Condo

~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!

Photo gallery for ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!

A living room with a blue sofa, a white coffee table, and a ceiling fan. There is a large window with a view of palm trees and a patio area with red chairs.
A living room with two blue sofas, a white coffee table, a large potted plant, and a painting on the wall.
A residential building with a white picket fence, surrounded by lush greenery and palm trees.
A kitchen with a black granite countertop, a stainless steel sink, and a chandelier. There is a dining area with a blue sofa and a TV mounted on the wall.
A narrow pathway flanked by lush greenery and a brick building with a white picket fence.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Duval Street

Popular amenities

  • Balcony
  • Swimming pool
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Garage parking available

Explore the area

View map
Key West, FL
  • Place, Harry S. Truman Little White House
    ‪2 min walk‬
  • Place, Duval Street
    ‪4 min walk‬
  • Place, Mallory Square
    ‪6 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪12 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Other Space 1

1 Double Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Garden

Add dates for prices

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Truman Annex
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (121 reviews)
Sunny & Beautiful 1st flr, Large In/Outdoors, 2BR K/T, 1 Bath, Truman Anx, Pool

About the area

Key West

Located in Key West, this condo is in the city centre. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting. Jet skiing, scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Map
Key West, FL

What's nearby

  • Key West Naval Station - 1 min walk - 0.2 km
  • Harry S. Truman Little White House - 2 min walk - 0.2 km
  • Duval Street - 4 min walk - 0.4 km
  • Mallory Square - 6 min walk - 0.6 km
  • Ernest Hemingway Home and Museum - 11 min walk - 0.9 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 13 min drive

Restaurants

  • ‪Margaritaville - ‬6 min walk
  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Key Lime Pie Factory - ‬6 min walk
  • ‪Wendy's - ‬5 min walk
  • ‪The Bull & Whistle Bar - ‬6 min walk

Frequently asked questions

Does ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! have a pool?

Yes, this property has a pool.

Is ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! pet-friendly?

No, pets are not allowed at this property.

How much is parking at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!?

On-site parking is available at the property.

What time is check-in at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!?

Check-in begins at 4:00 PM.

What time is check-out at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!?

Checkout is at 10:00 AM.

Where is ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! located?

Located in Old Town Key West, this condo building is within a 5-minute walk of Harry S. Truman Little White House and Duval Street. Mallory Square and Florida Keys Beaches are also within 15 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 78 out of 89 reviews
Rating 8 - Good. 9 out of 89 reviews
Rating 6 - Okay. 0 out of 89 reviews
Rating 4 - Poor. 0 out of 89 reviews
Rating 2 - Terrible. 2 out of 89 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!!
Stayed 7 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay. Most everything was walking distance. HKWVR staff very frinedly and helpful answering questions. Would definitely stay again!
Stayed 7 nights in Jul 2025
Response from VrboOwner on 4 August 2025
Thank you so much for the kind review of Fair Winds ~ and we hope you're already making plans to come back! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful and clean property in the heart of Key West. Walkable to everything.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 30 August 2025
We appreciate your taking the time to review us so kindly! We hope you're already making plans to come back and see us again, and soon! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

The house look exactly in the photos. Very clean and a great location.

Very pleased with our booking.
Stayed 7 nights in Aug 2021
Response from VrboOwner on 18 August 2021
So happy you were pleased!! Come and stay with us again! (and again). ;) ~ Jennifer & Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was beautiful and very clean. Plenty of room for my family of four. The check in process was easy and the seamless. The location is close enough to Duval Street but far enough to not hear the noise. The pool is nice but small. We enjoyed our stay!!
Stayed 7 nights in Aug 2025
Response from VrboOwner on 30 August 2025
We hope you're already making plans to come and stay with us again! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A perfect getaway

Loved our stay! Fair winds is a perfect location for key west! Quiet and easy accessibility to everything nearby. Very safe and comfortable.
Stayed 7 nights in Mar 2024
Response from VrboOwner on 3 April 2024
What a great review and we thank you for taking the time to do so! Hope we'll see you again, and soon! There's still more memories to be made in Key West. Jennifer & Team @ Historic Key West Vacation Rentals
From a partner site

