SEA-NIC VIEW ~ A Boater's Haven!

SEA-NIC VIEW ~ Peacefully Located 2 Bedroom, 2 Bathroom Oceanfront 3rd Floor Condo w/ Private Boat Slip, Heated Community Pool, Parking, Sandy Beach and Convenience to Shopping and More!

Location

30 Hilton Haven Rd. #6
33040 Key West , FL
United States
24° 33' 48.708" N, 81° 46' 53.868" W
See map: Google Maps
Florida US

SEA-NIC VIEW ~ A Boater's Haven!

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Perfection

Reviewed by Luis L. on 2025-06-09
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Great location, clean, quiet, great neighborhood
Manager response on 2025-06-10 - Response from Best of Key West Rentals
Thank you for this short and sweet review, we are thrilled you enjoyed your stay so much and look forward to welcoming you next time you visit our little island!

Perfection

Reviewed by Luis L. on 2025-05-02
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Absolutely beautiful. Great communication. Clean and well taken care of
Manager response on 2025-05-02 - Response from Best of Key West Rentals
Thank you so much for the kind words Travis! We're thrilled you found the property beautiful and well maintained, and that communication met your expectations. We’d love to host you again in the future!

great place to stay

Reviewed by Brian C. on 2023-03-06
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
great location, very nice accommodations...will plan to return next year....
Manager response on 2023-03-07 - Response from Best of Key West Rentals
Thank you for this wonderful review Brian, 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.

Great Place

Reviewed by Brian C. on 2024-03-05
Overall satisfaction
Cleanliness
Location
Property condition
Recommend to Others
Great month in Key West ....this is a wonderful location....Most of the neighbors are friendly and nice. Easy to get an Uber to go downtown, but nice and quiet at condo..
Manager response on 2024-03-06 - Response from Best of Key West Rentals
Thank you for this fantastic review Brian! We hope to welcome you again next year!

Hilton Haven rental

Reviewed by Kevin D. on 2024-04-02
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We stayed at 30 Hilton Haven for the month of March and it was amazing. The views were spectacular and it was close enough to get to downtown quickly but far enough away from all the hustle and chatter. Truman and Co. We're great and we're there every step of the way with answers to any question we had. I would definitely stay here again and would certainly use Truman & Co. For my next rental.
Manager response on 2024-04-11 - Response from Best of Key West Rentals
Thank you for this wonderful review Kevin, we are so glad you enjoyed the property so much and look forward to welcoming you again next time you are in Key West.

Great views, great location

Reviewed by Tanya M. on 2024-07-15
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This unit was very nice to stay in. Room for 5 or 6 to eat, relax, sleep, and soak in the Key West experience. Having a place for a boat and a pool to use make it extra special. The road is a dead end road, so it’s quiet, but close enough to bike, drive, or Uber to the busier parts of Key West. It is on the third floor, so pack light or in smaller suitcases to make it easier to get to the unit. Neighbors and other guests were all very friendly. We would stay here again. I wish the unit had a couple of bikes to use, but you can bring your own or rent from a local shop.
Manager response on 2024-07-16 - Response from Best of Key West Rentals
Thank you for your wonderful review Tanya. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

SEA-NIC VIEW ~ 2 BR/2Ba Water-front views, Heated Pool Access and Dockage!

Unit Code: SEA

SEA-NIC VIEW ~ A Boater's Haven!

SEA-NIC VIEW ~ Peacefully Located 2 Bedroom, 2 Bathroom Oceanfront 3rd Floor Condo w/ Private Boat Slip, Heated Community Pool, Parking, Sandy Beach and Convenience to Shopping and More!
IT'S A SWELL LIFE… Endless island treasures engulf this oceanfront haven which is your one stop destination for a complete Key West experience. Peacefully tucked away at the end of a private road, this community overlooks the lively Garrison Bight Marina nestled within nature’s surroundings, offering every imaginable amenity including convenience to shopping, dining and more! Imagine your worries washing away as you get lost in time mesmerized by the sparkling Gulf of Mexico, brimming a with water sports and yachts gently rolling in. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES… This quintessential island retreat is located on the 3rd floor of the complex, possessing a Key West vibe as soon as you step through the front door with tropical views all around. Find a spacious Great Room with an updated and fully equipped kitchen, featuring stainless steel appliances perfect for serving up your home-made meals to enjoy at the dining table for 4 or casually at the breakfast bar for 2. Settle into a good movie with comfy living area furnishings, a flat screen TV and 2 sets of French doors that can be perched open for sultry island breezes. Tile flooring and ceiling fans throughout keep this space airy and cool. SLEEPING ARRANGEMENTS… Snuggle into a king bed within the primary suite with plush linens, a flat screen TV, en suite bathroom with a soaking tub and separate shower, single sleeper convertible ottoman and writing desk for those working remotely. Marvel over your oceanfront views right from your bed and ease the doors open to your private balcony with seating to enjoy your morning cup of coffee with views of the pool and dock. The 2nd guest suite has a queen size bed, steps to a hallway bathroom with a shower tub combo, flat screen TV and direct access to the 2nd veranda overlooking Garrison Bight Marina. A queen sofa sleeper resides in the living room area. OUTDOOR LIVING… Enjoy the rare perk of a private 28 ft. boat slip on the dock just steps from this unit (trailers are not allowed to be stored on property – please inquire for local suggestions). This unobstructed slip allows for seamless navigation out to open turquoise waters. Clean your catch at the dock with a cocktail in hand as the sun sets in the distance and grill up your savory dinner. Dig your toes into the warm, sandy beach and find your serenity with just the sounds of the sea by your side. A refreshing dip in the heated community pool, a hammock swaying in the breeze and an evening beach bonfire are sure to calm your senses. PARKING... One convenient parking spot is available making coming and going ideal. 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). A TRULY REMARKABLE TROPICAL EXPERIENCE AWAITS!
October 2025
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DatesPrice
10/26/2025 - 10/31/2025$143 /nt
11/01/2025 - 11/30/2025$226 /nt
12/01/2025 - 12/31/2025$215 /nt
01/01/2026 - 01/31/2026$304 /nt
02/01/2026 - 02/28/2026$432 /nt
03/01/2026 - 03/31/2026$358 /nt
04/01/2026 - 04/30/2026$250 /nt
05/01/2026 - 07/31/2026$188 /nt
08/01/2026 - 09/30/2026$179 /nt
10/01/2026 - 10/26/2026$233 /nt
5.0000
(15 Review)

Perfection

May 2025
, Cocoa, FL US

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

Great location, clean, quiet, great neighborhood

Manager's Response

Thank you for this short and sweet review, we are thrilled you enjoyed your stay so much and look forward to welcoming you next time you visit our little island!

Perfection

May 2025
, Cocoa, FL United States

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

Great location, clean, quiet, great neighborhood

Manager's Response

Thank you for this short and sweet review, we are thrilled you enjoyed your stay so much and look forward to welcoming you next time you visit our little island!

Perfection

May 2025
, Cocoa, FL United States

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

Great location, clean, quiet, great neighborhood

Manager's Response

Thank you for this short and sweet review, we are thrilled you enjoyed your stay so much and look forward to welcoming you next time you visit our little island!

Perfection

May 2025
, Cocoa, FL United States

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

Great location, clean, quiet, great neighborhood

Manager's Response

Thank you for this short and sweet review, we are thrilled you enjoyed your stay so much and look forward to welcoming you next time you visit our little island!

Perfection

March 2025
, Cocoa, FL US

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

Absolutely beautiful. Great communication. Clean and well taken care of

Manager's Response

Thank you so much for the kind words Travis! We're thrilled you found the property beautiful and well maintained, and that communication met your expectations. We’d love to host you again in the future!

Perfection

March 2025
, Cocoa, FL United States

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

Absolutely beautiful. Great communication. Clean and well taken care of

Manager's Response

Thank you so much for the kind words Travis! We're thrilled you found the property beautiful and well maintained, and that communication met your expectations. We’d love to host you again in the future!

Perfection

March 2025
, Cocoa, FL United States

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

Absolutely beautiful. Great communication. Clean and well taken care of

Manager's Response

Thank you so much for the kind words Travis! We're thrilled you found the property beautiful and well maintained, and that communication met your expectations. We’d love to host you again in the future!

Perfection

March 2025
, Cocoa, FL United States

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

Absolutely beautiful. Great communication. Clean and well taken care of

Manager's Response

Thank you so much for the kind words Travis! We're thrilled you found the property beautiful and well maintained, and that communication met your expectations. We’d love to host you again in the future!

Perfection

March 2025
, Cocoa, FL United States

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

Absolutely beautiful. Great communication. Clean and well taken care of

Manager's Response

Thank you so much for the kind words Travis! We're thrilled you found the property beautiful and well maintained, and that communication met your expectations. We’d love to host you again in the future!

Great views, great location

June 2024
, Naples, FL US

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

This unit was very nice to stay in. Room for 5 or 6 to eat, relax, sleep, and soak in the Key West experience. Having a place for a boat and a pool to use make it extra special. The road is a dead end road, so it’s quiet, but close enough to bike, drive, or Uber to the busier parts of Key West. It is on the third floor, so pack light or in smaller suitcases to make it easier to get to the unit. Neighbors and other guests were all very friendly. We would stay here again. I wish the unit had a couple of bikes to use, but you can bring your own or rent from a local shop.

Manager's Response

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

Hilton Haven rental

March 2024
, Key West, FL United States

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

We stayed at 30 Hilton Haven for the month of March and it was amazing. The views were spectacular and it was close enough to get to downtown quickly but far enough away from all the hustle and chatter. Truman and Co. We're great and we're there every step of the way with answers to any question we had. I would definitely stay here again and would certainly use Truman & Co. For my next rental.

Manager's Response

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

Great Place

February 2024
, Fort Waynw, IN Unknown

Overall
5
Cleanliness
5
Location
5
Property condition
5

Great month in Key West ....this is a wonderful location....Most of the neighbors are friendly and nice. Easy to get an Uber to go downtown, but nice and quiet at condo..

Manager's Response

Thank you for this fantastic review Brian! We hope to welcome you again next year!

Great Place

February 2024
, Fort wayne, IN US

Overall
5
Cleanliness
5
Location
5
Property condition
5

Great month in Key West ....this is a wonderful location....Most of the neighbors are friendly and nice. Easy to get an Uber to go downtown, but nice and quiet at condo..

Manager's Response

Thank you for this fantastic review Brian! We hope to welcome you again next year!

great place to stay

January 2023
, Fort Waynw, IN US

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

great location, very nice accommodations...will plan to return next year....

Manager's Response

Thank you for this wonderful review Brian, 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.

great place to stay

January 2023
, Fort Waynw, IN Unknown

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

great location, very nice accommodations...will plan to return next year....

Manager's Response

Thank you for this wonderful review Brian, 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.

Leave a Review
2 Bed
2 Baths
Sleeps 6

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GILLEY'S PLACE ~ Old Town Charm!

GILLEY'S PLACE ~ Charming and Fully Renovated 1 Bedroom, 1 Bathroom Cottage in Old Town Key West with Great Outdoor Entertaining Space!

Location

1122 Stump Ln.
33040 Key West , FL
United States
24° 33' 35.424" N, 81° 47' 40.452" W
See map: Google Maps
Florida US

GILLEY'S PLACE ~ Old Town Charm!

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Fully Renovated Conch Shack

Reviewed by Unknown on 2025-01-18
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Vaulted ceiling throughout, porch, and double sliding glass doors to back deck really expand the living space. We walked or biked to everything in Old Town. Nice, quiet neighborhood. Rental team was excellent. Will stay here again!
Manager response on 2025-01-24 - Response from Best of Key West Rentals
Thank you for your wonderful review Sharon. We enjoyed hosting you and hope to see you back in Key West again soon!

House is perfect!!

Reviewed by Pam L. on 2024-10-16
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This house was perfect. Location is fantastic, walking distance to just about everything. House was very clean, comfortable and the avocado tree is a bonus. Kitchen very well equipped. Property Manager was responsive, efficient and professional. Loved it!! Hope to return next year!! Thanks for everything!
Manager response on 2024-10-17 - Response from Best of Key West Rentals
Thank you so much for this fantastic review Pam, it was truly a pleasure to host you and we are looking forward to welcoming you again next year!

A little jewel box

Reviewed by Ruth Ann S. on 2023-04-20
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Gilley’s Place was perfectly located, and beautifully decorated. It was brand new, clean and charming. A well stocked kitchen, and a good sized bathroom made this an easy small house for a months stay. The management team was very responsive and helpful. Five stars all around!
Manager response on 2023-05-01 - Response from Best of Key West Rentals
Thank you for your fantastic review Ruth. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Great spot!

Reviewed by Susan K. on 2024-02-02
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We really enjoyed our month at Gilley’s Place. The house is small but had everything that we needed. The management company was very responsive and checked in to make sure that we had everything that we needed. The home feels new and it was just right for the two of us. Exceptional shower!
Manager response on 2024-02-05 - Response from Best of Key West Rentals
Thank you for your review Susan. We are thrilled you loved this home and hope to host you again soon! Thank you for being our guest!

Key West stay

Reviewed by Timothy S. on 2024-01-04
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Perfect location. Absolutely charming home. A pleasant added surprise were the kind and welcoming neighbors!
Manager response on 2024-01-04 - Response from Best of Key West Rentals
Thank you for taking the time to post a review of our property Timothy. We are so happy to hear that you enjoyed your time at Gilley's Place. Our goal is always to exceed your expectations! If there's anything we can help you with during your next visit, please don't hesitate to let us know.

A Must Stay

Reviewed by Catherine C. on 2023-12-04
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
I had the privilege of staying at his place for the span of two months. It really felt like home. The kitchen and home in general is fully stocked with everything you may need and the backyard/porch is decked out with outdoor furniture and a grill which I regret that I didn’t use more! The home is very fresh, clean, light and well decorated. While the bedroom was on the smaller side, the large shower and bright living and kitchen space really made the home feel larger. It’s absolute perfect for two people to enjoy key west but also feel secluded on a tucked away little lane. I biked to work every day, the location was amazing.The owners as well as management team were so helpful and there for anything you need. I hope to stay again soon in the future!
Manager response on 2023-12-04 - Response from Best of Key West Rentals
Thank you for this great review Catherine! We are thrilled you enjoyed the property and hope to host you again in the future!

Great location very cute brand new cottage

Reviewed by Elizabeth J. on 2022-05-11
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Fabulous peaceful extremely new and beautifully equipped - a real find. Would not hesitate to recommend it.
Manager response on 2022-05-12 - Response from Best of Key West Rentals
Thank you for your fantastic review Elizabeth. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Cozy, Cozy, Cozy!

Reviewed by Rene C. on 2023-02-16
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others

Very nice, clean and cozy place on a quiet street.
Manager response on 2023-02-16 - Response from Best of Key West Rentals
Thank you for this great review Rene! We are thrilled you enjoyed the property and hope to host you again in the future!

GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!

Unit Code: GI

GILLEY'S PLACE ~ Old Town Charm!

GILLEY'S PLACE ~ Charming and Fully Renovated 1 Bedroom, 1 Bathroom Cottage in Old Town Key West with Great Outdoor Entertaining Space!
AN ESCAPE LIKE NO OTHER… Disconnect from the real world and reconnect with each other in this picture perfect, quaint cottage tucked away on a quiet and vibrant lane of Old Town. Your Paradise awaits just beyond a lovely white picket fence inviting you into a lush and luxuriant setting to call your island home. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE AMENITIES AND FURNISHINGS... A private, covered front porch beckons your lighthearted chit chat as you take in your tropical surroundings with your morning coffee in hand. Slip inside to a fully renovated and bright Great Room with cool hardwood flooring, cathedral ceilings and breathtaking natural lighting. Plush furnishings surround a flat screen TV, allowing you to sink in for your binging pleasure. A fully equipped kitchen with a stylish blue backsplash will calm your senses as you whip up your favorite dish and craft up your cocktail at the enticing bar area with bar seating for 3. Bring the outdoors in as you perch the sliding doors open for the best of both worlds! SLEEPING ARRANGEMENTS... Find your sleeping sanctuary just off the Great Room with a cozy queen bed with sumptuous linens for a peaceful night’s rest. An en suite full bathroom features a stunning walk-in glass shower with beautiful blue tiling within this nautical dwelling. A sofa sleeper resides in the living area for additional sleeping arrangements. OUTDOOR LIVING... Bring your fresh cooked cuisine outdoors on a private back deck enveloped in abundant, vibrant foliage with a sweet breeze by your side. A gas grill is provided to grill up your fresh catch of the day. Bike or stroll through this quaint neighborhood of beautiful, historic homes and enjoy just a short ride into town to all that Key West has to offer. 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) 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. BOOKING DATES... This home is available only 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). START LIVING ON ISLAND TIME…
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December 2025
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Age 18 and under.
DatesPrice
10/26/2025 - 10/31/2025$136 /nt
11/01/2025 - 11/30/2025$143 /nt
12/01/2025 - 12/31/2025$187 /nt
01/01/2026 - 01/31/2026$367 /nt
02/01/2026 - 02/28/2026$358 /nt
03/01/2026 - 03/31/2026$304 /nt
04/01/2026 - 04/30/2026$261 /nt
05/01/2026 - 07/31/2026$143 /nt
08/01/2026 - 08/31/2026$136 /nt
09/01/2026 - 10/26/2026$150 /nt
5.0000
(8 Review)

Fully Renovated Conch Shack

November 2024
, Key West, FL US

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

Vaulted ceiling throughout, porch, and double sliding glass doors to back deck really expand the living space. We walked or biked to everything in Old Town. Nice, quiet neighborhood. Rental team was excellent. Will stay here again!

Manager's Response

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

House is perfect!!

September 2024
, York, ME US

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

This house was perfect. Location is fantastic, walking distance to just about everything. House was very clean, comfortable and the avocado tree is a bonus. Kitchen very well equipped. Property Manager was responsive, efficient and professional. Loved it!! Hope to return next year!! Thanks for everything!

Manager's Response

Thank you so much for this fantastic review Pam, it was truly a pleasure to host you and we are looking forward to welcoming you again next year!

Great spot!

January 2024
, South Egremont, MA US

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

We really enjoyed our month at Gilley’s Place. The house is small but had everything that we needed. The management company was very responsive and checked in to make sure that we had everything that we needed. The home feels new and it was just right for the two of us. Exceptional shower!

Manager's Response

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

Key West stay

December 2023
, Carlisle, PA US

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

Perfect location. Absolutely charming home. A pleasant added surprise were the kind and welcoming neighbors!

Manager's Response

Thank you for taking the time to post a review of our property Timothy. We are so happy to hear that you enjoyed your time at Gilley's Place. Our goal is always to exceed your expectations! If there's anything we can help you with during your next visit, please don't hesitate to let us know.

