Row Wrapper 2

SMOOTH SAILING ~ Steps To Everything!

5.0000
(17 Reviews)

Capacity

2 Bedrooms
1 Bath
Sleeps 4

Search Availability

About

A TRUMAN ANNEX DREAM...
Come discover this beautifully renovated condo within the desirable Shipyard neighborhood in the Truman Annex area pairing comfort and modern luxuries at your fingertips. A cozy home base with just steps to the lively Key West action, this home is sure to make you never want to leave. 
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS AND AMENITIES…
Slip inside from an inviting front porch up to the 2nd level to a cheery and open Great Room bringing your loved ones together. Brand new furnishings surround the living area with a cozy place to hang for card night or your favorite movies on the flat screen TV. Craft up your meals and cocktails in the beautifully designed kitchen with stainless steel appliances and sprawl out at the dining table. Balconies lie off both the front and back of the unit with lush, sunny views and a table for 4. 

SLEEPING ARRANGEMENTS…
Sleep tight in the twin guest room that can be converted to a king upon request. The primary guest room comes with a king bed and access to the outdoor balcony to enjoy views of the vibrant neighborhood over a morning cup of coffee. Both rooms come with closet storage, a flat screen TV and share a hallway bathroom with a shower. A sofa sleeper occupies the living area.

OUTDOOR LIVING…
This home offers an incredibly peaceful escape allowing for the best kind of R & R on your island retreat. Although just walking distance to Mallory Square, Ft. Zachary Taylor and all the lively action, a parking spot is available for seamless coming and going should you head out for a scenic drive. The unit also offers a refreshing community pool lined with lounge chairs and is just steps away from the Truman Waterfront Park. 

PARKING!
This home does offer parking for one vehicle, but oversized trucks and extra large SUV's are not permitted and will have to park outside of this community.

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!

TIME TO UNWIND...

Features

Amenities

  • Parking
  • Free Wifi
  • Coffee Maker
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Communal Pool
  • Central Air
  • Washer & Dryer

Rental Type and Location

  • Condominium
  • Parking
  • Truman Annex
  • Best of Key West Rentals
  • Key West
  • Key West, FL

Duration

  • Nightly

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
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Map

Reviews

Leave a Review

Everything We Hoped For

September 2024
, Crestwood, KY US

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

Smooth Sailing is a beautiful unit in a quiet and safe community, within walking distance of Old Town. The ease of checkin and checkout was greatly appreciated and communication from the agency was timely, consistent and extremely helpful for all our needs. Highly recommend and we will be back!

Charming Condo in great location

July 2024
, Allen, TX US

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

Thoroughly enjoyed our stay at the Smooth Sailing - Steps to Everything condo! It looked exactly like the photos, was clean and comfortable. Very walkable to most locations - except for the high humidity in July. Close enough to the action, but still quiet. The pool is close by and feels great after a hot day out. Management responded quickly to a couple of requests we texted about. Would definitely recommend this charming place.

Lovely unit in Shipyard

March 2024
, Las Vegas, NV United States

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

The location and the furnishings in this Shipyard unit make for a relaxing stay in Key West.

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!

Nice Condo near the water

December 2023
, Mechanicsburg, PA United States

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

We rented in Truman Annex many times but this is our first time here. It is clean, ,well maintained and updated nicely. The bathroom and kitchen are renovated and look great. The location in the Shipyard is perfect. A quiet spot, not far from the pool, and overlooking Truman Park and the waterfront.
We would stay again but i would recommend the owner install a full size mirror somewhere in the condo. Perhaps on the thermostat wall to enlarge the space. There is only one mirror in the unit and that is in the bath. It was just my wife and I staying, but it would have been difficult if we stayed with another couple.
There are 2 bedrooms and we used the bedroom with the king size bed. It needs to be replaced and in our opinion is too big for the room. The TV on the wall and the king bed makes it tight in that room. There are 3 large TVs in the unit and we did not use any. For us, no time for TV as there is so much to do in Key West. For downtime, you can relax on the 2 balconies and even the front porch.
Overall, one of the nicest condos we rented in over 15 years going to Key West.

Manager's Response

Robert thank you for your feedback on your recent stay. 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!

Loved this place!

May 2023
, Chagrin Falls , OH US

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

The layout of this place was great! I had three women staying in this place and it was great! Everything was well thought out.

Manager's Response

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

Funtastic!

April 2023
, W St Paul, MN US

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

Super clean and comfortable! Loved the balconies and the parking was convenient. Close to everything! Manager Brian, was in contact and made the arrival and departure seamless.

Manager's Response

Thank you for your review Tom, 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.

Smooth Sailing

February 2023
, Lewes, DE United States

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

Excellent property in the perfect location

Manager's Response

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

Updated townhouse in great location!

February 2023
, Lititz, PA United States

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

Excellent communication from Brian at Best Rentals in Key West. Updated townhouse was beautiful, clean and well stocked. Beds were comfortable. Neighborhood was quiet every night. Great overall experience! AC problem on day 1 but property manager arranged for tech service and full repair within an hour of my text message. Bravo!!

Manager's Response

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

My Own Private Margaritaville

December 2022
, Grand Blanc, MI US

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

Really enjoyed the condo - close to EVERYTHING - Walkable EVERYWHERE. I will book again in the future.

Manager's Response

Thank you for this wonderful review Neil, 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.

Awesome Stay

April 2022
, Saraland, AL US

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

It was convenient to Duval Street and many other locations!!

Manager's Response

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

Truman Annex 104

April 2022
, Evans, GA US

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

Excellent facility and quiet yet central location, walkable to all main attractions in downtown Key West.

Manager's Response

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

Fantastic

March 2022
, Lino Lakes, MN US

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

Relaxing , quiet when needed to be but fun and so much to do just steps away! Home was perfect with great patios and space !

Manager's Response

Stephanie, 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!

Fantastic

March 2022
, Lino Lakes, MN United States

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

Relaxing , quiet when needed to be but fun and so much to do just steps away! Home was perfect with great patios and space !

Manager's Response

Stephanie, 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 condo

February 2022
, Markle, IN US

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

Our rental was perfectly located such that we did not need to rent bikes or a golf cart, let alone worry about parking.
The unit was nicely renovated and very clean.
The community pool was welcoming and clean.

Manager's Response

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

Life is Good at this Truman Annex rental

February 2022
, Montague, MA Unknown

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

Three ladies from MA vacationed here for a week.
The Shipyard area of Truman Annex is clean, quiet and charming.
Our unit was nicely decorated and we used many of the generously equipped features.
We thought there was no ice maker. The property manager sent Brian to help us turn it on and find the coffee maker we needed to get our mornings started! Brian was very friendly and offered to solve any other problems.
There are lovely porches at each end of the unit where we could gather, we were able to eat meals inside or out in the fresh air, and enough space each of us could have some privacy if wanted.
The location put us near Mallory Square, the Bahama Village, and an array of enjoyable restaurants. The Truman Waterfront Park is a wonderful new area to enjoy.
One of us took advantage of the community pool. I relished the quiet and feeling we were secure. Yes, five stars is deserved.

Manager's Response

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

Very nice

January 2022
, columbus, OH United States

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

I have stayed at the Turman Annex several times and this place was great. Very clean and everything works. Only down fall but not a big deal if not cooking no dishwasher.

Manager's Response

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

Great stay at Smooth Sailing

January 2022
, Greensboro, NC US

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

We had a very relaxing stay. We have stayed all over the island and as we had hoped Truman Annex was perfect. The place was clean and had a new feeling. Thank you.

Manager's Response

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