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
WEEKLY RENTAL: This property has a 7 night minimum stay.
**Beginning January, 2026, Fair Winds will be a MONTHLY (28 nights within the same month) RENTAL. 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.
***Staying for a month or longer? Request a quote for a minimum of 28 nights to see our discounted “monthly” rates.
***Guests must be 25 years of age or older unless accompanied by an adult.
***Managed by Historic Key West Vacation Rentals***
**Beginning January, 2026, Fair Winds will be a MONTHLY (28 nights within the same month) RENTAL. 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.
***Staying for a month or longer? Request a quote for a minimum of 28 nights to see our discounted “monthly” rates.
***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!
Family friendly
Map of Key West, FL
Things to know
Additional fees to expect
Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.
Booking feeNo booking fees, easy credit card payments.
Service feeThis helps Vrbo provide a safer and more secure booking experience.
TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.
Customer support
Customer support is handled by our partner Vrbo
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Top rated by guests
9.6Outstanding
(88 Ratings)
Great location, immaculate rentals, helpful staff, comfortable beds, fantastic stay!
From real guest reviews summarized by AIDon't miss out! Price and availability may change