A Must Stay

October 2023
, Fort Lauderdale, FL United States

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

I had the privilege of staying at his place for the span of two months. It really felt like home. The kitchen and home in general is fully stocked with everything you may need and the backyard/porch is decked out with outdoor furniture and a grill which I regret that I didn’t use more! The home is very fresh, clean, light and well decorated. While the bedroom was on the smaller side, the large shower and bright living and kitchen space really made the home feel larger. It’s absolute perfect for two people to enjoy key west but also feel secluded on a tucked away little lane. I biked to work every day, the location was amazing.The owners as well as management team were so helpful and there for anything you need. I hope to stay again soon in the future!

Manager's Response

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

A little jewel box

March 2023
, Westhampton Beach, NY United States

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

Gilley’s Place was perfectly located, and beautifully decorated. It was brand new, clean and charming. A well stocked kitchen, and a good sized bathroom made this an easy small house for a months stay. The management team was very responsive and helpful. Five stars all around!

Manager's Response

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

Cozy, Cozy, Cozy!

January 2023
, Bromont, QC CA

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


Very nice, clean and cozy place on a quiet street.

Manager's Response

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

Great location very cute brand new cottage

April 2022
, London W4 1DB, United Kingdom

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

Fabulous peaceful extremely new and beautifully equipped - a real find. Would not hesitate to recommend it.

Manager's Response

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

Leave a Review
1 Bed
1 Bath
Sleeps 2

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ISLAND OASIS ~ Stylish!

ISLAND OASIS ~ Dog Friendly 2 Bedroom, 2 Bath Townhome w/ Private, Heated Pool and Off Street Parking! Perfectly Located for All Things Key West!

Location

613 Amelia St.
33040 Key West , FL
United States
24° 33' 3.312" N, 81° 47' 46.968" W
See map: Google Maps
Florida US

ISLAND OASIS ~ Stylish!

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Perfect Get Away

Reviewed by Jennifer S. on 2025-07-18
Overall satisfaction
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Recommend to Others
We stayed at the Island Oasis for 4 nights in July. We had 4 adults, and the house was perfect for our stay. It was an extremely easy process from booking, check-in, and check-out. The management company was great with quick communication and the concierge was very helpful. The location of the house was perfect for walking to Duval Street area and we felt very safe. I would definitely stay here again.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you so much for your wonderful review! We're thrilled to hear Island Oasis was a perfect fit for your group and that you found the location convenient and safe. It's great to know our team and concierge service helped make your stay smooth and enjoyable. We’d love to welcome you back anytime!

A Great House with Good Privacy!

Reviewed by Mark N. on 2025-07-07
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Recommend to Others
A very nice house in a quiet area. Walking distance to Duval street and the beach. Loved the layout and enjoyed the private pool. The house is not big but it's good for two couples or a family.
very nice kitchen, living area and backyard patio.
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for your kind review! We're so glad to hear you enjoyed the quiet location, private pool, and the layout of the home. It sounds like it was a great fit for your group. We'd love to host you again on your next trip to Key West!

Location, location, location!

Reviewed by Unknown on 2025-01-04
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Property condition
Recommend to Others
Close to everything. It was nice to walk to the end of the street to get Cuban coffee every morning. Walk a few more blocks you're on Duval and a bit further to the Southernmost Point.

A few things could be upgraded in the home itself. Primary bedroom bed was very worn and squeaked every time you move. The guest bedroom beds are on wheels and roll across the floor. I read a review from a long time ago with the same issue. Thought it would have been addressed but was not.
The shower heads in both bathrooms could be better. Both are the rain style which are hard to rinse soap off with low water pressure.
Kitchen was fully stocked with cookware and dishes etc. The cooking utensils were poor quality. Plastic breaking off in food as we were cooking.
We used washer and dryer mid-week. Took us 2 hours to dry 6 towels. It was very old. Needs to be changed out.

Otherwise, the house was clean and in a great location.
Manager response on 2025-01-05 - Response from Best of Key West Rentals
Thank you for your feedback on your recent stay Ryan. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will rely back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!

Great house

Reviewed by Unknown on 2025-02-12
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Recommend to Others
The house was very clean, well kept, and was just as it appears in the pictures. We couldn’t have been happier with it.
Manager response on 2025-02-12 - Response from Best of Key West Rentals
Peirce we really appreciate you leaving such a nice review after your stay. We are thrilled you enjoyed this home so much and hope to have the chance to welcome you again next time you visit the southernmost island!

Never Disappoints

Reviewed by Unknown on 2025-02-25
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Recommend to Others
Rental was exactly as advertised. Great location. Close to everything but quiet. Shana was so helpful and quick to respond. I definitely recommend this property
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for the kind words! We're so glad to hear the rental met your expectations and that the location offered the perfect balance of convenience and peace. We'd love to host you again anytime!

Key West Vaca

Reviewed by Jed D. on 2025-04-10
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We had a great time. Nice place. A few issues need to be addressed. The towels and wash rags supplied were old, hard and discolored. New, softer ones would be nice. The safe in the closet didn't work. In the master bedroom, the AC vents or something in the ducts rattled and we didn't sleep well. In the downstairs half bathroom, the cold water didn't work and the toilet handle is not working. Since you asked, for what we paid I think the place could use a "freshening up".
Manager response on 2025-07-28 - Response from Best of Key West Rentals
Thank you for your feedback — we’re glad to hear you had a great time overall, and we appreciate you bringing these issues to our attention. We’re sorry to hear about the towels and maintenance concerns, and we’ve made note of all your comments so our team can follow up and ensure improvements are made. Your input helps us continue to improve the guest experience, and we hope to have the opportunity to welcome you back in the future!

The perfect place for my 50th birthday weekend!

Reviewed by Shae W. on 2024-10-07
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Island Oasis was the perfect spot for my husband and I to stay with my best friend and her husband! We stayed there for my 50th birthday weekend and were very comfortable. Both bedrooms had comfy king beds and ensuite bathrooms. The kitchen had everything we needed and we really enjoyed the outdoor area with private pool! It was so nice to come in from a day of walking around and be able to take a dip in the pool. The location is great, within walking distance to a lot of places but far enough away from Duval to escape the noise. Our concierge team was so attentive and helped us make reservations and made recommendations. I would definitely stay again!
Manager response on 2025-01-06 - 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!

Fabulous Key West Home

Reviewed by Unknown on 2024-09-20
Overall satisfaction
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Cleanliness
Location
Property condition
Recommend to Others
This place is wonderful and as pictured. Beautiful private pool, very clean and close to but not to close the Duvall, shopping and restaurants.

Rental company was great and so easy to communicate with. Would definitely stay here again.
Manager response on 2025-01-06 - 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!

1st time in Key West!

Reviewed by Renee C. on 2024-06-18
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The house was perfect for our stay. Communication was prompt, the location was perfect, the property was clean and everything we expected. Thank you!
Manager response on 2025-01-06 - Response from Best of Key West Rentals
Thank you for your wonderful review. We are thrilled you loved this home and hope to host you again soon!

Best Key West stay!

Reviewed by Carl T. on 2024-09-14
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Incredible place. Absolutely private pool with 6 foot end (I didn’t realize it has a deep end!), incredibly clean, and over the top nice. Best nightly rental I’ve ever booked.
Manager response on 2025-01-06 - Response from Best of Key West Rentals
Thank you for your wonderful review. We are thrilled you loved this home and hope to host you again soon!

Prefect!!!

Reviewed by Unknown on 2024-07-06
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The house,location,and management were PERFECT!!! we will definitely stay with you again!
Manager response on 2025-01-06 - 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!

Excellent stay!

Reviewed by Unknown on 2024-08-25
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The house was beautiful and pristine and the service exceeded my expectations! Great location and seamless experience. Would definitely stay with them again.
Manager response on 2025-01-06 - Response from Best of Key West Rentals
Thank you for your wonderful review. We are thrilled you loved this home and hope to host you again soon!

Great Place!

Reviewed by Olga T. on 2024-08-13
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Great place for our family! The host was responsive and the house had everything we needed.
Manager response on 2025-01-06 - 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!

Amazing

Reviewed by Bradley K. on 2024-11-13
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Perfect house my wife and I , and another couple . Great location ! Will definitely be returning !
Manager response on 2025-01-06 - 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!

Lovely Property

Reviewed by Brad S. on 2023-01-26
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Ideal location. Close to all hot spots but quiet and secluded.
Manager response on 2023-02-27 - Response from Best of Key West Rentals
Thank you for this great review Brad! We are thrilled you enjoyed the property and hope to host you again in the future!

Island Oasis

Reviewed by Unknown on 2023-03-16
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We had a lovely time. House in great location. The house could use some upgrades. Quiet peaceful neighborhood. Amelia Street is not pretty but it’s a wide street, not a lot of car traffic, and the parking lot is convenient if needed and there are lots of restaurants nearby. The pool was clean and a wonderful amenity to have, as well as the garden.

Great time in Key West with friends

Reviewed by Calvin M. on 2023-01-28
Overall satisfaction
Services from rental manager
Cleanliness
Location
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Recommend to Others
Island Oasis was everything we thought it would be. The Truman and Co Team was very helpful and took care of all of our needs. This was our second time to stay within this complex. The home is in a great location, the pool was a great place to end the day exploring Key West. We would give it a 5 out of 5. Looking forward to our next trip.
Manager response on 2023-02-27 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us Calvin! We would love to welcome you back!

Great Vacation Home

Reviewed by Chad T. on 2023-01-21
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Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We loved the place and we are already talking about coming back!
Manager response on 2023-02-27 - Response from Best of Key West Rentals
Thank you for this wonderful review Chad, 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.

Perfect Getaway

Reviewed by RYAN R. on 2023-04-24
Overall satisfaction
Services from rental manager
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Location
Property condition
Recommend to Others
This little gem is a couple blocks from some of the best food in KW! Breakfast and the Conch and the Cuban...dinner at any number of places within short waling distance (el Siboney!). Bike rentals-3 small blocks away. Drugstore with everything you forgot only 2 blocks away. Yet this place is tucked off the main roads to stay quiet and secluded. Pool was perfect for relaxing after biking all day. Bed was comfortable, showers nice and clean. Everything was as perfect as it could be. And the rental company was always quick to answer any question or concern! The PERFECT sport for a island vacation!
Manager response on 2023-12-05 - Response from Best of Key West Rentals
Thank you for your wonderful review Ryan. We are thrilled you loved this home and hope to host you again soon!

Great house, super location, excellent service

Reviewed by John H. on 2023-07-31
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Loved this place. Location is close to Duval. but quiet. Plenty of street parking in addition to the one dedicated spot. House was spotless clean. Nice furniture. Pool is a big plus. Service from the agent was tops. The blender broke while preparing dinner at 7, and they brought over another in less than 10 minutes.
Manager response on 2023-12-13 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us John! We would love to welcome you back!

Great time in Key West

Reviewed by Hardie T. on 2023-10-24
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We had a great experience at our rental. The property manager was very easy to get ahold of. He was able to accommodate an early check-in, and offered to convert the twin bedroom into a king size bed.

The backyard and pool area was really nice and the property is tucked away but conveniently located to so many great spots.
Manager response on 2023-12-13 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us Hardie! We would love to welcome you back!

Island Oasis is a Gem!

Reviewed by Unknown on 2023-12-31
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Cleanliness
Location
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Recommend to Others
Wonderful property. Walk to everything Key West has to offer. Perfect private deck and pool. Management was responsive and on top of everything.
Manager response on 2025-01-06 - 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!

Clean, Convenient, Great Pool

Reviewed by Unknown on 2024-03-24
Overall satisfaction
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Cleanliness
Location
Property condition
Recommend to Others
Two bedrooms. Convenient location. Heated pool.
Manager response on 2025-01-06 - Response from Best of Key West Rentals
Thank you for your wonderful review. We are thrilled you loved this home and hope to host you again soon!

Perfect Get Away at the Island Oasis/Key West

Reviewed by Tiffany W. on 2024-02-28
Overall satisfaction
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Location
Property condition
Recommend to Others
Loved this place! Perfect location, cozy home, nice set up, clean, all essentials, with parking. Rental company easy to work with and property manager very friendly. Thank you!
Manager response on 2025-01-06 - 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!

Wonderful Home!

Reviewed by Unknown on 2024-04-21
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Cleanliness
Location
Property condition
Recommend to Others
The home was beautiful and comfortable. It was the ideal place to retreat after a busy day in Key West.
The location could not have been better. There was parking right next to front door but it was walkable to Duvall St.
Manager response on 2025-01-06 - 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!

Key West February Getaway

Reviewed by Karl S. on 2024-03-02
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Location
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Recommend to Others
Great!
Manager response on 2025-01-06 - Response from Best of Key West Rentals
Thank you for this short and sweet five star review, we hope to have the pleasure to host you again next time you visit the island.

Nice & Clean

Reviewed by Jacky T. on 2024-02-05
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Great Location. Walking distance to all the action, yet quiet nights away from all the action.
Manager response on 2025-01-06 - 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!

Fun trip at end of February

Reviewed by Phillip N. on 2024-03-09
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Location
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Recommend to Others
We greatly enjoyed a short getaway to Key West when it was cold at home. This property was easy to access from Truman with our car and close to Zachary Taylor Park and Beach. We walked to Duvall and got great exercise and food and drink but far enough away to avoid large crowds. It was perfect for my wife and two adult children to experience Mallory Square and Bahia Honda and see fun sea creatures!
Manager response on 2025-01-06 - 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!

Location Location!

Reviewed by J & D A. on 2024-04-26
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Lovely cottage within walking distance of everything! Great pool, comfortable beds and had everything we needed.
Manager response on 2025-01-06 - 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!

Awesome Stay--Would do it again

Reviewed by IRA H. on 2022-10-13
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Close to everything but far enough it wasnt noisey. Very private back yard/pool..Great attenttive management. Would definitely recommend this place.
Manager response on 2022-11-08 - Response from Best of Key West Rentals
Thank you for your wonderful review Ira. We enjoyed hosting you and hope to see you back in Key West again soon!

Great place to stay!

Reviewed by Mary K. on 2023-01-11
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We had a great stay at island oasis. The house was clean, well laid out, pool space was great, and stocked of all the basics. The location is great off the main roads but very walkable, we walked a lot! The management company was very helpful, was involved as much or as little as you’d like. We booked a fishing trip and had other communications with the staff and they were very nice to deal it every time. The only down side to the property I won’t want to stay any more than 4 people. There isn’t any separate space besides the living room/dining room (one room) inside. If you needed to work or needed any privacy it’s just the bedrooms. Fantastic stay for the four of us was very happy with it!
Manager response on 2023-02-27 - Response from Best of Key West Rentals
Thank you for your fantastic review Mary. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!

Unit Code: IS

ISLAND OASIS ~ Stylish!

