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

Top rated by guests
Bright, open, and sunny living area.
View of living and dining area.
Enjoy the bright cheerful decor.
Fully equipped and updated kitchen.
End unit windows abound.
review stars
9.6Outstanding
(88 Ratings)
Great location, immaculate rentals, helpful staff, comfortable beds, fantastic stay!
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
9.6 / 10.0
Outstanding(88 Ratings)

Apartment in Key West, FL

6 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this apartment rental

**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.

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

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

Air conditioning
Pool
Non-smoking
TV
Coffee/tea maker
Refridgerator
Kitchen
Balcony/Terrace
WiFi/Internet
Microwave
Dishwasher
Washing machine
Dryer
Patio
Kitchenware
No pets allowed
Garden
Oven
Stove
Laundry services
Bath or shower
Ironing facilities
Towels
Hairdryer

Map of Key West, FL


Ratings and reviews

9.6 / 10.0
Outstanding(88 Ratings)
review starsSummary of reviews
Great location, immaculate rentals, helpful staff, comfortable beds, fantastic stay!
From real guest reviews summarized by AI
10.0 / 10.0Outstanding·Dec 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.
10.0 / 10.0Outstanding·Aug 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!!
10.0 / 10.0Outstanding·Aug 2025
Beautiful and clean property in the heart of Key West. Walkable to everything.
10.0 / 10.0Outstanding·Aug 2025
Great place to stay. Most everything was walking distance. HKWVR staff very frinedly and helpful answering questions. Would definitely stay again!

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FAQs

Is parking included with this apartment?

Parking is not specified as an available amenity at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this apartment?

Yes, a swimming pool is available for use at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!. Enjoy the water!

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

Unfortunately, this apartment is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!?

We found 24 amenities for this rental. This includes air conditioning, pool, non-smoking, tv, and coffee/tea maker.


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