POSITIVE VIBES ~ Sweet!

POSITIVE VIBES ~ Adorable 2 Bedroom, 1 Bathroom Cottage in Lush Surroundings and Outdoor Space!

Location

832 Johnson Ln.
33040 Key West , FL
United States
24° 33' 16.488" N, 81° 47' 40.524" W
See map: Google Maps
Florida US

POSITIVE VIBES ~ Sweet!

Request More Information

My October stay

Reviewed by Matthew K. on 2024-11-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Just wanted to say that I had a great time. The rental was clean, neat and updated. It had everything I needed to have an enjoyable stay.
Manager response on 2025-05-23 - Response from Best of Key West Rentals
Thank you for your review! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Frequent Guest - Love this Place!

Reviewed by Chris A. on 2024-05-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We have stayed at Positive Vibes multiple times. We love the cottage, the location, and the phenomenal service of Best of Key West. We already have 2 more trips to the cottage planned over the next year and can’t wait to enjoy its comfortable and relaxing “mojo”.

If you are looking for a great place to spend a month or more in Key West, this is a great option. We love it!
Manager response on 2024-06-29 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us! We would love to welcome you back!

Old Town Key West Cottage

Reviewed by Unknown on 2023-12-20
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Cute cottage and fantastic location for walking to many activities, restaurants, museums, sightseeing. Nice fenced in area for my small dog.
Manager response on 2024-06-29 - Response from Best of Key West Rentals
Thank you for your review, we are so glad the property met your needs while staying with us. We hope you'll stay with us again next time you visit Key West.

Positive Vibes!

Reviewed by Jeffrey H. on 2023-11-20
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Beautiful place, fantastic experience renting!!!
Manager response on 2023-12-05 - Response from Best of Key West Rentals
Thank you for this short but sweet five star review Jeffrey, we hope to have the pleasure to host you again next time you visit the island.

Quiet and Relaxing

Reviewed by Chris A. on 2023-05-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great little cottage tucked away on a quiet lane. Just far enough from Duval to get away from the crowds, but close enough to walk and get involved in the fun. We have stayed here before and we love Positive Vibes. Great home for a couple. The management company is awesome and very responsive. We will be back!
Manager response on 2023-12-05 - Response from Best of Key West Rentals
Thank you for your wonderful review Thomas. We are thrilled you loved this home and hope to host you again soon!

Positive Vibes really is charming!

Reviewed by Carl G. on 2023-01-20
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The home is beautifully located on a very quiet lane and is very well appointed. There were no surprises and the home is well maintained. Management company personnel could not be more friendly or helpful!
Manager response on 2023-02-24 - Response from Best of Key West Rentals
Thank you for your wonderful review Carl. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Paradise at Positive Vibes

Reviewed by Chris A. on 2022-11-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We have rented numerous properties over the years in Key West, and this property was one of our favorites. Great location, quiet lane, near Duval and all of the fun, but still far enough to give you a relaxing quiet evening if you want it. The house itself has two great bedrooms, a nice kitchen, and an outdoor area that is awesome and private. We loved our stay here and we have already reserved it again!
Manager response on 2022-12-02 - Response from Best of Key West Rentals
Thank you for this wonderful review Thomas, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Wonderful and Cozy Cottage

Reviewed by Kimberley S. on 2022-08-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Positive Vibes is tucked away on a delightful, narrow lane in a central location that makes most locations in Old Town and the White Street Gallery District easily walkable. (There is parking out front, and I kept my car there unused for almost all of our two-month stay.)

The cottage has two comfortable bedrooms. One is at the front of the house, with a door opening up to the front porch. There is a side entrance that can easily be used as the front door/main entrance instead.

The back and sides of the house are fenced and gated, and the back yard features a covered patio with seating and a dining table protected by an umbrella. The back yard has a beautiful garden with ginger and other plants, making it a pleasant place to relax.

The washer and dryer are indoors in the hallway by the main/side entrance. The kitchen has bar seating and is next to the living room.

As always, our property manager, Shana, was incredibly helpful and immediately responsive to any questions or concerns.

My family loves this neighborhood and tries to stay here at least once a year. The house is comfy and was suited for our needs (My husband and me with our small dog and cat, and with a brief visit by our son and his friend. We would definitely rent it again.
Manager response on 2022-09-09 - Response from Best of Key West Rentals
Thank you for your fantastic review Kimberley. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Private lane to enjoy the Key West experience

Reviewed by Steve B. on 2022-04-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
A small house that fit our needs. We loved the neighborhood and the neighbors.
Manager response on 2022-04-26 - Response from Best of Key West Rentals
It is wonderful to read you enjoyed this property and its neighbors so much. We hope your wife felt inspired and you both left with great new memories of your time in Key West!

February in Paradise

Reviewed by Unknown on 2022-03-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The home was very nice and cozy. Our pups loved their walks and ability to play in the fenced yard. Fully equipped and well furnished. While parking was an issue upin arrival - the property manager stayed on top of it and problem was resolved quickly. We have already reserved for next year.
Manager response on 2022-03-18 - Response from Best of Key West Rentals
Thank you for your fantastic review Madonna. It was a pleasure hosting you and we look forward to welcoming you again next year!

POSITIVE VIBES ~ Charming 2 BR, 1 Ba Cottage in Peaceful Area w/ Parking!

Unit Code: POS

POSITIVE VIBES ~ Sweet!

POSITIVE VIBES ~ Adorable 2 Bedroom, 1 Bathroom Cottage in Lush Surroundings and Outdoor Space!
LOST ON ISLAND TIME… Treasure your time together within this charming Key West cottage tucked away on this peaceful and vibrant lane in the iconic Old Town district. As you step inside a lifetime of memories are created as your loved ones come together for a unique and blissful getaway. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES… Showcasing a nautical lifestyle with modern amenities, this retreat allows you to truly live in the present. Enjoy a front porch boasting island views at every corner as you wave hello to friendly neighbors passing by. Within the home you will find an updated and fully equipped kitchen with stainless steel appliances and granite counters. Enjoy bar seating for 3 or take your treats outside and dine al fresco in the welcoming breeze. The adjacent living area is complete with cozy furnishings and a flat screen TV for movie nights. SLEEPING ARRANGEMENTS… Find a king bedroom with a flat screen TV located at the front of the home which can also be accessed from the front porch. Steps away is another guestroom outfitted with a queen bed and a flat screen TV. A full bathroom with a glass shower resides just outside both guestrooms. OUTDOOR LIVING… Indulge in island time within this lush and vibrant outdoor setting beckoning you in for more. Unwind with a good book on the plush outdoor furniture and stroll around by foot in this peaceful neighborhood. PARKING... This home allows parking for one vehicle. PETS... Pets up to 30 pounds are considered and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). TIME TO LIVE IN THE PRESENT…
June 2026
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Age 18 and under.
DatesPrice
06/12/2026 - 06/30/2026$150 /nt
07/01/2026 - 07/31/2026$136 /nt
08/01/2026 - 09/30/2026$150 /nt
10/01/2026 - 10/31/2026$161 /nt
11/01/2026 - 11/30/2026$179 /nt
12/01/2026 - 12/31/2026$197 /nt
01/01/2027 - 01/31/2027$286 /nt
02/01/2027 - 02/28/2027$304 /nt
03/01/2027 - 03/31/2027$286 /nt
04/01/2027 - 04/30/2027$197 /nt
05/01/2027 - 06/12/2027$161 /nt
4.7333
(15 Review)

My October stay

October 2024
, Winsted, CT US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Just wanted to say that I had a great time. The rental was clean, neat and updated. It had everything I needed to have an enjoyable stay.

Manager's Response

Thank you for your review! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Frequent Guest - Love this Place!

March 2024
, Columbia, MO United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We have stayed at Positive Vibes multiple times. We love the cottage, the location, and the phenomenal service of Best of Key West. We already have 2 more trips to the cottage planned over the next year and can’t wait to enjoy its comfortable and relaxing “mojo”.

If you are looking for a great place to spend a month or more in Key West, this is a great option. We love it!

Manager's Response

We are so happy to read you had such a good stay with us! We would love to welcome you back!

Frequent Guest - Love this Place!

March 2024
, Columbia, MO US

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We have stayed at Positive Vibes multiple times. We love the cottage, the location, and the phenomenal service of Best of Key West. We already have 2 more trips to the cottage planned over the next year and can’t wait to enjoy its comfortable and relaxing “mojo”.

If you are looking for a great place to spend a month or more in Key West, this is a great option. We love it!

Manager's Response

We are so happy to read you had such a good stay with us! We would love to welcome you back!

Old Town Key West Cottage

November 2023
, Denver, CO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Cute cottage and fantastic location for walking to many activities, restaurants, museums, sightseeing. Nice fenced in area for my small dog.

Manager's Response

Thank you for your review, we are so glad the property met your needs while staying with us. We hope you'll stay with us again next time you visit Key West.

Positive Vibes!

September 2023
, Marienville, PA, PA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Beautiful place, fantastic experience renting!!!

Manager's Response

Thank you for this short but sweet five star review Jeffrey, we hope to have the pleasure to host you again next time you visit the island.

Quiet and Relaxing

April 2023
, Columbia, MO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great little cottage tucked away on a quiet lane. Just far enough from Duval to get away from the crowds, but close enough to walk and get involved in the fun. We have stayed here before and we love Positive Vibes. Great home for a couple. The management company is awesome and very responsive. We will be back!

Manager's Response

Thank you for your wonderful review Thomas. We are thrilled you loved this home and hope to host you again soon!

Quiet and Relaxing

April 2023
, Columbia, MO US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great little cottage tucked away on a quiet lane. Just far enough from Duval to get away from the crowds, but close enough to walk and get involved in the fun. We have stayed here before and we love Positive Vibes. Great home for a couple. The management company is awesome and very responsive. We will be back!

Manager's Response

Thank you for your wonderful review Thomas. We are thrilled you loved this home and hope to host you again soon!

Positive Vibes really is charming!

December 2022
, Westford, MA Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The home is beautifully located on a very quiet lane and is very well appointed. There were no surprises and the home is well maintained. Management company personnel could not be more friendly or helpful!

Manager's Response

Thank you for your wonderful review Carl. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Positive Vibes really is charming!

December 2022
, Westford, MA Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The home is beautifully located on a very quiet lane and is very well appointed. There were no surprises and the home is well maintained. Management company personnel could not be more friendly or helpful!

Manager's Response

Thank you for your wonderful review Carl. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Paradise at Positive Vibes

October 2022
, Columbia, MO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We have rented numerous properties over the years in Key West, and this property was one of our favorites. Great location, quiet lane, near Duval and all of the fun, but still far enough to give you a relaxing quiet evening if you want it. The house itself has two great bedrooms, a nice kitchen, and an outdoor area that is awesome and private. We loved our stay here and we have already reserved it again!

Manager's Response

Thank you for this wonderful review Thomas, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Paradise at Positive Vibes

October 2022
, Columbia, MO US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We have rented numerous properties over the years in Key West, and this property was one of our favorites. Great location, quiet lane, near Duval and all of the fun, but still far enough to give you a relaxing quiet evening if you want it. The house itself has two great bedrooms, a nice kitchen, and an outdoor area that is awesome and private. We loved our stay here and we have already reserved it again!

Manager's Response

Thank you for this wonderful review Thomas, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Wonderful and Cozy Cottage

June 2022
, North Palm Beach, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Positive Vibes is tucked away on a delightful, narrow lane in a central location that makes most locations in Old Town and the White Street Gallery District easily walkable. (There is parking out front, and I kept my car there unused for almost all of our two-month stay.)

The cottage has two comfortable bedrooms. One is at the front of the house, with a door opening up to the front porch. There is a side entrance that can easily be used as the front door/main entrance instead.

The back and sides of the house are fenced and gated, and the back yard features a covered patio with seating and a dining table protected by an umbrella. The back yard has a beautiful garden with ginger and other plants, making it a pleasant place to relax.

The washer and dryer are indoors in the hallway by the main/side entrance. The kitchen has bar seating and is next to the living room.

As always, our property manager, Shana, was incredibly helpful and immediately responsive to any questions or concerns.

My family loves this neighborhood and tries to stay here at least once a year. The house is comfy and was suited for our needs (My husband and me with our small dog and cat, and with a brief visit by our son and his friend. We would definitely rent it again.

Manager's Response

Thank you for your fantastic review Kimberley. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Private lane to enjoy the Key West experience

March 2022
, bloomfield township, MI US

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

A small house that fit our needs. We loved the neighborhood and the neighbors.

Manager's Response

It is wonderful to read you enjoyed this property and its neighbors so much. We hope your wife felt inspired and you both left with great new memories of your time in Key West!

Private lane to enjoy the Key West experience

March 2022
, bloomfield township, MI Unknown

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

A small house that fit our needs. We loved the neighborhood and the neighbors.

Manager's Response

It is wonderful to read you enjoyed this property and its neighbors so much. We hope your wife felt inspired and you both left with great new memories of your time in Key West!

February in Paradise

February 2022
, Pawleys Island, SC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The home was very nice and cozy. Our pups loved their walks and ability to play in the fenced yard. Fully equipped and well furnished. While parking was an issue upin arrival - the property manager stayed on top of it and problem was resolved quickly. We have already reserved for next year.

Manager's Response

Thank you for your fantastic review Madonna. It was a pleasure hosting you and we look forward to welcoming you again next year!

Leave a Review
2 Bed
1 Bath
Sleeps 4

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GOOD FEELIN ~ Island Life!

GOOD FEELIN ~ Charming 2 Bedroom, 2 Bathroom Home w/ Backyard Cottage in Peaceful Key West Neighborhood!

Location

830 Johnson Ln.
33040 Key West , FL
United States
24° 33' 16.344" N, 81° 47' 40.74" W
See map: Google Maps
Florida US

GOOD FEELIN ~ Island Life!

Request More Information

Love Key West!

Reviewed by Susan C. on 2026-04-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
I couldn't have asked for a better trip. Spent a month in this adorable property. Had friends visit who were able stay in the separate cottage.
Manager response on 2026-04-06 - Response from Best of Key West Rentals
Thank you for the kind words Susan! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.

wonderful rental!

Reviewed by Maggie W. on 2023-04-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We truly enjoyed this rental! The location is great, we walked everywhere. The property is clean, comfortable and served all our purposes very well. We loved the private and beautiful seating area, and the little guest house was just perfect for our visitors. We'd highly recommend this rental!
Manager response on 2023-04-07 - Response from Best of Key West Rentals
Thank you for sharing a review of your recent experience Maggie. Our team here at Best of Key West Rentals is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you. We hope you’ll visit us again soon.

Month in paradise

Reviewed by Jodi F. on 2022-03-22
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Location of the home was perfect as I could walk everywhere. The Lane is quiet and friendly. Outdoor seating area was very comfortable and where most time spent.
Manager response on 2022-04-05 - Response from Best of Key West Rentals
Thank you for your wonderful review Jodi. We enjoyed hosting you and hope to see you back in Key West again soon!

Key West wonderful!

Reviewed by Jenny A. on 2022-02-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great month vacation in Key West! The home was convenient and we could walk everywhere. Nice quiet street not far from Duval. The home was clean and well stocked with everything you could need. The property manager Shana was wonderful and easy to reach. There were even bikes at the house to use. So much to do in Key West! We really enjoyed the Hemingway home, Little White House, sunset cruises, Mallory Square sunsets and all the live music and wonderful food.
Manager response on 2022-02-17 - Response from Best of Key West Rentals
Thank you for your review Jenny. We are so thrilled to hear how much you loved this home and enjoyed your Key West experience! We hope to host you again next time you visit!

Wonderful for groups or hosting friends/family

Reviewed by Kimberley S. on 2021-09-26
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Good Feelin’ is a terrific rental for large families, a group of friends, or a couple (like my husband and me) who have family and friends come for visits in the back cottage. It is made up of two Conch cottages with a large shared outdoor space between them.

The front cottage is comfortable, with a main bedroom, a smaller bedroom upstairs in the loft (accessible by a built-in ladder), a bathroom, full kitchen (fully stocked), and living area. There is bar seating at the counter.

There is a large patio/deck out back with a full-size dining table and chairs, a comfortable seating area, and a barbecue. This is all enclosed with fences and gates, in case you have pets.

The back cottage has a small seating area (with pull-out couch), small kitchenette, bedroom, and bathroom. It’s an ideal guest quarters. The back cottage can be accessed by the side gate to allow guests to come and go freely. The laundry is in a shed next to the back cottage.

The neighborhood is wonderful—it’s a quiet, narrow lane with incredibly friendly neighbors. It is centrally-located, so it is easy to walk most places in Old Town. There is an on-street parking space in front of the house. Other no-charge spaces can be found on Truman, Windsor by the church, and about every fifth space around the cemetery, which is a block away.

There are bikes along the side of the house in case you want to go for a ride.

While we were there, there was a plumbing issue in the back cottage that has now been resolved. The reason I mention it is that the staff of Best of Key West went out of their way to get a plumber and cleaning service there promptly to deal with the situation. If you need anything, you will always get a wuick and friendly response.

I will add I felt safe walking my dog late at night in this neighborhood. I felt our neighbors were looking out for us, too, as much of the time I was there alone (with my pets).
Manager response on 2021-10-06 - Response from Best of Key West Rentals
Thank you for this wonderful review Kimberley, we are so glad you enjoyed the property so much and look forward to welcoming you again next time you are in Key West!

GOOD FEELIN ~ Charming 2 BR/2 Ba Home Conveniently Located w/ Parking!

Unit Code: GF

GOOD FEELIN ~ Island Life!

GOOD FEELIN ~ Charming 2 Bedroom, 2 Bathroom Home w/ Backyard Cottage in Peaceful Key West Neighborhood!
SPOIL YOURSELF… Come unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of swaying palm trees beneath sunny skies will draw you into this picturesque dream you’ve been craving for within this quaint Old Town sanctuary. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENTITIES… Step onto a lovely front porch pulling you out of reality and into island time washing all your worries away. Inside you will be greeted with cheery surroundings and cool wood flooring within this cozy space bringing the everyone together. An updated kitchen featuring stainless steel appliances and granite counters graciously opens up to a living room equipped with comfortable furnishings and a flat screen TV. Enjoy bar seating for 4 or take your treats outside to dine together welcomed by a sweet tropical breeze. SLEEPING ARRANGEMENTS… Find a spacious queen bedroom equipped with a flat screen TV and a bathroom with a shower/tub combination that also opens up to the hallway for convenience. Perched above this room is a loft with a queen bed. Beyond the outdoor living space lies a roomy 1-bedroom cottage with a flat screen TV, full kitchen, en suite bathroom with a shower/tub combination and a queen bed. Enjoy a queen sofa sleeper in the cottage for additional visiting guests. OUTOOR LIVING… Come unwind in this desirable outdoor space offering a wonderful place to lounge and enjoy the simple treasures of island life. Grill up your fresh catch of the day and sip on your cocktail beneath the stars. Enjoy an outdoor shower to wash the day away. This home is just a short bike ride to all the beloved Key West attractions. PARKING... This home allows parking for one vehicle. PETS... Pets are considered up to 30 pounds and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). COME AND STAY A WHILE…
June 2026
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DatesPrice
06/12/2026 - 06/30/2026$136 /nt
07/01/2026 - 07/31/2026$143 /nt
08/01/2026 - 09/30/2026$161 /nt
10/01/2026 - 10/31/2026$179 /nt
11/01/2026 - 11/30/2026$197 /nt
12/01/2026 - 12/31/2026$215 /nt
01/01/2027 - 01/31/2027$322 /nt
02/01/2027 - 02/28/2027$358 /nt
03/01/2027 - 03/31/2027$322 /nt
04/01/2027 - 04/30/2027$215 /nt
05/01/2027 - 06/12/2027$179 /nt
5.0000
(5 Review)

Love Key West!

March 2026
, Tinton Falls, NJ US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

I couldn't have asked for a better trip. Spent a month in this adorable property. Had friends visit who were able stay in the separate cottage.

Manager's Response

Thank you for the kind words Susan! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.

wonderful rental!

March 2023
, AUBURN, NY US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We truly enjoyed this rental! The location is great, we walked everywhere. The property is clean, comfortable and served all our purposes very well. We loved the private and beautiful seating area, and the little guest house was just perfect for our visitors. We'd highly recommend this rental!

Manager's Response

Thank you for sharing a review of your recent experience Maggie. Our team here at Best of Key West Rentals is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you. We hope you’ll visit us again soon.

Month in paradise

January 2022
, Lancaster, PA United States

Overall
5
Services from rental manager
4
Cleanliness
5
Location
5
Property condition
4

Location of the home was perfect as I could walk everywhere. The Lane is quiet and friendly. Outdoor seating area was very comfortable and where most time spent.

Manager's Response

Thank you for your wonderful review Jodi. We enjoyed hosting you and hope to see you back in Key West again soon!

Key West wonderful!

January 2022
, Matthews, NC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great month vacation in Key West! The home was convenient and we could walk everywhere. Nice quiet street not far from Duval. The home was clean and well stocked with everything you could need. The property manager Shana was wonderful and easy to reach. There were even bikes at the house to use. So much to do in Key West! We really enjoyed the Hemingway home, Little White House, sunset cruises, Mallory Square sunsets and all the live music and wonderful food.

Manager's Response

Thank you for your review Jenny. We are so thrilled to hear how much you loved this home and enjoyed your Key West experience! We hope to host you again next time you visit!

Wonderful for groups or hosting friends/family

July 2021
, North Palm Beach, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Good Feelin’ is a terrific rental for large families, a group of friends, or a couple (like my husband and me) who have family and friends come for visits in the back cottage. It is made up of two Conch cottages with a large shared outdoor space between them.

The front cottage is comfortable, with a main bedroom, a smaller bedroom upstairs in the loft (accessible by a built-in ladder), a bathroom, full kitchen (fully stocked), and living area. There is bar seating at the counter.

There is a large patio/deck out back with a full-size dining table and chairs, a comfortable seating area, and a barbecue. This is all enclosed with fences and gates, in case you have pets.

The back cottage has a small seating area (with pull-out couch), small kitchenette, bedroom, and bathroom. It’s an ideal guest quarters. The back cottage can be accessed by the side gate to allow guests to come and go freely. The laundry is in a shed next to the back cottage.