ISLAND OASIS ~ Dog Friendly 2 Bedroom, 2 Bath Townhome w/ Private, Heated Pool and Off Street Parking! Perfectly Located for All Things Key West!
YOUR SOUTHERN SANCTUARY... Find your serenity in this stylish and cheery townhome, just a short distance away from the stunning beaches of Key West and all the fun on Duval St. This tropical refuge hosts the right amount of southern hospitality to wash away your real world worries. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES... Step in to find this sweet surprise of nautical decor with comfortable furnishings in a fun-loving space infused with natural lighting all around. This cheery space greets you with a cozy sectional surrounding a flat screen TV to gather around for lazy evenings together. A fully equipped kitchen allows for seamless meal prep that can be enjoyed around the dining table for 6. Open the large sliders to take advantage of this incredible indoor/outdoor space. SLEEPING ARRANGEMENTS... Head up to the 2nd level to find the primary suite with a king bed, flat screen TV and en suite bathroom with a shower and double sink vanity. Just down the hall is a room with 2 twin beds that can convert to a king upon request, a flat screen TV and en suite bathroom with a shower. There is a sleeper sofa in the great room for additional sleeping arrangements with the convenience of a powder room steps away. OUTDOOR LIVING... Indulge in your private island oasis out on the back pool deck as you catch some rays and enjoy the sweet breeze. Rinse off the day in the refreshing private pool (comes heated in the cooler months) and enjoy a good book out on the covered porch with seating. A gas grill, wet bar and outdoor shower complete your tranquil escape. PARKING... Although perfectly located within walking distance of most everything, this home comes with a parking spot for those wanting to head out for a scenic drive. PETS... Dogs are permitted. 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. COME STAY A WHILE...
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Age 18 and under.
DatesPrice
10/26/2025 - 10/26/2025$319 /nt
10/27/2025 - 10/27/2025$281 /nt
10/28/2025 - 10/28/2025$293 /nt
10/29/2025 - 10/29/2025$326 /nt
10/30/2025 - 10/30/2025$321 /nt
10/31/2025 - 10/31/2025$423 /nt
11/01/2025 - 11/01/2025$470 /nt
11/02/2025 - 11/02/2025$410 /nt
11/03/2025 - 11/03/2025$401 /nt
11/04/2025 - 11/04/2025$405 /nt
11/05/2025 - 11/05/2025$519 /nt
11/06/2025 - 11/06/2025$699 /nt
11/07/2025 - 11/07/2025$741 /nt
11/08/2025 - 11/08/2025$760 /nt
11/09/2025 - 11/09/2025$772 /nt
11/10/2025 - 11/10/2025$571 /nt
11/11/2025 - 11/11/2025$599 /nt
11/12/2025 - 11/12/2025$619 /nt
11/13/2025 - 11/13/2025$749 /nt
11/14/2025 - 11/14/2025$814 /nt
11/15/2025 - 11/15/2025$746 /nt
11/16/2025 - 11/16/2025$677 /nt
11/17/2025 - 11/17/2025$613 /nt
11/18/2025 - 11/18/2025$625 /nt
11/19/2025 - 11/19/2025$646 /nt
11/20/2025 - 11/20/2025$718 /nt
11/21/2025 - 11/21/2025$779 /nt
11/22/2025 - 11/22/2025$861 /nt
11/23/2025 - 11/23/2025$643 /nt
11/24/2025 - 11/24/2025$493 /nt
11/25/2025 - 11/25/2025$728 /nt
11/26/2025 - 11/26/2025$905 /nt
11/27/2025 - 11/27/2025$919 /nt
11/28/2025 - 11/28/2025$980 /nt
11/29/2025 - 11/29/2025$790 /nt
11/30/2025 - 11/30/2025$564 /nt
12/01/2025 - 12/01/2025$591 /nt
12/02/2025 - 12/02/2025$536 /nt
12/03/2025 - 12/03/2025$572 /nt
12/04/2025 - 12/04/2025$714 /nt
12/05/2025 - 12/05/2025$875 /nt
12/06/2025 - 12/06/2025$763 /nt
12/07/2025 - 12/07/2025$733 /nt
12/08/2025 - 12/08/2025$671 /nt
12/09/2025 - 12/09/2025$652 /nt
12/10/2025 - 12/10/2025$663 /nt
12/11/2025 - 12/11/2025$759 /nt
12/12/2025 - 12/12/2025$1,086 /nt
12/13/2025 - 12/13/2025$836 /nt
12/14/2025 - 12/14/2025$732 /nt
12/15/2025 - 12/15/2025$594 /nt
12/16/2025 - 12/16/2025$559 /nt
12/17/2025 - 12/17/2025$621 /nt
12/18/2025 - 12/18/2025$705 /nt
12/19/2025 - 12/19/2025$944 /nt
12/20/2025 - 12/20/2025$685 /nt
12/21/2025 - 12/21/2025$989 /nt
12/22/2025 - 12/22/2025$1,001 /nt
12/23/2025 - 12/23/2025$1,035 /nt
12/24/2025 - 12/24/2025$1,233 /nt
12/25/2025 - 12/25/2025$788 /nt
12/26/2025 - 12/26/2025$1,553 /nt
12/27/2025 - 12/27/2025$1,769 /nt
12/28/2025 - 12/28/2025$1,943 /nt
12/29/2025 - 12/29/2025$1,988 /nt
12/30/2025 - 12/30/2025$2,016 /nt
12/31/2025 - 12/31/2025$1,804 /nt
01/01/2026 - 01/01/2026$1,647 /nt
01/02/2026 - 01/02/2026$1,349 /nt
01/03/2026 - 01/03/2026$1,355 /nt
01/04/2026 - 01/04/2026$1,247 /nt
01/05/2026 - 01/05/2026$803 /nt
01/06/2026 - 01/06/2026$893 /nt
01/07/2026 - 01/07/2026$873 /nt
01/08/2026 - 01/08/2026$888 /nt
01/09/2026 - 01/09/2026$1,046 /nt
01/10/2026 - 01/10/2026$1,061 /nt
01/11/2026 - 01/11/2026$1,008 /nt
01/12/2026 - 01/12/2026$926 /nt
01/13/2026 - 01/13/2026$903 /nt
01/14/2026 - 01/14/2026$947 /nt
01/15/2026 - 01/15/2026$1,095 /nt
01/16/2026 - 01/16/2026$1,207 /nt
01/17/2026 - 01/17/2026$1,377 /nt
01/18/2026 - 01/18/2026$1,180 /nt
01/19/2026 - 01/19/2026$946 /nt
01/20/2026 - 01/20/2026$925 /nt
01/21/2026 - 01/21/2026$944 /nt
01/22/2026 - 01/22/2026$1,008 /nt
01/23/2026 - 01/23/2026$1,077 /nt
01/24/2026 - 01/24/2026$1,101 /nt
01/25/2026 - 01/25/2026$750 /nt
01/26/2026 - 01/26/2026$953 /nt
01/27/2026 - 01/27/2026$956 /nt
01/28/2026 - 01/28/2026$1,117 /nt
01/29/2026 - 01/29/2026$1,209 /nt
01/30/2026 - 01/30/2026$1,119 /nt
01/31/2026 - 01/31/2026$1,134 /nt
02/01/2026 - 02/01/2026$907 /nt
02/02/2026 - 02/02/2026$876 /nt
02/03/2026 - 02/03/2026$888 /nt
02/04/2026 - 02/04/2026$931 /nt
02/05/2026 - 02/05/2026$1,014 /nt
02/06/2026 - 02/06/2026$1,069 /nt
02/07/2026 - 02/07/2026$1,098 /nt
02/08/2026 - 02/08/2026$1,010 /nt
02/09/2026 - 02/09/2026$999 /nt
02/10/2026 - 02/10/2026$1,014 /nt
02/11/2026 - 02/11/2026$1,048 /nt
02/12/2026 - 02/12/2026$1,111 /nt
02/13/2026 - 02/13/2026$1,234 /nt
02/14/2026 - 02/14/2026$1,457 /nt
02/15/2026 - 02/15/2026$1,563 /nt
02/16/2026 - 02/16/2026$1,336 /nt
02/17/2026 - 02/17/2026$1,230 /nt
02/18/2026 - 02/18/2026$1,269 /nt
02/19/2026 - 02/19/2026$1,334 /nt
02/20/2026 - 02/20/2026$1,377 /nt
02/21/2026 - 02/21/2026$1,390 /nt
02/22/2026 - 02/22/2026$1,315 /nt
02/23/2026 - 02/23/2026$1,281 /nt
02/24/2026 - 02/24/2026$1,268 /nt
02/25/2026 - 02/25/2026$1,281 /nt
02/26/2026 - 02/26/2026$1,312 /nt
02/27/2026 - 02/27/2026$1,326 /nt
02/28/2026 - 02/28/2026$1,318 /nt
03/01/2026 - 03/01/2026$1,245 /nt
03/02/2026 - 03/02/2026$1,215 /nt
03/03/2026 - 03/03/2026$1,196 /nt
03/04/2026 - 03/04/2026$1,219 /nt
03/05/2026 - 03/05/2026$1,262 /nt
03/06/2026 - 03/06/2026$1,451 /nt
03/07/2026 - 03/07/2026$1,459 /nt
03/08/2026 - 03/09/2026$1,402 /nt
03/10/2026 - 03/10/2026$1,391 /nt
03/11/2026 - 03/11/2026$1,421 /nt
03/12/2026 - 03/12/2026$1,465 /nt
03/13/2026 - 03/14/2026$1,490 /nt
03/15/2026 - 03/15/2026$1,250 /nt
03/16/2026 - 03/16/2026$1,241 /nt
03/17/2026 - 03/17/2026$1,213 /nt
03/18/2026 - 03/18/2026$1,229 /nt
03/19/2026 - 03/19/2026$1,264 /nt
03/20/2026 - 03/20/2026$1,277 /nt
03/21/2026 - 03/21/2026$1,268 /nt
03/22/2026 - 03/22/2026$1,165 /nt
03/23/2026 - 03/23/2026$1,159 /nt
03/24/2026 - 03/24/2026$1,138 /nt
03/25/2026 - 03/25/2026$1,165 /nt
03/26/2026 - 03/26/2026$1,217 /nt
03/27/2026 - 03/27/2026$1,604 /nt
03/28/2026 - 03/28/2026$1,603 /nt
03/29/2026 - 03/29/2026$1,481 /nt
03/30/2026 - 03/30/2026$1,116 /nt
03/31/2026 - 03/31/2026$1,092 /nt
04/01/2026 - 04/01/2026$1,107 /nt
04/02/2026 - 04/02/2026$1,252 /nt
04/03/2026 - 04/03/2026$1,281 /nt
04/04/2026 - 04/04/2026$1,274 /nt
04/05/2026 - 04/05/2026$1,131 /nt
04/06/2026 - 04/06/2026$1,107 /nt
04/07/2026 - 04/07/2026$998 /nt
04/08/2026 - 04/08/2026$1,014 /nt
04/09/2026 - 04/09/2026$1,094 /nt
04/10/2026 - 04/10/2026$1,133 /nt
04/11/2026 - 04/11/2026$1,118 /nt
04/12/2026 - 04/12/2026$942 /nt
04/13/2026 - 04/13/2026$881 /nt
04/14/2026 - 04/14/2026$847 /nt
04/15/2026 - 04/15/2026$858 /nt
04/16/2026 - 04/16/2026$965 /nt
04/17/2026 - 04/17/2026$1,072 /nt
04/18/2026 - 04/18/2026$1,075 /nt
04/19/2026 - 04/19/2026$897 /nt
04/20/2026 - 04/20/2026$789 /nt
04/21/2026 - 04/21/2026$771 /nt
04/22/2026 - 04/22/2026$914 /nt
04/23/2026 - 04/23/2026$1,052 /nt
04/24/2026 - 04/24/2026$1,236 /nt
04/25/2026 - 04/25/2026$1,246 /nt
04/26/2026 - 04/26/2026$1,038 /nt
04/27/2026 - 04/27/2026$837 /nt
04/28/2026 - 04/28/2026$847 /nt
04/29/2026 - 04/29/2026$934 /nt
04/30/2026 - 04/30/2026$1,087 /nt
05/01/2026 - 05/01/2026$1,159 /nt
05/02/2026 - 05/02/2026$1,162 /nt
05/03/2026 - 05/03/2026$945 /nt
05/04/2026 - 05/04/2026$858 /nt
05/05/2026 - 05/05/2026$828 /nt
05/06/2026 - 05/06/2026$891 /nt
05/07/2026 - 05/07/2026$1,062 /nt
05/08/2026 - 05/08/2026$1,152 /nt
05/09/2026 - 05/09/2026$1,162 /nt
05/10/2026 - 05/10/2026$959 /nt
05/11/2026 - 05/11/2026$873 /nt
05/12/2026 - 05/12/2026$842 /nt
05/13/2026 - 05/13/2026$881 /nt
05/14/2026 - 05/14/2026$1,052 /nt
05/15/2026 - 05/15/2026$1,143 /nt
05/16/2026 - 05/16/2026$1,148 /nt
05/17/2026 - 05/17/2026$957 /nt
05/18/2026 - 05/18/2026$879 /nt
05/19/2026 - 05/19/2026$835 /nt
05/20/2026 - 05/20/2026$847 /nt
05/21/2026 - 05/21/2026$1,021 /nt
05/22/2026 - 05/22/2026$1,225 /nt
05/23/2026 - 05/23/2026$1,232 /nt
05/24/2026 - 05/24/2026$1,043 /nt
05/25/2026 - 05/25/2026$969 /nt
05/26/2026 - 05/26/2026$818 /nt
05/27/2026 - 05/27/2026$812 /nt
05/28/2026 - 05/28/2026$961 /nt
05/29/2026 - 05/29/2026$1,065 /nt
05/30/2026 - 05/30/2026$1,062 /nt
05/31/2026 - 05/31/2026$859 /nt
06/01/2026 - 06/01/2026$794 /nt
06/02/2026 - 06/02/2026$851 /nt
06/03/2026 - 06/03/2026$849 /nt
06/04/2026 - 06/04/2026$1,007 /nt
06/05/2026 - 06/05/2026$1,125 /nt
06/06/2026 - 06/06/2026$1,148 /nt
06/07/2026 - 06/07/2026$957 /nt
06/08/2026 - 06/08/2026$821 /nt
06/09/2026 - 06/09/2026$812 /nt
06/10/2026 - 06/10/2026$831 /nt
06/11/2026 - 06/11/2026$975 /nt
06/12/2026 - 06/13/2026$1,058 /nt
06/14/2026 - 06/14/2026$832 /nt
06/15/2026 - 06/15/2026$768 /nt
06/16/2026 - 06/16/2026$750 /nt
06/17/2026 - 06/17/2026$766 /nt
06/18/2026 - 06/18/2026$906 /nt
06/19/2026 - 06/19/2026$1,016 /nt
06/20/2026 - 06/20/2026$1,021 /nt
06/21/2026 - 06/21/2026$805 /nt
06/22/2026 - 06/22/2026$778 /nt
06/23/2026 - 06/23/2026$728 /nt
06/24/2026 - 06/24/2026$761 /nt
06/25/2026 - 06/25/2026$901 /nt
06/26/2026 - 06/26/2026$941 /nt
06/27/2026 - 06/27/2026$933 /nt
06/28/2026 - 06/28/2026$712 /nt
06/29/2026 - 06/29/2026$689 /nt
06/30/2026 - 06/30/2026$682 /nt
07/01/2026 - 07/01/2026$729 /nt
07/02/2026 - 07/02/2026$1,067 /nt
07/03/2026 - 07/03/2026$1,122 /nt
07/04/2026 - 07/04/2026$1,144 /nt
07/05/2026 - 07/05/2026$954 /nt
07/06/2026 - 07/06/2026$961 /nt
07/07/2026 - 07/07/2026$763 /nt
07/08/2026 - 07/08/2026$795 /nt
07/09/2026 - 07/09/2026$923 /nt
07/10/2026 - 07/11/2026$986 /nt
07/12/2026 - 07/12/2026$766 /nt
07/13/2026 - 07/13/2026$761 /nt
07/14/2026 - 07/14/2026$749 /nt
07/15/2026 - 07/15/2026$766 /nt
07/16/2026 - 07/16/2026$888 /nt
07/17/2026 - 07/17/2026$961 /nt
07/18/2026 - 07/18/2026$981 /nt
07/19/2026 - 07/19/2026$761 /nt
07/20/2026 - 07/20/2026$735 /nt
07/21/2026 - 07/21/2026$780 /nt
07/22/2026 - 07/22/2026$798 /nt
07/23/2026 - 07/23/2026$967 /nt
07/24/2026 - 07/24/2026$1,070 /nt
07/25/2026 - 07/25/2026$1,446 /nt
07/26/2026 - 07/26/2026$1,444 /nt
07/27/2026 - 07/27/2026$1,398 /nt
07/28/2026 - 07/28/2026$1,372 /nt
07/29/2026 - 07/29/2026$1,324 /nt
07/30/2026 - 07/30/2026$1,478 /nt
07/31/2026 - 07/31/2026$1,413 /nt
08/01/2026 - 08/01/2026$1,312 /nt
08/02/2026 - 08/02/2026$1,042 /nt
08/03/2026 - 08/03/2026$699 /nt
08/04/2026 - 08/04/2026$682 /nt
08/05/2026 - 08/05/2026$712 /nt
08/06/2026 - 08/06/2026$880 /nt
08/07/2026 - 08/07/2026$1,014 /nt
08/08/2026 - 08/08/2026$1,043 /nt
08/09/2026 - 08/09/2026$798 /nt
08/10/2026 - 08/10/2026$730 /nt
08/11/2026 - 08/11/2026$716 /nt
08/12/2026 - 08/12/2026$752 /nt
08/13/2026 - 08/13/2026$936 /nt
08/14/2026 - 08/14/2026$1,071 /nt
08/15/2026 - 08/15/2026$1,066 /nt
08/16/2026 - 08/16/2026$783 /nt
08/17/2026 - 08/17/2026$687 /nt
08/18/2026 - 08/18/2026$630 /nt
08/19/2026 - 08/19/2026$629 /nt
08/20/2026 - 08/20/2026$795 /nt
08/21/2026 - 08/21/2026$927 /nt
08/22/2026 - 08/22/2026$919 /nt
08/23/2026 - 08/23/2026$644 /nt
08/24/2026 - 08/24/2026$558 /nt
08/25/2026 - 08/25/2026$519 /nt
08/26/2026 - 08/26/2026$520 /nt
08/27/2026 - 08/27/2026$695 /nt
08/28/2026 - 08/28/2026$831 /nt
08/29/2026 - 08/29/2026$828 /nt
08/30/2026 - 08/30/2026$557 /nt
08/31/2026 - 08/31/2026$450 /nt
09/01/2026 - 09/01/2026$453 /nt
09/02/2026 - 09/02/2026$458 /nt
09/03/2026 - 09/03/2026$628 /nt
09/04/2026 - 09/04/2026$978 /nt
09/05/2026 - 09/05/2026$990 /nt
09/06/2026 - 09/06/2026$748 /nt
09/07/2026 - 09/07/2026$660 /nt
09/08/2026 - 09/08/2026$374 /nt
09/09/2026 - 09/09/2026$384 /nt
09/10/2026 - 09/10/2026$553 /nt
09/11/2026 - 09/11/2026$697 /nt
09/12/2026 - 09/12/2026$719 /nt
09/13/2026 - 09/13/2026$492 /nt
09/14/2026 - 09/14/2026$405 /nt
09/15/2026 - 09/15/2026$382 /nt
09/16/2026 - 09/16/2026$412 /nt
09/17/2026 - 09/17/2026$574 /nt
09/18/2026 - 09/18/2026$713 /nt
09/19/2026 - 09/19/2026$733 /nt
09/20/2026 - 09/20/2026$501 /nt
09/21/2026 - 09/21/2026$414 /nt
09/22/2026 - 09/22/2026$388 /nt
09/23/2026 - 09/23/2026$438 /nt
09/24/2026 - 09/24/2026$598 /nt
09/25/2026 - 09/25/2026$738 /nt
09/26/2026 - 09/26/2026$761 /nt
09/27/2026 - 09/27/2026$535 /nt
09/28/2026 - 09/28/2026$439 /nt
09/29/2026 - 09/29/2026$408 /nt
09/30/2026 - 09/30/2026$463 /nt
10/01/2026 - 10/01/2026$614 /nt
10/02/2026 - 10/02/2026$756 /nt
10/03/2026 - 10/03/2026$772 /nt
10/04/2026 - 10/04/2026$544 /nt
10/05/2026 - 10/05/2026$449 /nt
10/06/2026 - 10/06/2026$421 /nt
10/07/2026 - 10/07/2026$506 /nt
10/08/2026 - 10/08/2026$676 /nt
10/09/2026 - 10/09/2026$892 /nt
10/10/2026 - 10/10/2026$915 /nt
10/11/2026 - 10/11/2026$696 /nt
10/12/2026 - 10/12/2026$603 /nt
10/13/2026 - 10/13/2026$521 /nt
10/14/2026 - 10/14/2026$606 /nt
10/15/2026 - 10/15/2026$761 /nt
10/16/2026 - 10/16/2026$1,205 /nt
10/17/2026 - 10/17/2026$1,194 /nt
10/18/2026 - 10/18/2026$958 /nt
10/19/2026 - 10/19/2026$856 /nt
10/20/2026 - 10/20/2026$836 /nt
10/21/2026 - 10/21/2026$943 /nt
10/22/2026 - 10/22/2026$1,111 /nt
10/23/2026 - 10/24/2026$1,262 /nt
10/25/2026 - 10/25/2026$1,043 /nt
10/26/2026 - 10/26/2026$665 /nt
4.9063
(32 Review)

Perfect Get Away

July 2025
, Canton, GA United States

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

We stayed at the Island Oasis for 4 nights in July. We had 4 adults, and the house was perfect for our stay. It was an extremely easy process from booking, check-in, and check-out. The management company was great with quick communication and the concierge was very helpful. The location of the house was perfect for walking to Duval Street area and we felt very safe. I would definitely stay here again.

Manager's Response

Thank you so much for your wonderful review! We're thrilled to hear Island Oasis was a perfect fit for your group and that you found the location convenient and safe. It's great to know our team and concierge service helped make your stay smooth and enjoyable. We’d love to welcome you back anytime!

A Great House with Good Privacy!

July 2025
, Long Beach, CA US

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

A very nice house in a quiet area. Walking distance to Duval street and the beach. Loved the layout and enjoyed the private pool. The house is not big but it's good for two couples or a family.
very nice kitchen, living area and backyard patio.

Manager's Response

Thank you for your kind review! We're so glad to hear you enjoyed the quiet location, private pool, and the layout of the home. It sounds like it was a great fit for your group. We'd love to host you again on your next trip to Key West!

Key West Vaca

April 2025
, Metairie, LA United States

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

We had a great time. Nice place. A few issues need to be addressed. The towels and wash rags supplied were old, hard and discolored. New, softer ones would be nice. The safe in the closet didn't work. In the master bedroom, the AC vents or something in the ducts rattled and we didn't sleep well. In the downstairs half bathroom, the cold water didn't work and the toilet handle is not working. Since you asked, for what we paid I think the place could use a "freshening up".

