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

Key West, Florida
$310 avg/night Minimum Stay 28 Nights
Bed 2

Bed

Bath 2

Bath

Home Condo

Property Type

Sleep 6

Max Sleeps

Night 28 nights

Min Stay

**Beginning 12/22/25, Fair Winds will be a MONTHLY RENTAL (28 nights within the same month). Stay a month and live like a local!

THE PROPERTY: As you open the white picket gate to this three-story townhouse, your tropical courtyard and outdoor dining area will delight you. Through the oversized French doors with transoms, you will find your living room, dining area, updated kitchen and half bath. This home has more windows than most as well as vaulted ceilings, adding sunshine and volume to the open concept living area. A comfortably furnished family room with TV lead to the dining table with seating for 4-6. The galley-style kitchen has everything you need to prepare a meal or snack.

The second-floor primary bedroom is beautifully furnished and includes bedside lamps, nightstands, TV, closet and dresser storage. The ensuite bath is tiled and has a shower/tub combination. Open the French doors enjoy morning coffee on your private balcony.
The guest bedroom is sunny and bright on the third floor. Twin beds can be combined to form a king upon request. A TV, bedside table, lamp, closet, and dresser storage are also provided.

History aficionados will appreciate The Truman Annex. Formerly an Army installation and later a Naval station, it was also President Harry S. Truman’s winter home. The park-like setting with an abundance of palm trees and white picket fences is a source of pride and splendor in Key West.

Whether you spend a day at the pool or a night on Duval Street, you won’t be disappointed with this townhouse or its unbeatable location. Come stay a while at Fair Winds at the Foundry.

BED CONFIGURATION: The primary king ensuite is on the second floor. The third floor ensuite guest bedroom has two twin beds that can be joined to create a king bed. A sleeper sofa in the living room can accommodate 2.

OUTDOOR AMENITIES: Share a fabulous pool with guests of the Foundry. Enjoy cocktails on the patio or grill up the daily catch on the gas grill.

PARKING: There is a dedicated covered parking space for one vehicle that may not exceed 18’ long x 80” wide. This is strictly enforced so be sure your vehicle is appropriately sized.

LOCATION: Tucked away in the exclusive, historic Truman Annex, this home in Old Town is close to everything. Within walking distance are galleries, shops, restaurants on and off Duval Street, sunsets at Mallory Square and the Truman Waterfront Park. Bike to Fort Zachary Taylor State Park’s beach, stroll to the Key West Harbor or walk to the Tropic Cinema and catch a film.

PETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).

SMOKING: This is a non-smoking home and property.

***Guests must be 25 years of age or older unless accompanied by an adult.

***Please note that the cleaning fee includes a full mid-stay clean***

***Managed by Historic Key West Vacation Rentals***

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1527 Sq Ft (142 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Limited Onsite Parking (max 1 Space) Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • POOL/SPA

    Shared/communal Pool
  • BATHROOMS

    2.5 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Cycling Nearby Fishing Nearby Jet Skiing Nearby Marina Nearby Sailing Nearby Scuba Diving Nearby Water Skiing Nearby Windsurfing Nearby
  • ENTERTAINMENT

    TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In The City Center
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • suzan s.

    Submitted Dec 1, 2025

    Stayed Nov 23, 2025

    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.

  • John F.

    Submitted Aug 29, 2025

    Stayed Aug 16, 2025

    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!!

  • JILL T.

    Submitted Aug 27, 2025

    Stayed Aug 9, 2025

    Beautiful and clean property in the heart of Key West. Walkable to everything.

  • michelle b.

    Submitted Aug 1, 2025

    Stayed Jul 25, 2025

    Great place to stay. Most everything was walking distance. HKWVR staff very frinedly and helpful answering questions. Would definitely stay again!

  • KATIE F.

    Submitted Jun 9, 2025

    Stayed May 22, 2025

    Great location!!

  • Ronda P.

    Submitted Mar 6, 2025

    Stayed Feb 19, 2025

    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've been coming to KW for 20 years and have found this property to be one of the best. From its location to all the amenities - they have thought of everything. I work from home and even the wifi could keep up with all my reports. It would be nice to have a book with check in and check out information - I felt bad for asking questions, that with a little looking thru my emails, I could have found BUT when you are in Key West you forget all your worries! Great property and we will rent it again (and when we get our house built, we will send our overflow guest in this direction!).

  • Luke M.

    Submitted Feb 15, 2025

    Stayed Feb 1, 2025

    We had an excellent stay at The Foundry in Key West! Its location cannot be beat as it is within walking distance of just about everything you might want to do while visiting the city. We were only minutes from the excitement of Duval street, but when back at the property you wouldn’t know it. The Foundry was always peaceful and relaxing at any given time of day. We also loved all the amenities it provided us. The full kitchen and gas grill were perfect for nights when we didn’t feel like going out to a restaurant. We loved how each bedroom was on its own floor with a full bathroom attached and that there was even a half bath on the ground floor as well. Having a washer and dryer in the unit was especially convenient for a week long stay. The staff were very helpful any time we had questions and we felt right at home the whole time. Would definitely book a property with Historic Key West Vacation Rentals again!

  • Denise T.

    Submitted May 13, 2024

    Stayed Dec 31, 1969

    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

  • Kelly O.

    Submitted Apr 6, 2024

    Stayed Dec 31, 1969

    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!

  • Fred B.

    Submitted Mar 26, 2024

    Stayed Dec 31, 1969

    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: Terrific property in a great location. The 33 steps to the 3rd floor bedroom were a bit of an issue. The AC went out one day and the temp soared into the 90's. However, with one phone call, a maintenance man came to our unit even though it was after he had gone home for the day and within a few hours, the AC unit was repaired. The one thing I did not like was the hassle created by their check in and check out policy. You cannot gain access to your unit until 4:00pm (we arrived at noon) and must be completely out of the unit by 10:00am (our flight was at 6:00pm). The mgmt co allowed us to store our luggage at their office during the before and after hours; however, the office is two miles away from the unit. So, we had to Uber our luggage from the airport to the mgmt co's office, then Uber into town for lunch and wait the four hours until the unit became available. We then had to Uber back to the office to retrieve our luggage and then take another Uber with our luggage to our unit. We then had to repeat the process upon departure. In all, it required 8 separate Ubers - an expensive hassle. It would have been so much better service if someone at the office would have simply driven our luggage to and from the unit or if we could have stored our luggage on site. Nevertheless, I am already looking forward to our next visit.

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Total

Includes taxes and fees
$310+
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