The neighborhood is wonderful—it’s a quiet, narrow lane with incredibly friendly neighbors. It is centrally-located, so it is easy to walk most places in Old Town. There is an on-street parking space in front of the house. Other no-charge spaces can be found on Truman, Windsor by the church, and about every fifth space around the cemetery, which is a block away.

There are bikes along the side of the house in case you want to go for a ride.

While we were there, there was a plumbing issue in the back cottage that has now been resolved. The reason I mention it is that the staff of Best of Key West went out of their way to get a plumber and cleaning service there promptly to deal with the situation. If you need anything, you will always get a wuick and friendly response.

I will add I felt safe walking my dog late at night in this neighborhood. I felt our neighbors were looking out for us, too, as much of the time I was there alone (with my pets).

Manager's Response

Thank you for this wonderful review Kimberley, we are so glad you enjoyed the property so much and look forward to welcoming you again next time you are in Key West!

Leave a Review
2 Bed
2 Baths
Sleeps 6

Search Availability

OUR HAPPY PLACE ~ Cloud 9!

OUR HAPPY PLACE ~ 2 Bedroom, 2 Bath Condo Steps from Beach and Community Pool in Quiet Location!

Location

1800 Atlantic Blvd. C222
33040 Key West , FL
United States
24° 33' 2.5848" N, 81° 46' 39.0648" W
See map: Google Maps
Florida US

OUR HAPPY PLACE ~ Cloud 9!

Request More Information

Year 5 and coming back again!

Reviewed by Joe L. on 2026-03-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
1800 Atlantic Association is making structural and water/drainage improvements to all units at the property.
Manager response on 2026-03-03 - Response from Best of Key West Rentals
Thank you for the kind words! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.

Winter Escape

Reviewed by Joe L. on 2026-02-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This is my fifth year renting this condo for January and February. Enjoy the location and ocean view from the balcony. The unit and furniture needs some updating..
Manager response on 2026-02-17 - Response from Best of Key West Rentals
Thank you for the kind words Joe! We’re so happy you enjoyed your stay in paradise, and we’d be thrilled to welcome you back for another unforgettable visit.

Our KW happy place

Reviewed by Elaine H. on 2025-05-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This is a review for the 2 month stay March-April 2025. The unit was a perfect fit for our needs. Thank you for upgrading the window treatments in the main bedroom. The room darkening drapes kept the room cooler with the afternoon sun. We especially were pleased with the upgrade provided to the cable system and how the transition was handled including recognizing the inconvenience of the 5 day interruption of services. We definitely noticed the positive impact of the new management service in the building...clean, better care of landscape and pool and the beach front looks wonderful making it much more inviting to use. One suggestion...with our extended stay we do spend more time in the unit, especially in the evenings and the living room furniture is not the most comfortable. An update here would go a long way to enhance the unit. Would like to give a shout out the Whitney Olado who continues to be prompt with her responses and always helpful. Once again a positive experience at 1800!
Manager response on 2025-05-05 - Response from Best of Key West Rentals
Elaine, thank you so much for your thoughtful and detailed review! We’re thrilled to hear the unit was a great fit and that the updates—especially the window treatments and cable system—made a noticeable difference during your stay. We're also glad you appreciated the improvements in building management and the care taken with the property overall. We truly value your suggestion regarding the living room furniture and will be sharing that feedback with the owner for consideration. And thank you for the kind words about Whitney—she’ll be happy to hear her efforts made a positive impact. We look forward to welcoming you back to YOUR Key West happy place!

key West our “happy place”

Reviewed by Elaine H. on 2024-05-08
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Our stay was from March 1st 2024 to May 1st 2024. We found Our Happy Place to fit our needs, comfortable, spacious, bright and well appointed. We have been coming to KW for over 20 years and have mainly stayed in Old Town. We found 1800 Atlantic to be a sweet spot and really enjoyed the lovely outdoor amenities, especially the lovely views pool side and the lush gardens leading to the waterfront. We truly felt it was a quiet get-away spot but close enough to town with use of bikes or ride share. Plenty of excellent walking options for our morning walks.
The appliances were all in good working order, kitchen well furnished with necessary gadgets, and ample storage. Beds were very comfortable, linens new and fresh.
A few minor suggestions...the window treatments in the primary bedroom would benefit being room darkening. Although the sheers gave the room an airy feeling the afternoon sun heated the floor tiles and the room making the room very warm, making use of the air conditioning a necessity. With a stay of 2 months we did a lot of living in this space and found the living room furniture not the most comfortable. The addition of one very comfy chair would make a huge difference.
Our property manager Whitney was always very responsive and a great problem solver. We really appreciated her keeping tabs of our arrival and facilitating an earlier check-in.
All in all we had a great experience and look forward to our return visit in 2025!
Manager response on 2024-05-08 - Response from Best of Key West Rentals
Thank you for your review Elain. It was a pleasure hosting you. We really appreciate you taking the time to share your feedback and being so open with us, all your suggestions have been shane with the owner. We are glad you felt home at Our Happy Place and plan on returning next year! We look forward to welcoming you again!

Great Two Months!

Reviewed by Joe L. on 2024-03-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
My property Manager Whitney.was terrific as she has been in past years that I have rented this condo. I look forward to be back in January and February 2025.
Manager response on 2024-03-19 - Response from Best of Key West Rentals
Thank you for your fantastic review Joe. It was a pleasure hosting you and we look forward to welcoming you again next year!

Third Time A Charm

Reviewed by Joe L. on 2023-03-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
I rented this condo for January and February. It is ideally situated for me as I am on a walker. The only issue, was the elevator failed on three occasions. Whitney, our property manager was terrific. She promptly and courteously addressed any concern that I brought to her attention. After the third breakdown the elevator operated efficiently.
Manager response on 2023-03-20 - Response from Best of Key West Rentals
Thank you for this great review Joe! We are thrilled you enjoyed the property and relieved the elevator was repaired for good so you could comfortably get around. We hope to host you again next time you need warmth and sunshine!

Our Happy Place - After Adjustments

Reviewed by Joe L. on 2022-02-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Upon arrival, no box spring, bed was too low for me , Shana, my manager was excellent. She arranged for two box springs, at my cost, and had them installed. Each request I had she answered and resolved promptly and professionally. She made my stay as comfortable as possible for me being mobility challenged.
Manager response on 2022-02-08 - Response from Best of Key West Rentals
Thank you for your review Joe, it was a pleasure hosting you and we look forward to welcoming you again next year!

OUR HAPPY PLACE ~ Adorable 2 Bedroom, 2 Bath Condo Steps from the Beach!

Unit Code: OHP

OUR HAPPY PLACE ~ Cloud 9!

OUR HAPPY PLACE ~ 2 Bedroom, 2 Bath Condo Steps from Beach and Community Pool in Quiet Location!
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through May 2026. A 12 person crew will be working section-by-section from 8am-6pm, 5 days a week, and Saturdays will be weather make-up days as-needed. Please understand there will most likely be some amount of noise heard throughout the community. Our rentals have been priced to offset noise issues or any other inconvenience due to the construction project. UNFORGETTABLE KEY WEST… Allow your Key West creation to unfold within this charming and tranquil retreat embracing the quintessential island spirit of the Keys. Possessing every luxury one could desire within a fun loving space, this setting is sure to wash all your real world worries away. Take a journey through this slice of Paradise located in the community of 1800 Atlantic offering the right amount of R & R from within your private abode with just steps to putting your toes in the sandy beaches. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES… Step into this spacious condo with nautical charm immediately pulling you into island time. An open concept brings the whole family together allowing for unforgettable memories to be created. A large kitchen with plenty of counter space, stainless-steel appliances and a cafe table for 2 makes meal prep a breeze. The indoor dining area allows for 6 as you come together after a fun filled day being followed by movie night on cozy living room furnishings. The unit is accessible by an elevator or the stairs. SLEEPING ARRANGEMENTS… Enjoy a comfortable king guestroom with a TV with access to a hallway bathroom with a shower/tub combination. The primary suite is outfitted with a king bed, TV and an en suite full bathroom with a large shower/tub combination. Both rooms open to a balcony showcasing lush courtyard views beyond. Enjoy a sofa sleeper in the Great Room. OUTDOOR LIVING… Take your happy hour out on the balcony and soak up the island breeze with courtyard views and a sliver of the blue ocean beyond. A heated, saltwater community pool is equipped with plenty of loungers and views of the sparkling ocean. Tennis courts reside on property as well as a community grill and fitness center. Enjoy being located in these peaceful surroundings with just a short ride into town! PARKING... Enjoy one covered parking space in the garage (larger SUV's may not fit). Plenty of additional parking available in the open lots in front of the units at no additional cost. PETS... This is not a pet-friendly home. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). ISLAND TIME…
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DatesPrice
06/12/2026 - 06/30/2026$125 /nt
07/01/2026 - 07/31/2026$136 /nt
08/01/2026 - 09/30/2026$161 /nt
10/01/2026 - 10/31/2026$179 /nt
11/01/2026 - 11/30/2026$197 /nt
12/01/2026 - 12/31/2026$250 /nt
01/01/2027 - 01/31/2027$429 /nt
02/01/2027 - 02/28/2027$465 /nt
03/01/2027 - 03/31/2027$429 /nt
04/01/2027 - 04/30/2027$268 /nt
05/01/2027 - 06/12/2027$161 /nt
4.8889
(9 Review)

Year 5 and coming back again!

February 2026
, Thornton, PA United States

Overall
5
Property condition
4
Location
5
Cleanliness
4
Services from rental manager
5

1800 Atlantic Association is making structural and water/drainage improvements to all units at the property.

Manager's Response

Thank you for the kind words! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.

Winter Escape

January 2026
, Thornton, PA United States

Overall
5
Property condition
3
Location
5
Cleanliness
5
Services from rental manager
5

This is my fifth year renting this condo for January and February. Enjoy the location and ocean view from the balcony. The unit and furniture needs some updating..

Manager's Response

Thank you for the kind words Joe! We’re so happy you enjoyed your stay in paradise, and we’d be thrilled to welcome you back for another unforgettable visit.

Our KW happy place

March 2025
, Newport, RI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

This is a review for the 2 month stay March-April 2025. The unit was a perfect fit for our needs. Thank you for upgrading the window treatments in the main bedroom. The room darkening drapes kept the room cooler with the afternoon sun. We especially were pleased with the upgrade provided to the cable system and how the transition was handled including recognizing the inconvenience of the 5 day interruption of services. We definitely noticed the positive impact of the new management service in the building...clean, better care of landscape and pool and the beach front looks wonderful making it much more inviting to use. One suggestion...with our extended stay we do spend more time in the unit, especially in the evenings and the living room furniture is not the most comfortable. An update here would go a long way to enhance the unit. Would like to give a shout out the Whitney Olado who continues to be prompt with her responses and always helpful. Once again a positive experience at 1800!

Manager's Response

Elaine, thank you so much for your thoughtful and detailed review! We’re thrilled to hear the unit was a great fit and that the updates—especially the window treatments and cable system—made a noticeable difference during your stay. We're also glad you appreciated the improvements in building management and the care taken with the property overall.


We truly value your suggestion regarding the living room furniture and will be sharing that feedback with the owner for consideration. And thank you for the kind words about Whitney—she’ll be happy to hear her efforts made a positive impact. We look forward to welcoming you back to YOUR Key West happy place!

Our KW happy place

March 2025
, Newport, RI United States

Overall
5
Property condition
4
Location
5
Cleanliness
5
Services from rental manager
5

This is a review for the 2 month stay March-April 2025. The unit was a perfect fit for our needs. Thank you for upgrading the window treatments in the main bedroom. The room darkening drapes kept the room cooler with the afternoon sun. We especially were pleased with the upgrade provided to the cable system and how the transition was handled including recognizing the inconvenience of the 5 day interruption of services. We definitely noticed the positive impact of the new management service in the building...clean, better care of landscape and pool and the beach front looks wonderful making it much more inviting to use. One suggestion...with our extended stay we do spend more time in the unit, especially in the evenings and the living room furniture is not the most comfortable. An update here would go a long way to enhance the unit. Would like to give a shout out the Whitney Olado who continues to be prompt with her responses and always helpful. Once again a positive experience at 1800!

Manager's Response

Elaine, thank you so much for your thoughtful and detailed review! We’re thrilled to hear the unit was a great fit and that the updates—especially the window treatments and cable system—made a noticeable difference during your stay. We're also glad you appreciated the improvements in building management and the care taken with the property overall.


We truly value your suggestion regarding the living room furniture and will be sharing that feedback with the owner for consideration. And thank you for the kind words about Whitney—she’ll be happy to hear her efforts made a positive impact. We look forward to welcoming you back to YOUR Key West happy place!

key West our “happy place”

April 2024
, Newport, RI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Our stay was from March 1st 2024 to May 1st 2024. We found Our Happy Place to fit our needs, comfortable, spacious, bright and well appointed. We have been coming to KW for over 20 years and have mainly stayed in Old Town. We found 1800 Atlantic to be a sweet spot and really enjoyed the lovely outdoor amenities, especially the lovely views pool side and the lush gardens leading to the waterfront. We truly felt it was a quiet get-away spot but close enough to town with use of bikes or ride share. Plenty of excellent walking options for our morning walks.
The appliances were all in good working order, kitchen well furnished with necessary gadgets, and ample storage. Beds were very comfortable, linens new and fresh.
A few minor suggestions...the window treatments in the primary bedroom would benefit being room darkening. Although the sheers gave the room an airy feeling the afternoon sun heated the floor tiles and the room making the room very warm, making use of the air conditioning a necessity. With a stay of 2 months we did a lot of living in this space and found the living room furniture not the most comfortable. The addition of one very comfy chair would make a huge difference.
Our property manager Whitney was always very responsive and a great problem solver. We really appreciated her keeping tabs of our arrival and facilitating an earlier check-in.
All in all we had a great experience and look forward to our return visit in 2025!

Manager's Response

Thank you for your review Elain. It was a pleasure hosting you. We really appreciate you taking the time to share your feedback and being so open with us, all your suggestions have been shane with the owner.

We are glad you felt home at Our Happy Place and plan on returning next year! We look forward to welcoming you again!

key West our “happy place”

April 2024
, Newport, RI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Our stay was from March 1st 2024 to May 1st 2024. We found Our Happy Place to fit our needs, comfortable, spacious, bright and well appointed. We have been coming to KW for over 20 years and have mainly stayed in Old Town. We found 1800 Atlantic to be a sweet spot and really enjoyed the lovely outdoor amenities, especially the lovely views pool side and the lush gardens leading to the waterfront. We truly felt it was a quiet get-away spot but close enough to town with use of bikes or ride share. Plenty of excellent walking options for our morning walks.
The appliances were all in good working order, kitchen well furnished with necessary gadgets, and ample storage. Beds were very comfortable, linens new and fresh.
A few minor suggestions...the window treatments in the primary bedroom would benefit being room darkening. Although the sheers gave the room an airy feeling the afternoon sun heated the floor tiles and the room making the room very warm, making use of the air conditioning a necessity. With a stay of 2 months we did a lot of living in this space and found the living room furniture not the most comfortable. The addition of one very comfy chair would make a huge difference.
Our property manager Whitney was always very responsive and a great problem solver. We really appreciated her keeping tabs of our arrival and facilitating an earlier check-in.
All in all we had a great experience and look forward to our return visit in 2025!

Manager's Response

Thank you for your review Elain. It was a pleasure hosting you. We really appreciate you taking the time to share your feedback and being so open with us, all your suggestions have been shane with the owner.

We are glad you felt home at Our Happy Place and plan on returning next year! We look forward to welcoming you again!

Great Two Months!

February 2024
, Thornton, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

My property Manager Whitney.was terrific as she has been in past years that I have rented this condo. I look forward to be back in January and February 2025.

Manager's Response

Thank you for your fantastic review Joe. It was a pleasure hosting you and we look forward to welcoming you again next year!

Third Time A Charm

February 2023
, Thornton, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

I rented this condo for January and February. It is ideally situated for me as I am on a walker. The only issue, was the elevator failed on three occasions. Whitney, our property manager was terrific. She promptly and courteously addressed any concern that I brought to her attention. After the third breakdown the elevator operated efficiently.

Manager's Response

Thank you for this great review Joe! We are thrilled you enjoyed the property and relieved the elevator was repaired for good so you could comfortably get around. We hope to host you again next time you need warmth and sunshine!

Our Happy Place - After Adjustments

January 2022
, Thornton, PA United States

Overall
4
Services from rental manager
5
Cleanliness
4
Location
4
Property condition
1

Upon arrival, no box spring, bed was too low for me , Shana, my manager was excellent. She arranged for two box springs, at my cost, and had them installed. Each request I had she answered and resolved promptly and professionally. She made my stay as comfortable as possible for me being mobility challenged.

Manager's Response

Thank you for your review Joe, it was a pleasure hosting you and we look forward to welcoming you again next year!

Leave a Review
2 Bed
2 Baths
Sleeps 6

Search Availability

CLOUD 9 ~ No Passport Required!

CLOUD 9 ~ 4 Bedroom, 3.5 Bathroom Retreat with 2 Off Street Parking Spots and Incredible Outdoor Oasis w/ Pool! A Short Distance to Sandy Key West Beaches!

Location

1211 Margaret St.
33040 Key West , FL
United States
24° 33' 6.444" N, 81° 47' 33.576" W
See map: Google Maps
Florida US

CLOUD 9 ~ No Passport Required!

Request More Information

What a joy!

Reviewed by Rachelle B. on 2024-07-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This home was so comfortable and clean! It has amazing space for guests coming and going. The property management team was very good. The countertops in the kitchen were a little warm, but everything else was perfecto! ��✨ #homeawayfromhome #cozyvibes #perfecto
Manager response on 2024-07-05 - Response from Best of Key West Rentals
Thank you for your fantastic review Rachelle. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

2nd year at Cloud 9

Reviewed by Unknown on 2023-12-20
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We returned to Cloud 9 for the month of November and had a wonderful time. A few minor problems at the beginning of our stay were quickly addressed, and the house was comfortable for 3 couples during one week, and 4 adults and 3 kids over Thanksgiving. The pool and outside area are great, the kitchen well-appointed, and common spaces are comfortable.
The one caution I would offer is that the 4th “bedroom” in the pool house is not particularly comfortable. It’s damp smelling and requires a dehumidifier to be running 24/7. There are no closets in the room. We used it for our teenage grandson, and used the bathroom there as a spare shower, but I wouldn’t count on it as an option for a couple.
Location is great, walkable to everything.
Manager response on 2024-06-05 - Response from Best of Key West Rentals
Thank you for this great review! We are thrilled you enjoyed the property and hope to host you again in the future!

Great month long celebration!

Reviewed by Unknown on 2022-12-07
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We rented Cloud Nine for the month, knowing that we’d have a variety of friends and family of all ages staying at various times during the month. The house is flexible, and accommodated all our needs. The large outside table and retractable awning made the backyard a perfect place for happy hour, and the pool was big enough for the kids to play.
Manager response on 2022-12-08 - Response from Best of Key West Rentals
Ruth, we are so happy you found this property and ideal for your month long celebration in Key West. We hope you'll stay with us again next time you visit! Thank you for being our guest!

Great Home!

Reviewed by Unknown on 2021-08-30
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Cloud 9 was a great house monthly rental. Location in Old Town was great and close to marinas, Duval and the beach. Great off street parking and well appointed home. This was our second time renting from Truman & Company and they are great. Very responsive!
Manager response on 2021-09-07 - Response from Best of Key West Rentals
Thank you for this wonderful review Searing, we are thrilled you enjoyed every aspect of your stay and look forward to the next time you visit the island!

You should rent this house now!

Reviewed by Kristina D. on 2020-10-19
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This house had everything to feel like a home. It was so well appointed from the salt water pool to the spaciousness of the house. Its welcoming and beautiful. There is off street parking and its two doors down from our favorite cuban restaurant and a short bike ride or even a walk to neighborhood grocery, beach, fishing pier and Duval street. The management company was super responsive and kind and the complimentary concierge service was extremely knowledgeable about the island and suggestions that fit our wants. We loved our time there and wish we were still there.
Manager response on 2020-10-20 - Response from Best of Key West Rentals
Wow! Thank you for your wonderful review. We enjoyed hosting you in this incredible Key West dream home and hope to see you again next year!

The BEST home in 11 years of vacationing in Key West

Reviewed by John P. on 2020-08-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Part of me doesn't want to say how great this home is, because I get the feeling it will become so popular it won't be available for our yearly return to Key West. But being perfectly honest we have stayed 1 month in Key West every year for the last 11 years and rented 7 different homes. Cloud 9 is by far the best most comfortable home we have rented. We also loved the location. We always stay in Old Town, but many of the streets are busy. Cloud 9 is on a quiet street within a 10 min walk of the beach. We have also worked with several Key West rental companies over the years and Wendy Zintsmaster's team was among the best.
Manager response on 2020-08-13 - Response from Best of Key West Rentals
Thank you so much for your amazing review! We are so happy that you enjoyed Cloud 9 and can't wait to see you return next year.

CLOUD 9 ~ 4 Bedroom, 3.5 Bathroom with Off Street Parking and Pool!

Unit Code: CL

CLOUD 9 ~ No Passport Required!