Manager's Response

Thank you for your feedback — we’re glad to hear you had a great time overall, and we appreciate you bringing these issues to our attention. We’re sorry to hear about the towels and maintenance concerns, and we’ve made note of all your comments so our team can follow up and ensure improvements are made. Your input helps us continue to improve the guest experience, and we hope to have the opportunity to welcome you back in the future!

Never Disappoints

January 2025
, Lexington, Kentucky United States

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

Rental was exactly as advertised. Great location. Close to everything but quiet. Shana was so helpful and quick to respond. I definitely recommend this property

Never Disappoints

January 2025
, Lexington, Kentucky United States

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

Rental was exactly as advertised. Great location. Close to everything but quiet. Shana was so helpful and quick to respond. I definitely recommend this property

Manager's Response

Thank you for the kind words! We're so glad to hear the rental met your expectations and that the location offered the perfect balance of convenience and peace. We'd love to host you again anytime!

Great house

January 2025
, New York, NY US

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

The house was very clean, well kept, and was just as it appears in the pictures. We couldn’t have been happier with it.

Manager's Response

Peirce we really appreciate you leaving such a nice review after your stay. We are thrilled you enjoyed this home so much and hope to have the chance to welcome you again next time you visit the southernmost island!

Location, location, location!

December 2024
, Sarasota, FL US

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

Close to everything. It was nice to walk to the end of the street to get Cuban coffee every morning. Walk a few more blocks you're on Duval and a bit further to the Southernmost Point.

A few things could be upgraded in the home itself. Primary bedroom bed was very worn and squeaked every time you move. The guest bedroom beds are on wheels and roll across the floor. I read a review from a long time ago with the same issue. Thought it would have been addressed but was not.
The shower heads in both bathrooms could be better. Both are the rain style which are hard to rinse soap off with low water pressure.
Kitchen was fully stocked with cookware and dishes etc. The cooking utensils were poor quality. Plastic breaking off in food as we were cooking.
We used washer and dryer mid-week. Took us 2 hours to dry 6 towels. It was very old. Needs to be changed out.

Otherwise, the house was clean and in a great location.

Manager's Response

Thank you for your feedback on your recent stay Ryan. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will rely back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!

Amazing

November 2024
, Indianapolis, IN US

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

Perfect house my wife and I , and another couple . Great location ! Will definitely be returning !

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!

The perfect place for my 50th birthday weekend!

October 2024
, Cairo, GA US

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

Island Oasis was the perfect spot for my husband and I to stay with my best friend and her husband! We stayed there for my 50th birthday weekend and were very comfortable. Both bedrooms had comfy king beds and ensuite bathrooms. The kitchen had everything we needed and we really enjoyed the outdoor area with private pool! It was so nice to come in from a day of walking around and be able to take a dip in the pool. The location is great, within walking distance to a lot of places but far enough away from Duval to escape the noise. Our concierge team was so attentive and helped us make reservations and made recommendations. I would definitely stay again!

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!

Fabulous Key West Home

September 2024
, HEBER SPRINGS, AR United States

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

This place is wonderful and as pictured. Beautiful private pool, very clean and close to but not to close the Duvall, shopping and restaurants.

Rental company was great and so easy to communicate with. Would definitely stay here again.

Manager's Response

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

Fabulous Key West Home

September 2024
, Heber Springs, AR US

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

This place is wonderful and as pictured. Beautiful private pool, very clean and close to but not to close the Duvall, shopping and restaurants.

Rental company was great and so easy to communicate with. Would definitely stay here again.

Manager's Response

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

Best Key West stay!

September 2024
, New Market, AL US

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

Incredible place. Absolutely private pool with 6 foot end (I didn’t realize it has a deep end!), incredibly clean, and over the top nice. Best nightly rental I’ve ever booked.

Manager's Response

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

Excellent stay!

August 2024
, Orlando, FL US

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

The house was beautiful and pristine and the service exceeded my expectations! Great location and seamless experience. Would definitely stay with them again.

Manager's Response

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

Great Place!

August 2024
, Venice, FL United States

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

Great place for our family! The host was responsive and the house had everything we needed.

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!

Prefect!!!

June 2024
, North Charleston, SC US

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

The house,location,and management were PERFECT!!! we will definitely stay with you again!

Manager's Response

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

1st time in Key West!

June 2024
, Sneads ferry, NC US

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

The house was perfect for our stay. Communication was prompt, the location was perfect, the property was clean and everything we expected. Thank you!

Manager's Response

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

Wonderful Home!

April 2024
, Athens, GA US

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

The home was beautiful and comfortable. It was the ideal place to retreat after a busy day in Key West.
The location could not have been better. There was parking right next to front door but it was walkable to Duvall St.

Manager's Response

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

Clean, Convenient, Great Pool

March 2024
, Succasunna, NJ United States

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

Two bedrooms. Convenient location. Heated pool.

Manager's Response

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

Fun trip at end of February

February 2024
, Signal Mountain, TN Unknown

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

We greatly enjoyed a short getaway to Key West when it was cold at home. This property was easy to access from Truman with our car and close to Zachary Taylor Park and Beach. We walked to Duvall and got great exercise and food and drink but far enough away to avoid large crowds. It was perfect for my wife and two adult children to experience Mallory Square and Bahia Honda and see fun sea creatures!

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!

Perfect Get Away at the Island Oasis/Key West

February 2024
, Bloomingdale, IL US

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

Loved this place! Perfect location, cozy home, nice set up, clean, all essentials, with parking. Rental company easy to work with and property manager very friendly. Thank you!

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 February Getaway

February 2024
, Washington, NC US

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

Great!

Manager's Response

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

Nice & Clean

January 2024
, Milan, OH US

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

Great Location. Walking distance to all the action, yet quiet nights away from all the action.

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!

Island Oasis is a Gem!

December 2023
, Los Angeles, CA US

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

Wonderful property. Walk to everything Key West has to offer. Perfect private deck and pool. Management was responsive and on top of everything.

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!

Great time in Key West

September 2023
, chicago, IL US

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

We had a great experience at our rental. The property manager was very easy to get ahold of. He was able to accommodate an early check-in, and offered to convert the twin bedroom into a king size bed.

The backyard and pool area was really nice and the property is tucked away but conveniently located to so many great spots.

Manager's Response

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

Great house, super location, excellent service

July 2023
, Palm Beach Gardens, FL US

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

Loved this place. Location is close to Duval. but quiet. Plenty of street parking in addition to the one dedicated spot. House was spotless clean. Nice furniture. Pool is a big plus. Service from the agent was tops. The blender broke while preparing dinner at 7, and they brought over another in less than 10 minutes.

Manager's Response

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

Perfect Getaway

April 2023
, Clarksville, TN US

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

This little gem is a couple blocks from some of the best food in KW! Breakfast and the Conch and the Cuban...dinner at any number of places within short waling distance (el Siboney!). Bike rentals-3 small blocks away. Drugstore with everything you forgot only 2 blocks away. Yet this place is tucked off the main roads to stay quiet and secluded. Pool was perfect for relaxing after biking all day. Bed was comfortable, showers nice and clean. Everything was as perfect as it could be. And the rental company was always quick to answer any question or concern! The PERFECT sport for a island vacation!

Manager's Response

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

Island Oasis

March 2023
, Huntington, NY United States

Overall
4
Services from rental manager
5
Cleanliness
2
Location
5
Property condition
2

We had a lovely time. House in great location. The house could use some upgrades. Quiet peaceful neighborhood. Amelia Street is not pretty but it’s a wide street, not a lot of car traffic, and the parking lot is convenient if needed and there are lots of restaurants nearby. The pool was clean and a wonderful amenity to have, as well as the garden.

Great time in Key West with friends

January 2023
, Cullman, AL US

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

Island Oasis was everything we thought it would be. The Truman and Co Team was very helpful and took care of all of our needs. This was our second time to stay within this complex. The home is in a great location, the pool was a great place to end the day exploring Key West. We would give it a 5 out of 5. Looking forward to our next trip.

Manager's Response

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

Great Vacation Home

January 2023
, McHenry, MD US

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

We loved the place and we are already talking about coming back!

Manager's Response

Thank you for this wonderful review Chad, 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.

Great place to stay!

January 2023
, Lancaster, PA US

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

We had a great stay at island oasis. The house was clean, well laid out, pool space was great, and stocked of all the basics. The location is great off the main roads but very walkable, we walked a lot! The management company was very helpful, was involved as much or as little as you’d like. We booked a fishing trip and had other communications with the staff and they were very nice to deal it every time. The only down side to the property I won’t want to stay any more than 4 people. There isn’t any separate space besides the living room/dining room (one room) inside. If you needed to work or needed any privacy it’s just the bedrooms. Fantastic stay for the four of us was very happy with it!

Manager's Response

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

Lovely Property

December 2022
, Louisville, KY US

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

Ideal location. Close to all hot spots but quiet and secluded.

Manager's Response

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

Awesome Stay--Would do it again

October 2022
, SUFFOLK, VA United States

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

Close to everything but far enough it wasnt noisey. Very private back yard/pool..Great attenttive management. Would definitely recommend this place.

Manager's Response

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

Leave a Review
2 Bed
2.5 Baths
Sleeps 6

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EBB AND FLO ~ Paradise!

EBB AND FLO ~ Renovated 4 Bed/3 Bath Home in Old Town Location with Incredible Pool Deck Area and Outdoor Dining!

Location

917 United St.
33040 Key West , FL
United States
24° 33' 6.9948" N, 81° 47' 29.2128" W
See map: Google Maps
Florida US

EBB AND FLO ~ Paradise!

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Ebb & Flo 2025

Reviewed by jeffrey c. on 2025-05-17
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The property is very well maintained and sits in a great location close to everything old town has. This is the 4th time staying here and have not been disappointed. Shana the property manager is very helpful and responds very quick to any questions. Hope to rent for 2025.
Manager response on 2025-05-19 - Response from Best of Key West Rentals
Thank you so much for your wonderful review! We're thrilled to hear that you enjoyed your stay at Ebb & Flo and appreciate your loyalty. It's great to know that our location and the property's maintenance have met your expectations. We look forward to welcoming you back for your next stay in 2025! Safe travels until then!

Long stay at Ebb and Flow

Reviewed by Janet & Frank D. on 2025-01-21
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The house is very centrally located and an easy walk or bike ride to anywhere in Key West. Nice newer model bikes were included in the rental which made it even easier. The property was immaculate and beautifully furnished. There is an outside bar area with a TV and a beautiful heated pool.
Manager response on 2025-01-21 - Response from Best of Key West Rentals
Thank you for your review Janet & Frank, 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. Thank you for being amazing guests!

I don't do titles

Reviewed by Mary Lou S. on 2023-04-15
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Ebb and Flo is a great house! The location is great, easy to walk to restaurants, stores, groceries, coffee, the beach. The location could not be better. We did have a plumbing issue, but the property company handled it very quickly and very well, there was a plumber there quickly and he was, also great. The outdoor space is excellent, the pool is very nice, the bar and dining area are very useful. The rooms and bathrooms are all very nice, and the kitchen is very well outfitted. We were able to cook there with no issues. all in all a great house.
Manager response on 2023-05-01 - Response from Best of Key West Rentals
Thank you for your fantastic review Mary Lou. It was a pleasure hosting you! We are so glad you enjoyed the outdoors as well of the location and we look forward to welcoming you again next time you visit the island!

Backyard Oasis

Reviewed by Michelle T. on 2023-03-16
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We honestly didn't spend much awake time in this house, which is a shame because the kitchen is spectacular. It was hard to be inside when the yard at this house is just a dream. The bar and table area has a fridge and ice maker- never needed to go inside! This house is very well appointed, close to Higgs beach, walking distance to everything, and has plenty of room for friends and family.
Manager response on 2023-03-20 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us Michelle! Please reach out to us for your next Key West vacation, we would love to welcome you back! Thank you for being our guest!

Another fantastic stay!

Reviewed by Charles G. on 2024-07-06
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This was our second time at Ebb and Flo and we had another great stay. The house is perfect to have the family together and the location is quiet but within walking distance to Duval. Shana was great to communicate with and made everything incredibly easy for us! (And the four bikes were super convenient to have!)
Manager response on 2024-07-07 - Response from Best of Key West Rentals
Thank you for this wonderful review Charles, we are so glad you enjoyed the property so much you stayed with us again this year! We look forward to welcoming you again next time you are in Key West!

Ebb & Flo

Reviewed by Unknown on 2024-04-03
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Ebb & Flo is a very nice vacation rental and is located in an area in walking distance to many restaurants, etc. Unfortunately, the landscaper doesn’t come as often as noted on the sheet for guests in the rental. When he does come, he does a good job. The pool maintenance company does a great job! It would be nice if the bedrooms had access to Direct TV like is available in the family room and outside in the pool area.
Manager response on 2024-07-22 - Response from Best of Key West Rentals
Thank you for your feedback on your recent stay Thomas. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will relay back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!

Captain’s Choice

Reviewed by Unknown on 2020-03-16
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Wonderful home, very well maintained. Property Manager was excellent, responded within minutes. House was spotless. Stayed two months, the house was excellent.
Manager response on 2020-03-17 - Response from Best of Key West Rentals
Dear Patricia, Thank you for your wonderful review. We are so thrilled to hear how much you loved this home. We enjoyed hosting you and look forward to your return back. Best Regards, Wendy Zintsmaster and Team

Key West Stay

Reviewed by Larry G. on 2022-02-02
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
My wife and I rented this house for the month of January. Love the area and the pool and outdoor area. Only downside house is located on a very busy road.
Manager response on 2022-02-07 - Response from Best of Key West Rentals
Thank you for your review Larry, we are glad you enjoyed the property and hope to welcome you again next time you visit the island!

Paradise on key west

Reviewed by Andrea S. on 2022-03-31
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Ebb & Flo was just about perfect! Perfect space, location, privacy, and the outdoor space is incomparable to anywhere I’ve stayed. Our 3 adult children filtered in and out over the month with their significant others and all were impressed with the accommodations. The property management company, Shana in particular, was top notch! Shana responded immediately to any questions we had and was a wonderful comforting resource. We loved the location as it’s quiet and a bit removed from Duval street but it’s a quick walk anywhere. We did end up renting a golf cart which was so much fun. My husband biked to Higgs Beach every day for pickle ball. It too was close by. The house was very clean and we loved every minute of our 28 day stay.
Manager response on 2022-04-19 - Response from Best of Key West Rentals
Thank you for your wonderful review Andrea. We really enjoyed hosting you and hope to see you back in Key West again soon!

Ebb and flo paradise

Reviewed by Elaine N. on 2022-06-15
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The place was perfect for my needs. The management was above and beyond. Would most definitely rent it again.
Manager response on 2022-06-20 - Response from Best of Key West Rentals
Thank you for your incredible review Elaine! 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!

EBB AND FLO ~ Newly Renovated Retreat in Old Town with Incredible Pool!

Unit Code: EF

EBB AND FLO ~ Paradise!

EBB AND FLO ~ Renovated 4 Bed/3 Bath Home in Old Town Location with Incredible Pool Deck Area and Outdoor Dining!
OLD TOWN KEY WEST… Surround yourself in this newly renovated gem located in the desirable Casa Marina neighborhood nearing the Southernmost Point of the U.S. This tropical retreat begs for entertainment in the exceptional outdoor living space and resides steps away from high end galleries, the beautiful beaches of Key West and some of the most coveted dining downtown! ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… Lush vegetation surrounds this island retreat welcoming you into your escape from reality. A private, covered front porch greets you as you enter the home in to a cheery seating area with an indoor dining table and writing desk nearby. Steps away is the fully equipped kitchen with charming brick accent walls and casual bar top dining. Cozy furnishings surround a flat screen TV just steps away. Tile flooring throughout this home will keep you cool during a warm island afternoon. SLEEPING ARRANGEMENTS… Totaling 4 bedrooms, this home is perfect for families and couples traveling together. Sleep tight in the twin bed guestroom of which can be converted to a king upon request. A cozy queen bedroom lies steps away. Both rooms come with TVs and share a bathroom with a walk in glass shower. The primary king suite is equipped with a flat screen TV and en suite bathroom with a walk in glass shower. French doors lead out to the lush outdoor garden for your morning cup of coffee. The living space includes a sofa sleeper for visiting guests. There is a 4th bedroom poolside that comes with 2 twins and an en suite bathroom with a shower. OUTDOOR LIVING… Step through the French doors of the kitchen to your pristine outdoor oasis which makes for the ideal 5 o’clock happy hour with plenty of space to lounge and entertain. An outdoor TV, ice maker and refrigerator complete the outdoor wet bar. Grill up your fresh catch of the day and catch some rays on the spacious pool deck in the privacy of your fenced in backyard. The saltwater pool comes heated in the winter months and has the option of being chilled during the months of June-August at an additional charge if requested. Rinse off in the outdoor shower before heading out on the town. PARKING AND BIKES... Two off-street parking spaces make parking your vehicle a breeze, and 4 bikes are also provided. PETS... Dogs are considered, no cats 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. 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 IS AWAITING YOUR ARRIVAL…
October 2025
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DatesPrice
10/26/2025 - 10/31/2025$425 /nt
11/01/2025 - 11/30/2025$484 /nt
12/01/2025 - 12/31/2025$542 /nt
01/01/2026 - 01/31/2026$750 /nt
02/01/2026 - 02/28/2026$858 /nt
03/01/2026 - 03/31/2026$764 /nt
04/01/2026 - 04/30/2026$572 /nt
05/01/2026 - 07/31/2026$475 /nt
08/01/2026 - 09/30/2026$429 /nt
10/01/2026 - 10/26/2026$447 /nt
4.9091
(11 Review)

Ebb & Flo 2025

April 2025
, cheswick, PA Unknown

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

The property is very well maintained and sits in a great location close to everything old town has. This is the 4th time staying here and have not been disappointed. Shana the property manager is very helpful and responds very quick to any questions. Hope to rent for 2025.

Manager's Response

Thank you so much for your wonderful review! We're thrilled to hear that you enjoyed your stay at Ebb & Flo and appreciate your loyalty. It's great to know that our location and the property's maintenance have met your expectations. We look forward to welcoming you back for your next stay in 2025! Safe travels until then!

Long stay at Ebb and Flow

December 2024
, Barnegat, NJ Unknown

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

The house is very centrally located and an easy walk or bike ride to anywhere in Key West. Nice newer model bikes were included in the rental which made it even easier. The property was immaculate and beautifully furnished. There is an outside bar area with a TV and a beautiful heated pool.

Manager's Response

Thank you for your review Janet & Frank, 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. Thank you for being amazing guests!

Another fantastic stay!