10/10 Excellent

Quiet and lovely venue

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Such a beautiful and peaceful location. A quiet place but so very close to everything we were looking for: easy walk to beach, Mallory Square, Duval Street restaurants, Truman Little White House, and Hemingway House. We hardly used our car! We would definitely stay here again.
Response from VrboOwner on 12 December 2025
Starting in December 22, 2025, Fair Winds @ the Foundry will be a monthly rental; we hope you'll come and stay with us for a month and live like a local! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Truman Annex

We enjoyed our week here. Property was accurately described and the location is perfect. Plenty of room to stretch out and nice quiet area but still walking distance to Duval.
Stayed 7 nights in Feb 2022
Response from VrboOwner on 25 February 2022
We are so happy you enjoyed your time at Fair Winds! We think it's a pretty great home and in a great location as well. Hope you're already making plans to come and see us again, and soon! ~ Jennifer & Team Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location

Great Location. Everything was great until the A/C quit working but they were on top of it and had it working in no time.
Stayed 10 nights in Apr 2022
Response from VrboOwner on 31 May 2022
Sorry to hear the A/C quit but so happy to hear we got right on it! A/C is important. :) Let us know when you're coming back to see us again! ~ Jennifer & Historic Key West Vacation Rentals Team
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice townhouse

Pretty townhome centrally located in old town.
Stayed 7 nights in Nov 2022
Response from VrboOwner on 19 November 2022
Danielle, thank you for your review! Fairwinds is in a great location and the parking space and shared pool are great amenities! Come back to our little island paradise when you can! Cindy & the HKWVR team
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key west

Wonderful week.
Stayed 8 nights in Mar 2023
Response from VrboOwner on 20 March 2023
Oh, that's so nice to hear! Come and stay at Fair Winds at the Foundry again and have another wonderful week! We're here. ~ Jennifer @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful time in Key West

The rental property was comfortable, clean, well appointed and in a terrific neighborhood...easy access to all that Key West has to offer. We didn't even need a car. Key West is a fun and happy place!
Stayed 28 nights in Feb 2024
Response from VrboOwner on 7 March 2024
Thank you for the nice review of Fair Winds at the Foundry! Please tell us when you'll be back to make some more memories. ~ Jennifer & Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely gem close walking distance to duval.

Such a great location! Of all our stays so far in Key West (which is many) this was one of my top choices. Easy to get anywhere and parking for the unit was right outside and covered. I would recommend it to anyone unless you can’t climb stairs ;)
Stayed 7 nights in Oct 2021
Response from VrboOwner on 5 November 2021
Heather, thank you very much for your review. Fairwinds is in a great location and the parking space is a great perk. We are pleased you enjoyed your stay. Please come back soon for more Key West adventures! Cindy & the HKWVR team
From a partner site

10/10 Excellent

Perfect!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Absolutely perfect rental for our family of 4. Amazing location, everything you need!
Response from VrboOwner on 22 August 2023
So nice to hear that you enjoyed your time at Fair Winds! Please bring the family back soon and make some more memories. ~ Jennifer & Team HKWVR
From a partner site

10/10 Excellent

Great vacation

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our second time at Fair Winds and we are very pleased. It is clean and located close to all the best places to see. We will definitely be going back
Response from VrboOwner on 14 May 2024
Third time will definitely be the charm, so please hurry back! ~ Jennifer & Team @ HKWVR
From a partner site

10/10 Excellent

Great location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wonderful location within Truman Annex with easy walking access to the waterfront and Mallory Square. Comfortable and charming decor.
Response from VrboOwner on 21 April 2023
We are so happy you enjoyed Fair Winds at the Foundry, and we agree on its comfort and charm! We hope you're already making plans to come back and see us again, and soon. ~ Jennifer & Team HKWVR
From a partner site