CLOUD 9 ~ 4 Bedroom, 3.5 Bathroom Retreat with 2 Off Street Parking Spots and Incredible Outdoor Oasis w/ Pool! A Short Distance to Sandy Key West Beaches!
NO PASSPORT REQUIRED… A lovingly restored island retreat with luxurious coastal flair, this home’s aesthetic beauty draws you in to a world of tranquility. This home is also known as "Hunter House" in the name of Blake Hunter for his generous donation to a local organization. Spacious by design with 4 bedrooms and 3.5 bathrooms, a lifetime of memories await as your loved ones come together in this gem set a world apart from reality. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES… An adorable glance to your picture-perfect getaway catches your eye as you pull up to 2 off street parking with views of your long awaited dream home. A quaint sunroom begins your journey with seating for your 5 o’clock happy hour. Step foot into an attractive, open Great Room area with cozy furnishings, a flat screen TV and rich hard wood flooring throughout. A crisp, gourmet kitchen follows with ample lighted cabinetry, a gas stove, granite counters, stainless steel appliances and bar seating for 4. Dining for 6 lies just beyond overlooking your outdoor tropical oasis. SLEEPING ARRANGEMENTS… Two comfortable bedrooms occupy the first level of the home sharing a full bathroom with a walk in shower. The first bedroom comes with a queen bed and the other with a king bed. The private king master suite lies up the stairs equipped with a large walk in closet, writing desk and en suite full bathroom with double vanity sinks, a walk in shower and clawfoot tub. Soak up the pristine backyard views from the master suite’s very own balcony with seating for two. Visiting guests can experience a poolside cottage featuring a queen bed, mini fridge and en suite full bathroom with a shower. Additional sleeping arrangements can be found on the sofa sleeper downstairs with a powder room just off the dining area. Apple TV's are provided in guest rooms so you can log in to catch up on all your Netflix favorites! OUTDOOR LIVING… Sunny days are best spent out on the spacious outdoor deck surrounding a sparkling, heated pool and natural beauty of swaying palms all around. Cool off under the retractable awning and enjoy your fresh catch al fresco with seating for 6. Just a short distance to the sandy beaches of Key West and all the adored attractions, this home is the ideal destination for island perfection. PARKING... Two off street parking spaces are available for this home. PETS... One pet per reservation, 30 pound non-shedding dogs are considered. No kitties please! Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. A pet fee is required. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). A TROPICAL DREAM…
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Age 18 and under.
DatesPrice
06/12/2026 - 06/30/2026$268 /nt
07/01/2026 - 07/31/2026$483 /nt
08/01/2026 - 09/30/2026$322 /nt
10/01/2026 - 10/31/2026$500 /nt
11/01/2026 - 11/30/2026$600 /nt
12/01/2026 - 12/31/2026$625 /nt
01/01/2027 - 01/31/2027$804 /nt
02/01/2027 - 02/28/2027$893 /nt
03/01/2027 - 03/31/2027$804 /nt
04/01/2027 - 04/30/2027$500 /nt
05/01/2027 - 06/12/2027$375 /nt
4.8750
(8 Review)

What a joy!

May 2024
, Independence, MO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This home was so comfortable and clean! It has amazing space for guests coming and going. The property management team was very good. The countertops in the kitchen were a little warm, but everything else was perfecto! ✨ #homeawayfromhome #cozyvibes #perfecto

Manager's Response

Thank you for your fantastic review Rachelle. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

2nd year at Cloud 9

November 2023
, Baltimore, MD Unknown

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

We returned to Cloud 9 for the month of November and had a wonderful time. A few minor problems at the beginning of our stay were quickly addressed, and the house was comfortable for 3 couples during one week, and 4 adults and 3 kids over Thanksgiving. The pool and outside area are great, the kitchen well-appointed, and common spaces are comfortable.
The one caution I would offer is that the 4th “bedroom” in the pool house is not particularly comfortable. It’s damp smelling and requires a dehumidifier to be running 24/7. There are no closets in the room. We used it for our teenage grandson, and used the bathroom there as a spare shower, but I wouldn’t count on it as an option for a couple.
Location is great, walkable to everything.

Manager's Response

Thank you for this great review! We are thrilled you enjoyed the property and hope to host you again in the future!

Great month long celebration!

November 2022
, Baltimore, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
5

We rented Cloud Nine for the month, knowing that we’d have a variety of friends and family of all ages staying at various times during the month. The house is flexible, and accommodated all our needs. The large outside table and retractable awning made the backyard a perfect place for happy hour, and the pool was big enough for the kids to play.

Manager's Response

Ruth, we are so happy you found this property and ideal for your month long celebration in Key West. We hope you'll stay with us again next time you visit! Thank you for being our guest!

Great month long celebration!

November 2022
, Baltimore, MD Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
5

We rented Cloud Nine for the month, knowing that we’d have a variety of friends and family of all ages staying at various times during the month. The house is flexible, and accommodated all our needs. The large outside table and retractable awning made the backyard a perfect place for happy hour, and the pool was big enough for the kids to play.

Manager's Response

Ruth, we are so happy you found this property and ideal for your month long celebration in Key West. We hope you'll stay with us again next time you visit! Thank you for being our guest!

Great Home!

July 2021
, Tampa, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Cloud 9 was a great house monthly rental. Location in Old Town was great and close to marinas, Duval and the beach. Great off street parking and well appointed home. This was our second time renting from Truman & Company and they are great. Very responsive!

Manager's Response

Thank you for this wonderful review Searing, we are thrilled you enjoyed every aspect of your stay and look forward to the next time you visit the island!

Great Home!

July 2021
, Tampa, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Cloud 9 was a great house monthly rental. Location in Old Town was great and close to marinas, Duval and the beach. Great off street parking and well appointed home. This was our second time renting from Truman & Company and they are great. Very responsive!

Manager's Response

Thank you for this wonderful review Searing, we are thrilled you enjoyed every aspect of your stay and look forward to the next time you visit the island!

You should rent this house now!

September 2020
, cedar park, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house had everything to feel like a home. It was so well appointed from the salt water pool to the spaciousness of the house. Its welcoming and beautiful. There is off street parking and its two doors down from our favorite cuban restaurant and a short bike ride or even a walk to neighborhood grocery, beach, fishing pier and Duval street. The management company was super responsive and kind and the complimentary concierge service was extremely knowledgeable about the island and suggestions that fit our wants. We loved our time there and wish we were still there.

Manager's Response

Wow! Thank you for your wonderful review. We enjoyed hosting you in this incredible Key West dream home and hope to see you again next year!

The BEST home in 11 years of vacationing in Key West

July 2020

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Part of me doesn't want to say how great this home is, because I get the feeling it will become so popular it won't be available for our yearly return to Key West. But being perfectly honest we have stayed 1 month in Key West every year for the last 11 years and rented 7 different homes. Cloud 9 is by far the best most comfortable home we have rented. We also loved the location. We always stay in Old Town, but many of the streets are busy. Cloud 9 is on a quiet street within a 10 min walk of the beach. We have also worked with several Key West rental companies over the years and Wendy Zintsmaster's team was among the best.

Manager's Response

Thank you so much for your amazing review! We are so happy that you enjoyed Cloud 9 and can't wait to see you return next year.

Leave a Review
4 Bed
3.5 Baths
Sleeps 10

Search Availability

ISLAND DAZE ~ Good Vibes!

ISLAND DAZE ~ Newly Renovated 2 Bedroom Cottage Just Steps to Duval St. with Lush Outdoor Area! Nestled on A Tranquil Lane for Island Serenity!

Location

512 Louisa St.
33040 Key West , FL
United States
24° 32' 55.968" N, 81° 47' 49.164" W
See map: Google Maps
Florida US

ISLAND DAZE ~ Good Vibes!

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Memorable Memorial Day

Reviewed by Loren K. on 2026-06-10
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The house is beautifully decorated and extremely comfortable. The yard area is stunning and a perfect morning hangout with coffee or prosecco. It is steps from Duval by the Southern most point. Gorgeous, comfortable, spotless, and would definitely stay again. The kitchen has the cutest eclectic selection of glassware as well. There are two neighborhood cats (clearly with collars and used to people) who like to come hang out in the morning. They are very friendly and watching them play together is hilarious.
Manager response on 2026-06-12 - Response from Best of Key West Rentals
We’re grateful for your glowing review Loren! It was such a pleasure to host you, and we’re already looking forward to your return to the island.

Wonderful house in a super location

Reviewed by Cathey L. on 2026-04-30
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
House was extremely clean with lots of amenities. Can't beat the location, right off of Duval St. We could walk to most everything we wanted.
Manager response on 2026-05-04 - Response from Best of Key West Rentals
We’re so glad you had a great time with us Cathey. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

Great Rental!

Reviewed by Stephen C. on 2026-04-22
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
From reservations to check out, everything was wonderful. The house is quaint, clean, comfortable and in a great location, just a half block off Duval Street.
Manager response on 2026-04-22 - Response from Best of Key West Rentals
We’re so glad you had a great time with us Stephen. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

Girls Trip

Reviewed by Linda S. on 2026-03-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Home was clean and very nice. Great location-steps to Duval St. Would stay here again!
Manager response on 2026-03-16 - Response from Best of Key West Rentals
Thanks so much for the lovely feedback Linda! We’re happy to hear you enjoyed the property and would love to host you again in the future.

Location location location

Reviewed by Unknown on 2026-03-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had a wonderful time! This place is close to everything. Restaurants, stores, transportation, beach, it’s within 5 blocks. The rental company was fantastic. Our property manager was even better. The place was very clean and well kept. Couldn’t be happier with the stay.
Manager response on 2026-03-03 - Response from Best of Key West Rentals
Your kind words mean the world to us Karen! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

Perfect Location and Adorable Oasis

Reviewed by Unknown on 2026-02-10
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Loved this house. House was small, but very comfortable. Right off Duvall so close to everything, but on a very quiet and calm little street. Adorable, cool back yard oasis. Everything was clean and well-thought out. Thank you.
Manager response on 2026-02-12 - Response from Best of Key West Rentals
We so appreciate your kind review Constance! We are delighted that you loved the home, back yard and location. Please come back soon as our guest!

Our Happy Place

Reviewed by Deborah W. on 2026-01-04
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This is my families “Happy Place.” We have visited Island Daze multiple times. It is clean, spacious, and has a wonderful secluded backyard. Its location is prime real estate. It is a bike ride or walk to all the beaches, restaurants, attractions, bars, and places to watch sunsets. The properties management is top notch.
Manager response on 2026-01-06 - Response from Best of Key West Rentals
We are so thrilled to have you as a valued repeat guest Deborah! Thank you so much for the glowing review! You are always a pleasure to host and we look forward to welcoming you back many times in the future!

Hidden Gem in Old Town Key West

Reviewed by Debra M. on 2025-12-28
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We stayed 4 nights at the Island Daze and loved it! The place is quaint, clean, and thoughtfully maintained. The decor is tasteful and fits the Old Town vibe without feeling dated or fussy.

The cottage had ample room for five people, which can be hard to find in Key West. The location in Old Town was a big win. We could walk to restaurants, shops, and the main sights without needing to drive.
One of our favorite parts was the backyard. It made it feel like we were tucked away, even though we were right in the middle of everything. We especially enjoyed having coffee out there in the early mornings. It was peaceful and made the stay feel like a true getaway.

If you want a charming, convenient Old Town stay that feels comfortable and well cared for, this is a great option.
Manager response on 2025-12-29 - Response from Best of Key West Rentals
We’re so glad you had a great time with us Debra! it was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

December Fun in Key West

Reviewed by Jill-Ann P. on 2025-12-08
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We loved our rental very much. It had everything we needed. Great location and quiet.
Manager response on 2025-12-09 - Response from Best of Key West Rentals
Jill-Ann, your kind words mean the world to us! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

Wonderful Trip

Reviewed by James S. on 2025-11-13
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We enjoy staying at the quaint and well appointed Island Daze home in Key West. The property was clean, the location was perfect and the team from Best of Key West Rentals were great! Overall, it was an easy process, with clear communication before and during our trip that made for a great getaway!
Manager response on 2025-11-18 - Response from Best of Key West Rentals
James, we’re so glad you had a great time with us, it was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

gGreat getaway!!

Reviewed by John F. on 2025-11-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This rental was nicely equipped and located in a quiet spot 150 ft from Duval. Quick access to restaurants and shops.
Manager response on 2025-11-03 - Response from Best of Key West Rentals
John, thank you for your 5 star review! We are happy to hear that the home was equipped with everything you needed and that the location was up to your expectations. Please come back again as our guest!

Awesome home!

Reviewed by Mary Ann W. on 2025-09-26
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This was the perfect place to stay for my first trip to Key West. The property looks identical to the photos. The location was perfect,just a few houses away from the quieter end of Duval St. There were cute little breakfast places right at the end of the street. The Southernmost Point marker was under construction and it ended up being moved to only a couple of blocks away from us. My sister and I weren't into the party scene so this house was perfect for us.
Manager response on 2025-09-30 - Response from Best of Key West Rentals
Mary Ann, we’re so glad you had a great time with us, it was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

Great Little Get Away

Reviewed by Unknown on 2025-09-22
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Property was as advertised and very accommodating. Amenities were great and location was a perfect walk to everywhere!
We would definitely rent again!
Manager response on 2025-09-23 - Response from Best of Key West Rentals
Stacey, your kind words mean the world to us! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

Island Daze for the win!

Reviewed by Unknown on 2023-10-09
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had a great experience when we stayed in this cute little home in Key West. My husband and I rented it to stay with his brother and his wife for a long weekend. It is very well appointed and was clean as a whistle! Shana, the property manager, is delightful and was very helpful! The backyard is a peaceful oasis... we had a lot of fun watching the iguana that was hanging out there to have an afternoon snack several times. We slept in the bedroom that is right inside the front door. The bed was so comfortable!! High quality bath towels in both bathrooms. Will definitely be sharing this location with friends!
Manager response on 2024-02-21 - Response from Best of Key West Rentals
David we are so glad you had a great stay and will be sharing your experience with your friends! We look forward to welcoming you again next time you visit the island!

Awesome Stay!

Reviewed by Sheryl R. on 2023-08-19
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We loved staying at Island Daze! This place was amazing, centrally located (but not right in the middle of party town), spacious and clean. The beds were super comfortable and the space was equipped with anything needed for cooking, laundry and outdoor grilling. Our family would definitely stay here again. Our host was also very responsive and accommodating.
Manager response on 2023-08-31 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us Sheryl! We would love to welcome you back!

Super clean. Very friendly staff

Reviewed by J cesar R. on 2023-08-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
It was a super clean , communication was awesome. They even let us get into the property earlier then the check in time.
Manager response on 2023-08-31 - Response from Best of Key West Rentals
Thank you for your review. We are so thrilled to hear how much you loved this home and hope to see you again!

Island Daze

Reviewed by John M. on 2024-01-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Very good. the unit was clean and appointed nicely. we will be back.
Manager response on 2024-02-21 - Response from Best of Key West Rentals
We love it when guests enjoyed their stay so much they plan on coming back! Thank you for being our guest John!

Just Perfect

Reviewed by Brian O. on 2023-10-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We stayed two nights and nothing could make it more perfect. Fantastic location walkable to every place of interest we wanted to see. The house is squeaky clean, charmingly decorated Very functional floor plan and the backyard is a lovely private oasis. Would never be happy staying anywhere else in Key West. Perfect Also management was in regular touch to help with anything. Great stay
Manager response on 2024-02-21 - Response from Best of Key West Rentals
What a wonderful review Brian, thank you so much! Please let us know as soon as you plan a trip back, we'll make sure it is as perfect as this one! Thank you for being our guest!

Amazing Property!!

Reviewed by Shaun Y. on 2023-12-19
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We travelled to Key West for a few days. This house was amazing! Very clean, good beds, amazing location! We will definitely be renting this place again!
Manager response on 2024-02-21 - Response from Best of Key West Rentals
We really enjoyed hosting you Shaun. We are so happy you are planning on coming back, we look forward to welcoming you again!

Very Nice & Great Location!

Reviewed by Sharon B. on 2024-01-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great place, beds comfy and nice location with easy access to all the sights. Very quiet and nice to have parking. Appreciated being able to use the washer & dryer. A few things were dirty, but that was just a minor complaint. Would prefer an 11:00 vs. 10 a.m checkout which seems a bit early. Very professional and responsive management - thank you! ~ Addition of jacuzzi would be great for rainy, colder days.
Manager response on 2024-02-21 - Response from Best of Key West Rentals
Sharon thank you for taking the time to review your stay at Island Daze, we are so glad you enjoyed your stay and will relay your suggestions to the owner. Please come visit again!

Key West Long Weekend

Reviewed by Alissa B. on 2024-04-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Island Daze is presented beautifully! We had a wonderful time and really enjoyed the outdoor seating, cold AC, and hot showers! Can’t wait to come back again! Dan was responsive and helped get us checked in earlier than check in time and was very communicative throughout our stay.
Manager response on 2024-07-22 - Response from Best of Key West Rentals
Thank you for your review. We are thrilled you loved this home and hope to host you again soon!

Island days

Reviewed by Trudi R. on 2024-01-19
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Two bedroom cottage
Manager response on 2024-02-21 - Response from Best of Key West Rentals
Thank you for your 5 star review Trudi! Please come visit us again soon!

Island Daze

Reviewed by Unknown on 2024-09-22
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had a wonderful time. The home was clean and the beds and pillows comfortable my biggest priorities. A few suggestions from a frequent traveler to KW is that the windows need replacing. Keeping the kitchen/family room cool at the temp suggested was not feasible with sunroom windows that have openings. The bard door bedroom doesn't allow for privacy for two couples and made the vacation time sleeping not ideal. A real door would have been much better. A Vent is needed in the bathroom along with some shelving for guests toiletries. A laundry basket in both bedrooms and a luggage valet. The home is great just a few additions would make it perfect. Till next time.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you so much for your detailed and thoughtful review! We’re happy to hear you had a wonderful stay and that the home was clean and comfortable—especially the beds and pillows, which we know make a big difference. As a frequent visitor to Key West, your insights are incredibly helpful and will be taken into consideration as we continue to improve the guest experience. Thank you again for staying with us—looking forward to welcoming you back next time!

Little cottage big on charm and convenience

Reviewed by Unknown on 2024-02-04
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Overall, the cottage provided amble space for our 4 guests. Located on quiet street yet we could walk/ride bikes to shops restaurants attractions Easy rental process & very friendly staff. would stay here again
Manager response on 2024-02-21 - Response from Best of Key West Rentals
Tricia thank you so much for your review, we are thrilled you had a great time at Island Daze and would love to welcome you again next time you are in Key West!

Key West getaway

Reviewed by Debra M. on 2023-12-07
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Island daze was very clean and location was great. Close to everything. The management company was so helpful and convenient to check in. I would stay again when we return and highly recommend renting the property.
Manager response on 2024-02-21 - Response from Best of Key West Rentals
Debra thank you for this great review! We would love to welcome you again!

Great Place in Key West

Reviewed by Unknown on 2024-10-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The house was great for 4 people. The front bathroom is quite small without much storage fir toiletries. The beds were AMAZING. It was hot while we were there and the little room ac couldn't keep up. We were glad we brought a fan to help at night. We like to be extra cool when sleeping. Great location. 3 great restaurants within minutes of house.
Manager response on 2025-05-23 - Response from Best of Key West Rentals
Thank you for this great review! We are thrilled you enjoyed the property and hope to host you again in the future!

Great Key West Getaway

Reviewed by Judy C. on 2024-03-21
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Very comfortable 2BR house in Key West island decor, well-equipped kitchen, comfortable beds and convenient location. Nice backyard to sip coffee in the morning. Great Stay
Manager response on 2024-07-22 - Response from Best of Key West Rentals
We are so happy you found this property and its location ideal for your get away in Key West. We hope you'll stay with us again next time you visit!

Great place

Reviewed by Patricia H. on 2024-05-04
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Cute, clean, comfy houseand. Good communication with rental company and property manager.

Despite the houses being close together, the patio was private.

Great location.

Not very soundproof. When next door neighbors come home at night you can hear them clearly.

2nd bedroom is fairly small,but loved having 2 bedrooms both with king beds and their own bathrooms. The barn door for the 2nd bedroom didn't provide great privacy or sound barrier to rest of house.

Would recommend the house.
Manager response on 2024-07-22 - Response from Best of Key West Rentals
Thank you for this great review! We are thrilled you enjoyed the property and hope to host you again in the future!

GREAT Rental

Reviewed by Rachel B. on 2024-09-22
Recommend to Others
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This is a gem - perfect for four (or six I expect). Both bedrooms had king beds, two bathrooms, a wonderful kitchen, and a lovely backyard. It’s a quiet neighborhood with easy walking to Hemingway’s house, the beach, restaurants. Well appointed and clean.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for the lovely review! We're so glad you enjoyed the comfort, layout, and peaceful neighborhood of the home. It's wonderful to hear the location made it easy to explore all the nearby favorites. We'd love to host you again for another relaxing Key West getaway!

Great Place

Reviewed by Unknown on 2024-05-23
Recommend to Others
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We had a great time here and I highly recommend this rental. Place is convenient walking distance to everything. Back yard area was great to relax in and rooms were very comfortable.
Manager response on 2024-07-22 - Response from Best of Key West Rentals
Thank you for your review, we are so glad the property met your needs while staying with us. We hope you'll stay with us again next time you visit Key West.

Cute house

Reviewed by Amanda W. on 2024-06-13
Recommend to Others
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Overall satisfaction
Great little house and a great location. 2 king beds with bathrooms was why we chose was clean and had everything we needed.
Manager response on 2024-07-22 - Response from Best of Key West Rentals
We are so happy you found this property and its location ideal for your get away in Key West. We hope you'll stay with us again next time you visit!

Darling Cottage

Reviewed by Cathy C. on 2024-10-12
Recommend to Others
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Overall satisfaction
The cottage was perfect for two couples. Both bedrooms had attached baths. We were just three houses down from Duval Street and a few blocks from the beach.
The staff was great. Our home in Fort Myers was threatened by Hurricane Milton. We were able to extend our stay until it was safe to return home.
Manager response on 2025-05-23 - Response from Best of Key West Rentals
Thank you for your fantastic review. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

It IS a perfectly located cottage!

Reviewed by Unknown on 2024-06-24
Recommend to Others
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Cozy. Neat location within walking distance to everything Key West. So happy and satisfied calling this place home during our stay!
Manager response on 2024-07-22 - Response from Best of Key West Rentals
Thank you for your wonderful review Ed. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Island Daze

Reviewed by Unknown on 2024-06-20
Recommend to Others
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Location
Cleanliness
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Overall satisfaction
The property was very well maintained, and extremely convenient for all activities.
Manager response on 2024-07-22 - Response from Best of Key West Rentals
Thank you for this great review Joseph! We are thrilled you enjoyed the property and hope to host you again in the future!

Great Island Hideout in ideal location

Reviewed by Marc B. on 2025-02-21
Recommend to Others
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Great location, comfortable house in an ideal location. We enjoyed this beautiful place, with a nice outdoor sitting and barbecue area, very cosy and discrete place. Ideally located close to the beach and to all the commodities. We will be returning for sure.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for the wonderful review! We're so glad you enjoyed the comfort and privacy of the home, along with the outdoor space and unbeatable location. It’s great to hear it was the perfect island hideout for your trip. We’d be thrilled to welcome you back anytime!