June 2024
, Savannah, GA United States

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

This was our second time at Ebb and Flo and we had another great stay. The house is perfect to have the family together and the location is quiet but within walking distance to Duval. Shana was great to communicate with and made everything incredibly easy for us! (And the four bikes were super convenient to have!)

Manager's Response

Thank you for this wonderful review Charles, we are so glad you enjoyed the property so much you stayed with us again this year! We look forward to welcoming you again next time you are in Key West!

Ebb & Flo

March 2024
, Needham, MA Afghanistan

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

Ebb & Flo is a very nice vacation rental and is located in an area in walking distance to many restaurants, etc. Unfortunately, the landscaper doesn’t come as often as noted on the sheet for guests in the rental. When he does come, he does a good job. The pool maintenance company does a great job! It would be nice if the bedrooms had access to Direct TV like is available in the family room and outside in the pool area.

Manager's Response

Thank you for your feedback on your recent stay Thomas. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will relay back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!

I don't do titles

March 2023
, Wayne, PA United States

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

Ebb and Flo is a great house! The location is great, easy to walk to restaurants, stores, groceries, coffee, the beach. The location could not be better. We did have a plumbing issue, but the property company handled it very quickly and very well, there was a plumber there quickly and he was, also great. The outdoor space is excellent, the pool is very nice, the bar and dining area are very useful. The rooms and bathrooms are all very nice, and the kitchen is very well outfitted. We were able to cook there with no issues. all in all a great house.

Manager's Response

Thank you for your fantastic review Mary Lou. It was a pleasure hosting you! We are so glad you enjoyed the outdoors as well of the location and we look forward to welcoming you again next time you visit the island!

I don't do titles

March 2023
, Malvern, PA United States

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

Ebb and Flo is a great house! The location is great, easy to walk to restaurants, stores, groceries, coffee, the beach. The location could not be better. We did have a plumbing issue, but the property company handled it very quickly and very well, there was a plumber there quickly and he was, also great. The outdoor space is excellent, the pool is very nice, the bar and dining area are very useful. The rooms and bathrooms are all very nice, and the kitchen is very well outfitted. We were able to cook there with no issues. all in all a great house.

Manager's Response

Thank you for your fantastic review Mary Lou. It was a pleasure hosting you! We are so glad you enjoyed the outdoors as well of the location and we look forward to welcoming you again next time you visit the island!

Backyard Oasis

February 2023
, Minnetonka, MN United States

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

We honestly didn't spend much awake time in this house, which is a shame because the kitchen is spectacular. It was hard to be inside when the yard at this house is just a dream. The bar and table area has a fridge and ice maker- never needed to go inside! This house is very well appointed, close to Higgs beach, walking distance to everything, and has plenty of room for friends and family.

Manager's Response

We are so happy to read you had such a good stay with us Michelle! Please reach out to us for your next Key West vacation, we would love to welcome you back! Thank you for being our guest!

Ebb and flo paradise

May 2022
, Kamuela, HI US

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

The place was perfect for my needs. The management was above and beyond. Would most definitely rent it again.

Manager's Response

Thank you for your incredible review Elaine! 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!

Paradise on key west

March 2022
, Ocean city, NJ US

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

Ebb & Flo was just about perfect! Perfect space, location, privacy, and the outdoor space is incomparable to anywhere I’ve stayed. Our 3 adult children filtered in and out over the month with their significant others and all were impressed with the accommodations. The property management company, Shana in particular, was top notch! Shana responded immediately to any questions we had and was a wonderful comforting resource. We loved the location as it’s quiet and a bit removed from Duval street but it’s a quick walk anywhere. We did end up renting a golf cart which was so much fun. My husband biked to Higgs Beach every day for pickle ball. It too was close by. The house was very clean and we loved every minute of our 28 day stay.

Manager's Response

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

Key West Stay

January 2022
, Cornelius, NC United States

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

My wife and I rented this house for the month of January. Love the area and the pool and outdoor area. Only downside house is located on a very busy road.

Manager's Response

Thank you for your review Larry, we are glad you enjoyed the property and hope to welcome you again next time you visit the island!

Captain’s Choice

January 2020
, Murfreesboro , TN US

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

Wonderful home, very well maintained. Property Manager was excellent, responded within minutes. House was spotless. Stayed two months, the house was excellent.

Manager's Response

Dear Patricia,


Thank you for your wonderful review. We are so thrilled to hear how much you loved this home. We enjoyed hosting you and look forward to your return back.


Best Regards,


Wendy Zintsmaster and Team

Leave a Review
4 Bed
3 Baths
Sleeps 10

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BONITA EN ROSA ~ Peaceful Retreat!

BONITA EN ROSA ~ Adorable 2 Bedroom, 1 Bathroom Home with Lush Outdoor Space and Sparkling Pool Tucked Into Old Town District!

Location

1401 Duncan St. - BACK UNIT
33040 Key West , FL
United States
24° 33' 19.8" N, 81° 47' 15.216" W
See map: Google Maps
Florida US

BONITA EN ROSA ~ Peaceful Retreat!

Request More Information

BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w/ Pool!

Unit Code: BN

BONITA EN ROSA ~ Peaceful Retreat!

BONITA EN ROSA ~ Adorable 2 Bedroom, 1 Bathroom Home with Lush Outdoor Space and Sparkling Pool Tucked Into Old Town District!
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees. ISLAND TIME AWAITS… This tranquil island sanctuary calls your name awaiting peaceful moments and endless memories with your loved ones. Nestled within the Old Town district of Key West, this well appointed 2 bedroom, 1 bathroom home greets you with lush vegetation at every corner of this property creating a sensation of tranquility. Well equipped with all the everyday comforts of home paired with desirable modern luxuries, this haven is sure to welcome you into an unforgettable adventure.  ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… Step inside to find your cozy island abode boasting bright, natural lighting creating a cheery space. Sprawl out in the cozy living room that includes a flat screen TV and bookshelf full of novels for a rainy afternoon. A fully equipped kitchen lies nearby equipped with stainless steel appliances for meal prep which can be enjoyed at the indoor dining table for 4. Perch the doors open creating a lovely indoor/outdoor space with a sweet island breeze.  SLEEPING ARRANGEMENTS… The first guest room comes with a comfortable queen bed, flat screen TV and closet space for your belongings. The second guest room can be entered off the kitchen through double barn doors and includes a trundle bed, armoire storage and French doors leading out to the garden for your morning cup of coffee. Both guest rooms share a jack and jill full bathroom equipped with a walk in shower and newly refinished antique soaking tub. OUTDOOR LIVING… Find your serenity within the lush outdoor space as you calm your island soul in peaceful surroundings. Enjoy a dip pool which comes heated in the winter months followed by an evening under the stars in the rocking chairs or hammock. Grill out on the BBQ and dining al fresco with seating for 4 as you map out your next day's adventures. Peacefully located, this home allows for the best kind of R & R with only a short ride into town or the sandy beaches of Key West. 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. 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) 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. 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). FIND YOUR WANDERLUST…
October 2025
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DatesPrice
10/26/2025 - 10/31/2025$162 /nt
11/01/2025 - 11/30/2025$161 /nt
12/01/2025 - 12/31/2025$197 /nt
01/01/2026 - 01/31/2026$358 /nt
02/01/2026 - 02/28/2026$376 /nt
03/01/2026 - 03/31/2026$340 /nt
04/01/2026 - 04/30/2026$268 /nt
05/01/2026 - 07/31/2026$171 /nt
08/01/2026 - 09/30/2026$161 /nt
10/01/2026 - 10/26/2026$179 /nt
Leave a Review
2 Bed
1 Bath
Sleeps 4

Search Availability

LA PUERTA PEQUENA ~ Island Haven!

LA PUERTA PEQUENA ~ Adorable 1 Bedroom, 1 Bathroom with Loft in Peaceful and Convenient Old Town District!

Location

1211 Florida St. - FRONT UNIT
33040 Key West , FL
United States
24° 33' 19.8" N, 81° 47' 15.216" W
See map: Google Maps
Florida US

LA PUERTA PEQUENA ~ Island Haven!

Request More Information

Puerta Rosa

Reviewed by Jack N. on 2023-03-04
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
My one-month stay at Puerta Rosa was as good as can be expeced. It was clean, simply appointed with amenities, very accessible and not too expensive
Manager response on 2023-03-06 - Response from Best of Key West Rentals
Thank you for this great review Jack! We are thrilled you enjoyed the property and hope to host you again in the future!

LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w/ Loft in Old Town!

Unit Code: LU

LA PUERTA PEQUENA ~ Island Haven!

LA PUERTA PEQUENA ~ Adorable 1 Bedroom, 1 Bathroom with Loft in Peaceful and Convenient Old Town District!
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees. TRANQUILITY AWAITS… Nestled in the Old Town district of Key West, this picturesque island home awaits the creation of your tropical adventure. A bright and cheery space within a beautiful and lush Key West setting, this home is sure to allow all your worries to wash away. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… Walk up to a lovely porch, perfect for soaking up your peaceful surroundings with a coffee in hand as you watch neighbors passing by. Step inside to a an inviting living space with cozy furnishings and a flat screen TV. Find a small kitchen steps away to craft up your happy hour snacks and cocktails before a night out on the town. The washer/dryer is accessed from the exterior of the home and is shared with the rear unit. This property is equipped with a Ring Doorbell located next to the front door of the home. SLEEPING ARRANGEMENTS… Enjoy a peaceful night's rest in a comfortable full bed with a bathroom steps away with a shower tub combo. An upstairs loft with a twin mattress, or a queen Murphy bed down below can be used for additional sleeping arrangements. ***We recommend 3 adults max in this home. OUTDOOR LIVING… Peacefully located, this home allows for the best kind of R & R with only a short ride into town or the sandy beaches of Key West. 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. 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) 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. 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! **Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees. 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). SUN IS SHINING, THE WEATHER IS SWEET…
October 2025
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DatesPrice
10/26/2025 - 10/31/2025$103 /nt
11/01/2025 - 11/30/2025$102 /nt
12/01/2025 - 12/31/2025$108 /nt
01/01/2026 - 01/31/2026$215 /nt
02/01/2026 - 02/28/2026$250 /nt
03/01/2026 - 03/31/2026$215 /nt
04/01/2026 - 04/30/2026$161 /nt
05/01/2026 - 07/31/2026$143 /nt
08/01/2026 - 08/31/2026$125 /nt
09/01/2026 - 09/30/2026$136 /nt
10/01/2026 - 10/26/2026$143 /nt
4.0000
(1 Review)

Puerta Rosa

February 2023
, Maple Grove, MN US

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

My one-month stay at Puerta Rosa was as good as can be expeced. It was clean, simply appointed with amenities, very accessible and not too expensive

Manager's Response

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

Leave a Review
1 Bed
1 Bath
Sleeps 4

Search Availability

LA PUERTA ROSA~Tranquility!

LA PUERTA ROSA~ Charming 3 bed/2 bath Conch Home in Old Town with Private Outdoor Garden, Dip Pool and Parking Space! Your Tranquil Retreat for Endless Rest and Relaxation!

Location

1401 Duncan St.
33040 Key West , FL
United States
24° 33' 19.8" N, 81° 47' 15.216" W
See map: Google Maps
Florida US

LA PUERTA ROSA~Tranquility!

Request More Information

Excellent accommodations

Reviewed by Patricia G. on 2021-08-12
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We thoroughly enjoyed our stay here. It was quiet, comfortable and close to everything. The house is well equipped with everything one needs to feel at home and the pool and outside area are just perfect for Key West summers. Melanie, the property manager was extremely helpful and kind.
Manager response on 2021-08-17 - Response from Best of Key West Rentals
Thank you for this wonderful review Patricia, we are so glad you enjoyed the property and hope to welcome you again in the future.

Key West kitsch meets modern amenities

Reviewed by Unknown on 2020-11-17
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
I think this is the first rental house I've ever stayed in where the pictures actually matched the reality of the house. If you're thinking it looks like a small slice of paradise, it truly is!

The house was clean with plenty of initial supplies to get you through the first week. Check-in, as well as all interactions with the property manager, was quick and easy. The house location was perfect for us--residential and quiet, but a short 20 minute walk or 4 minute Uber to Duval or other hot spots. The best part is you are a five minute bike ride to Higgs beach and no more than 15 minutes to Smathers.

The backyard is the highlight of the house. The plunge pool is bigger than it looks and the owner has smartly created several seating areas throughout. Just wait until you're sitting on the deck, under the string lights, eating Key West spiced shrimp or something picked up from the local butcher a couple blocks away. (The grill works great too!)
Manager response on 2020-11-17 - Response from Best of Key West Rentals
Thank you for your incredible review. We enjoyed hosting you and hope to see you again!

So Soothing to my Soul

Reviewed by Tracy E. on 2020-04-03
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The moment I stepped up to the gate I knew I was home. This sanctuary on Duncan Street was truly a gift to my soul. The calm peaceful vibe that resonated from the beautiful landscape, the pool fountain and the pool, the bright welcoming kitchen and the perfectly decorated rooms could not be more to my taste. It was divinely planned for me to be "stuck" in key west at this beautiful magical home. I am forever grateful for my time spent exploring the simple daily pleasures of key west with La Puerta Rosa as my homebase. If you are seeking relaxation and a time for quiet reflection and peace in your soul...or just a beautiful home to spend time in while you vacation in Key West... Treat yourself to this home.
Manager response on 2020-04-03 - Response from Best of Key West Rentals
Dear Tracy, WOW! Thank you for this beautiful review on your recent stay at La Puerta Rosa. We are so thrilled to hear how much you loved this home and we hope to have the pleasure of hosting you again soon. Best Regards, Wendy Zintsmaster and Team

Great getaway!

Reviewed by Unknown on 2020-10-28
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We stayed here from July to mid-August and highly recommend! The house worked well for our needs and the outdoor space was perfect for days by the pool or relaxing and grilling in the evening.
Manager response on 2020-10-28 - Response from Best of Key West Rentals
Thank you for your wonderful review. We enjoyed hosting you in Paradise and hope to see you again soon!

Home away from Home

Reviewed by Unknown on 2020-10-05
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Thoroughly enjoyed our stay at La Puerta Rosa as it was like a home away from home for us. Highlights were the refreshing pool, the outdoor entertaining area and a spacious living room, kitchen and bathroom. The bedroom had a high ceiling and a very comfortable bed which was a great plus. The neighborhood is quiet and yet, you are in walking/cycling distance to cafe's, restaurants and Truman/Duval St. I would rent the cottage again particularly as our experience with the property manager and the neighbor very very positive. They have been extremely helpful and responded fast when we needed help.
Manager response on 2020-10-06 - Response from Best of Key West Rentals
Thank you for your wonderful review. We are so happy to hear how much you loved this home and hope to see you back soon!

LA PUERTA ROSA~Charming 3 bed/2 bath Conch Home in Old Town Key West!

Unit Code: LP

LA PUERTA ROSA~Tranquility!

LA PUERTA ROSA~ Charming 3 bed/2 bath Conch Home in Old Town with Private Outdoor Garden, Dip Pool and Parking Space! Your Tranquil Retreat for Endless Rest and Relaxation!
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees. TRANQUILITY AWAITS… Awaken your tropical senses in this well-appointed 3 bedroom, 2 bathroom retreat nestled into the Old Town district of Key West. Lush vegetation greets you at every corner of this property creating a sensation of tranquility. Well equipped with all the everyday home comforts enhanced by desirable modern luxuries, this haven is sure to make the most of your island vacation. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… This charming Conch sanctuary exudes bright and crisp décor representative of coastal living. Easy living can be achieved as you sprawl out in the cozy living room that includes a flat screen TV and bookshelf full of novels for a rainy afternoon. A fully equipped kitchen lies nearby showcasing stainless steel appliances for meal prep which can be enjoyed at the indoor dining table for 4. Perch the windows open as natural lighting pours through and invite the island breeze in creating a cheerful indoor/outdoor space. An additional living space is located at the front of this home equipped with a comfy seating area and small kitchen steps away. This property is equipped with a Ring Doorbell located next to the front door of the home. SLEEPING ARRANGEMENTS… The first guestroom comes with a comfortable queen bed, flat screen TV and closet space for your belongings. The second guestroom can be entered off the kitchen through double barn doors and includes a trundle bed, armoire storage and French doors leading out to the garden for your morning cup of coffee. Both guestrooms share a jack and jill full bathroom equipped with a walk in shower and newly refinished antique soaking tub. Residing within the front living area of this home is a full bed guest room and bathroom with a shower tub combo just steps away. An upstairs loft with a twin mattress or the sofa sleeper down below can be used for additional sleeping arrangements. OUTDOOR LIVING… Your dreamy outdoor oasis will fully complete your tropical vacation. A calming afternoon calls for unwinding in the heated dip pool followed by an evening under the stars in the rocking chairs or hammock. Enjoy grilling out on the BBQ and dining al fresco with seating for 4 as you map out your next day's adventures. A quaint front porch is the perfect spot for enjoying your cup of coffee as you watch neighbors pass by. Peacefully located, this home allows for the best kind of R & R with only a short ride into town or the sandy beaches of Key West. 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). SUN IS SHINING, THE WEATHER IS SWEET…
October 2025
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DatesPrice
10/26/2025 - 10/31/2025$242 /nt
11/01/2025 - 11/30/2025$215 /nt
12/01/2025 - 12/31/2025$243 /nt
01/01/2026 - 01/31/2026$500 /nt
02/01/2026 - 02/28/2026$572 /nt
03/01/2026 - 03/31/2026$543 /nt
04/01/2026 - 04/30/2026$358 /nt
05/01/2026 - 09/30/2026$250 /nt
10/01/2026 - 10/26/2026$268 /nt
5.0000
(5 Review)

Excellent accommodations

July 2021
, Frisco, TX United States

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

We thoroughly enjoyed our stay here. It was quiet, comfortable and close to everything. The house is well equipped with everything one needs to feel at home and the pool and outside area are just perfect for Key West summers. Melanie, the property manager was extremely helpful and kind.

Manager's Response

Thank you for this wonderful review Patricia, we are so glad you enjoyed the property and hope to welcome you again in the future.

Key West kitsch meets modern amenities

October 2020
, Edgewater, MD US

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

I think this is the first rental house I've ever stayed in where the pictures actually matched the reality of the house. If you're thinking it looks like a small slice of paradise, it truly is!

The house was clean with plenty of initial supplies to get you through the first week. Check-in, as well as all interactions with the property manager, was quick and easy. The house location was perfect for us--residential and quiet, but a short 20 minute walk or 4 minute Uber to Duval or other hot spots. The best part is you are a five minute bike ride to Higgs beach and no more than 15 minutes to Smathers.

The backyard is the highlight of the house. The plunge pool is bigger than it looks and the owner has smartly created several seating areas throughout. Just wait until you're sitting on the deck, under the string lights, eating Key West spiced shrimp or something picked up from the local butcher a couple blocks away. (The grill works great too!)

