~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! | Condo in Key West
2 Bedroom Condo in Truman Annex, Key West
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***
~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! is located in Truman Annex. ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! provides accommodation, featuring Security/Safety, Bedding/Linens, Air Conditioner, among other amenities. This Condo features Security/Safety, Bedding/Linens, Air Conditioner, to make your stay a comfortable one.
~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! has 2 Bedrooms , 2 Bathrooms, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Condo because of the excellent services rendered by the owner or manager of this Condo, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Condo has a friendly neighborhood, and the Truman Annex has interesting places to visit. If you want to learn more about the Condo in Truman Annex, such as places to visit and things to do nearby, you can check below to learn more.
Amenities
Policies
Reviews
FAQ's
Is this Truman Annex condo pet-friendly for guests?
No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.
Does the Truman Annex condo have a swimming pool?
Yes, this Truman Annex condo has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in Truman Annex condo?
Best-rates for the Truman Annex condo starts from $552 per night with includes Bedding/Linens, Air Conditioner, Parking, Fireplace/Heating, Child Friendly, Laundry, TV, Balcony/Terrace, Sports/Activities, Internet, Kitchen, Wellness Facilities, Barbecue/Outdoor Cooking, Pool, Security/Safety with all other facilities. RBO matches every traveller with their perfect accommodation, whether you are travelling with a group, friends, family, or pets.
Is Truman Annex condo a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this condo Good or guests have recommended them suitable for families. As reported by the owner or manager, the condo has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the Truman Annex condo wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Truman Annex condo has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the Truman Annex condo?
Based on the information reported by the owner or manager, the Truman Annex condo indicates 1 day stay policy at this condo. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for Truman Annex condo?
Based on the information reported by the owner or manager, details for the cancellation policy for the Truman Annex condo are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
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