Great cottage, great location, great management!

Reviewed by RonLynn R. on 2024-12-14
Recommend to Others
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Location
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Services from rental manager
Overall satisfaction
We came down for a getaway. Island Daze is better than the photos. Very clean, fresh and comfortable. Back yard is private and relaxing. We caught the Old Town Tram at the Southern most bouy. Toured, hit happy hours and had a great time. Wind caused a loud night but the property manager responded quickly and took care of the issue. This place is great and we would not hesitate to return. Thank you and we will see you again!!!
Manager response on 2025-05-23 - Response from Best of Key West Rentals
Thank you for your incredible review! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

On my bucket list!

Reviewed by Unknown on 2025-03-13
Recommend to Others
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This vacation rental was the perfect location to see Key West. The parking is very limited in the city so I would suggest to have a location to park your vehicle during your stay which was provided. The premises was accurate to the discretion. The downfall was the check in and check out times for the money you pay. It’s not a full 2 day stay. It’s more like a day and a half. Very expensive for a bucket list experience. Be prepared to pay.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for your feedback and for choosing our rental for such a special bucket list trip! We're so glad the location and included parking made it easy to explore Key West, and that the property lived up to your expectations. We understand your concern regarding check-in and check-out times. Like many vacation rentals, we need that time to ensure the home is thoroughly cleaned and prepared for each guest’s arrival. That said, we’re always reviewing ways to improve the guest experience and appreciate your perspective. We hope the memories made were well worth it and would love to welcome you back again in the future!

Great place to stay

Reviewed by Kenneth H. on 2025-04-28
Recommend to Others
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Overall satisfaction
The location and home were perfect for us. Had a really great time.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for the great review! We’re so happy to hear the home and location were a perfect fit. We'd love to have you back anytime!

5 Days April 2025

Reviewed by Jeff L. on 2025-04-28
Recommend to Others
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Location
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Overall satisfaction
Very enjoyable stay, great location, clean, quiet and comfortable. Great little backyard with plenty of shade... Wife and I stayed, had a great time.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for the kind words! We’re so glad you and your wife had a great time and enjoyed the peaceful backyard, comfort, and location. We'd love to welcome you back anytime!

Cute cottage in perfect location to beach & Duval. Modern & clean

Reviewed by Susan K. on 2025-04-26
Recommend to Others
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Location
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Overall satisfaction
Easy to book and check in.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for your kind review! We’re so glad you enjoyed the cottage and found the location convenient and the process smooth. We’d love to host you again on your next Key West visit!

Key West getaway

Reviewed by Luis C. on 2025-07-26
Recommend to Others
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Overall satisfaction
Great location. Very nice house. The parking is a little small, but we are able to make our Rav4 fit. Anything larger than that would be tight. When we return to Key West in the future we would definitely stay here again if it's available.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for the great feedback! We're glad you enjoyed the house and the fantastic location. Good to know your RAV4 fit—parking can definitely be tight in Key West. We'd be thrilled to host you again on your next visit!

Great Stay at Island Daze!

Reviewed by Sean N. on 2021-01-04
Recommend to Others
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Location
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Overall satisfaction
Location: The house was in a great part of Key West on a very quiet street about 200’ off Duval. We heard very little noise from the neighbors and felt very safe during our stay. It is a 2 blocks from the Southernmost Point “Buoy,” close to some good restaurants, a bike rental shop, and a quick (5 min) bike ride to Higgs beach, and 10 min. to Smathers and Fort Zachary Taylor Beach. It’s about a 10 minute bike ride down to Mallory Square down Duval or Simonton.

House: The pictures on the website were very accurate. The house was a good size and provided ample space for our 2 kids and 2 dogs. We used the bedroom close to the front of the house as the “Master” while our daughter took the other bedroom and our son slept on the couch. All of the beds were amazingly comfortable, and we slept great the entire time. The AC worked well and kept the house very cool with a ceiling fan in each room. The kitchen had everything needed during our stay (including a Kuireg and a regular coffee maker as well). The internet was very fast in most parts of the house. My son had his PS5 and was able to run it in the living room with few issues. We pulled ~100MB in most of the house but it was higher at times as well. There’s YouTube TV on all of the TV’s which were good sized at ~40-50.” The parking spot in front of the house was big enough to park my full size truck caddy corner.

Yard: The yard was a good size for Key West and had a Hot Tub, table, and a grill. Everything worked great. If you have dog(s) there is no grass in the backyard for their “bathroom.” We walked the dogs 2 minutes down the street to a bank that had plenty of grass for them though. We parked our rented bikes in the backyard with no issues.

Best of Key West rentals was very accommodating and responsive for the few needs we had. Overall we had no complaints at all. We’ve been to Key W
Manager response on 2021-01-12 - Response from Best of Key West Rentals
Thank you for your wonderful review. We enjoyed hosting you and hope to see you back in Key West again soon!

Island hide away

Reviewed by Unknown on 2021-11-18
Recommend to Others
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Location
Cleanliness
Services from rental manager
Overall satisfaction
The property is located in a great location, walking distance to many restaurants and shops. The property is well-appointed clean and has everything you'll need for your stay. The back patio is a little oasis, private and lush. The property management company was great from the time I booked the home till we checked out. I would stay there again.
Manager response on 2021-11-30 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us Mark! We would love to welcome you back!

Precious cottage right off Duval

Reviewed by Martha S. on 2021-01-15
Recommend to Others
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Overall satisfaction
We planned this vacation less than a month before Christmas and was so excited to find this precious cottage. It’s 1/2 block off Duval close to the Southern most point with great restaurants, galleries and shopping all within walking distance. Beds are comfortable, place was clean and had everything you needed.
Manager response on 2021-01-26 - Response from Best of Key West Rentals
Thank you for your kind words. We enjoyed hosting you and hope to see you again very soon!

Absolutely Wonderful

Reviewed by Nicole A. on 2021-04-26
Recommend to Others
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Location
Cleanliness
Services from rental manager
Overall satisfaction
We were a group of two couples and this property worked out perfectly for our stay. We were able to each have the privacy of our own bedroom and bathroom, and had plenty of common space to enjoy. The property was in great condition and the property manager was great. The location was great too, an easy walk to the Southernmost point area and a doable walk to the other end of Duval St. Be sure to stop at the Banana Cafe for breakfast!

Also, if you book with this company, take advantage of their concierge services, they were able to suggest and book some great activities!
Manager response on 2021-05-06 - Response from Best of Key West Rentals
Thank you for your review. We enjoyed hosting you and hope to see you again soon!

Great!

Reviewed by Rebekah C. on 2021-06-04
Recommend to Others
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Location
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Overall satisfaction
Our stay was great! Super clean and great location. We enjoyed the hot tub and outside patio area. The beds were extra comfy for the best night sleep. It was nice having our own parking too. The house had all the little extra touches we needed. thanks we will be back soon.
Manager response on 2021-06-07 - Response from Best of Key West Rentals
We are so glad your stay with us was great and look forward to welcoming you again soon!

Key West Celebration

Reviewed by Unknown on 2021-06-14
Recommend to Others
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Location
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Overall satisfaction
The location of the property was ideal for experiencing Duval St, yet quiet at night. The house was clean, in working order, and property management was very responsive. We had a wonderful time!
Manager response on 2021-06-15 - Response from Best of Key West Rentals
Thank you for your review Jennifer, we are so happy your stay with us was wonderful and hope you will come visit Key West again soon!

Beautiful little getaway

Reviewed by Unknown on 2021-05-31
Recommend to Others
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Overall satisfaction
Home exactly as pictured; fantastic location, lovely furnishings and fit our needs perfectly! Can’t wait to book our next stay! ⭐️⭐️⭐️⭐️⭐️
Manager response on 2021-06-01 - Response from Best of Key West Rentals
Thank you for your review. We are so happy you had a great time and hope to see you again!

Perfect!

Reviewed by Unknown on 2021-03-29
Recommend to Others
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Location
Cleanliness
Services from rental manager
Overall satisfaction
Absolutely perfect. The property is awesome and the complementary concierge service was amazing!
Manager response on 2021-03-30 - Response from Best of Key West Rentals
Thank you for your wonderful review. We hope to see you again soon!

island daze review

Reviewed by Unknown on 2022-03-03
Recommend to Others
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Location
Cleanliness
Services from rental manager
Overall satisfaction
great place; clean; staff very helpful in providing few things we found missing upon arrival. overall great experience
Manager response on 2022-03-04 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us Michael! We would love to welcome you back next time you plan to visit Key West!

Perfect Location

Reviewed by Hayley G. on 2021-07-28
Recommend to Others
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Overall satisfaction
This house was situated in the perfect location, just a block off of Duval Street. It was super cute and clean. We wouldn't hesitate to go back.
Manager response on 2021-08-04 - Response from Best of Key West Rentals
Thank you for your wonderful review. We hope to see you again soon!

A Great Stay in Historical Key West

Reviewed by Debra W. on 2021-05-16
Recommend to Others
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Overall satisfaction
Island Daze was a wonderful place for our family to stay while visiting Key West. it is a short walk/bike ride to white sand beaches, and an even shorter walk to Duvall Street, where one will find many shops and great food. The French Bakery on the corner of their street was a fantastic find for breakfast/lunch.
Manager response on 2021-05-17 - Response from Best of Key West Rentals
Thank you for your wonderful review. We hope to see you again soon in Paradise!

I cannot say enough!

Reviewed by Natasha P. on 2021-09-08
Recommend to Others
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Location
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Services from rental manager
Overall satisfaction
We absolutely LOVED this home. It’s location was perfect. The home was very clean and cutely decorated. The communication with the property manager was fantastic as well. We will absolutely be staying again!
Manager response on 2021-09-09 - Response from Best of Key West Rentals
Thank you for your review Natasha, we are so glad you enjoyed your stay with us and really look forward to welcoming you again!

50th Getaway

Reviewed by Unknown on 2021-10-31
Recommend to Others
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Location
Cleanliness
Services from rental manager
Overall satisfaction
Awesome two bedroom house just as seen in the pictures. Ideal location on the quiet end of Duval Street. Had a great time and would definitely stay here again.
Manager response on 2021-11-16 - Response from Best of Key West Rentals
We are so happy you enjoyed your stay so much Adam, we would love to host you again next time you visit key West!

Fantastic Stay in Key West

Reviewed by Don J. on 2022-01-19
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great Location
Perfect Set-up
Parking!
Great Time had by all
Manager response on 2022-01-20 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us Don! We would love to welcome you back!

Great Stay!!

Reviewed by Orlando H. on 2021-11-29
Recommend to Others
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Location
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Overall satisfaction
The host was MORE than accommodating and helped anytime we had any issues even after our stay. There were a few things that needed to be addressed before our stay (empty propane bottle in the grill, hot water issue) but it didn't ruin the stay. The host was very responsive and tried to help as soon as they were made aware. This was a great place with a great location!
Manager response on 2021-11-30 - Response from Best of Key West Rentals
Thank you for your review Orlando, we are glad you enjoyed your stay at Island Daze, we hope to welcome you at the property again!

Perfect Getaway

Reviewed by Brittney P. on 2021-07-17
Recommend to Others
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Overall satisfaction
The house was perfect for our girls trip! The house had everything we needed. The beds were comfy and extra mirrors in the hall helped when we were all getting ready. We loved how close it was to Duvall St.
Manager response on 2021-07-26 - Response from Best of Key West Rentals
Thank you for this great review Brittney! We are glad our property met all your group's need and hope to see you again next time you are on the island!

Fantastic!

Reviewed by Julie A. on 2021-09-29
Recommend to Others
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Location
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Overall satisfaction
This house was great! Super close to Duval and the Banana Cafe( went there for breakfast everyday!) easy access and parking for up to 5-6 scooters in front of the house. Wonderful temperature control and the bedroom/baths were more than adequate with plenty of space to unpack and the beds were both roomy and comfortable, slept great!
Manager response on 2021-10-06 - Response from Best of Key West Rentals
Thank you for your wonderful review Julie! We enjoyed hosting you and hope to see you back soon!

Wonderful stay at a wonderful cottage!

Reviewed by Carrington C. on 2022-04-28
Recommend to Others
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Overall satisfaction
We came her with another couple and thoroughly enjoyed our stay at Island Daze. Location was great, loved being on a small quiet street that was close to everything. Cottage was clean, cute and the AC was kicking! We would definitely stay here again when planning a trip to Key West!
Manager response on 2022-04-29 - Response from Best of Key West Rentals
Thank you for your fantastic review. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Best Location.

Reviewed by Peter T. on 2022-07-23
Recommend to Others
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Location
Cleanliness
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Overall satisfaction
Island Daze was half a block from Duval Street, but near the quieter part of town and it was great. The place was spotless, roomy with an at home feel. We wouldn't hesitate to stay here again!
Manager response on 2022-07-29 - Response from Best of Key West Rentals
Thank you for your wonderful review Peter. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Excellent Property in Key West

Reviewed by Unknown on 2022-05-01
Recommend to Others
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Overall satisfaction
Outstanding location. Perfect property for two couples. Close to everything and very private. Very clean and had everything we need. Property manager very helpful and engaging!
Manager response on 2022-05-13 - Response from Best of Key West Rentals
Thank you for your wonderful review Tina. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Island home review

Reviewed by Unknown on 2022-06-29
Recommend to Others
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Location
Cleanliness
Services from rental manager
Overall satisfaction
Place was conveniently located, on the quieter side of Duvall and kept updated and clean. Great long weekend get away place!
Manager response on 2022-07-29 - Response from Best of Key West Rentals
Thank you for this great review Lisa! We are thrilled you enjoyed the property and hope to host you again in the future!

Great Daze at Island Daze!

Reviewed by Julie W. on 2022-02-06
Recommend to Others
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This house is perfectly located right off the quiet end of Duval. The back yard offers a wonderful respite from the busy party vibe of the City. The home is beautifully decorated and is a peaceful oasis with a tropical feel. The property manager was super responsive and friendly. This was a perfect stay and if I’m ever back in Key West, I’ll hope to stay there again!
Manager response on 2022-02-24 - Response from Best of Key West Rentals
Thank you for your wonderful review Julie. We enjoyed hosting you and hope to see you back in Key West again soon!

An island gem!

Reviewed by Lynn C. on 2022-04-16
Recommend to Others
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Overall satisfaction
The house was in a wonderful location close to everything, but yet in a quiet neighborhood. It had everything you would need, was clean and the management company was very responsive. Would definitely stay here again.
Manager response on 2022-04-29 - Response from Best of Key West Rentals
Thank you for your wonderful review Lynn. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Great Time!

Reviewed by LeAnne W. on 2022-10-13
Recommend to Others
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Location
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Overall satisfaction
When we arrived the house was neat and tidy! It was a perfect location and convenient to everything.
Manager response on 2022-12-05 - Response from Best of Key West Rentals
Thank you for your review LeAnne. We are thrilled you loved this home and hope to host you again soon!

Great vacation

Reviewed by Rebekah G. on 2022-08-10
Recommend to Others
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Services from rental manager
Overall satisfaction
We had a great time, really well maintained property.
Manager response on 2022-09-09 - Response from Best of Key West Rentals
Thank you for your review Rebekah. We are so thrilled to hear how much you loved this home and hope to see you again!

Cute vacation house

Reviewed by Ann Y. on 2022-10-21
Recommend to Others
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Overall satisfaction
Great little house, wonderful location, and was very well equipped.
Manager response on 2022-12-05 - Response from Best of Key West Rentals
Thank you for your feedback on your recent stay Ann. We are so glad that you enjoyed your time spent at this home. Thank you again and please reach out to us for your next Key West vacation!

Island Daze 2023

Reviewed by Martha S. on 2023-05-18
Recommend to Others
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Overall satisfaction
A gem of a house! This is a return trip for us to this property and the new owners have kept the charm yet outfitted the home beautifully with KW style. The property manager came by to say hello upon our arrival and was delightful. I feel lucky to have re-discovered this property! A short walk (really) to Duval St and the delicious Banana Cafe and the bakery La Grigonote. Thank you team Island Daze!
Love KW and to be able to vacation here is a
Manager response on 2023-08-31 - Response from Best of Key West Rentals
Thank you for this great review Martha! We are thrilled you enjoyed the property and hope to host you again in the future!

Luisa Ave, Key West

Reviewed by Lois S. on 2023-03-24
Recommend to Others
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Overall satisfaction
Couldn’t have been more happy with this cottage. Great location, property manager was great, kitchen amenities were top notch, furnishings lovely and comfortable.
Manager response on 2023-08-31 - Response from Best of Key West Rentals
Thank you for this great review Lois! We are thrilled you enjoyed the property and hope to host you again in the future!

Great house...Great location

Reviewed by Curt D. on 2023-06-05
Recommend to Others
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Overall satisfaction
Came for vacation and our beach wedding and everything was perfect. We loved the house, private back yard and location was great. We would definitely stay again if we come back.
Manager response on 2023-08-31 - Response from Best of Key West Rentals
Thank you for your wonderful review Curt. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Beautiful home in a great location!

Reviewed by Cheryl G. on 2023-03-23
Recommend to Others
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Overall satisfaction
This home is a beautiful place to stay in a great location in Key West! In addition, the team that manages the home is super helpful. I highly recommend staying here when you visit Key West!
Manager response on 2023-08-31 - Response from Best of Key West Rentals
Thank you for your incredible review Cheryl! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Great Stay!

Reviewed by Unknown on 2023-03-13
Recommend to Others
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Overall satisfaction
What a great stay! Great place, location, and agency at a competitive price. No complaints and would love to stay again!
Manager response on 2023-08-31 - Response from Best of Key West Rentals
Thank you for your fantastic review Phi-Oanh. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

ISLAND DAZE ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 block to Duval!

Unit Code: ID

ISLAND DAZE ~ Good Vibes!