Manager's Response

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

Home away from Home

September 2020
, Key West, FL United States

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

Thoroughly enjoyed our stay at La Puerta Rosa as it was like a home away from home for us. Highlights were the refreshing pool, the outdoor entertaining area and a spacious living room, kitchen and bathroom. The bedroom had a high ceiling and a very comfortable bed which was a great plus. The neighborhood is quiet and yet, you are in walking/cycling distance to cafe's, restaurants and Truman/Duval St. I would rent the cottage again particularly as our experience with the property manager and the neighbor very very positive. They have been extremely helpful and responded fast when we needed help.

Manager's Response

Thank you for your wonderful review. We are so happy to hear how much you loved this home and hope to see you back soon!

Great getaway!

July 2020

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

We stayed here from July to mid-August and highly recommend! The house worked well for our needs and the outdoor space was perfect for days by the pool or relaxing and grilling in the evening.

Manager's Response

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

So Soothing to my Soul

February 2020
, Milwaukee, WI US

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

The moment I stepped up to the gate I knew I was home. This sanctuary on Duncan Street was truly a gift to my soul. The calm peaceful vibe that resonated from the beautiful landscape, the pool fountain and the pool, the bright welcoming kitchen and the perfectly decorated rooms could not be more to my taste. It was divinely planned for me to be "stuck" in key west at this beautiful magical home. I am forever grateful for my time spent exploring the simple daily pleasures of key west with La Puerta Rosa as my homebase. If you are seeking relaxation and a time for quiet reflection and peace in your soul...or just a beautiful home to spend time in while you vacation in Key West... Treat yourself to this home.

Manager's Response

Dear Tracy,


WOW! Thank you for this beautiful review on your recent stay at La Puerta Rosa. We are so thrilled to hear how much you loved this home and we hope to have the pleasure of hosting you again soon.


Best Regards,


Wendy Zintsmaster and Team

Leave a Review
3 Bed
2 Baths
Sleeps 6

Search Availability

SAILOR HOUSE ~ Steps to Duval!

SAILOR HOUSE ~ Grand Opening Rates! Adorable 2 Bedroom, 1.5 Bathroom Home with Charming Outdoor Space and Sundeck Just Steps to Everything on Duval St.!

Location

824 Center St.
33040 Key West , FL
United States
24° 33' 8.892" N, 81° 47' 58.344" W
See map: Google Maps
Florida US

SAILOR HOUSE ~ Steps to Duval!

Request More Information

Lovely - great location

Reviewed by Danny B. on 2025-10-17
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Would rent again
Manager response on 2025-10-23 - Response from Best of Key West Rentals
Danny, 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.

Don't hesitate. Book it now!

Reviewed by Unknown on 2025-04-14
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Sailor house is wonderful! Everything was exceptionally clean and comfortable. It is quiet and roomy. The host was very responsive when we asked a question and she even sent us something that we left behind. The house is only one block from Duval St. where there are endless restaurants, bars with live music & shops. We found a parking spot & left our car there for our entire stay. We rented bikes & either rode or walked everywhere we went. The beaches are very easily reachable with a bike. There is a nice sidewalk along the south side of the island that is situated right along the water & you can bike on it (about 3.5 miles). This is the best biking on the island because you don't deal with traffic. The Key West Cuban Coffee Shop that is on the corner just 1.5 blocks south from the Sailor House served a fabulous breakfast. Other great breakfast spots are La Grignote & Frenchie's Cafe. Blue Heaven was our favorite restaurant. Kari Wolf is an amazing performer who played at some of the bars.
Manager response on 2025-08-26 - Response from Best of Key West Rentals
We’re grateful for your glowing review Ellen! It was such a pleasure to host you, and we’re already looking forward to your return to the island.

A Nice Stay at Sailor House

Reviewed by Unknown on 2025-03-02
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Overall, it was wonderful experience staying at Sailor House. Communication with the property management was outstanding - very responsive. Things we loved: Being so close to Duval St yet on a quiet street. The outdoor space - spacious, private area in the back of the house where we had most of our meals (using the grill a lot); deck off the master bedroom is very private and sunny; front second floor porch with the swing. Master bedroom mattress was so comfortable. The kitchen is adequately equipped. The biggest drawback is the neighborhood, specifically a house directly across the street that was a bit shabby. And one day the couple living there had a huge argument right outside their house - yelling and using the "F" word a lot. This wouldn't deter us from staying at Sailor House again because the house itself and the proximity to Duval Street is great.
Manager response on 2025-08-26 - Response from Best of Key West Rentals
Thank you for your thoughtful feedback! We’re so glad you had a wonderful experience at Sailor House and that you enjoyed the many unique spaces it offers — from the sunny private deck off the master to the porch swing and spacious outdoor dining area. It’s great to hear the location and comfort of the home made your stay enjoyable. We also appreciate your kind words about our communication — it means a lot to us that you felt well taken care of during your visit. We regret to hear about the incident across the street and understand how that could have been unsettling. While this is outside of our control, we’re grateful that it didn’t take away from your overall enjoyment of the property. We’d be delighted to host you again and look forward to welcoming you back to Sailor House in the future!

Nice

Reviewed by Unknown on 2024-10-28
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Great place and perfect location. Quick walk to everything.
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!

Key West Experience

Reviewed by Unknown on 2025-03-11
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Our experience at the Sailor House in Key West was exceptional. The different outside sitting areas were fabulous, and yes we took advantage of all areas. The beds were very comfortable and the amenities provided met our needs. We were able to secure a parking spot in front of the house, otherwise it would have been a challenge. On our next visit to Key West we will definitely be staying here again.
Manager response on 2025-08-26 - Response from Best of Key West Rentals
We’re so glad you had a great time with us Lisa—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 Place

Reviewed by David A. on 2025-03-21
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Recommend to Others
Really enjoyed our stay at the Sailor House. Very nice place, with everything we needed for our stay. Also, a great location for all the festivities in Key West.
Manager response on 2025-08-26 - Response from Best of Key West Rentals
Thanks so much for the lovely feedback David! We’re happy to hear you enjoyed the property and would love to host you again in the future.

Amazing place close to everything

Reviewed by steven b. on 2023-10-14
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Recommend to Others
What a hidden gem. Just off Duval street, but you'd never know it, secluded feel, quiet neighborhood. The property Manger Brian was awesome. We will be staying here again next year, planning our trip already. You can't go wrong with this place.
Manager response on 2023-11-08 - Response from Best of Key West Rentals
Thank you for your review Steven. We are so thrilled to hear how much you loved this home and hope to see you again!

What a Great Find!

Reviewed by Unknown on 2023-10-19
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Recommend to Others
Our stay at Sailor House was better than we ever could have imagined. The house is clean and comfortable, and we loved sitting on the back deck. The location could not have been better - close to so many Key West attractions and our favorite restaurants. The outdoor shower, bathroom and laundry came in very handy. The only negative was that there is no designated parking. After one night in the parking garage, we were able to snag a spot right in front of the house, so it turned out to be a very minor issue. We would most definitely stay there again!
Manager response on 2023-11-08 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us Christa! We would love to welcome you back!

Charming Sailor House

Reviewed by Margaret S. on 2024-01-31
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Recommend to Others
What a beautiful little home in the heart of Key West. It is very evident that the home is very well cared for and it was extremely clean. We had a wonderful stay and so enjoyed getting to see and know Key West and all it offers. Shana, the manager, was very helpful. Only issue was the parking but once parked no need to move your vehicle because everything is within walking distance. Highly recommend this sweet spot
Manager response on 2024-05-23 - Response from Best of Key West Rentals
Thank you for taking the time to post a review of our property. We are so happy to hear that you enjoyed your time in Key West. Our goal is always to exceed your expectations! If there's anything we can help you with during your next visit, please don't hesitate to let us know.

Perfect Location

Reviewed by Kim C. on 2023-12-24
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Recommend to Others
This home was perfect for our one week vacation! It was just a block from everything you need and at the same time quiet. Home is so lovely and comfortable and has all the amenities you need. I would definitely stay here again! It was perfect!
Manager response on 2024-05-23 - Response from Best of Key West Rentals
Thank you for your wonderful review. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Great stay in Key West

Reviewed by Daisy S. on 2024-03-19
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Recommend to Others
Sailor House was excellent all around. Location perfect. House super clean. Beds very comfortable. The managing company went above and beyond to solve any problem we had. The only minor issue was parking. Street parking was full during our stay. We recommend parking in Old Town Parking Garage during your stay if street parking is not available.
Manager response on 2024-05-23 - Response from Best of Key West Rentals
Thank you for this great review Daisy! We are thrilled you enjoyed the property and hope to host you again in the future!

Sailor House Review

Reviewed by Russell J. on 2024-03-08
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Recommend to Others
A very clean, spacious and well-appointed house. Beds are super comfortable. Outside second bathroom a real plus for multiple guests. Location is great, just a block from Duval St., and on the quieter end. Host communication was excellent whenever needed. Overall, would highly recommend.
Manager response on 2024-05-23 - 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!

Sailor House enjoyed

Reviewed by Darlene S. on 2024-05-23
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Recommend to Others
This was our first time visiting Key West and we stayed at the Sailor House at the end of April. The home was very clean and comfortable, air conditioning worked well and the location was very convenient. All the lower and upper porches and decks were nice outside options to read a book or drink a morning coffee. A block away was a shop where we rented a bike one day and a golf cart for 4 hours another day. Moondog Cafe and El Siboney were our favorite restaurants just a short walk from the home. We very much enjoyed our stay at the Sailor House.
Manager response on 2024-05-23 - Response from Best of Key West Rentals
Thank you for your fantastic review Darlene. It was a pleasure hosting you and we hope to welcome you again next time you visit the island!

Was a very special place. We loved the location and the house.

Reviewed by Mark J. on 2024-09-22
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Recommend to Others
Perfect experience. Highly recommend and we will go back.
Manager response on 2025-08-26 - Response from Best of Key West Rentals
Your kind words mean the world to us Mark! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

Excellent location!

Reviewed by Tristal H. on 2021-12-03
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Recommend to Others
We couldn’t have stayed at a place with a better location. We parked our car when we arrived and didn’t move it till we left to go home. We walked everywhere and everything was so close. My favorite spot was the top deck where I’d watch the sun rise each morning. My only issue is there was no lock on the bathroom door and not much privacy when using the bathroom as the door had slats on it. We had such a great stay and this house, it had everything we needed. Would def stay here again. Thanks for the great trip!!
Manager response on 2021-12-03 - Response from Best of Key West Rentals
Tristal thank you for your review, we are thrilled you enjoyed the house so much! We are taking notes concerning the bathroom door and will plan to improve it. We hope to be able to host you again next time you visit the island.

Wonderful Experience.

Reviewed by Derek L. on 2021-12-16
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Recommend to Others
The house was awesome, clean, and perfect for a quick getaway. Brian the property manager was amazing!
Manager response on 2021-12-16 - Response from Best of Key West Rentals
Thank you for this great review Derek! We hope to have the pleasure to host you again next time you visit Key West!

Location, location, location

Reviewed by Donald D. on 2022-02-22
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Recommend to Others
Very well maintain property. Can’t say enough about the location. Aptly located on Center street, it truly is in the middle of everything thing in Key West. Within walking distance to everything. Was a little worried about the sliding doors for bedrooms, but was pleasantly surprised about noise levels between bedrooms. Loved the balconies and especially the back deck. Kitchen nicely stocked with utensils and pots and pans to do cooking if you’d like. New outdoor grill was a nice touch. We put everything to use and can say it was great. Thanks again.
Manager response on 2022-02-22 - Response from Best of Key West Rentals
Thank you for your wonderful review Donald. We enjoyed hosting you and hope to see you back in Key West again soon!

Great location and floor plan. Parking could have been an issue.

Reviewed by Unknown on 2022-04-24
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Recommend to Others
Fabulous! Again, the location could not have been better. 4 adults stayed plenty of room.
Manager response on 2022-04-26 - Response from Best of Key West Rentals
Thank you for your wonderful review Lori. We enjoyed hosting you and hope to see you back in Key West again soon!

A fun getaway

Reviewed by Unknown on 2022-08-03
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Recommend to Others
Sailors house was a perfect find. One block off Duval Street. Close to everything. House was charming and very clean clean. We had a wonderful time!!
Manager response on 2022-08-12 - Response from Best of Key West Rentals
Thank you for your fantastic review Susan. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

The best accommodations!

Reviewed by Mary D. on 2022-09-29
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Recommend to Others
Best accommodations in Key West!! Location! Clean! Adorable!
Manager response on 2022-10-06 - Response from Best of Key West Rentals
Thank you for this short but sweet five star review Mary, we hope to have the please to host you again next time you visit the island.

Lovely stay!

Reviewed by Mary Anne T. on 2023-01-24
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Recommend to Others
Was a delightful getaway. Was cared for and comfortable. Happy to recommend.
Manager response on 2023-02-27 - Response from Best of Key West Rentals
Thank you for your wonderful review Mary. We enjoyed hosting you and hope to see you back in Key West again soon!

Perfect House

Reviewed by Lori P. on 2023-01-10
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Location
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Recommend to Others
Amazing location, management was amazing. The house was very clean and the pictures posted looked exactly as good he house perfect
Manager response on 2023-01-10 - Response from Best of Key West Rentals
Thank you for this wonderful review Lori, 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.

Great location

Reviewed by John w. on 2023-02-09
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Recommend to Others
Perfectly clean and a great stay for 2couples! Very spacious first floor and 3 awesome outdoor areas to hang out, book it!
Manager response on 2023-02-27 - Response from Best of Key West Rentals
Thank you for your review John. We are so thrilled to hear how much you loved this home and hope to see you again!

Sailor House

Reviewed by Nancy C. on 2023-03-22
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Location
Property condition
Recommend to Others
Very good. The only downside was construction next door.
Manager response on 2023-11-08 - Response from Best of Key West Rentals
Thank you for taking the time to review your stay Nancy, sorry you had to deal with construction noise, it has since stopped and we are back to hearing live music and roosters' songs I promise! Please come visit us again soon!

Weekend Getaway 2023

Reviewed by Unknown on 2023-03-23
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Recommend to Others
We just stayed at the Sailor House the second week of March. The house was an absolute Key West dream! It was perfect just like the photos with every amenity you could possibly think of. The whole process of renting it was simple. Brian, the property manager, made everything so easy. He is very available to answer any questions you may have. You could not ask for a better location. It’s one block off Duval Street yet it was really quiet. We were there for our daughter’s 21st birthday. We had made reservations one month in advance at Nine One Five which to our delight was literally around the corner from the house. Excellent restaurant by the way! I have already recommended the Sailor House to all my family and friends.

Manager response on 2023-11-08 - Response from Best of Key West Rentals
Thank you for this great review Pamela! We are thrilled you enjoyed the property and hope to host you again in the future!

EXCELLENT ACCOMODATIONS!!

Reviewed by Tyler S. on 2023-05-11
Overall satisfaction
Services from rental manager
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Location
Property condition
Recommend to Others
Everything about the property was perfect and well kept! We would stay here again in a heartbeat!!
Manager response on 2023-11-08 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us Tyler! We would love to welcome you back!

Great Spot Great Place Great Time

Reviewed by Jack P. on 2023-06-13
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Services from rental manager
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Location
Property condition
Recommend to Others
The thoughtfulness and care put into the selection of pictures, decorations and furniture was evident. They brightened up the house and made it feel like a home rather than a rental. Very cozy and comfortable. The location is perfect for walking access to anything you need or would want to do; restaurants, shopping sight seeing, water activities, etc. The street is quiet and gives you the full Key West feel and experience. The house is clean, air conditioned and fully stocked with books, games, and everything you need in the kitchen for cooking and dining at home. Loved the patios, both upstairs and down. The manager Bryan was extremely helpful and always available with the answer to any question we had. Check-in and check-out was simple and easy. Would not hesitate to stay here again.
Manager response on 2023-11-08 - Response from Best of Key West Rentals
Thank you for this great review Jack! We are thrilled you enjoyed the property and hope to host you again in the future!

Delightful place to stay in Key west!

Reviewed by Catherine L. on 2023-10-10
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Location
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Recommend to Others
Could walk to everything we wanted to see from one end of Duval street to the other.
Manager response on 2023-11-08 - Response from Best of Key West Rentals
Thank you for your wonderful review. We are thrilled you loved this home and hope to host you again soon!

SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!

Unit Code: SH

SAILOR HOUSE ~ Steps to Duval!