10/10 Excellent

The Foundery

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very good. Very Enjoyable.
Stayed 7 nights in Jan 2020
Response from VrboOwner on 18 March 2020
Tom we are so happy you enjoyed Fairwinds at the Foundry and you stayed with us once again. Key West is a lovely place to enjoy the warm weather & get away from the ice cold winds.We look forward to seeing you whenever you can come back. Hoping it wil be soon! Cindy & the HKWVR team
From a partner site

8/10 Good

Wonderful Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great place to stay. Truman Annex is very quiet. The Foundry is a cool building and the kids enjoyed having their own separate space. We will be re-booking for next year!
Response from VrboOwner on 25 January 2023
Thank you Peter for your kind review of Fair Winds. We agree that the building is cool and the layout is great! We can't wait to see you again in sunny Key West! ~Lori and the Team @ HKWVR
From a partner site

10/10 Excellent

Paradise

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property was perfect. Easy check in and out. Art work in the condo was fantastic. Condo was well stocked and location was perfect.
Response from VrboOwner on 28 May 2022
Dear Joseph, Thank you so much for taking the time to share your feedback in regards with your most recent stay with us. We strive to provide all of our guests with an unforgettable experience and we are delighted to have accomplished that objective during your stay. We are thrilled you enjoyed your visit with us and hope to welcome you back for another great stay soon! Happy Holidays! Sincerely, Yoli and the HKWVR Team
From a partner site

10/10 Excellent

Relaxing vacation

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our vacation was so relaxing. The condo was very clean and spacious for the four of us. It was within walking distance to lots of very good restaurants and shopping. I would absolutely recommend this place to my friends.
Response from VrboOwner on 3 June 2023
Relaxing vacations are our goal for our guests. Please come and relax with us anytime! ~ Jennifer & Team HKWVR
From a partner site

10/10 Excellent

Perfect Home

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The house has a great location, is well maintained and tastefully decorated, and has a delightful patio. The staff at Historic Key West Vacation were the best we have ever dealt with in renting vacation homes.
Response from VrboOwner on 4 March 2023
Wow! Thank you for the super kind review of Fair Winds *and* us. I will pass this along to our crew ~ we love happy, nice guests. ~ Jennifer & Team HKWVR
From a partner site

8/10 Good

Convient location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location, close to everything Property worked very well for family The kitchen is somewhat under equipped and guest bedroom could use better lighting (as per the boys) Would stay at property again, over all satisfied
Stayed 7 nights in Aug 2019
From a partner site

10/10 Excellent

Great Location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved the location. The condo was clean worked well for our family of 4. Historic Key West did a great job of keeping us apprised of the check-in process, kept our bags when we arrived early and coordinated our bike drop off. Very happy with our stay. We will be back.
Response from VrboOwner on 5 January 2024
We are so happy you enjoyed your time and that we met (exceeded?) your expectations! Please come and stay with us again, anytime, but hopefully soon. ~ Jennifer & Team @ HKWVR
From a partner site

10/10 Excellent

Fair Winds at the Foundry - great location in Key West

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent stay at Fair Winds, great location, easily walkable to Old Town, harbor, Mallory Square and Zachary Taylor Park. Bonus of a parking space for our rental golf cart, a must when visiting Key West. We would certainly consider Fair Winds again on return trips.Historic Key West Vacations is a great management company, quickly responsive to questions and setting up information for arrival and departure.
Response from VrboOwner on 3 June 2023
We are so happy to hear you had a nice time at Fair Winds and that we were helpful in making your trip a good one. Come and stay with us anytime! ~ Team HKWVR
From a partner site

10/10 Excellent

Very happy!

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was our first time staying in Truman Annex & we could not be happier. The house was perfect for my family of four. We loved the location, the patio area and my daughters loved the privacy of the third floor bedroom that they had to themselves. The house was stocked with plenty of towels, extra pillows, blankets and beach towels and plenty of paper products to last the whole week. We are looking forward to coming back!
Response from VrboOwner on 6 April 2024
We are excited to hear that you'll be coming back ~ more memories are ready to be made here! ~ Jennifer & Team @ HKWVR
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