ISLAND DAZE ~ Newly Renovated 2 Bedroom Cottage Just Steps to Duval St. with Lush Outdoor Area! Nestled on A Tranquil Lane for Island Serenity!
ALLOW THE PERFECT VACATION TO UNFOLD... The epitome of laid-back, island living is found within this classic, Conch style home bringing endless charm to your tropical vacation. Steps from high end galleries, bars and restaurants, yet tucked away on a quaint and colorful lane, this home entails all the desired amenities that will truly immerse you into the Key West spirit. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES... A friendly front porch awaits your morning cup of coffee, so you can plan out your day while you gaze beyond at tropical surroundings and neighbors passing by. Inside you will find an inviting space with cozy furnishings and a flat screen TV to gather around on a lazy afternoon. A fully equipped kitchen is accompanied by an indoor dining area and bar seating to enjoy meals together. Perch the French doors open to bring the breezy outdoors inside. YouTube TV is offered so you can stream your favorite shows. SLEEPING ARRANGEMENTS... This newly renovated gem totals 2 king bedrooms and two en suite bathrooms - one with a shower and the other with a shower/tub combination. Each room is equipped with a cozy kings bed and a flat screen TV. A queen sofa sleeper allows for additional sleeping arrangements in the living room. OUTDOOR LIVING... Escape reality and explore this extraordinary hideaway! Your own private, lush backyard oasis is the perfect setting for your tranquil escape from reality. Complete with outdoor dining, a gas grill and peaceful surroundings for unwinding under the stars, this backyard dream immerses you into your island home away from home. PARKING... Although just steps to all the action, this home comes with 1 off street parking space making coming and going a breeze. PETS... Dogs are considered but no cats permitted and a pet fee is required. DISTANCES TO BEACHES... South Beach is 0.2 mi Higgs Beach is 0.8 mi Smathers Beach is 2 mi Fort Zachary Taylor Beach Is 1.4 mi All beaches have beach chair and umbrella rentals. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund. CREATE YOUR ISLAND STORY...
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DatesPrice
06/12/2026 - 06/12/2026$691 /nt
06/13/2026 - 06/13/2026$688 /nt
06/14/2026 - 06/14/2026$540 /nt
06/15/2026 - 06/16/2026$283 /nt
06/17/2026 - 06/17/2026$284 /nt
06/18/2026 - 06/18/2026$312 /nt
06/19/2026 - 06/19/2026$361 /nt
06/20/2026 - 06/20/2026$539 /nt
06/21/2026 - 06/21/2026$410 /nt
06/22/2026 - 06/22/2026$362 /nt
06/23/2026 - 06/23/2026$374 /nt
06/24/2026 - 06/24/2026$392 /nt
06/25/2026 - 06/25/2026$465 /nt
06/26/2026 - 06/26/2026$347 /nt
06/27/2026 - 06/27/2026$353 /nt
06/28/2026 - 07/01/2026$283 /nt
07/02/2026 - 07/02/2026$355 /nt
07/03/2026 - 07/03/2026$384 /nt
07/04/2026 - 07/04/2026$455 /nt
07/05/2026 - 07/05/2026$368 /nt
07/06/2026 - 07/06/2026$334 /nt
07/07/2026 - 07/07/2026$342 /nt
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07/10/2026 - 07/11/2026$452 /nt
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07/19/2026 - 07/19/2026$342 /nt
07/20/2026 - 07/20/2026$345 /nt
07/21/2026 - 07/21/2026$353 /nt
07/22/2026 - 07/22/2026$361 /nt
07/23/2026 - 07/23/2026$436 /nt
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07/25/2026 - 07/25/2026$536 /nt
07/26/2026 - 07/26/2026$345 /nt
07/27/2026 - 07/27/2026$424 /nt
07/28/2026 - 07/28/2026$452 /nt
07/29/2026 - 07/29/2026$430 /nt
07/30/2026 - 07/30/2026$498 /nt
07/31/2026 - 07/31/2026$542 /nt
08/01/2026 - 08/01/2026$546 /nt
08/02/2026 - 08/02/2026$422 /nt
08/03/2026 - 08/03/2026$303 /nt
08/04/2026 - 08/04/2026$287 /nt
08/05/2026 - 08/05/2026$283 /nt
08/06/2026 - 08/06/2026$325 /nt
08/07/2026 - 08/07/2026$438 /nt
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08/12/2026 - 08/12/2026$347 /nt
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08/15/2026 - 08/15/2026$562 /nt
08/16/2026 - 08/16/2026$412 /nt
08/17/2026 - 08/17/2026$334 /nt
08/18/2026 - 08/19/2026$283 /nt
08/20/2026 - 08/20/2026$349 /nt
08/21/2026 - 08/21/2026$410 /nt
08/22/2026 - 08/22/2026$402 /nt
08/23/2026 - 08/26/2026$283 /nt
08/27/2026 - 08/27/2026$304 /nt
08/28/2026 - 08/28/2026$372 /nt
08/29/2026 - 08/29/2026$321 /nt
08/30/2026 - 09/02/2026$283 /nt
09/03/2026 - 09/03/2026$336 /nt
09/04/2026 - 09/04/2026$534 /nt
09/05/2026 - 09/05/2026$607 /nt
09/06/2026 - 09/06/2026$493 /nt
09/07/2026 - 09/07/2026$283 /nt
09/08/2026 - 09/08/2026$323 /nt
09/09/2026 - 09/09/2026$441 /nt
09/10/2026 - 09/10/2026$299 /nt
09/11/2026 - 09/11/2026$378 /nt
09/12/2026 - 09/12/2026$345 /nt
09/13/2026 - 09/13/2026$410 /nt
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09/19/2026 - 09/22/2026$393 /nt
09/23/2026 - 09/23/2026$283 /nt
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09/26/2026 - 09/28/2026$445 /nt
09/29/2026 - 09/29/2026$447 /nt
09/30/2026 - 10/02/2026$428 /nt
10/03/2026 - 10/03/2026$341 /nt
10/04/2026 - 10/05/2026$417 /nt
10/06/2026 - 10/07/2026$452 /nt
10/08/2026 - 10/08/2026$450 /nt
10/09/2026 - 10/09/2026$482 /nt
10/10/2026 - 10/10/2026$519 /nt
10/11/2026 - 10/11/2026$389 /nt
10/12/2026 - 10/12/2026$341 /nt
10/13/2026 - 10/14/2026$347 /nt
10/15/2026 - 10/18/2026$964 /nt
10/19/2026 - 10/21/2026$1,172 /nt
10/22/2026 - 10/22/2026$1,289 /nt
10/23/2026 - 10/23/2026$1,030 /nt
10/24/2026 - 10/24/2026$1,114 /nt
10/25/2026 - 10/25/2026$770 /nt
10/26/2026 - 10/29/2026$699 /nt
10/30/2026 - 10/30/2026$806 /nt
10/31/2026 - 10/31/2026$650 /nt
11/01/2026 - 11/01/2026$1,238 /nt
11/02/2026 - 11/03/2026$1,151 /nt
11/04/2026 - 11/04/2026$1,196 /nt
11/05/2026 - 11/05/2026$1,307 /nt
11/06/2026 - 11/06/2026$1,498 /nt
11/07/2026 - 11/08/2026$1,112 /nt
11/09/2026 - 11/09/2026$428 /nt
11/10/2026 - 11/10/2026$551 /nt
11/11/2026 - 11/11/2026$489 /nt
11/12/2026 - 11/15/2026$591 /nt
11/16/2026 - 11/18/2026$444 /nt
11/19/2026 - 11/19/2026$781 /nt
11/20/2026 - 11/20/2026$816 /nt
11/21/2026 - 11/21/2026$860 /nt
11/22/2026 - 11/22/2026$781 /nt
11/23/2026 - 11/25/2026$631 /nt
11/26/2026 - 11/26/2026$1,102 /nt
11/27/2026 - 11/27/2026$1,161 /nt
11/28/2026 - 11/28/2026$1,200 /nt
11/29/2026 - 11/30/2026$829 /nt
12/01/2026 - 12/02/2026$568 /nt
12/03/2026 - 12/03/2026$591 /nt
12/04/2026 - 12/04/2026$796 /nt
12/05/2026 - 12/05/2026$835 /nt
12/06/2026 - 12/10/2026$796 /nt
12/11/2026 - 12/11/2026$957 /nt
12/12/2026 - 12/12/2026$994 /nt
12/13/2026 - 12/13/2026$868 /nt
12/14/2026 - 12/16/2026$763 /nt
12/17/2026 - 12/19/2026$591 /nt
12/20/2026 - 12/20/2026$494 /nt
12/21/2026 - 12/21/2026$511 /nt
12/22/2026 - 12/22/2026$904 /nt
12/23/2026 - 12/26/2026$1,493 /nt
12/27/2026 - 12/28/2026$1,177 /nt
12/29/2026 - 01/01/2027$1,372 /nt
01/02/2027 - 01/02/2027$857 /nt
01/03/2027 - 01/03/2027$861 /nt
01/04/2027 - 01/04/2027$835 /nt
01/05/2027 - 01/07/2027$1,014 /nt
01/08/2027 - 01/08/2027$1,065 /nt
01/09/2027 - 01/09/2027$1,088 /nt
01/10/2027 - 01/10/2027$977 /nt
01/11/2027 - 01/11/2027$891 /nt
01/12/2027 - 01/13/2027$859 /nt
01/14/2027 - 01/14/2027$1,044 /nt
01/15/2027 - 01/15/2027$1,099 /nt
01/16/2027 - 01/16/2027$1,121 /nt
01/17/2027 - 01/17/2027$1,049 /nt
01/18/2027 - 01/18/2027$1,044 /nt
01/19/2027 - 01/20/2027$877 /nt
01/21/2027 - 01/21/2027$912 /nt
01/22/2027 - 01/22/2027$1,010 /nt
01/23/2027 - 01/23/2027$1,035 /nt
01/24/2027 - 01/24/2027$907 /nt
01/25/2027 - 01/27/2027$903 /nt
01/28/2027 - 01/28/2027$995 /nt
01/29/2027 - 01/30/2027$790 /nt
01/31/2027 - 02/02/2027$980 /nt
02/03/2027 - 02/05/2027$1,017 /nt
02/06/2027 - 02/09/2027$1,052 /nt
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02/14/2027 - 02/17/2027$1,142 /nt
02/18/2027 - 02/26/2027$1,017 /nt
02/27/2027 - 02/28/2027$949 /nt
03/01/2027 - 03/03/2027$937 /nt
03/04/2027 - 03/07/2027$1,101 /nt
03/08/2027 - 03/08/2027$961 /nt
03/09/2027 - 03/10/2027$872 /nt
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03/12/2027 - 03/12/2027$1,272 /nt
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03/20/2027 - 03/22/2027$1,245 /nt
03/23/2027 - 03/25/2027$933 /nt
03/26/2027 - 03/29/2027$1,075 /nt
03/30/2027 - 03/31/2027$839 /nt
04/01/2027 - 04/01/2027$848 /nt
04/02/2027 - 04/02/2027$866 /nt
04/03/2027 - 04/04/2027$986 /nt
04/05/2027 - 04/06/2027$1,139 /nt
04/07/2027 - 04/08/2027$1,132 /nt
04/09/2027 - 04/10/2027$880 /nt
04/11/2027 - 04/11/2027$688 /nt
04/12/2027 - 04/12/2027$553 /nt
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04/16/2027 - 04/20/2027$828 /nt
04/21/2027 - 04/21/2027$712 /nt
04/22/2027 - 04/25/2027$794 /nt
04/26/2027 - 04/27/2027$829 /nt
04/28/2027 - 05/01/2027$839 /nt
05/02/2027 - 05/02/2027$712 /nt
05/03/2027 - 05/03/2027$666 /nt
05/04/2027 - 05/04/2027$625 /nt
05/05/2027 - 05/05/2027$494 /nt
05/06/2027 - 05/06/2027$597 /nt
05/07/2027 - 05/07/2027$666 /nt
05/08/2027 - 05/14/2027$787 /nt
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05/19/2027 - 05/19/2027$729 /nt
05/20/2027 - 05/23/2027$907 /nt
05/24/2027 - 05/24/2027$756 /nt
05/25/2027 - 05/25/2027$460 /nt
05/26/2027 - 05/26/2027$465 /nt
05/27/2027 - 05/27/2027$570 /nt
05/28/2027 - 05/28/2027$697 /nt
05/29/2027 - 05/29/2027$675 /nt
05/30/2027 - 05/30/2027$552 /nt
05/31/2027 - 06/01/2027$589 /nt
06/02/2027 - 06/03/2027$634 /nt
06/04/2027 - 06/04/2027$662 /nt
06/05/2027 - 06/05/2027$673 /nt
06/06/2027 - 06/06/2027$634 /nt
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06/08/2027 - 06/08/2027$452 /nt
06/09/2027 - 06/09/2027$458 /nt
06/10/2027 - 06/12/2027$747 /nt
4.9444
(72 Review)

Wonderful house in a super location

April 2026
, Austin, TX US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

House was extremely clean with lots of amenities. Can't beat the location, right off of Duval St. We could walk to most everything we wanted.

Manager's Response

We’re so glad you had a great time with us Cathey. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

Great Rental!

April 2026
, Virginia Beach, VA US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

From reservations to check out, everything was wonderful. The house is quaint, clean, comfortable and in a great location, just a half block off Duval Street.

Manager's Response

We’re so glad you had a great time with us Stephen. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

Girls Trip

March 2026
, Inver Grove Heights, MN US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

Home was clean and very nice. Great location-steps to Duval St. Would stay here again!

Manager's Response

Thanks so much for the lovely feedback Linda! We’re happy to hear you enjoyed the property and would love to host you again in the future.

Location location location

February 2026
, Gibsonia, PA US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

We had a wonderful time! This place is close to everything. Restaurants, stores, transportation, beach, it’s within 5 blocks. The rental company was fantastic. Our property manager was even better. The place was very clean and well kept. Couldn’t be happier with the stay.

Manager's Response

Your kind words mean the world to us Karen! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

Perfect Location and Adorable Oasis

January 2026
, Sanibel, FL Unknown

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

Loved this house. House was small, but very comfortable. Right off Duvall so close to everything, but on a very quiet and calm little street. Adorable, cool back yard oasis. Everything was clean and well-thought out. Thank you.

Manager's Response

We so appreciate your kind review Constance! We are delighted that you loved the home, back yard and location. Please come back soon as our guest!

Hidden Gem in Old Town Key West

December 2025
, Santa Barbara, CA US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

We stayed 4 nights at the Island Daze and loved it! The place is quaint, clean, and thoughtfully maintained. The decor is tasteful and fits the Old Town vibe without feeling dated or fussy.

The cottage had ample room for five people, which can be hard to find in Key West. The location in Old Town was a big win. We could walk to restaurants, shops, and the main sights without needing to drive.
One of our favorite parts was the backyard. It made it feel like we were tucked away, even though we were right in the middle of everything. We especially enjoyed having coffee out there in the early mornings. It was peaceful and made the stay feel like a true getaway.

If you want a charming, convenient Old Town stay that feels comfortable and well cared for, this is a great option.

Manager's Response

We’re so glad you had a great time with us Debra! it was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

Our Happy Place

December 2025
, River Vale, NJ United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

This is my families “Happy Place.” We have visited Island Daze multiple times. It is clean, spacious, and has a wonderful secluded backyard. Its location is prime real estate. It is a bike ride or walk to all the beaches, restaurants, attractions, bars, and places to watch sunsets. The properties management is top notch.

Manager's Response

We are so thrilled to have you as a valued repeat guest Deborah! Thank you so much for the glowing review! You are always a pleasure to host and we look forward to welcoming you back many times in the future!

December Fun in Key West

November 2025
, Salt Lake City, UT US

Overall
4
Property condition
4
Location
5
Cleanliness
5
Services from rental manager
5

We loved our rental very much. It had everything we needed. Great location and quiet.

Manager's Response

Jill-Ann, your kind words mean the world to us! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

Wonderful Trip

November 2025
, Maple Glen, PA US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

We enjoy staying at the quaint and well appointed Island Daze home in Key West. The property was clean, the location was perfect and the team from Best of Key West Rentals were great! Overall, it was an easy process, with clear communication before and during our trip that made for a great getaway!

Manager's Response

James, we’re so glad you had a great time with us, it was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

gGreat getaway!!

October 2025
, PALMETTO, AL US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

This rental was nicely equipped and located in a quiet spot 150 ft from Duval. Quick access to restaurants and shops.

Manager's Response

John, thank you for your 5 star review! We are happy to hear that the home was equipped with everything you needed and that the location was up to your expectations. Please come back again as our guest!

Awesome home!

September 2025
, Berea, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was the perfect place to stay for my first trip to Key West. The property looks identical to the photos. The location was perfect,just a few houses away from the quieter end of Duval St. There were cute little breakfast places right at the end of the street. The Southernmost Point marker was under construction and it ended up being moved to only a couple of blocks away from us. My sister and I weren't into the party scene so this house was perfect for us.

Manager's Response

Mary Ann, we’re so glad you had a great time with us, it was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

Great Little Get Away

August 2025
, sarasota, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Property was as advertised and very accommodating. Amenities were great and location was a perfect walk to everywhere!
We would definitely rent again!

Manager's Response

Stacey, your kind words mean the world to us! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

Best Weekend Ever

August 2025
, Lake Mary, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

super clean, updated little cottage. couldnt be in a better location. very well kept and updated. 2 king beds was a nice touch.

Key West getaway

July 2025
, Miami, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great location. Very nice house. The parking is a little small, but we are able to make our Rav4 fit. Anything larger than that would be tight. When we return to Key West in the future we would definitely stay here again if it's available.

Manager's Response

Thank you for the great feedback! We're glad you enjoyed the house and the fantastic location. Good to know your RAV4 fit—parking can definitely be tight in Key West. We'd be thrilled to host you again on your next visit!

Great place to stay

April 2025
, Broken Arrow, OK US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The location and home were perfect for us. Had a really great time.

Manager's Response

Thank you for the great review! We’re so happy to hear the home and location were a perfect fit. We'd love to have you back anytime!

Cute cottage in perfect location to beach & Duval. Modern & clean

April 2025
, United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Easy to book and check in.

Manager's Response

Thank you for your kind review! We’re so glad you enjoyed the cottage and found the location convenient and the process smooth. We’d love to host you again on your next Key West visit!

5 Days April 2025

April 2025
, Mississauga, ON CA

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very enjoyable stay, great location, clean, quiet and comfortable. Great little backyard with plenty of shade... Wife and I stayed, had a great time.

Manager's Response

Thank you for the kind words! We’re so glad you and your wife had a great time and enjoyed the peaceful backyard, comfort, and location. We'd love to welcome you back anytime!

Great Island Hideout in ideal location

January 2025
, Geneva, CH

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great location, comfortable house in an ideal location. We enjoyed this beautiful place, with a nice outdoor sitting and barbecue area, very cosy and discrete place. Ideally located close to the beach and to all the commodities. We will be returning for sure.

Manager's Response

Thank you for the wonderful review! We're so glad you enjoyed the comfort and privacy of the home, along with the outdoor space and unbeatable location. It’s great to hear it was the perfect island hideout for your trip. We’d be thrilled to welcome you back anytime!

Great cottage, great location, great management!

December 2024
, Lake Wales, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We came down for a getaway. Island Daze is better than the photos. Very clean, fresh and comfortable. Back yard is private and relaxing. We caught the Old Town Tram at the Southern most bouy. Toured, hit happy hours and had a great time. Wind caused a loud night but the property manager responded quickly and took care of the issue. This place is great and we would not hesitate to return. Thank you and we will see you again!!!

Manager's Response

Thank you for your incredible review! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Darling Cottage

October 2024
, Fort Myers, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The cottage was perfect for two couples. Both bedrooms had attached baths. We were just three houses down from Duval Street and a few blocks from the beach.
The staff was great. Our home in Fort Myers was threatened by Hurricane Milton. We were able to extend our stay until it was safe to return home.

Manager's Response

Thank you for your fantastic review. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Great Place in Key West

September 2024
, Millington, TN US

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was great for 4 people. The front bathroom is quite small without much storage fir toiletries. The beds were AMAZING. It was hot while we were there and the little room ac couldn't keep up. We were glad we brought a fan to help at night. We like to be extra cool when sleeping. Great location. 3 great restaurants within minutes of house.

Manager's Response

Thank you for this great review! We are thrilled you enjoyed the property and hope to host you again in the future!

Island Daze

September 2024
, Oconomowoc, WI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

We had a wonderful time. The home was clean and the beds and pillows comfortable my biggest priorities. A few suggestions from a frequent traveler to KW is that the windows need replacing. Keeping the kitchen/family room cool at the temp suggested was not feasible with sunroom windows that have openings. The bard door bedroom doesn't allow for privacy for two couples and made the vacation time sleeping not ideal. A real door would have been much better. A Vent is needed in the bathroom along with some shelving for guests toiletries. A laundry basket in both bedrooms and a luggage valet. The home is great just a few additions would make it perfect. Till next time.

Manager's Response

Thank you so much for your detailed and thoughtful review! We’re happy to hear you had a wonderful stay and that the home was clean and comfortable—especially the beds and pillows, which we know make a big difference.

As a frequent visitor to Key West, your insights are incredibly helpful and will be taken into consideration as we continue to improve the guest experience.

Thank you again for staying with us—looking forward to welcoming you back next time!

GREAT Rental

September 2024
, St. Louis, MO US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is a gem - perfect for four (or six I expect). Both bedrooms had king beds, two bathrooms, a wonderful kitchen, and a lovely backyard. It’s a quiet neighborhood with easy walking to Hemingway’s house, the beach, restaurants. Well appointed and clean.

Manager's Response

Thank you for the lovely review! We're so glad you enjoyed the comfort, layout, and peaceful neighborhood of the home. It's wonderful to hear the location made it easy to explore all the nearby favorites. We'd love to host you again for another relaxing Key West getaway!

It IS a perfectly located cottage!

June 2024
, Naples, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Cozy. Neat location within walking distance to everything Key West. So happy and satisfied calling this place home during our stay!

Manager's Response

Thank you for your wonderful review Ed. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Island Daze

June 2024
, Gulfport, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property was very well maintained, and extremely convenient for all activities.

Manager's Response

Thank you for this great review Joseph! We are thrilled you enjoyed the property and hope to host you again in the future!

Cute house

May 2024
, Weatherford, TX US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great little house and a great location. 2 king beds with bathrooms was why we chose was clean and had everything we needed.

Manager's Response

We are so happy you found this property and its location ideal for your get away in Key West. We hope you'll stay with us again next time you visit!

Great Place

May 2024
, Lincoln Park, NJ US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a great time here and I highly recommend this rental. Place is convenient walking distance to everything. Back yard area was great to relax in and rooms were very comfortable.

Manager's Response

Thank you for your review, we are so glad the property met your needs while staying with us. We hope you'll stay with us again next time you visit Key West.

Great place

April 2024
, Lombard, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Cute, clean, comfy houseand. Good communication with rental company and property manager.

Despite the houses being close together, the patio was private.

Great location.

Not very soundproof. When next door neighbors come home at night you can hear them clearly.

2nd bedroom is fairly small,but loved having 2 bedrooms both with king beds and their own bathrooms. The barn door for the 2nd bedroom didn't provide great privacy or sound barrier to rest of house.

Would recommend the house.

Manager's Response

Thank you for this great review! We are thrilled you enjoyed the property and hope to host you again in the future!

Key West Long Weekend

March 2024
, Alva, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Island Daze is presented beautifully! We had a wonderful time and really enjoyed the outdoor seating, cold AC, and hot showers! Can’t wait to come back again! Dan was responsive and helped get us checked in earlier than check in time and was very communicative throughout our stay.

Manager's Response

Thank you for your review. We are thrilled you loved this home and hope to host you again soon!

Great Key West Getaway

March 2024
, LARCHMONT, NY US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very comfortable 2BR house in Key West island decor, well-equipped kitchen, comfortable beds and convenient location. Nice backyard to sip coffee in the morning. Great Stay

Manager's Response

We are so happy you found this property and its location ideal for your get away in Key West. We hope you'll stay with us again next time you visit!

Island days

January 2024
, Taylors, SC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Two bedroom cottage

Manager's Response

Thank you for your 5 star review Trudi! Please come visit us again soon!

Island Daze

December 2023
, Pensacola, FL, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very good. the unit was clean and appointed nicely. we will be back.

Manager's Response

We love it when guests enjoyed their stay so much they plan on coming back! Thank you for being our guest John!

Very Nice & Great Location!

December 2023
, Sandia Park, NM United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4

Great place, beds comfy and nice location with easy access to all the sights. Very quiet and nice to have parking. Appreciated being able to use the washer & dryer. A few things were dirty, but that was just a minor complaint. Would prefer an 11:00 vs. 10 a.m checkout which seems a bit early. Very professional and responsive management - thank you! ~ Addition of jacuzzi would be great for rainy, colder days.

Manager's Response

Sharon thank you for taking the time to review your stay at Island Daze, we are so glad you enjoyed your stay and will relay your suggestions to the owner. Please come visit again!

Little cottage big on charm and convenience

December 2023
, Suffolk, VA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Overall, the cottage provided amble space for our 4 guests. Located on quiet street yet we could walk/ride bikes to shops restaurants attractions Easy rental process & very friendly staff. would stay here again

Manager's Response

Tricia thank you so much for your review, we are thrilled you had a great time at Island Daze and would love to welcome you again next time you are in Key West!

Amazing Property!!

December 2023
, OSTRANDER, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We travelled to Key West for a few days. This house was amazing! Very clean, good beds, amazing location! We will definitely be renting this place again!

Manager's Response

We really enjoyed hosting you Shaun. We are so happy you are planning on coming back, we look forward to welcoming you again!

Key West getaway

December 2023
, Natrona Hts, PA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Island daze was very clean and location was great. Close to everything. The management company was so helpful and convenient to check in. I would stay again when we return and highly recommend renting the property.

Manager's Response

Debra thank you for this great review! We would love to welcome you again!

Just Perfect

October 2023
, Calgary, AB CA

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We stayed two nights and nothing could make it more perfect. Fantastic location walkable to every place of interest we wanted to see. The house is squeaky clean, charmingly decorated Very functional floor plan and the backyard is a lovely private oasis. Would never be happy staying anywhere else in Key West. Perfect Also management was in regular touch to help with anything. Great stay

Manager's Response

What a wonderful review Brian, thank you so much! Please let us know as soon as you plan a trip back, we'll make sure it is as perfect as this one! Thank you for being our guest!