SAILOR HOUSE ~ Grand Opening Rates! Adorable 2 Bedroom, 1.5 Bathroom Home with Charming Outdoor Space and Sundeck Just Steps to Everything on Duval St.!
FAR FROM ORDINARY... Extraordinary moments and blissful surroundings lie ahead for your Key West adventure as you soak in an alternate reality full of sunshine and serenity. Nestled just 1 block off the fun-loving Duval St., this cozy retreat makes your time in Paradise hard to leave with everything at your fingertips such as all the highly adored restaurants, bars and attractions. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... Greeted by swaying palms and lush greenery surrounding this charming tropical getaway, the stress of the real world instantly washes away. A front porch begins your time calling for a good book as you unwind and watch neighbors passing by. Find a bright and open Great Room inside outfitted with comfortable furnishings, a writing desk and a flat screen TV. A fully equipped kitchen area includes a table for 4 and bar top seating for 3. SLEEPING ARRANGEMENTS... Follow the stairs up to two comfortable guest rooms lying beyond charming barn doors for your peaceful night's rest. The first room comes with a queen bed and a TV with direct access to the front balcony with a charming swing to overlook the vibrant neighborhood. The second room comes with a king bed and a TV , as well as access to a rear facing private sundeck with loungers for your lazy days. Full bathroom with shower is located on the second floor. An additional half bathroom lies outside off the back porch area. OUTDOOR LIVING... Slip outside from the kitchen area to your covered, tranquil outdoor oasis. Grill up your fresh catch of the day to be enjoyed at the outdoor table for 4. Enjoy an outdoor shower so you can rinse off after a fun summer day out on the town. This property is just a stone's throw from the famous Duval St. making your time in Paradise practically perfect. 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. 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. PARADISE AT YOUR FINGERTIPS...
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Age 18 and under.
DatesPrice
10/26/2025 - 10/30/2025$278 /nt
10/31/2025 - 10/31/2025$295 /nt
11/01/2025 - 11/01/2025$328 /nt
11/02/2025 - 11/02/2025$286 /nt
11/03/2025 - 11/04/2025$278 /nt
11/05/2025 - 11/05/2025$343 /nt
11/06/2025 - 11/06/2025$479 /nt
11/07/2025 - 11/07/2025$517 /nt
11/08/2025 - 11/08/2025$530 /nt
11/09/2025 - 11/09/2025$431 /nt
11/10/2025 - 11/10/2025$319 /nt
11/11/2025 - 11/11/2025$284 /nt
11/12/2025 - 11/12/2025$293 /nt
11/13/2025 - 11/13/2025$355 /nt
11/14/2025 - 11/14/2025$385 /nt
11/15/2025 - 11/15/2025$392 /nt
11/16/2025 - 11/16/2025$336 /nt
11/17/2025 - 11/17/2025$291 /nt
11/18/2025 - 11/18/2025$296 /nt
11/19/2025 - 11/19/2025$306 /nt
11/20/2025 - 11/20/2025$340 /nt
11/21/2025 - 11/21/2025$369 /nt
11/22/2025 - 11/22/2025$408 /nt
11/23/2025 - 11/23/2025$328 /nt
11/24/2025 - 11/24/2025$310 /nt
11/25/2025 - 11/25/2025$346 /nt
11/26/2025 - 11/26/2025$410 /nt
11/27/2025 - 11/27/2025$416 /nt
11/28/2025 - 11/28/2025$442 /nt
11/29/2025 - 11/29/2025$428 /nt
11/30/2025 - 12/03/2025$278 /nt
12/04/2025 - 12/04/2025$322 /nt
12/05/2025 - 12/05/2025$415 /nt
12/06/2025 - 12/06/2025$382 /nt
12/07/2025 - 12/07/2025$331 /nt
12/08/2025 - 12/08/2025$303 /nt
12/09/2025 - 12/09/2025$295 /nt
12/10/2025 - 12/10/2025$298 /nt
12/11/2025 - 12/11/2025$343 /nt
12/12/2025 - 12/12/2025$490 /nt
12/13/2025 - 12/13/2025$467 /nt
12/14/2025 - 12/14/2025$408 /nt
12/15/2025 - 12/16/2025$278 /nt
12/17/2025 - 12/17/2025$280 /nt
12/18/2025 - 12/18/2025$318 /nt
12/19/2025 - 12/19/2025$448 /nt
12/20/2025 - 12/20/2025$456 /nt
12/21/2025 - 12/21/2025$469 /nt
12/22/2025 - 12/22/2025$475 /nt
12/23/2025 - 12/23/2025$491 /nt
12/24/2025 - 12/24/2025$584 /nt
12/25/2025 - 12/25/2025$598 /nt
12/26/2025 - 12/26/2025$736 /nt
12/27/2025 - 12/27/2025$838 /nt
12/28/2025 - 12/28/2025$921 /nt
12/29/2025 - 12/29/2025$942 /nt
12/30/2025 - 12/30/2025$955 /nt
12/31/2025 - 12/31/2025$941 /nt
01/01/2026 - 01/01/2026$805 /nt
01/02/2026 - 01/02/2026$639 /nt
01/03/2026 - 01/03/2026$643 /nt
01/04/2026 - 01/04/2026$743 /nt
01/05/2026 - 01/05/2026$525 /nt
01/06/2026 - 01/06/2026$442 /nt
01/07/2026 - 01/07/2026$461 /nt
01/08/2026 - 01/08/2026$495 /nt
01/09/2026 - 01/09/2026$565 /nt
01/10/2026 - 01/10/2026$583 /nt
01/11/2026 - 01/11/2026$593 /nt
01/12/2026 - 01/12/2026$517 /nt
01/13/2026 - 01/13/2026$503 /nt
01/14/2026 - 01/14/2026$528 /nt
01/15/2026 - 01/15/2026$735 /nt
01/16/2026 - 01/16/2026$844 /nt
01/17/2026 - 01/17/2026$993 /nt
01/18/2026 - 01/18/2026$806 /nt
01/19/2026 - 01/19/2026$598 /nt
01/20/2026 - 01/20/2026$668 /nt
01/21/2026 - 01/21/2026$682 /nt
01/22/2026 - 01/22/2026$728 /nt
01/23/2026 - 01/23/2026$779 /nt
01/24/2026 - 01/24/2026$794 /nt
01/25/2026 - 01/25/2026$541 /nt
01/26/2026 - 01/26/2026$688 /nt
01/27/2026 - 01/27/2026$690 /nt
01/28/2026 - 01/28/2026$806 /nt
01/29/2026 - 01/29/2026$872 /nt
01/30/2026 - 01/30/2026$807 /nt
01/31/2026 - 01/31/2026$817 /nt
02/01/2026 - 02/01/2026$653 /nt
02/02/2026 - 02/02/2026$631 /nt
02/03/2026 - 02/03/2026$640 /nt
02/04/2026 - 02/04/2026$671 /nt
02/05/2026 - 02/05/2026$733 /nt
02/06/2026 - 02/06/2026$771 /nt
02/07/2026 - 02/07/2026$792 /nt
02/08/2026 - 02/08/2026$729 /nt
02/09/2026 - 02/09/2026$721 /nt
02/10/2026 - 02/10/2026$733 /nt
02/11/2026 - 02/11/2026$757 /nt
02/12/2026 - 02/12/2026$802 /nt
02/13/2026 - 02/13/2026$892 /nt
02/14/2026 - 02/14/2026$789 /nt
02/15/2026 - 02/15/2026$840 /nt
02/16/2026 - 02/16/2026$746 /nt
02/17/2026 - 02/17/2026$686 /nt
02/18/2026 - 02/18/2026$708 /nt
02/19/2026 - 02/19/2026$745 /nt
02/20/2026 - 02/20/2026$768 /nt
02/21/2026 - 02/21/2026$774 /nt
02/22/2026 - 02/22/2026$733 /nt
02/23/2026 - 02/23/2026$714 /nt
02/24/2026 - 02/24/2026$707 /nt
02/25/2026 - 02/25/2026$714 /nt
02/26/2026 - 02/26/2026$731 /nt
02/27/2026 - 02/27/2026$740 /nt
02/28/2026 - 02/28/2026$735 /nt
03/01/2026 - 03/01/2026$694 /nt
03/02/2026 - 03/02/2026$678 /nt
03/03/2026 - 03/03/2026$668 /nt
03/04/2026 - 03/04/2026$681 /nt
03/05/2026 - 03/05/2026$704 /nt
03/06/2026 - 03/06/2026$808 /nt
03/07/2026 - 03/07/2026$813 /nt
03/08/2026 - 03/09/2026$781 /nt
03/10/2026 - 03/10/2026$776 /nt
03/11/2026 - 03/11/2026$792 /nt
03/12/2026 - 03/12/2026$816 /nt
03/13/2026 - 03/13/2026$832 /nt
03/14/2026 - 03/14/2026$831 /nt
03/15/2026 - 03/15/2026$698 /nt
03/16/2026 - 03/16/2026$691 /nt
03/17/2026 - 03/17/2026$676 /nt
03/18/2026 - 03/18/2026$685 /nt
03/19/2026 - 03/19/2026$705 /nt
03/20/2026 - 03/20/2026$711 /nt
03/21/2026 - 03/21/2026$707 /nt
03/22/2026 - 03/22/2026$650 /nt
03/23/2026 - 03/23/2026$646 /nt
03/24/2026 - 03/24/2026$634 /nt
03/25/2026 - 03/25/2026$616 /nt
03/26/2026 - 03/26/2026$603 /nt
03/27/2026 - 03/28/2026$894 /nt
03/29/2026 - 03/29/2026$826 /nt
03/30/2026 - 03/30/2026$622 /nt
03/31/2026 - 03/31/2026$609 /nt
04/01/2026 - 04/01/2026$582 /nt
04/02/2026 - 04/02/2026$676 /nt
04/03/2026 - 04/03/2026$715 /nt
04/04/2026 - 04/04/2026$711 /nt
04/05/2026 - 04/05/2026$631 /nt
04/06/2026 - 04/06/2026$618 /nt
04/07/2026 - 04/07/2026$556 /nt
04/08/2026 - 04/08/2026$566 /nt
04/09/2026 - 04/09/2026$610 /nt
04/10/2026 - 04/10/2026$632 /nt
04/11/2026 - 04/11/2026$624 /nt
04/12/2026 - 04/12/2026$526 /nt
04/13/2026 - 04/13/2026$491 /nt
04/14/2026 - 04/14/2026$472 /nt
04/15/2026 - 04/15/2026$479 /nt
04/16/2026 - 04/16/2026$538 /nt
04/17/2026 - 04/17/2026$597 /nt
04/18/2026 - 04/18/2026$600 /nt
04/19/2026 - 04/19/2026$501 /nt
04/20/2026 - 04/20/2026$441 /nt
04/21/2026 - 04/21/2026$430 /nt
04/22/2026 - 04/22/2026$509 /nt
04/23/2026 - 04/23/2026$587 /nt
04/24/2026 - 04/24/2026$690 /nt
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04/27/2026 - 04/27/2026$509 /nt
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06/28/2026 - 06/28/2026$397 /nt
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07/01/2026 - 07/01/2026$407 /nt
07/02/2026 - 07/02/2026$595 /nt
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10/26/2026 - 10/26/2026$370 /nt
4.9643
(28 Review)

Lovely - great location

October 2025
, Dallas, TX United States

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

Would rent again

Manager's Response

Danny, 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.

Don't hesitate. Book it now!

March 2025
, Marathon, WI US

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

Sailor house is wonderful! Everything was exceptionally clean and comfortable. It is quiet and roomy. The host was very responsive when we asked a question and she even sent us something that we left behind. The house is only one block from Duval St. where there are endless restaurants, bars with live music & shops. We found a parking spot & left our car there for our entire stay. We rented bikes & either rode or walked everywhere we went. The beaches are very easily reachable with a bike. There is a nice sidewalk along the south side of the island that is situated right along the water & you can bike on it (about 3.5 miles). This is the best biking on the island because you don't deal with traffic. The Key West Cuban Coffee Shop that is on the corner just 1.5 blocks south from the Sailor House served a fabulous breakfast. Other great breakfast spots are La Grignote & Frenchie's Cafe. Blue Heaven was our favorite restaurant. Kari Wolf is an amazing performer who played at some of the bars.

Manager's Response

We’re grateful for your glowing review Ellen! It was such a pleasure to host you, and we’re already looking forward to your return to the island.

Great Place

March 2025
, Carolina Beach, NC US

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

Really enjoyed our stay at the Sailor House. Very nice place, with everything we needed for our stay. Also, a great location for all the festivities in Key West.

Manager's Response

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

Key West Experience

February 2025
, Portsmouth, VA United States

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

Our experience at the Sailor House in Key West was exceptional. The different outside sitting areas were fabulous, and yes we took advantage of all areas. The beds were very comfortable and the amenities provided met our needs. We were able to secure a parking spot in front of the house, otherwise it would have been a challenge. On our next visit to Key West we will definitely be staying here again.

Manager's Response

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

A Nice Stay at Sailor House

February 2025
, South Dartmouth, MA US

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

Overall, it was wonderful experience staying at Sailor House. Communication with the property management was outstanding - very responsive. Things we loved: Being so close to Duval St yet on a quiet street. The outdoor space - spacious, private area in the back of the house where we had most of our meals (using the grill a lot); deck off the master bedroom is very private and sunny; front second floor porch with the swing. Master bedroom mattress was so comfortable. The kitchen is adequately equipped. The biggest drawback is the neighborhood, specifically a house directly across the street that was a bit shabby. And one day the couple living there had a huge argument right outside their house - yelling and using the "F" word a lot. This wouldn't deter us from staying at Sailor House again because the house itself and the proximity to Duval Street is great.

Manager's Response

Thank you for your thoughtful feedback! We’re so glad you had a wonderful experience at Sailor House and that you enjoyed the many unique spaces it offers — from the sunny private deck off the master to the porch swing and spacious outdoor dining area. It’s great to hear the location and comfort of the home made your stay enjoyable.

We also appreciate your kind words about our communication — it means a lot to us that you felt well taken care of during your visit.

We regret to hear about the incident across the street and understand how that could have been unsettling. While this is outside of our control, we’re grateful that it didn’t take away from your overall enjoyment of the property.

We’d be delighted to host you again and look forward to welcoming you back to Sailor House in the future!

Nice

October 2024
, Woodstock, IL United States

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

Great place and perfect location. Quick walk to everything.

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!

Was a very special place. We loved the location and the house.

September 2024
, Moseley, VA US

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

Perfect experience. Highly recommend and we will go back.

Manager's Response

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

Sailor House enjoyed

April 2024
, SHELBURNE, VT US

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

This was our first time visiting Key West and we stayed at the Sailor House at the end of April. The home was very clean and comfortable, air conditioning worked well and the location was very convenient. All the lower and upper porches and decks were nice outside options to read a book or drink a morning coffee. A block away was a shop where we rented a bike one day and a golf cart for 4 hours another day. Moondog Cafe and El Siboney were our favorite restaurants just a short walk from the home. We very much enjoyed our stay at the Sailor House.

Manager's Response

Thank you for your fantastic review Darlene. It was a pleasure hosting you and we hope to welcome you again next time you visit the island!

Great stay in Key West

February 2024
, Miami, FL US

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

Sailor House was excellent all around. Location perfect. House super clean. Beds very comfortable. The managing company went above and beyond to solve any problem we had. The only minor issue was parking. Street parking was full during our stay. We recommend parking in Old Town Parking Garage during your stay if street parking is not available.

Manager's Response

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

Sailor House Review

February 2024
, Baldwinsville, NY US

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

A very clean, spacious and well-appointed house. Beds are super comfortable. Outside second bathroom a real plus for multiple guests. Location is great, just a block from Duval St., and on the quieter end. Host communication was excellent whenever needed. Overall, would highly recommend.

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!

Charming Sailor House

January 2024
, Twin Falls, ID US

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

What a beautiful little home in the heart of Key West. It is very evident that the home is very well cared for and it was extremely clean. We had a wonderful stay and so enjoyed getting to see and know Key West and all it offers. Shana, the manager, was very helpful. Only issue was the parking but once parked no need to move your vehicle because everything is within walking distance. Highly recommend this sweet spot

Manager's Response

Thank you for taking the time to post a review of our property. We are so happy to hear that you enjoyed your time in Key West. Our goal is always to exceed your expectations! If there's anything we can help you with during your next visit, please don't hesitate to let us know.

Perfect Location

December 2023
, Manchester, NH US

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

This home was perfect for our one week vacation! It was just a block from everything you need and at the same time quiet. Home is so lovely and comfortable and has all the amenities you need. I would definitely stay here again! It was perfect!

Manager's Response

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

What a Great Find!

October 2023
, Royal Palm Beach, FL US

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

Our stay at Sailor House was better than we ever could have imagined. The house is clean and comfortable, and we loved sitting on the back deck. The location could not have been better - close to so many Key West attractions and our favorite restaurants. The outdoor shower, bathroom and laundry came in very handy. The only negative was that there is no designated parking. After one night in the parking garage, we were able to snag a spot right in front of the house, so it turned out to be a very minor issue. We would most definitely stay there again!

Manager's Response

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

Amazing place close to everything

September 2023
, crystal, MN US

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

What a hidden gem. Just off Duval street, but you'd never know it, secluded feel, quiet neighborhood. The property Manger Brian was awesome. We will be staying here again next year, planning our trip already. You can't go wrong with this place.

Manager's Response

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

Delightful place to stay in Key west!

September 2023
, Boca Raton, FL US

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

Could walk to everything we wanted to see from one end of Duval street to the other.

Manager's Response

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

Great Spot Great Place Great Time

June 2023
, Downingtown, PA US

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

The thoughtfulness and care put into the selection of pictures, decorations and furniture was evident. They brightened up the house and made it feel like a home rather than a rental. Very cozy and comfortable. The location is perfect for walking access to anything you need or would want to do; restaurants, shopping sight seeing, water activities, etc. The street is quiet and gives you the full Key West feel and experience. The house is clean, air conditioned and fully stocked with books, games, and everything you need in the kitchen for cooking and dining at home. Loved the patios, both upstairs and down. The manager Bryan was extremely helpful and always available with the answer to any question we had. Check-in and check-out was simple and easy. Would not hesitate to stay here again.

Manager's Response

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

EXCELLENT ACCOMODATIONS!!

May 2023
, Feazee, MN US

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

Everything about the property was perfect and well kept! We would stay here again in a heartbeat!!

Manager's Response

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

Sailor House

March 2023
, Media, PA US

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

Very good. The only downside was construction next door.

Manager's Response

Thank you for taking the time to review your stay Nancy, sorry you had to deal with construction noise, it has since stopped and we are back to hearing live music and roosters' songs I promise! Please come visit us again soon!

Weekend Getaway 2023

March 2023
, Dania Beach , FL United States

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

We just stayed at the Sailor House the second week of March. The house was an absolute Key West dream! It was perfect just like the photos with every amenity you could possibly think of. The whole process of renting it was simple. Brian, the property manager, made everything so easy. He is very available to answer any questions you may have. You could not ask for a better location. It’s one block off Duval Street yet it was really quiet. We were there for our daughter’s 21st birthday. We had made reservations one month in advance at Nine One Five which to our delight was literally around the corner from the house. Excellent restaurant by the way! I have already recommended the Sailor House to all my family and friends.

Manager's Response

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

Great location

February 2023
, Columbus, OH US

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

Perfectly clean and a great stay for 2couples! Very spacious first floor and 3 awesome outdoor areas to hang out, book it!

Manager's Response

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

Lovely stay!

January 2023
, Sharon, CT US

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

Was a delightful getaway. Was cared for and comfortable. Happy to recommend.

Manager's Response

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

Perfect House

December 2022
, Brockport, NY US

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

Amazing location, management was amazing. The house was very clean and the pictures posted looked exactly as good he house perfect

Manager's Response

Thank you for this wonderful review Lori, 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.

The best accommodations!

September 2022
, Vineland, NJ US

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

Best accommodations in Key West!! Location! Clean! Adorable!

Manager's Response

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

A fun getaway

July 2022
, East islip, NY US

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

Sailors house was a perfect find. One block off Duval Street. Close to everything. House was charming and very clean clean. We had a wonderful time!!

Manager's Response

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

Great location and floor plan. Parking could have been an issue.

April 2022
, monroe, LA US

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

Fabulous! Again, the location could not have been better. 4 adults stayed plenty of room.

Manager's Response

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

Location, location, location

February 2022
, Arlington, TX US

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

Very well maintain property. Can’t say enough about the location. Aptly located on Center street, it truly is in the middle of everything thing in Key West. Within walking distance to everything. Was a little worried about the sliding doors for bedrooms, but was pleasantly surprised about noise levels between bedrooms. Loved the balconies and especially the back deck. Kitchen nicely stocked with utensils and pots and pans to do cooking if you’d like. New outdoor grill was a nice touch. We put everything to use and can say it was great. Thanks again.

Manager's Response

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

Wonderful Experience.

November 2021
, Warwick, RI US

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

The house was awesome, clean, and perfect for a quick getaway. Brian the property manager was amazing!

Manager's Response

Thank you for this great review Derek! We hope to have the pleasure to host you again next time you visit Key West!

Excellent location!

