~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex

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: Located where the Gulf meets the Atlantic, this is the upscale vacation home you have been looking for! Stroll down your private entrance in the Historic Truman Annex to this elegantly decorated single family home. With Serena and Lily touches throughout, this sophisticated space is flooded with natural light. As you enter the home, you will be greeted by a serene ambiance and alluring art. A convenient first floor powder room is on the right of the entry area. Moving into the striking white kitchen, you will enjoy stainless steel Bosch appliances, an induction oven, a farm sink, and bench seating under the waterfall peninsula. The open concept dining area and living room are where you will find spectacular furnishings, a large screen, wall mounted TV as well as generous room to entertain guests. Two sets of French doors with transom windows lead out to your private, partially covered patio. Enjoy dinner or cocktails while surrounded by the privacy of lush foliage and palm trees. Comfortably furnished and fenced, this space provides a respite from the excitement of Duval Street.
Upstairs are two King bedrooms. The stunning, primary ensuite bedroom is complete with bedside tables, lamps, ceiling fan, wall-mounted TV, and closets. Two sets of French doors lead to a covered balcony where you can enjoy morning coffee while listening to the sounds of the island. The primary ensuite bath is a beautiful space with double sinks, waterfall faucets, tiled, glass walk in shower and natural light. At the end of the hall is the second bedroom. This charming space is adorned with nightstands, bedside lighting, ceiling fan and closet. Its hall bathroom has a unique silver glass vessel sink with waterfall faucet and a dazzling, tiled, walk-in shower. Decorated in shades of the sea, with amenities expected in a luxury rental, you are sure to enjoy your holiday in this select paradise.

BED CONFIGURATION: Both bedrooms, located on the second floor, have king size beds and ceiling fans. The primary bedroom has two closets and an ensuite bath with double sinks and a gorgeous walk-in shower. This room also boasts a covered deck. The second bedroom has an ample closet and hall bath with a spacious walk-in shower. A queen sleeper sofa is in the living room.

OUTDOOR AMENITIES: The home’s comfortably furnished paver patio and grill can be enjoyed rain or shine. The heated community pool is a short stroll away. The pool area has lounge chairs, tables with umbrellas and restrooms for your convenience.

PARKING: One highly coveted, designated parking space is just steps from the home. Note vehicle must NOT exceed 18' long or 80" wide, strictly enforced.

LOCATION: Tucked away in the exclusive, historic Truman Annex, this home is a mere two blocks from Duval Street. The Truman Waterfront Park is nearby. Restaurants, shopping, and entertainment are all within walking distance.

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.
***Staying for a month or longer? Request a quote for a minimum of 28 nights to see our discounted "monthly" rates.
***Managed by Historic Key West Vacation Rentals***