Island Daze for the win!

October 2023
, Fort Myers, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a great experience when we stayed in this cute little home in Key West. My husband and I rented it to stay with his brother and his wife for a long weekend. It is very well appointed and was clean as a whistle! Shana, the property manager, is delightful and was very helpful! The backyard is a peaceful oasis... we had a lot of fun watching the iguana that was hanging out there to have an afternoon snack several times. We slept in the bedroom that is right inside the front door. The bed was so comfortable!! High quality bath towels in both bathrooms. Will definitely be sharing this location with friends!

Manager's Response

David we are so glad you had a great stay and will be sharing your experience with your friends! We look forward to welcoming you again next time you visit the island!

Super clean. Very friendly staff

August 2023
, Clewiston, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

It was a super clean , communication was awesome. They even let us get into the property earlier then the check in time.

Manager's Response

Thank you for your review. We are so thrilled to hear how much you loved this home and hope to see you again!

Awesome Stay!

July 2023
, Wellington, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We loved staying at Island Daze! This place was amazing, centrally located (but not right in the middle of party town), spacious and clean. The beds were super comfortable and the space was equipped with anything needed for cooking, laundry and outdoor grilling. Our family would definitely stay here again. Our host was also very responsive and accommodating.

Manager's Response

We are so happy to read you had such a good stay with us Sheryl! We would love to welcome you back!

Great house...Great location

May 2023
, Palatine, IL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Came for vacation and our beach wedding and everything was perfect. We loved the house, private back yard and location was great. We would definitely stay again if we come back.

Manager's Response

Thank you for your wonderful review Curt. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Island Daze 2023

April 2023
, Vineyard Haven, MA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

A gem of a house! This is a return trip for us to this property and the new owners have kept the charm yet outfitted the home beautifully with KW style. The property manager came by to say hello upon our arrival and was delightful. I feel lucky to have re-discovered this property! A short walk (really) to Duval St and the delicious Banana Cafe and the bakery La Grigonote. Thank you team Island Daze!
Love KW and to be able to vacation here is a

Manager's Response

Thank you for this great review Martha! We are thrilled you enjoyed the property and hope to host you again in the future!

Island Daze 2023

April 2023
, Vineyard Haven, MA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

A gem of a house! This is a return trip for us to this property and the new owners have kept the charm yet outfitted the home beautifully with KW style. The property manager came by to say hello upon our arrival and was delightful. I feel lucky to have re-discovered this property! A short walk (really) to Duval St and the delicious Banana Cafe and the bakery La Grigonote. Thank you team Island Daze!
Love KW and to be able to vacation here is a

Manager's Response

Thank you for this great review Martha! We are thrilled you enjoyed the property and hope to host you again in the future!

Beautiful home in a great location!

March 2023
, Lake Mary, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This home is a beautiful place to stay in a great location in Key West! In addition, the team that manages the home is super helpful. I highly recommend staying here when you visit Key West!

Manager's Response

Thank you for your incredible review Cheryl! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Great Stay!

March 2023
, Lancaster, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

What a great stay! Great place, location, and agency at a competitive price. No complaints and would love to stay again!

Manager's Response

Thank you for your fantastic review Phi-Oanh. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Luisa Ave, Key West

February 2023
, Richmond, VA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Couldn’t have been more happy with this cottage. Great location, property manager was great, kitchen amenities were top notch, furnishings lovely and comfortable.

Manager's Response

Thank you for this great review Lois! We are thrilled you enjoyed the property and hope to host you again in the future!

Cute vacation house

October 2022
, Columbia, MD US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Great little house, wonderful location, and was very well equipped.

Manager's Response

Thank you for your feedback on your recent stay Ann. We are so glad that you enjoyed your time spent at this home. Thank you again and please reach out to us for your next Key West vacation!

Great Time!

October 2022
, WAKE FOREST, NC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

When we arrived the house was neat and tidy! It was a perfect location and convenient to everything.

Manager's Response

Thank you for your review LeAnne. We are thrilled you loved this home and hope to host you again soon!

Great vacation

August 2022
, Three Rivers, MI US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a great time, really well maintained property.

Manager's Response

Thank you for your review Rebekah. We are so thrilled to hear how much you loved this home and hope to see you again!

Best Location.

July 2022
, WELLINGTON, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Island Daze was half a block from Duval Street, but near the quieter part of town and it was great. The place was spotless, roomy with an at home feel. We wouldn't hesitate to stay here again!

Manager's Response

Thank you for your wonderful review Peter. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Island home review

June 2022
, Reisterstown, MD Afghanistan

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
3

Place was conveniently located, on the quieter side of Duvall and kept updated and clean. Great long weekend get away place!

Manager's Response

Thank you for this great review Lisa! We are thrilled you enjoyed the property and hope to host you again in the future!

Excellent Property in Key West

April 2022
, Oshkosh, WI US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Outstanding location. Perfect property for two couples. Close to everything and very private. Very clean and had everything we need. Property manager very helpful and engaging!

Manager's Response

Thank you for your wonderful review Tina. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Wonderful stay at a wonderful cottage!

April 2022
, Charlotte, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We came her with another couple and thoroughly enjoyed our stay at Island Daze. Location was great, loved being on a small quiet street that was close to everything. Cottage was clean, cute and the AC was kicking! We would definitely stay here again when planning a trip to Key West!

Manager's Response

Thank you for your fantastic review. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

An island gem!

April 2022
, Arlington, VA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was in a wonderful location close to everything, but yet in a quiet neighborhood. It had everything you would need, was clean and the management company was very responsive. Would definitely stay here again.

Manager's Response

Thank you for your wonderful review Lynn. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

island daze review

February 2022
, Ann arbor, MI US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
3

great place; clean; staff very helpful in providing few things we found missing upon arrival. overall great experience

Manager's Response

We are so happy to read you had such a good stay with us Michael! We would love to welcome you back next time you plan to visit Key West!

Great Daze at Island Daze!

February 2022
, Catskill, NY US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house is perfectly located right off the quiet end of Duval. The back yard offers a wonderful respite from the busy party vibe of the City. The home is beautifully decorated and is a peaceful oasis with a tropical feel. The property manager was super responsive and friendly. This was a perfect stay and if I’m ever back in Key West, I’ll hope to stay there again!

Manager's Response

Thank you for your wonderful review Julie. We enjoyed hosting you and hope to see you back in Key West again soon!

Fantastic Stay in Key West

December 2021
, Excelsior , MN US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great Location
Perfect Set-up
Parking!
Great Time had by all

Manager's Response

We are so happy to read you had such a good stay with us Don! We would love to welcome you back!

Great Stay!!

November 2021
, Rosharon , TX US

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The host was MORE than accommodating and helped anytime we had any issues even after our stay. There were a few things that needed to be addressed before our stay (empty propane bottle in the grill, hot water issue) but it didn't ruin the stay. The host was very responsive and tried to help as soon as they were made aware. This was a great place with a great location!

Manager's Response

Thank you for your review Orlando, we are glad you enjoyed your stay at Island Daze, we hope to welcome you at the property again!

Island hide away

October 2021
, chagrin falls, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property is located in a great location, walking distance to many restaurants and shops. The property is well-appointed clean and has everything you'll need for your stay. The back patio is a little oasis, private and lush. The property management company was great from the time I booked the home till we checked out. I would stay there again.

Manager's Response

We are so happy to read you had such a good stay with us Mark! We would love to welcome you back!

50th Getaway

October 2021
, Peru, IL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Awesome two bedroom house just as seen in the pictures. Ideal location on the quiet end of Duval Street. Had a great time and would definitely stay here again.

Manager's Response

We are so happy you enjoyed your stay so much Adam, we would love to host you again next time you visit key West!

Fantastic!

September 2021
, NAPERVILLE, IL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house was great! Super close to Duval and the Banana Cafe( went there for breakfast everyday!) easy access and parking for up to 5-6 scooters in front of the house. Wonderful temperature control and the bedroom/baths were more than adequate with plenty of space to unpack and the beds were both roomy and comfortable, slept great!

Manager's Response

Thank you for your wonderful review Julie! We enjoyed hosting you and hope to see you back soon!

I cannot say enough!

September 2021
, Peoria Heights, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We absolutely LOVED this home. It’s location was perfect. The home was very clean and cutely decorated. The communication with the property manager was fantastic as well. We will absolutely be staying again!

Manager's Response

Thank you for your review Natasha, we are so glad you enjoyed your stay with us and really look forward to welcoming you again!

Perfect Getaway

July 2021
, Tulsa, OK US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was perfect for our girls trip! The house had everything we needed. The beds were comfy and extra mirrors in the hall helped when we were all getting ready. We loved how close it was to Duvall St.

Manager's Response

Thank you for this great review Brittney! We are glad our property met all your group's need and hope to see you again next time you are on the island!

Perfect Location

July 2021
, Port St Lucie , FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house was situated in the perfect location, just a block off of Duval Street. It was super cute and clean. We wouldn't hesitate to go back.

Manager's Response

Thank you for your wonderful review. We hope to see you again soon!

Key West Celebration

June 2021
, Escondido, CA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The location of the property was ideal for experiencing Duval St, yet quiet at night. The house was clean, in working order, and property management was very responsive. We had a wonderful time!

Manager's Response

Thank you for your review Jennifer, we are so happy your stay with us was wonderful and hope you will come visit Key West again soon!

Beautiful little getaway

May 2021
, Jonesboro , GA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Home exactly as pictured; fantastic location, lovely furnishings and fit our needs perfectly! Can’t wait to book our next stay! ⭐️⭐️⭐️⭐️⭐️

Manager's Response

Thank you for your review. We are so happy you had a great time and hope to see you again!

Great!

May 2021
, Maryville , TN US

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our stay was great! Super clean and great location. We enjoyed the hot tub and outside patio area. The beds were extra comfy for the best night sleep. It was nice having our own parking too. The house had all the little extra touches we needed. thanks we will be back soon.

Manager's Response

We are so glad your stay with us was great and look forward to welcoming you again soon!

A Great Stay in Historical Key West

May 2021
, Long Beach , CA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Island Daze was a wonderful place for our family to stay while visiting Key West. it is a short walk/bike ride to white sand beaches, and an even shorter walk to Duvall Street, where one will find many shops and great food. The French Bakery on the corner of their street was a fantastic find for breakfast/lunch.

Manager's Response

Thank you for your wonderful review. We hope to see you again soon in Paradise!

Absolutely Wonderful

April 2021
, Tomah, WI US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We were a group of two couples and this property worked out perfectly for our stay. We were able to each have the privacy of our own bedroom and bathroom, and had plenty of common space to enjoy. The property was in great condition and the property manager was great. The location was great too, an easy walk to the Southernmost point area and a doable walk to the other end of Duval St. Be sure to stop at the Banana Cafe for breakfast!

Also, if you book with this company, take advantage of their concierge services, they were able to suggest and book some great activities!

Manager's Response

Thank you for your review. We enjoyed hosting you and hope to see you again soon!

Perfect!

March 2021
, Riverside, IL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Absolutely perfect. The property is awesome and the complementary concierge service was amazing!

Manager's Response

Thank you for your wonderful review. We hope to see you again soon!

Precious cottage right off Duval

December 2020
, Cataula, GA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We planned this vacation less than a month before Christmas and was so excited to find this precious cottage. It’s 1/2 block off Duval close to the Southern most point with great restaurants, galleries and shopping all within walking distance. Beds are comfortable, place was clean and had everything you needed.

Manager's Response

Thank you for your kind words. We enjoyed hosting you and hope to see you again very soon!

Great Stay at Island Daze!

December 2020
, Westerville, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Location: The house was in a great part of Key West on a very quiet street about 200’ off Duval. We heard very little noise from the neighbors and felt very safe during our stay. It is a 2 blocks from the Southernmost Point “Buoy,” close to some good restaurants, a bike rental shop, and a quick (5 min) bike ride to Higgs beach, and 10 min. to Smathers and Fort Zachary Taylor Beach. It’s about a 10 minute bike ride down to Mallory Square down Duval or Simonton.

House: The pictures on the website were very accurate. The house was a good size and provided ample space for our 2 kids and 2 dogs. We used the bedroom close to the front of the house as the “Master” while our daughter took the other bedroom and our son slept on the couch. All of the beds were amazingly comfortable, and we slept great the entire time. The AC worked well and kept the house very cool with a ceiling fan in each room. The kitchen had everything needed during our stay (including a Kuireg and a regular coffee maker as well). The internet was very fast in most parts of the house. My son had his PS5 and was able to run it in the living room with few issues. We pulled ~100MB in most of the house but it was higher at times as well. There’s YouTube TV on all of the TV’s which were good sized at ~40-50.” The parking spot in front of the house was big enough to park my full size truck caddy corner.

Yard: The yard was a good size for Key West and had a Hot Tub, table, and a grill. Everything worked great. If you have dog(s) there is no grass in the backyard for their “bathroom.” We walked the dogs 2 minutes down the street to a bank that had plenty of grass for them though. We parked our rented bikes in the backyard with no issues.

Best of Key West rentals was very accommodating and responsive for the few needs we had. Overall we had no complaints at all. We’ve been to Key W

Manager's Response

Thank you for your wonderful review. We enjoyed hosting you and hope to see you back in Key West again soon!

Leave a Review
2 Bed
2 Baths
Sleeps 6

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INTO THE MYSTIC ~ Charming!

INTO THE MYSTIC ~ Charming 2 Bedroom, 3 Bathroom Townhome w/ Shared Pool within Lush Community Close to Everything!

Location

607 Virginia St.
33040 Key West , FL
United States
24° 33' 3.78" N, 81° 47' 50.028" W
See map: Google Maps
Florida US

INTO THE MYSTIC ~ Charming!

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Checks every box

Reviewed by Tony P. on 2021-03-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We rented the home for 3 months, perfect location only a block away from Duval. Walk to everywhere within minutes. Many outstanding restaurants nearby. The house is well laid out, roomy, and in fantastic condition. Bright and airy feel to it set on very lovely grounds. Parking in your own driveway made it super easy.
Manager response on 2021-03-30 - Response from Best of Key West Rentals
Thank you for your review. Please come back and see us soon!

INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w/ Community Pool!

Unit Code: IM

INTO THE MYSTIC ~ Charming!

INTO THE MYSTIC ~ Charming 2 Bedroom, 3 Bathroom Townhome w/ Shared Pool within Lush Community Close to Everything!
YOUR PEACEFUL PARADISE AWAITS… Find this unmatched island escape tucked away in the lust and intimate Southernmost Cabana Community in the Old Town district of Key West. Convenient location with high end finishings and endless amenities, this home is sure to complete your well awaited tropical getaway in style!   ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… Pull up to your tropical abode boasting vibrant vegetation all around immersing you into the island lifestyle. Step onto your own front porch with rocking chairs for your morning cup of coffee as you appreciate your serene surroundings. Inside you will be greeted by a cheery, open great room showcasing tile flooring and natural lighting all around. Prepare your meals together in a fully equipped kitchen complete with granite counters and stainless-steel appliances with bar seating for 3 and a nearby dining table for 4. Snuggle up on cozy living room furnishings with a flat screen TV available and stunning garden views beyond a set of French doors to your outdoor Paradise. SLEEPING ARRANGEMENTS... Follow the stairs up to a king bedroom with a flat screen TV and an en suite bathroom with a shower. Down the hall you will find another guest room equipped with a queen bed, flat screen TV, an en suite bathroom with a shower and your own private balcony. An additional full bathroom with a shower lies off the kitchen area downstairs. OUTDOOR LIVING... Your own slice of paradise is available as you step out onto your own back porch with an inviting seating area and grill for your fresh catch of the day. Take a stroll through the quaint community and find your tranquil heated community pool with a waterfall and surrounding loungers. Take a short bike ride or walk down to the unique treasures of Duval Street or sneak away to a nearby beach. The home also comes with a parking spot right out front of the unit. PETS... No pets please. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). TIME TO UNWIND…
June 2026
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DatesPrice
06/12/2026 - 07/31/2026$188 /nt
08/01/2026 - 09/30/2026$179 /nt
10/01/2026 - 10/31/2026$197 /nt
11/01/2026 - 11/30/2026$215 /nt
12/01/2026 - 12/31/2026$429 /nt
01/01/2027 - 03/31/2027$572 /nt
04/01/2027 - 04/30/2027$250 /nt
05/01/2027 - 06/12/2027$197 /nt
5.0000
(1 Review)

Checks every box

January 2021
, Boston, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We rented the home for 3 months, perfect location only a block away from Duval. Walk to everywhere within minutes. Many outstanding restaurants nearby. The house is well laid out, roomy, and in fantastic condition. Bright and airy feel to it set on very lovely grounds. Parking in your own driveway made it super easy.

Manager's Response

Thank you for your review. Please come back and see us soon!

Leave a Review
2 Bed
3 Baths
Sleeps 4

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PINEAPPLE BREEZE ~ Perfection!

PINEAPPLE BREEZE ~ JUST RENOVATED 3 Bedroom, 2 Bathroom Home in The Meadows with Private Backyard Pool Area! Upscale Living in Sunshiny Paradise!

Location

1221 Olivia St.
33040 Key West , FL
United States
24° 33' 27.108" N, 81° 47' 28.68" W
See map: Google Maps
Florida US

PINEAPPLE BREEZE ~ Perfection!

Request More Information

Pineapple Breeze Was Truly Perfection!

Reviewed by Martha S. on 2024-12-21
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Outstanding home! Beautifully decorated, immaculate and the level of comfort was exceptional! Above average for a rental property! Thank you to both the owners for the privilage and their care to provide the perfect Key West vibe and the rental company who's attention to every detail made for a wonderful experience. I hated to leave.
Manager response on 2024-12-22 - Response from Best of Key West Rentals
Thank you for your incredible review! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Pineapple Breeze is Fabulous

Reviewed by Unknown on 2020-03-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Pineapple Breeze has been newly renovated and it is a spacious,spotless, beautifully decorated home. The kitchen is well laid out, with new appliances and equipment, and basic food items in the cupboard. The beds are comfortable with new mattresses. We used the pool daily and ate most of our meals in the lovely backyard. The outdoor shower is a great feature. The location is quiet on Olivia Street and we were able to find on-street parking easily. There is a parking space for a small car. The location is not close to Duval Street but we enjoyed the walk and it is a short bikeride. The management was helpful and responded immediately to any questions or requests. We will be back next year.
Manager response on 2020-03-24 - Response from Best of Key West Rentals
Dear Karen, WOW! Thank you for your incredible review. We are so thrilled to hear how much you loved this home. We are so excited to see you back again next year! Best Regards, Wendy Zintsmaster and Team

Relaxing getaway at Pineapple Breeze...

Reviewed by Amanda B. on 2020-02-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had an amazing time in Key West and our stay at Pineapple Breeze was great! The house is in a great location which made it easy for us to ride bikes everywhere in town. The house was clean and well-maintained and had a great layout for us and our visitors. The house has a great relaxing feel inside and we felt right at home. They kept the pool maintained weekly and if we needed something our property manager Brian was readily available and took care of it for us quickly. The booking process was easy and they kept us well informed if any changes were going to occur. Everything was handled professionally from the beginning of our booking to the end of our stay. I would highly recommend Pineapple Breeze and Truman and Company. We can't wait to come back and visit next year!
Manager response on 2020-02-07 - Response from Best of Key West Rentals
Dear Amanda, Wow, thank you for your incredible review! We are so thrilled to hear how much you loved this wonderful Key West home. We enjoyed hosting you in Paradise and hope to see you back again next year! Best Regards, Wendy Zintsmaster and Team

PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!

Unit Code: PB

PINEAPPLE BREEZE ~ Perfection!

PINEAPPLE BREEZE ~ JUST RENOVATED 3 Bedroom, 2 Bathroom Home in The Meadows with Private Backyard Pool Area! Upscale Living in Sunshiny Paradise!
PICTURE PERFECT PARADISE... This newly renovated retreat is nestled in the highly sought-after neighborhood of The Meadows. A beautiful balance of modern luxuries mixed with vibrant surroundings connect you to your personal Paradise. Exceptional attention to detail and all the desired amenities set this home apart from everything else. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES... Immerse yourself in island time as you enter the white picket fence and gaze at your private front porch perfect for enjoying your morning coffee. Greeted by elegant designer décor showcasing an upscale Key West flare and accents of Dade County Pine, this natural light filled home exudes happiness. An inviting Florida room flooded with sunshine invites a lazy day of lounging with a good book or serves as additional sleeping. Bamboo floors, breezy ceiling fans and cozy furnishings along with a TV fill the open living area. Steps away is your top of the line kitchen featuring stainless-steel appliances, custom cabinetry and granite countertops complete with a breakfast bar with seating for 2. Come together for dinner around the dining table for 4 or open the French doors and dine al fresco! SLEEPING ARRANGEMENTS... Enjoy 3 bedrooms in total equipped with flat screen tv's. Two of the guest rooms (one with a King Bed and one with a Queen bed) share a hallway as well as an over-sized pineapple inspired bathroom, featuring a double sink vanity and extra large glass shower. On the other end of the home is a poolside retreat with a King Size Bed, TV and private bathroom complete with a shower/tub combination. Beautiful French doors open wide to your backyard patio and pool to let the outside beauty in - this is true paradise living! OUTDOOR LIVING... French doors open from the kitchen to a backyard dream that's perfect for entertaining. A calming afternoon calls for a dip in the heated pool or a rinse in the adorable outdoor shower as you are accompanied by swaying palms in the breeze. Sip cocktails under the twinkling light at the outdoor dining table for 4 and toast to another day in Paradise. Private and tranquil, yet just a short bike ride away from all the island favorite restaurants, bars and galleries making your island vacation feeling complete. PARKING... There is a small private parking spot plus ample on street parking to accommodate your stay. PETS... The owner will consider dogs up to 45 pounds (no more than 3) and a pet fee is required. Cats will not be accepted. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). YOU'LL NEVER WANT TO LEAVE...
June 2026
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DatesPrice
06/12/2026 - 06/30/2026$250 /nt
07/01/2026 - 07/31/2026$268 /nt
08/01/2026 - 09/30/2026$304 /nt
10/01/2026 - 10/31/2026$358 /nt
11/01/2026 - 11/30/2026$429 /nt
12/01/2026 - 12/31/2026$536 /nt
01/01/2027 - 01/31/2027$715 /nt
02/01/2027 - 02/28/2027$750 /nt
03/01/2027 - 03/31/2027$715 /nt
04/01/2027 - 04/30/2027$429 /nt
05/01/2027 - 06/12/2027$304 /nt
5.0000
(4 Review)

Pineapple Breeze Was Truly Perfection!