November 2021
, Apollo beach, FL US

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

We couldn’t have stayed at a place with a better location. We parked our car when we arrived and didn’t move it till we left to go home. We walked everywhere and everything was so close. My favorite spot was the top deck where I’d watch the sun rise each morning. My only issue is there was no lock on the bathroom door and not much privacy when using the bathroom as the door had slats on it. We had such a great stay and this house, it had everything we needed. Would def stay here again. Thanks for the great trip!!

Manager's Response

Tristal thank you for your review, we are thrilled you enjoyed the house so much! We are taking notes concerning the bathroom door and will plan to improve it. We hope to be able to host you again next time you visit the island.

Leave a Review
2 Bed
1.5 Baths
Sleeps 4

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CROOKED PALM ~ Island Sophisticated!

CROOKED PALM ~ Newly Renovated 3 Bedroom, 3 Bathroom Home in Old Town District w/ Heated Pool and Compact Car Parking!

Location

733 Poorhouse Ln.
33040 Key West , FL
United States
24° 33' 16.848" N, 81° 47' 49.092" W
See map: Google Maps
Florida US

CROOKED PALM ~ Island Sophisticated!

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January 2025 Stay

Reviewed by Robert V. on 2025-02-03
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This is our third January we rented the property. Great property and location. We already are booked for next year.
Manager response on 2025-02-05 - Response from Best of Key West Rentals
Thank you for this fantastic review Robert, we are always thrilled to host you at Crooked Palm. We look forward to welcoming you again next year! Thank you for being our guest!

Fabulous

Reviewed by Theodore T. P. on 2024-04-01
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The house, Crooked Palm, was wonderful. clean,, well equipped, well located, charming
Especially appreciated Shana Yoest from Truman & Co. She was SO HELPFUL on several occasions: squeeking alarm, packages, etc. Even on weekends!
Manager response on 2024-04-01 - Response from Best of Key West Rentals
Thank you for your wonderful review Theodore, we are thrilled you enjoyed your stay so much and hope to welcome you again next time you visit Key West!

Crooked Palm - A Piece of Key West Heaven

Reviewed by Robert V. on 2023-02-16
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The house and the location were awesome. The rooms were spacious and there was plenty of closet space. We especially loved the outdoor living space. Having a parking spot was an added feature. The house is laid out well.
Manager response on 2023-02-16 - Response from Best of Key West Rentals
Thank you for your wonderful review Robert. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Crooked Palm - A Piece of Key West Heaven in Old Town

Reviewed by Robert V. on 2024-02-02
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We loved the property and the location. Walking distance to everything. This was our second year renting the Crooked Palm and we already booked it for next year. Added bonus is having a parking spot.
Manager response on 2024-02-05 - Response from Best of Key West Rentals
Thank you for your wonderful review Robert. We enjoyed hosting you again and look forward to seeing you back in Key West again next year!

CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w/ Pool & Compact Parking!

Unit Code: CR

CROOKED PALM ~ Island Sophisticated!

CROOKED PALM ~ Newly Renovated 3 Bedroom, 3 Bathroom Home in Old Town District w/ Heated Pool and Compact Car Parking!
LET THE REAL WORLD SLIP AWAY... Experience quintessential island serenity within this charming and newly renovated home tucked away in the Old Town district of Key West. A laid back vibe with every desirable amenity at your fingertips, this retreat is sure to capture your tropical soul.  ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES... Step onto your quaint front porch calling your name for a good book as you sip on your morning cup of coffee. Totalling 3 bedrooms and 3 bathrooms this home seamlessly suits a comfortable month long stay in Paradise. Step in to find an open and cheery space showcasing cool hardwood flooring, impeccable interior design with Dade County Pine accents, bright natural light from all around and stunning cathedral ceilings creating a happy space for everyone to gather. A fully equipped kitchen boasting top of the line appliances makes meal prep a breeze as you gather around for happy hour with a cocktail in hand at the bar area for 4. Cozy living room furnishings lie steps away with a flat screen TV for lazy nights in.  This property is equipped with a Ring Doorbell located next to the front door of the home. SLEEPING ARRANGEMENTS... The first guestroom comes with a king bed with plush linens, a flat screen TV and a stunning en suite full bathroom with a shower. The second guestroom resides off the Great Room and comes with a cozy king bed with access to the outdoor area and a nearby hallway bathroom with a shower/tub combination. Step outside to find a charming poolside cottage with a queen bed, a flat screen TV and en suite full bathroom with a shower. OUTDOOR LIVING... Truly immerse yourself in your private and magical outdoor oasis as you cool off in the sparkling pool (comes heated in the winter months) with a sweet island breeze and attractive landscaping surrounding you. Grill up your fresh catch of the day to be enjoyed around a table for 6 with a flat screen smart TV and a bluetooth speaker for your island tunes. Enjoy parking for 1 compact vehicle so you can come and go at your leisure (owner's golf cart is parked in driveway and not available for guest use). PETS... The owner prefers no pets, but may consider a dog under 30 pounds. 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). PARADISE AT YOUR FINGERTIPS...
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DatesPrice
10/26/2025 - 10/31/2025$451 /nt
11/01/2025 - 11/30/2025$322 /nt
12/01/2025 - 12/31/2025$358 /nt
01/01/2026 - 01/31/2026$804 /nt
02/01/2026 - 02/28/2026$901 /nt
03/01/2026 - 03/31/2026$815 /nt
04/01/2026 - 04/30/2026$600 /nt
05/01/2026 - 07/31/2026$447 /nt
08/01/2026 - 09/30/2026$429 /nt
10/01/2026 - 10/26/2026$500 /nt
5.0000
(4 Review)

January 2025 Stay

January 2025
, Fort Lauderdale, FL US

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

This is our third January we rented the property. Great property and location. We already are booked for next year.

Manager's Response

Thank you for this fantastic review Robert, we are always thrilled to host you at Crooked Palm. We look forward to welcoming you again next year! Thank you for being our guest!

Fabulous

March 2024
, Sag Harbor, NY US

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

The house, Crooked Palm, was wonderful. clean,, well equipped, well located, charming
Especially appreciated Shana Yoest from Truman & Co. She was SO HELPFUL on several occasions: squeeking alarm, packages, etc. Even on weekends!

Manager's Response

Thank you for your wonderful review Theodore, we are thrilled you enjoyed your stay so much and hope to welcome you again next time you visit Key West!

Crooked Palm - A Piece of Key West Heaven in Old Town

January 2024
, Fort Lauderdale, FL US

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

We loved the property and the location. Walking distance to everything. This was our second year renting the Crooked Palm and we already booked it for next year. Added bonus is having a parking spot.

Manager's Response

Thank you for your wonderful review Robert. We enjoyed hosting you again and look forward to seeing you back in Key West again next year!

Crooked Palm - A Piece of Key West Heaven

January 2023
, Fort Lauderdale, FL US

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

The house and the location were awesome. The rooms were spacious and there was plenty of closet space. We especially loved the outdoor living space. Having a parking spot was an added feature. The house is laid out well.

Manager's Response

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

Leave a Review
3 Bed
3 Baths
Sleeps 6

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SECOND WIND ~ The Sweet Life!

SECOND WIND ~ Adorable 2 Bedroom, 2 Bathroom Home Located in the Peaceful Neighborhood of The Meadows with a Heated Pool and Parking! Enjoy Your Dreamy Backyard Oasis in Paradise!

Location

1309 Albury St.
33040 Key West , FL
United States
24° 33' 27.324" N, 81° 47' 24.612" W
See map: Google Maps
Florida US

SECOND WIND ~ The Sweet Life!

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Great experience

Reviewed by Unknown on 2025-05-08
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
I spent two months at this property and loved it. It is a peaceful neighborhood, and the property is beautiful—just as advertised in the pictures. I recommend it highly. Also, the property manager and management company are first rate and very responsive.
Manager response on 2025-05-08 - Response from Best of Key West Rentals
Thank you so much for your kind words Peirce! We're thrilled to hear you had such a great experience during your two-month stay. It’s wonderful to know the home and neighborhood met your expectations and that our team could make your time here even more enjoyable. We truly appreciate your recommendation and hope to welcome you back anytime you're in Key West!

Perfect Key West Cottage

Reviewed by Unknown on 2025-01-06
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Absolutely wonderful stay at the lovely Second Wind Cottage. This was our 5th visit to Key West and Second Wind has been our favorite place the stay so far! Great location, short bike ride or walk to beaches, marinas, restaurants, etc. Convenient to park for walking our labradoodle. The cottage was well appointed, wonderfully landscaped and comfortable. Thank you to the owners and property manager Melanie for a lovely visit!
Manager response on 2025-01-06 - Response from Best of Key West Rentals
Thank you for your incredible review Susan! 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!

Second Stay at Second Wind.

Reviewed by Unknown on 2023-03-19
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This was our second stay at this deluxe house on Albury Street. The perfect home in Key West. We brought our bikes and never drove our car again for the month. You are an easy bike ride from Duval Street and all it has to offer. Once you are home in this private little oasis the fun really begins. The back yard and pool are very secluded and very beautiful. A tropical heaven!
Manager response on 2023-03-21 - Response from Best of Key West Rentals
Thank you for your wonderful review Dwight. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

March 2023 Second Wind Stay

Reviewed by John H. on 2023-04-04
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Beautiful cottage in great location in Key West. Rental team superb throughout, property manager Brian was great and immediately responded to any issues or concerns. Highly recommend.
Manager response on 2023-04-07 - Response from Best of Key West Rentals
Thank you for sharing a review of your recent experience John. 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.

A pleasant stay at Second Wind

Reviewed by Alan R. on 2023-12-22
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We're having a terrific time. We've been here for 7 weeks with 10 days to go. The location is perfect for us, in a quiet neighbourhood (the Meadows) but an easy walk or bike ride to anything we want to do. The house itself is bright and airy. The housekeeping and pool/landscaping services are excellent. The property management team has been very helpful and are quick to respond. If we could make some minor suggestions, they would be: to add towel racks to the principal bathrooms and more dishware, especially saucers for the cups, in the kitchen (which is very well-appointed otherwise). The addition of a light over the dining room table would be helpful. We find the living room sofa a bit too deep to be comfortable for TV viewing. These are relatively minor issues and we've loved our stay here.
Manager response on 2024-07-19 - Response from Best of Key West Rentals
Thank you for your feedback on your winter stay Alan. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will rely back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!

Perfect house for the summer

Reviewed by John R. on 2024-09-01
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We rented this house for 3 months, and was close enough to all the action, and also super convenient for parking and access to the park to walk our dogs twice a day. We loved it. Not to mention a pool to cool down in!
Manager response on 2024-09-01 - Response from Best of Key West Rentals
Thank you for your wonderful review John. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Wonderful trip

Reviewed by Melissa S. on 2022-06-24
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Second Wind property was a wonderful respite from the cold climes of Wyoming. The location and proximity was perfect for us. The neighborhood was quiet, neighbors lovely, house was comfortable.
Team Truman and Company are excellent!
Manager response on 2022-06-27 - Response from Best of Key West Rentals
Thank you for your incredible review Melissa! 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!

Wonderful Retreat

Reviewed by Vincent Z. on 2022-07-06
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Everything was exactly as we hoped it would be. Good location with off street parking (a definite plus). The one problem that we had (lock problem) was quickly and efficiently solved by Brian. Definitely would recommend to friends ��.
Manager response on 2022-07-15 - Response from Best of Key West Rentals
Thank you for this great review Vincent! We are thrilled you enjoyed the property and hope to host you again in the future!

Best vacation!

Reviewed by Marion C. on 2023-02-16
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Brian was helpfull I loved my stay and I even rebooked for next year
Manager response on 2023-02-17 - Response from Best of Key West Rentals
Thank you for your wonderful review Merci! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next year. Thank you for being our guest!

SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!

Unit Code: SW

SECOND WIND ~ The Sweet Life!

SECOND WIND ~ Adorable 2 Bedroom, 2 Bathroom Home Located in the Peaceful Neighborhood of The Meadows with a Heated Pool and Parking! Enjoy Your Dreamy Backyard Oasis in Paradise!
CATCH YOUR SECOND WIND… Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambiance. Equipped with 2 bedrooms and 2 bathrooms, this home welcomes you into a peaceful setting within the desirable district of The Meadows. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS & AMENITIES… Welcome in to an inviting, open floor plan boasting vaulted ceilings, hardwood floors and stunning wooden beams ready to entertain your crew for your getaway to Paradise. A fully equipped kitchen allows for seamless meal prep to enjoy together at the dining table for 6. Enjoy the bright and cheery living space with cozy furnishings and a TV for your lazy days in with gorgeous views beyond pocket doors of your outdoor oasis. This home is equipped with Youtube TV for live steaming. SLEEPING ARRANGEMENTS… Sleep tight in one of two cozy king bedrooms both equipped with storage space and flat screen TVs. The primary suite comes with an en suite bathroom with a double sink vanity and jet tub/shower combination. The second bathroom lies in the hallway with a shower/tub combination. OUTDOOR LIVING… Soak up your surroundings as you head out to your private backyard dream tucked within lush and vibrant foliage. Cool off in the pool which comes heated in the winter month and dine al fresco in the island breeze equipped with a gas grill. Lounge on your private front porch over your morning cup of coffee as you dream of your days adventures ahead. The Meadows district is a charming and convenient location to downtown Key West, yet tucked away for a peaceful evenings rest. PARKING... There is one parking space making coming and going a breeze. PETS... Dogs are considered at this home. 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). YOUR SLICE OF PARADISE AWAITS…
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DatesPrice
10/26/2025 - 10/31/2025$255 /nt
11/01/2025 - 11/30/2025$258 /nt
12/01/2025 - 12/31/2025$250 /nt
01/01/2026 - 01/31/2026$667 /nt
02/01/2026 - 02/28/2026$751 /nt
03/01/2026 - 03/31/2026$625 /nt
04/01/2026 - 04/30/2026$411 /nt
05/01/2026 - 07/31/2026$286 /nt
08/01/2026 - 09/30/2026$268 /nt
10/01/2026 - 10/26/2026$286 /nt
5.0000
(13 Review)

Great experience

April 2025
, United States

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

I spent two months at this property and loved it. It is a peaceful neighborhood, and the property is beautiful—just as advertised in the pictures. I recommend it highly. Also, the property manager and management company are first rate and very responsive.

Manager's Response

Thank you so much for your kind words Peirce! We're thrilled to hear you had such a great experience during your two-month stay. It’s wonderful to know the home and neighborhood met your expectations and that our team could make your time here even more enjoyable. We truly appreciate your recommendation and hope to welcome you back anytime you're in Key West!

Perfect Key West Cottage

December 2024
, Huntsville, AL United States

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

Absolutely wonderful stay at the lovely Second Wind Cottage. This was our 5th visit to Key West and Second Wind has been our favorite place the stay so far! Great location, short bike ride or walk to beaches, marinas, restaurants, etc. Convenient to park for walking our labradoodle. The cottage was well appointed, wonderfully landscaped and comfortable. Thank you to the owners and property manager Melanie for a lovely visit!

Manager's Response

Thank you for your incredible review Susan! 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!

Perfect house for the summer

August 2024
, WEST TISBURY, MA US

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

We rented this house for 3 months, and was close enough to all the action, and also super convenient for parking and access to the park to walk our dogs twice a day. We loved it. Not to mention a pool to cool down in!

Manager's Response

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

A pleasant stay at Second Wind

November 2023
, Toronto, ON Canada

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

We're having a terrific time. We've been here for 7 weeks with 10 days to go. The location is perfect for us, in a quiet neighbourhood (the Meadows) but an easy walk or bike ride to anything we want to do. The house itself is bright and airy. The housekeeping and pool/landscaping services are excellent. The property management team has been very helpful and are quick to respond. If we could make some minor suggestions, they would be: to add towel racks to the principal bathrooms and more dishware, especially saucers for the cups, in the kitchen (which is very well-appointed otherwise). The addition of a light over the dining room table would be helpful. We find the living room sofa a bit too deep to be comfortable for TV viewing. These are relatively minor issues and we've loved our stay here.

A pleasant stay at Second Wind

November 2023
, Toronto, ON United States

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

We're having a terrific time. We've been here for 7 weeks with 10 days to go. The location is perfect for us, in a quiet neighbourhood (the Meadows) but an easy walk or bike ride to anything we want to do. The house itself is bright and airy. The housekeeping and pool/landscaping services are excellent. The property management team has been very helpful and are quick to respond. If we could make some minor suggestions, they would be: to add towel racks to the principal bathrooms and more dishware, especially saucers for the cups, in the kitchen (which is very well-appointed otherwise). The addition of a light over the dining room table would be helpful. We find the living room sofa a bit too deep to be comfortable for TV viewing. These are relatively minor issues and we've loved our stay here.

Manager's Response

Thank you for your feedback on your winter stay Alan. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will rely back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!

March 2023 Second Wind Stay

March 2023
, Locust Hill, VA United States

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

Beautiful cottage in great location in Key West. Rental team superb throughout, property manager Brian was great and immediately responded to any issues or concerns. Highly recommend.

Manager's Response

Thank you for sharing a review of your recent experience John. 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.

Second Stay at Second Wind.

February 2023
, United States

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

This was our second stay at this deluxe house on Albury Street. The perfect home in Key West. We brought our bikes and never drove our car again for the month. You are an easy bike ride from Duval Street and all it has to offer. Once you are home in this private little oasis the fun really begins. The back yard and pool are very secluded and very beautiful. A tropical heaven!

Manager's Response

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

Best vacation!

January 2023
, Montreal, Quebec United States

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

Brian was helpfull I loved my stay and I even rebooked for next year

Manager's Response

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

Best vacation!

January 2023
, Montreal, Quebec United States

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

Brian was helpfull I loved my stay and I even rebooked for next year

Manager's Response

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

Wonderful Retreat

June 2022
, Sarasota , FL United States

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

Everything was exactly as we hoped it would be. Good location with off street parking (a definite plus). The one problem that we had (lock problem) was quickly and efficiently solved by Brian. Definitely would recommend to friends .

Manager's Response

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

Wonderful Retreat

June 2022
, Sarasota , FL United States

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

Everything was exactly as we hoped it would be. Good location with off street parking (a definite plus). The one problem that we had (lock problem) was quickly and efficiently solved by Brian. Definitely would recommend to friends .

Manager's Response

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

Wonderful trip

April 2022
, Paradise Valley, AZ US

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

Second Wind property was a wonderful respite from the cold climes of Wyoming. The location and proximity was perfect for us. The neighborhood was quiet, neighbors lovely, house was comfortable.
Team Truman and Company are excellent!

Manager's Response

Thank you for your incredible review Melissa! 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!

Wonderful trip

April 2022
, Paradise Valley, AZ US

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

Second Wind property was a wonderful respite from the cold climes of Wyoming. The location and proximity was perfect for us. The neighborhood was quiet, neighbors lovely, house was comfortable.
Team Truman and Company are excellent!

Manager's Response

Thank you for your incredible review Melissa! 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!

Leave a Review
2 Bed
2 Baths
Sleeps 4

Search Availability

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