October 2024
, Vineyard Haven, MA Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Outstanding home! Beautifully decorated, immaculate and the level of comfort was exceptional! Above average for a rental property! Thank you to both the owners for the privilage and their care to provide the perfect Key West vibe and the rental company who's attention to every detail made for a wonderful experience. I hated to leave.

Manager's Response

Thank you for your incredible review! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Pineapple Breeze is Fabulous

February 2020
, Huntsville, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Breeze has been newly renovated and it is a spacious,spotless, beautifully decorated home. The kitchen is well laid out, with new appliances and equipment, and basic food items in the cupboard. The beds are comfortable with new mattresses. We used the pool daily and ate most of our meals in the lovely backyard. The outdoor shower is a great feature. The location is quiet on Olivia Street and we were able to find on-street parking easily. There is a parking space for a small car. The location is not close to Duval Street but we enjoyed the walk and it is a short bikeride. The management was helpful and responded immediately to any questions or requests. We will be back next year.

Manager's Response

Dear Karen,


WOW! Thank you for your incredible review. We are so thrilled to hear how much you loved this home. We are so excited to see you back again next year!


Best Regards,


Wendy Zintsmaster and Team

Pineapple Breeze is Fabulous

February 2020
, Huntsville, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Breeze has been newly renovated and it is a spacious,spotless, beautifully decorated home. The kitchen is well laid out, with new appliances and equipment, and basic food items in the cupboard. The beds are comfortable with new mattresses. We used the pool daily and ate most of our meals in the lovely backyard. The outdoor shower is a great feature. The location is quiet on Olivia Street and we were able to find on-street parking easily. There is a parking space for a small car. The location is not close to Duval Street but we enjoyed the walk and it is a short bikeride. The management was helpful and responded immediately to any questions or requests. We will be back next year.

Manager's Response

Dear Karen,


WOW! Thank you for your incredible review. We are so thrilled to hear how much you loved this home. We are so excited to see you back again next year!


Best Regards,


Wendy Zintsmaster and Team

Relaxing getaway at Pineapple Breeze...

January 2020
, Newburyport, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had an amazing time in Key West and our stay at Pineapple Breeze was great! The house is in a great location which made it easy for us to ride bikes everywhere in town. The house was clean and well-maintained and had a great layout for us and our visitors. The house has a great relaxing feel inside and we felt right at home. They kept the pool maintained weekly and if we needed something our property manager Brian was readily available and took care of it for us quickly. The booking process was easy and they kept us well informed if any changes were going to occur. Everything was handled professionally from the beginning of our booking to the end of our stay. I would highly recommend Pineapple Breeze and Truman and Company. We can't wait to come back and visit next year!

Manager's Response

Dear Amanda,


Wow, thank you for your incredible review! We are so thrilled to hear how much you loved this wonderful Key West home. We enjoyed hosting you in Paradise and hope to see you back again next year!


Best Regards,


Wendy Zintsmaster and Team

Leave a Review
3 Bed
2 Baths
Sleeps 6

Search Availability

SOUTHERN CROSS ~ Royal!

SOUTHERN CROSS ~ Charming 3 Bedroom, 2.5 Bathroom Home Located in a Peaceful Area with Pool and Off Street Parking Space!

Location

1219 Royal St.
33040 Key West , FL
United States
24° 33' 4.32" N, 81° 47' 35.16" W
See map: Google Maps
Florida US

SOUTHERN CROSS ~ Royal!

Request More Information

Always an excellent stay

Reviewed by Unknown on 2026-02-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This was our 4th year renting Southern Cross and still love it! Love the home, very comfortably laid out (could use a bit more kitchen prep items), fabulous pool/deck and location.
Manager response on 2026-02-02 - Response from Best of Key West Rentals
We truly appreciate your review Scott! It makes us happy to know you loved this home, and we’d be delighted to host you again anytime.

Love the Southern Cross

Reviewed by Unknown on 2025-02-20
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This was our 3rd winter (2 months) at Southern Cross and it continues to be our preferred place to stay on the island. We are looking forward to our return this December (2025) & January (2026)! The kitchen could use a little TLC however; updated flatware, plates, equipment & most of the outlets & overhead lights didn't work (again, didn't on our previous stay either). Would be great if the LED overhead lights could be replaced with more visibly appealing bulbs. Unfortunately, the pool & landscape lighting were challenges (they didn't work during most of our stay) & it took quite a bit of communication with the property manager (who seemed to be annoyed by our contact, sorry to say) to eventually be repaired. Just in time for our departure. Not a deal breaker whatsoever, but love the lights/atmosphere when they work. Don't get me wrong, we LOVE the property! We would love to purchase it in fact, so these are not complaints, simply constructive criticism. We do recommend this property highly!
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you so much for your continued loyalty to Southern Cross—it truly means a lot to us! We're thrilled to hear it's become your preferred winter retreat and that you're already looking forward to returning this December. We really appreciate your detailed feedback about the kitchen, lighting, and landscape features. Your insights help us identify areas where we can make meaningful improvements, and we’ll absolutely be reviewing these items with our team. We're especially sorry to hear that communication around the lighting repair felt less than welcoming—that’s not the experience we aim to provide, and we’ll work to ensure future interactions are more supportive and responsive. We’re so glad you continue to enjoy the property overall, and your kind words and ongoing support mean everything. Looking forward to welcoming you back soon!

Great stay at Southern Cross

Reviewed by MIke S. on 2024-12-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Spent a month at your beautiful home - great location, private back yard, and wonderful amenities.
Manager response on 2024-12-18 - Response from Best of Key West Rentals
Thank you for your review Mike. We are so thrilled to hear how much you loved this home and hope to see you again!

Review of Southern Cross

Reviewed by Unknown on 2024-04-08
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The home, location, cleanliness of the house was great! The concierge team (especially Natalie) were on top of every detail and responsive with each question. My only disappointment was the condition of the pool and the tree constantly dropping leaves. We were constantly clearing leaves from the pool deck, furniture and the pool itself. Overall though a great stay!
Manager response on 2024-04-11 - Response from Best of Key West Rentals
We are so happy you found this property and its location ideal for your get away in Key West Hilary. We are glad our team was able to provide you with the best service. We are sorry the wind and seasonal changes of the landscape caused leafs to fall daily. We hope this won't keep your from staying with us again next time you visit Key West!

Love the Southern Cross

Reviewed by Unknown on 2024-02-04
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This was our second month long rental at Southern Cross and love it! So far, our favorite long term rental in Key West (we've rented 2 other homes for month+ stays). Well equipped, comfortable layout, excellent location and we love the privacy of the pool area (can't wait for the construction at the home behind is finally over!) There are some spots that need a little TLC but nothing functional. Shanna is an amazing property manager (& we know as we own a vacation property management company on Cape Cod! She's GREAT! The whole team at Truman is great! Very helpful & kind)
Manager response on 2024-02-05 - Response from Best of Key West Rentals
Thank you so much for your kind words Scott. We really appreciate you taking the time out to share your experience with us — and we agree, Shana is truly a gem to have on our team! We count ourselves lucky for guests like you. We look forward to working with you again in the future!

Absolutely wonderful

Reviewed by Jeannine K. on 2023-06-26
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This house was perfect for our stay! We were able to walk everywhere. I like this location because it's not on Duval, but doesn't take long to walk there. It's also close to the pickleball courts, El Siboney, and the cemetery.
The house is spacious. The laundry room is large and there is an amazing walk in closet in the master bedroom. I work from home and was able to find quiet places to work during the day with reliable internet.
We only had a couple of very minor issues and the property manager took care of them same day!
I would definitely recommend this home!
Manager response on 2023-12-05 - Response from Best of Key West Rentals
Thank you for this wonderful review Jeannine, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

When you see the Southern Cross for the 1st time You understand

Reviewed by Unknown on 2023-02-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Loved it! We've rented with T&Co for 5 years now, 3 homes, this is by far the best. Great location, beautiful, comfortable & well appointed. LOVE the pool deck & cabana. We rarely got out of the pool, except to eat at the MANY amazing restaurants on island. Please fix the main TV though, we barely watch TV & when we tried to (watch) it was frustrating & nearly impossible. Otherwise, love the property & look forward to our return next January.
Manager response on 2023-02-03 - Response from Best of Key West Rentals
Thank you for sharing a review of your recent experience at Southern Cross Scott! Our team here at Best of Key West Rentals is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you over the years. We look forward to hosting you again next year. Thank you for being our guest!

Perfection

Reviewed by Unknown on 2021-12-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The house exceeded our expectations. Exactly as advertised only better. Location was perfect. Comfortable beds, nice pool. Stocked with everything you need.
Manager response on 2021-12-03 - Response from Best of Key West Rentals
Thank you for this wonderful review Bruce, we are thrilled you enjoyed the property and look forward to welcoming you again next time you are in Key West!

Slice of Paradise in Key West

Reviewed by Diana F. on 2021-02-07
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had the great fortune of spending 2 amazing months at this slice of heaven. The house is fully stocked with everything you need to cook and clean. Love that it has starter laundry detergents, soaps, cleaners, etc. The design is open, airy and beautiful. The owner should be an interior decorator if she isn’t already! Everything is clean and new or like new! The back deck was done so thoughtfully too, with orchids planted in all the trees that were so beautiful. Really nice touches throughout. Loved the pool house to be able to use as an office to separate work and home. The outdoor shower was amazing to start the day with. The location can’t be beat, smack in the middle of town walking distance from everything! We will always remember the time we spent at Royal Street fondly.
Manager response on 2021-02-08 - Response from Best of Key West Rentals
Thank you for this incredible review. We loved hosting you in Paradise and hope to see you again soon!

SOUTHERN CROSS ~ Conveniently Located 3 Bedroom, 2.5 Bathroom Gem w/ Pool

Unit Code: SOU

SOUTHERN CROSS ~ Royal!

SOUTHERN CROSS ~ Charming 3 Bedroom, 2.5 Bathroom Home Located in a Peaceful Area with Pool and Off Street Parking Space!
SOUTHERN HOSPITALITY... Find your luxurious, island retreat nestled in the heart of Old Town, just blocks from the beautiful beaches and minutes from town. An upscale refuge designed to surpass all of your expectations boasting an ideal entertaining space within an enchanting tropical setting. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES... Although conveniently located, this home comes with the perk of one off street parking spot so you can come and go as you please. Pull up to this attractive abode with swaying palms greeting you in the island breeze. Step inside to find an open concept layout boasting cathedral ceilings, hardwood flooring and cheery natural lighting throughout bringing the outdoors inside. Find an updated and fully equipped kitchen with stainless steel appliance, granite counters, a wine chiller and bar seating for 2. The living space is filled with comfortable furnishings and a flat screen TV. All the TVs in this house are smart TVs available for your log in information. This property is equipped with security cameras located on the front of the home facing the yard. SLEEPING ARRANGEMENTS... The main house offers two guest rooms beginning with a queen bedroom with a flat screen TV and an en suite full bathroom with a walk in glass shower that can also be accessed by the main hallway. A king master suite is located off the Great Room and comes with a flat screen TV, French doors to your private backyard and an en suite full bathroom with a walk in glass shower. A poolside cottage comes furnished with a queen bed, half bath and an adjoining room with a twin sofa sleeper and writing desk. OUTDOOR LIVING... An awe inspiring, sparkling pool greets you in this incredibly lush backyard area - a heat option is available during winter months. Savor your surroundings in a lounge chair and dine al fresco together in the evenings. Rinse off in the outdoor shower which can also be accessed from the cottage and head into town for all the fun! Serviced every Friday. PARKING... Enjoy an off street parking space inside the gates. PETS... This is NOT a pet friendly home. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). SIMPLY HEAVENLY...
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Age 18 and under.
DatesPrice
06/12/2026 - 06/30/2026$250 /nt
07/01/2026 - 07/31/2026$268 /nt
08/01/2026 - 08/31/2026$304 /nt
09/01/2026 - 09/30/2026$268 /nt
10/01/2026 - 10/31/2026$340 /nt
11/01/2026 - 11/30/2026$447 /nt
12/01/2026 - 12/31/2026$536 /nt
01/01/2027 - 01/31/2027$715 /nt
02/01/2027 - 02/28/2027$804 /nt
03/01/2027 - 03/31/2027$750 /nt
04/01/2027 - 04/30/2027$500 /nt
05/01/2027 - 06/12/2027$322 /nt
4.9231
(13 Review)

Always an excellent stay

January 2026
, Tierra Verde, FL United States

Overall
5
Property condition
4
Location
5
Cleanliness
5
Services from rental manager
5

This was our 4th year renting Southern Cross and still love it! Love the home, very comfortably laid out (could use a bit more kitchen prep items), fabulous pool/deck and location.

Manager's Response

We truly appreciate your review Scott! It makes us happy to know you loved this home, and we’d be delighted to host you again anytime.

Always an excellent stay

January 2026
, Tierra Verde, FL Unknown

Overall
5
Property condition
4
Location
5
Cleanliness
5
Services from rental manager
5

This was our 4th year renting Southern Cross and still love it! Love the home, very comfortably laid out (could use a bit more kitchen prep items), fabulous pool/deck and location.

Manager's Response

We truly appreciate your review Scott! It makes us happy to know you loved this home, and we’d be delighted to host you again anytime.

Love the Southern Cross

January 2025
, Tierra Verde , FL United States

Overall
5
Services from rental manager
3
Cleanliness
5
Location
5
Property condition
4

This was our 3rd winter (2 months) at Southern Cross and it continues to be our preferred place to stay on the island. We are looking forward to our return this December (2025) & January (2026)! The kitchen could use a little TLC however; updated flatware, plates, equipment & most of the outlets & overhead lights didn't work (again, didn't on our previous stay either). Would be great if the LED overhead lights could be replaced with more visibly appealing bulbs. Unfortunately, the pool & landscape lighting were challenges (they didn't work during most of our stay) & it took quite a bit of communication with the property manager (who seemed to be annoyed by our contact, sorry to say) to eventually be repaired. Just in time for our departure. Not a deal breaker whatsoever, but love the lights/atmosphere when they work. Don't get me wrong, we LOVE the property! We would love to purchase it in fact, so these are not complaints, simply constructive criticism. We do recommend this property highly!

Manager's Response

Thank you so much for your continued loyalty to Southern Cross—it truly means a lot to us! We're thrilled to hear it's become your preferred winter retreat and that you're already looking forward to returning this December.

We really appreciate your detailed feedback about the kitchen, lighting, and landscape features. Your insights help us identify areas where we can make meaningful improvements, and we’ll absolutely be reviewing these items with our team. We're especially sorry to hear that communication around the lighting repair felt less than welcoming—that’s not the experience we aim to provide, and we’ll work to ensure future interactions are more supportive and responsive.

We’re so glad you continue to enjoy the property overall, and your kind words and ongoing support mean everything. Looking forward to welcoming you back soon!

Love the Southern Cross

January 2025
, Tierra Verde, FL United States

Overall
5
Property condition
4
Location
5
Cleanliness
5
Services from rental manager
3

This was our 3rd winter (2 months) at Southern Cross and it continues to be our preferred place to stay on the island. We are looking forward to our return this December (2025) & January (2026)! The kitchen could use a little TLC however; updated flatware, plates, equipment & most of the outlets & overhead lights didn't work (again, didn't on our previous stay either). Would be great if the LED overhead lights could be replaced with more visibly appealing bulbs. Unfortunately, the pool & landscape lighting were challenges (they didn't work during most of our stay) & it took quite a bit of communication with the property manager (who seemed to be annoyed by our contact, sorry to say) to eventually be repaired. Just in time for our departure. Not a deal breaker whatsoever, but love the lights/atmosphere when they work. Don't get me wrong, we LOVE the property! We would love to purchase it in fact, so these are not complaints, simply constructive criticism. We do recommend this property highly!

Manager's Response

Thank you so much for your continued loyalty to Southern Cross—it truly means a lot to us! We're thrilled to hear it's become your preferred winter retreat and that you're already looking forward to returning this December.

We really appreciate your detailed feedback about the kitchen, lighting, and landscape features. Your insights help us identify areas where we can make meaningful improvements, and we’ll absolutely be reviewing these items with our team. We're especially sorry to hear that communication around the lighting repair felt less than welcoming—that’s not the experience we aim to provide, and we’ll work to ensure future interactions are more supportive and responsive.

We’re so glad you continue to enjoy the property overall, and your kind words and ongoing support mean everything. Looking forward to welcoming you back soon!

Great stay at Southern Cross

November 2024
, Cincinnati, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Spent a month at your beautiful home - great location, private back yard, and wonderful amenities.

Manager's Response

Thank you for your review Mike. We are so thrilled to hear how much you loved this home and hope to see you again!

Review of Southern Cross

March 2024
, Madison, NJ US

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

The home, location, cleanliness of the house was great! The concierge team (especially Natalie) were on top of every detail and responsive with each question. My only disappointment was the condition of the pool and the tree constantly dropping leaves. We were constantly clearing leaves from the pool deck, furniture and the pool itself. Overall though a great stay!

Manager's Response

We are so happy you found this property and its location ideal for your get away in Key West Hilary. We are glad our team was able to provide you with the best service. We are sorry the wind and seasonal changes of the landscape caused leafs to fall daily. We hope this won't keep your from staying with us again next time you visit Key West!

Love the Southern Cross

December 2023
, Tierra Verde, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

This was our second month long rental at Southern Cross and love it! So far, our favorite long term rental in Key West (we've rented 2 other homes for month+ stays). Well equipped, comfortable layout, excellent location and we love the privacy of the pool area (can't wait for the construction at the home behind is finally over!) There are some spots that need a little TLC but nothing functional. Shanna is an amazing property manager (& we know as we own a vacation property management company on Cape Cod! She's GREAT! The whole team at Truman is great! Very helpful & kind)

Manager's Response

Thank you so much for your kind words Scott. We really appreciate you taking the time out to share your experience with us — and we agree, Shana is truly a gem to have on our team! We count ourselves lucky for guests like you. We look forward to working with you again in the future!

Love the Southern Cross

December 2023
, Tierra Verde , FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

This was our second month long rental at Southern Cross and love it! So far, our favorite long term rental in Key West (we've rented 2 other homes for month+ stays). Well equipped, comfortable layout, excellent location and we love the privacy of the pool area (can't wait for the construction at the home behind is finally over!) There are some spots that need a little TLC but nothing functional. Shanna is an amazing property manager (& we know as we own a vacation property management company on Cape Cod! She's GREAT! The whole team at Truman is great! Very helpful & kind)

Manager's Response

Thank you so much for your kind words Scott. We really appreciate you taking the time out to share your experience with us — and we agree, Shana is truly a gem to have on our team! We count ourselves lucky for guests like you. We look forward to working with you again in the future!

Absolutely wonderful

May 2023
, Columbus, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house was perfect for our stay! We were able to walk everywhere. I like this location because it's not on Duval, but doesn't take long to walk there. It's also close to the pickleball courts, El Siboney, and the cemetery.
The house is spacious. The laundry room is large and there is an amazing walk in closet in the master bedroom. I work from home and was able to find quiet places to work during the day with reliable internet.
We only had a couple of very minor issues and the property manager took care of them same day!
I would definitely recommend this home!

Manager's Response

Thank you for this wonderful review Jeannine, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

When you see the Southern Cross for the 1st time You understand

December 2022
, Tierra Verde, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Loved it! We've rented with T&Co for 5 years now, 3 homes, this is by far the best. Great location, beautiful, comfortable & well appointed. LOVE the pool deck & cabana. We rarely got out of the pool, except to eat at the MANY amazing restaurants on island. Please fix the main TV though, we barely watch TV & when we tried to (watch) it was frustrating & nearly impossible. Otherwise, love the property & look forward to our return next January.

Manager's Response

Thank you for sharing a review of your recent experience at Southern Cross Scott! Our team here at Best of Key West Rentals is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you over the years. We look forward to hosting you again next year. Thank you for being our guest!

When you see the Southern Cross for the 1st time You understand

December 2022
, Tierra Verde , FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Loved it! We've rented with T&Co for 5 years now, 3 homes, this is by far the best. Great location, beautiful, comfortable & well appointed. LOVE the pool deck & cabana. We rarely got out of the pool, except to eat at the MANY amazing restaurants on island. Please fix the main TV though, we barely watch TV & when we tried to (watch) it was frustrating & nearly impossible. Otherwise, love the property & look forward to our return next January.

Manager's Response

Thank you for sharing a review of your recent experience at Southern Cross Scott! Our team here at Best of Key West Rentals is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you over the years. We look forward to hosting you again next year. Thank you for being our guest!

Perfection

November 2021
, Crestwood, KY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house exceeded our expectations. Exactly as advertised only better. Location was perfect. Comfortable beds, nice pool. Stocked with everything you need.

Manager's Response

Thank you for this wonderful review Bruce, we are thrilled you enjoyed the property and look forward to welcoming you again next time you are in Key West!

Slice of Paradise in Key West

January 2021
, Riverhead, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had the great fortune of spending 2 amazing months at this slice of heaven. The house is fully stocked with everything you need to cook and clean. Love that it has starter laundry detergents, soaps, cleaners, etc. The design is open, airy and beautiful. The owner should be an interior decorator if she isn’t already! Everything is clean and new or like new! The back deck was done so thoughtfully too, with orchids planted in all the trees that were so beautiful. Really nice touches throughout. Loved the pool house to be able to use as an office to separate work and home. The outdoor shower was amazing to start the day with. The location can’t be beat, smack in the middle of town walking distance from everything! We will always remember the time we spent at Royal Street fondly.

Manager's Response

Thank you for this incredible review. We loved hosting you in Paradise and hope to see you again soon!

Leave a Review
3 Bed
2.5 Baths
Sleeps 7

Search Availability

BAREFOOT BUNGALOW~Escape Reality!

BAREFOOT BUNGALOW~Peacefully and Centrally Located 2 Bedroom Home with Office and Outdoor Area w/ Large, Heated Private Pool and Tiki Hut!

Location

2328 Staples Ave.
33040 Key West , FL
United States
24° 33' 30.42" N, 81° 46' 33.096" W
See map: Google Maps
Florida US

BAREFOOT BUNGALOW~Escape Reality!

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Home away from bome

Reviewed by George D. on 2025-06-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Barefoot Bungalow is what is what they advertise. Have been coming here for three straigt years now . We stay for a month and the location is perfect with easy accesse to the whole island.Very good managment sevice when needed.If you want a home away from home vacation, this is the place.
Manager response on 2025-06-16 - Response from Best of Key West Rentals
George, thank you so much for your kind words and for being a loyal guest at Barefoot Bungalow for three years running! We're thrilled to hear the home continues to meet your expectations and feels like your home away from home. The location truly is a gem, and we're glad our management team has been able to support you when needed. We look forward to welcoming you back for many more relaxing stays on the island!

Comfortable

Reviewed by Jane R. on 2025-01-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This property suited my needs very nicely. I brought my bike and cycling is the perfect way to navigate Key West. This property is not in Old Town but in a neighborhood mostly inhabited by locals and I like that. The house and yard are lovely, I enjoyed cooking in the kitchen. Both the front porch and pool areas are pleasant places to spend time. I’ve booked it again and am looking forward to revisiting.
Manager response on 2025-01-04 - Response from Best of Key West Rentals
Thank you for your wonderful review Jane. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Home away from bome

Reviewed by George D. on 2024-06-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This has been our second year at Barefoot Bungalow so that says alot in itself. The property is exactly what you see and the maintainence service is good. The property manager is great,there for you at any time and takes care of anything that might pop up.The property is in an area that makes you feel like a conch.Hope skip and a jump to anywhere on the island.Spent many a day just relaxing by the pool.This is where I come to decompress for a month after a 11 months of work.Definetly will be back next year! My home Key West home.
Manager response on 2024-06-04 - Response from Best of Key West Rentals
Thank you for this wonderful review George, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Excellent place to stay!

Reviewed by Steven V. on 2023-03-22
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This home is an excellent place to stay in Key West. It's in a quiet neighborhood but still only minutes from Old Town. Nothing is far away in Key West. We rented the home for a month so we had plenty of time to form an opinion. The interior is clean and updated. Cable TV throughout the home, internet, even a pool table. With the exception of a hot tub, the exterior of the home had everything. Heated pool, covered living area w/cable tv, tiki bar w/refrigerator, grill, outdoor shower. Everything you would want for a Key West stay. We had a few issues with the pool but our property manager, Whitney, quickly addressed the issues. Ultimately the pool heater stopped working and Whitney was quick to address the issue. She responded to our text messages immediately and had service personnel out to the home as soon as possible. She was always available when we had concerns or questions. Don't wait, rent this home!!
Manager response on 2023-03-23 - Response from Best of Key West Rentals
Thank you for this wonderful review Steven, we are so glad you enjoyed the property so much! We look forward to welcoming you again next time you are in Key West.

Wonderful month at Barefoot Bungalow!

Reviewed by Unknown on 2022-05-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The minute we walked into the property and looked around; we knew we had made the correct decision for our month's stay in KW. The photos were on spot with what we saw upon check-in. The backyard area was very nice with plenty of room and different areas to enjoy. We truly enjoyed the outdoor shower, and we rarely used the inside showers even though they were extremely nice. Kitchen was well stocked with everything you needed to cook at home which we did quite frequently. Pool was lovely and Andrea the pool lady was very nice and friendly when she came to clean the pool weekly. Our property contact was Whitney and she responded to any needs we had almost immediately by text. The property is in New Town and as someone who lived in KW for 5 years, we knew the proximity to the Old Town area and some of our favorite places. However, even though we were aware of the location that would be the only downside. We had a car but parking in Old Town is difficult and can get a little pricey for a month. We still really enjoyed our stay. Our dog Teddy came with us, and he was right at home. It is a nice area, and it was easy to take a walk with our dog or to ride our electric bikes to the beach.
Overall, I thought the place was great and we would come back!
Manager response on 2022-05-19 - Response from Best of Key West Rentals
Thank you for your wonderful review Rebecca. It was a pleasure hosting you both and sweet Teddy, we hope to welcome you again next time you visit paradise! Thank you for being our guests!

Spring Getaway

Reviewed by Unknown on 2022-04-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Small home with charm. Enjoyed our stay but needs bed & outdoor furniture updates. Location was good - but we had car. Great pool and well maintained. Our property manager was outstanding and most importantly the house and it’s linens and kitchen contents were very clean.
Manager response on 2022-04-28 - Response from Best of Key West Rentals
Thank you for your fantastic review Peter. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Key West Barefoot Bungalow Best Vacation

Reviewed by Jim T. on 2021-03-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
My wife and I had the best Key West vacation experience and Barefoot Bungalow was a major contributing factor. When I booked I was worried about the accommodations and location but both were great. We walked to the Shanna Key local bar about 5 blocks away for some local favor and the food was very good. Melanie was very helpful and her list of restaurants were spot on. I would add the Hogfish bar and grill on Stock Island to her list and get the fish and chips. Don't bother with Louies backyard they were so **** rude they must not need the money.
We have already recommended this property to friends!
Manager response on 2021-03-12 - Response from Best of Key West Rentals
Thank you for your review! We enjoyed hosting you and hope to see you back again soon!

It can't get better than this.

Reviewed by Charles H. on 2021-01-04
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This was the most incredible place we have ever stayed. It was decorated by a real professional. The pool is perfect and the home has great features all the way around. The lighting and landscaping are as good as it can get. The kitchen has more than enough for gourmet cooking. The outside grill and bar really make for a great experience. There is more space than you will ever need. The office is a great bonus. We will be back next year! Truman and Company/Zintmaster is top drawer. They answered every call within minutes, even on the weekends.
Manager response on 2021-01-12 - Response from Best of Key West Rentals
Thank you for your wonderful review. We enjoyed hosting you and hope to see you back in Key West again soon!

Charming!

Reviewed by Sandra E. on 2020-11-22
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had a wonderful stay at the charming Barefoot Bungalow. It is so comfortable we felt right at home on the first day. Well equipped kitchen, both inside and outside grill area. The beds are very comfortable, although they really could fit queen size in the rooms rather than the very small full size. The pool is awesome and the outdoor shower is such a treat! Kudos to Wendy Zintsmaster and Team! Their attention to detail and guest services is stellar. Melanie was always available for whatever we needed - even searching for a dog sitter! We will happily book again!
Manager response on 2020-12-02 - Response from Best of Key West Rentals
Thank you for your wonderful review! The beds are in fact queen size beds. Please come back and see us soon!

BAREFOOT BUNGALOW~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!

Unit Code: BAR

BAREFOOT BUNGALOW~Escape Reality!

BAREFOOT BUNGALOW~Peacefully and Centrally Located 2 Bedroom Home with Office and Outdoor Area w/ Large, Heated Private Pool and Tiki Hut!
IMAGINE PARADISE… Picture your very own tropical estate enhanced with luxurious perks to include an expansive outdoor oasis with a large pool and tiki hut! This adorable private residence is centrally located area of “Mid Town” offering tranquil surroundings just a short distance to everything! ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES… A vibrant first impression greets you to this island hideaway with front porch seating to soak up the serene surroundings. Step inside to find an open space showcasing tile flooring throughout and coastal decor. A cozy seating area with a tv begins your journey with a fully equipped and renovated kitchen steps away. Granite counters, gorgeous custom cabinetry, stainless steel appliances and bar seating for 3 occupy this cheery space. Adjacent to the kitchen is a light filled, air-conditioned sunroom equipped with comfortable furnishings, a pool table and TV. An office room is also available for those working remotely. Cable is offered in the living room. The guest rooms and outside TVs are smart TVs. SLEEPING ARRANGEMENTS… Enjoy a peaceful evening’s rest in either queen guest room – both equipped with a flat screen TV and ceiling fans to keep you cool. The shared hallway bathroom comes with a walk-in glass shower. An additional full bathroom with a walk-in glass shower is located right off the sunroom. OUTDOOR LIVING… This dream home come true is surrounded by mature landscaping, a large heated private pool and a charming tiki hut with plenty of bar and dining seating for the whole crew for incredible entertaining. Rinse off the the outdoor shower, catch an island breeze in one of the loungers and enjoy a movie on the flat screen TV. PARKING... Plenty of street parking is available here on the 2300 Block of Staples Ave. PETS... This home is NOT pet friendly. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). LET THE STRESS MELT AWAY…
June 2026
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DatesPrice
06/12/2026 - 06/30/2026$179 /nt
07/01/2026 - 09/30/2026$197 /nt
10/01/2026 - 10/31/2026$250 /nt
11/01/2026 - 11/30/2026$268 /nt
12/01/2026 - 12/31/2026$286 /nt
01/01/2027 - 01/31/2027$600 /nt
02/01/2027 - 02/28/2027$643 /nt
03/01/2027 - 03/31/2027$600 /nt
04/01/2027 - 04/30/2027$304 /nt
05/01/2027 - 06/12/2027$233 /nt
4.8182
(11 Review)

Home away from bome

May 2025
, Delaware, OH Unknown

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
3

Barefoot Bungalow is what is what they advertise. Have been coming here for three straigt years now . We stay for a month and the location is perfect with easy accesse to the whole island.Very good managment sevice when needed.If you want a home away from home vacation, this is the place.

Manager's Response

George, thank you so much for your kind words and for being a loyal guest at Barefoot Bungalow for three years running! We're thrilled to hear the home continues to meet your expectations and feels like your home away from home. The location truly is a gem, and we're glad our management team has been able to support you when needed. We look forward to welcoming you back for many more relaxing stays on the island!

Comfortable

December 2024
, Plainwell, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This property suited my needs very nicely. I brought my bike and cycling is the perfect way to navigate Key West. This property is not in Old Town but in a neighborhood mostly inhabited by locals and I like that. The house and yard are lovely, I enjoyed cooking in the kitchen. Both the front porch and pool areas are pleasant places to spend time. I’ve booked it again and am looking forward to revisiting.

Manager's Response

Thank you for your wonderful review Jane. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Home away from bome

April 2024
, Delaware, OH US

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4

This has been our second year at Barefoot Bungalow so that says alot in itself. The property is exactly what you see and the maintainence service is good. The property manager is great,there for you at any time and takes care of anything that might pop up.The property is in an area that makes you feel like a conch.Hope skip and a jump to anywhere on the island.Spent many a day just relaxing by the pool.This is where I come to decompress for a month after a 11 months of work.Definetly will be back next year! My home Key West home.

Manager's Response

Thank you for this wonderful review George, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Excellent place to stay!

February 2023
, Washington, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This home is an excellent place to stay in Key West. It's in a quiet neighborhood but still only minutes from Old Town. Nothing is far away in Key West. We rented the home for a month so we had plenty of time to form an opinion. The interior is clean and updated. Cable TV throughout the home, internet, even a pool table. With the exception of a hot tub, the exterior of the home had everything. Heated pool, covered living area w/cable tv, tiki bar w/refrigerator, grill, outdoor shower. Everything you would want for a Key West stay. We had a few issues with the pool but our property manager, Whitney, quickly addressed the issues. Ultimately the pool heater stopped working and Whitney was quick to address the issue. She responded to our text messages immediately and had service personnel out to the home as soon as possible. She was always available when we had concerns or questions. Don't wait, rent this home!!

Manager's Response

Thank you for this wonderful review Steven, we are so glad you enjoyed the property so much! We look forward to welcoming you again next time you are in Key West.

Excellent place to stay!

February 2023
, Washington, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This home is an excellent place to stay in Key West. It's in a quiet neighborhood but still only minutes from Old Town. Nothing is far away in Key West. We rented the home for a month so we had plenty of time to form an opinion. The interior is clean and updated. Cable TV throughout the home, internet, even a pool table. With the exception of a hot tub, the exterior of the home had everything. Heated pool, covered living area w/cable tv, tiki bar w/refrigerator, grill, outdoor shower. Everything you would want for a Key West stay. We had a few issues with the pool but our property manager, Whitney, quickly addressed the issues. Ultimately the pool heater stopped working and Whitney was quick to address the issue. She responded to our text messages immediately and had service personnel out to the home as soon as possible. She was always available when we had concerns or questions. Don't wait, rent this home!!

Manager's Response

Thank you for this wonderful review Steven, we are so glad you enjoyed the property so much! We look forward to welcoming you again next time you are in Key West.

Wonderful month at Barefoot Bungalow!

April 2022
, Indianapolis, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
5

The minute we walked into the property and looked around; we knew we had made the correct decision for our month's stay in KW. The photos were on spot with what we saw upon check-in. The backyard area was very nice with plenty of room and different areas to enjoy. We truly enjoyed the outdoor shower, and we rarely used the inside showers even though they were extremely nice. Kitchen was well stocked with everything you needed to cook at home which we did quite frequently. Pool was lovely and Andrea the pool lady was very nice and friendly when she came to clean the pool weekly. Our property contact was Whitney and she responded to any needs we had almost immediately by text. The property is in New Town and as someone who lived in KW for 5 years, we knew the proximity to the Old Town area and some of our favorite places. However, even though we were aware of the location that would be the only downside. We had a car but parking in Old Town is difficult and can get a little pricey for a month. We still really enjoyed our stay. Our dog Teddy came with us, and he was right at home. It is a nice area, and it was easy to take a walk with our dog or to ride our electric bikes to the beach.
Overall, I thought the place was great and we would come back!

Manager's Response

Thank you for your wonderful review Rebecca. It was a pleasure hosting you both and sweet Teddy, we hope to welcome you again next time you visit paradise! Thank you for being our guests!

Wonderful month at Barefoot Bungalow!

April 2022
, Indianapolis, Indiana United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
5

The minute we walked into the property and looked around; we knew we had made the correct decision for our month's stay in KW. The photos were on spot with what we saw upon check-in. The backyard area was very nice with plenty of room and different areas to enjoy. We truly enjoyed the outdoor shower, and we rarely used the inside showers even though they were extremely nice. Kitchen was well stocked with everything you needed to cook at home which we did quite frequently. Pool was lovely and Andrea the pool lady was very nice and friendly when she came to clean the pool weekly. Our property contact was Whitney and she responded to any needs we had almost immediately by text. The property is in New Town and as someone who lived in KW for 5 years, we knew the proximity to the Old Town area and some of our favorite places. However, even though we were aware of the location that would be the only downside. We had a car but parking in Old Town is difficult and can get a little pricey for a month. We still really enjoyed our stay. Our dog Teddy came with us, and he was right at home. It is a nice area, and it was easy to take a walk with our dog or to ride our electric bikes to the beach.
Overall, I thought the place was great and we would come back!

Manager's Response

Thank you for your wonderful review Rebecca. It was a pleasure hosting you both and sweet Teddy, we hope to welcome you again next time you visit paradise! Thank you for being our guests!

Spring Getaway

March 2022
, Watersmeet , MI United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
3

Small home with charm. Enjoyed our stay but needs bed & outdoor furniture updates. Location was good - but we had car. Great pool and well maintained. Our property manager was outstanding and most importantly the house and it’s linens and kitchen contents were very clean.

Manager's Response

Thank you for your fantastic review Peter. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Key West Barefoot Bungalow Best Vacation

January 2021

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

My wife and I had the best Key West vacation experience and Barefoot Bungalow was a major contributing factor. When I booked I was worried about the accommodations and location but both were great. We walked to the Shanna Key local bar about 5 blocks away for some local favor and the food was very good. Melanie was very helpful and her list of restaurants were spot on. I would add the Hogfish bar and grill on Stock Island to her list and get the fish and chips. Don't bother with Louies backyard they were so **** rude they must not need the money.
We have already recommended this property to friends!

Manager's Response

Thank you for your review! We enjoyed hosting you and hope to see you back again soon!

It can't get better than this.

December 2020
, Shady Side, MD US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was the most incredible place we have ever stayed. It was decorated by a real professional. The pool is perfect and the home has great features all the way around. The lighting and landscaping are as good as it can get. The kitchen has more than enough for gourmet cooking. The outside grill and bar really make for a great experience. There is more space than you will ever need. The office is a great bonus. We will be back next year! Truman and Company/Zintmaster is top drawer. They answered every call within minutes, even on the weekends.

Manager's Response

Thank you for your wonderful review. We enjoyed hosting you and hope to see you back in Key West again soon!

Charming!

October 2020
, Alleyton, TX US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a wonderful stay at the charming Barefoot Bungalow. It is so comfortable we felt right at home on the first day. Well equipped kitchen, both inside and outside grill area. The beds are very comfortable, although they really could fit queen size in the rooms rather than the very small full size. The pool is awesome and the outdoor shower is such a treat! Kudos to Wendy Zintsmaster and Team! Their attention to detail and guest services is stellar. Melanie was always available for whatever we needed - even searching for a dog sitter! We will happily book again!

Manager's Response

Thank you for your wonderful review! The beds are in fact queen size beds. Please come back and see us soon!

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2 Bed
2 Baths
Sleeps 4

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CABIN FEVER ~ Vintage!

CABIN FEVER ~ Charming First Floor Unit--1 Bedroom, 1 Bathroom with Updated Kitchen in The Meadows Neighborhood with Community Pool!

Location

1203 Newton St. #2
33040 Key West , FL
United States
24° 33' 31.5" N, 81° 47' 33.612" W
See map: Google Maps
Florida US

CABIN FEVER ~ Vintage!

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Great little place!

Reviewed by Bill K. on 2025-03-19
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
My wife and I stayed here two months. It was clean, property management group was awsome! Always there any time we needed them, which was not very often! Great location. Generaly very easy parking.
Manager response on 2025-03-20 - Response from Best of Key West Rentals
Thank you for your fantastic review Bill. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Cabin Fever was Great!

Reviewed by Bill K. on 2025-02-18
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Our rental for January and February 2025 was great. Nice place. Very quiet. Great location. We loved the neighborhood here. Generally quite easy to park. Parking in other parts of town can be difficult, but not here! Property was very clean. Management was awesome! They were always there if we needed anything. They took great care of us from the beginning. I would definately recommend them to friends.
Manager response on 2025-02-24 - Response from Best of Key West Rentals
Thank you for your incredible review Bill! We are so thrilled to hear how much you love this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Cabin Fever

Reviewed by Unknown on 2022-03-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Adequate for our needs
Manager response on 2022-03-08 - Response from Best of Key West Rentals
Thank you for your review Philip. We enjoyed hosting you and hope to see you back in Key West again soon!

CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!

Unit Code: CF

CABIN FEVER ~ Vintage!

CABIN FEVER ~ Charming First Floor Unit--1 Bedroom, 1 Bathroom with Updated Kitchen in The Meadows Neighborhood with Community Pool!
SIMPLISTIC ELEGANCE... Enjoy easy island living in this quaint and cozy Key West gem located in the attractive community of The Meadows. A charming hideaway tucked within quiet surroundings with the opportunity to fully live like a local! ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… Immerse yourself in this cozy layout on the first floor with nautical accents and vintage Dade County walls throughout. Large windows attract incredible natural lighting in this cherry space with comfortable furnishings and a flat screen TV for lazy afternoons. A fully equipped and updated kitchen with a funky backsplash allow for all your meal prep and cocktail crafting to be enjoyed at a small table within the living space or out on the front patio. There is a coin laundry in the shed by the pool area. SLEEPING ARRANGEMENTS… Step through a modern barn door to find the a queen guest room with French doors that lead you out to the screened in patio for your morning cup of coffee. A very stylish full bathroom with gorgeous tile work and a walk in shower lies just off of the living room area. OUTDOOR LIVING… A second entrance from the kitchen area takes you out to your outdoor tropical oasis. Steps away you will find a friendly community pool (not heated) with plenty of loungers to soak up the island rays. Park your bike on the side of the building and stroll in town to meet old friends and new. There are local laundromat and laundry services are available nearby! PARKING... This home does not have designated parking but there is on street parking in the surrounding neighborhood.  Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates. PETS... This is NOT a pet friendly property. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). AUTHENTIC KEY WEST...
June 2026
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Age 18 and under.
DatesPrice
06/12/2026 - 06/30/2026$108 /nt
07/01/2026 - 07/31/2026$114 /nt
08/01/2026 - 09/30/2026$119 /nt
10/01/2026 - 10/31/2026$136 /nt
11/01/2026 - 11/30/2026$143 /nt
12/01/2026 - 12/31/2026$150 /nt
01/01/2027 - 01/31/2027$250 /nt
02/01/2027 - 02/28/2027$268 /nt
03/01/2027 - 04/30/2027$250 /nt
05/01/2027 - 06/12/2027$150 /nt
4.2500
(4 Review)

Great little place!

February 2025
, Greenfield, WI Unknown

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

My wife and I stayed here two months. It was clean, property management group was awsome! Always there any time we needed them, which was not very often! Great location. Generaly very easy parking.

Manager's Response

Thank you for your fantastic review Bill. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Cabin Fever was Great!

January 2025
, Greenfield, WI Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Our rental for January and February 2025 was great. Nice place. Very quiet. Great location. We loved the neighborhood here. Generally quite easy to park. Parking in other parts of town can be difficult, but not here! Property was very clean. Management was awesome! They were always there if we needed anything. They took great care of us from the beginning. I would definately recommend them to friends.

Manager's Response

Thank you for your incredible review Bill! We are so thrilled to hear how much you love this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Cabin Fever

January 2022
, Cedar Knolls , NJ US

Overall
4
Services from rental manager
5
Cleanliness
4
Location
4
Property condition
4

Adequate for our needs

Manager's Response

Thank you for your review Philip. We enjoyed hosting you and hope to see you back in Key West again soon!

Cabin Fever

January 2022
, Cedar Knolls , NJ US

Overall
4
Services from rental manager
5
Cleanliness
4
Location
4
Property condition
4

Adequate for our needs

Manager's Response

Thank you for your review Philip. We enjoyed hosting you and hope to see you back in Key West again soon!

Leave a Review
1 Bed
1 Bath
Sleeps 2

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