Availability details can be found on the Historic Hideaways website.

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Property Description

Summer Specials!

Truman Annex Properties are going to Monthly (or longer) rentals beginning January 1, 2026 because of changing licensing. To find/book these units for any period in 2026 you must use 30 as your ‘minimum nights’ to have them pull up and show pricing and to book. Please call our office with any questions.

This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket fences give the Annex a lovely park-like atmosphere. Don't be surprised if you see exotic birds like the snowy egret taking a stroll right in the Shipyard gardens. All this tranquility makes it hard to imagine that Duval Street, Key West's central artery of entertainment is a mere two blocks away.

The two-story white wooden structure at Shipyard has a condo below and above. Yours is above and features front and back balconies. Either is ideal for enjoying what locals call sweet weather, a cup of coffee, or that newspaper or novel you brought along. If you're thinking of a swim, a heated pool with spacious patio is just steps away. For your convenience and comfort, the "Shipyard Residents Only" pool area provides chaise lounges, high-speed internet, bathrooms, and shower. If you prefer the real beach, the sun and sea breezes at Fort Zachary Taylor are right in the neighborhood. At the beach, have a sandwich and beer at the snack bar or rent an umbrella and chairs to watch the world of swimmers, divers, sailors, kayakers, and jet skiers pass by.

But wait, you aren't even unpacked yet. Enter your vacation home from the front porch, unlock the door to your left, and head up the carpeted stair case. At the top you'll find a welcoming, fluid open floor plan that combines the kitchen, dining area, and living room. A door at the back of the kitchen opens to the front balcony and the living room door leads to the back balcony. The galley kitchen has everything you need to cook a meal at the stove. There's plenty of cupboard space above and every appliance conveniently tucked in below.

Next to the kitchen, the dining area provides a round, glass-topped table, colorful table linens, and four chairs. Sitting here you can enjoy the view out the French doors to the back balcony with blue sky and palm trees beyond. Or take your meal outside using the balcony's dining table and chairs. The living area features a bamboo couch, coffee table, and arm chair, all the same warm honey color as the Travertine tile floors. Colorful fish add tropical decoration to the walls. A "Casablanca" fan whirs above, circulating air throughout. In fact white ceiling fans cool every room whether you're using the central air conditioning or not. A corner-situated TV provides convenient viewing from the couch or chair. Need more seating? Just bring in the dining area chairs.

Just off the living/dining area are the master bedroom, which features a queen bed, chest of drawers, wall-mounted TV, and plenty of natural light from a large window; a full bath; and a second bedroom with twin beds. Each bedroom offers plenty of closet and drawer space for your flip-flops, shorts, swimwear, sunglasses, camera, hat, you name it.

Once you've settled in, the free-spirited fun of America's only Caribbean island awaits you at the Historic Seaport, on Duval, at the Southernmost Point, or at the beaches along the Atlantic. Check out the tours, museums, water sports, shopping, bars, and over two hundred restaurants, many with open-air seating, some right on the water. While your condo comes with reserved parking, you don't really need a car. From your central location, everything is easily accessible by foot, bike, pedicab, or taxi. Strolling Duval, you might find yourself posing for a photo-op with a pirate, a six-foot-tall drag queen, a Hemingway look-alike, or maybe even Jimmy Buffet in person.

When you've had enough for one day and head back to your condo to relax and plan for the next day, make one last stop at the Green Parrot for a little live music, a libation, and free popcorn among writers, artists, locals, and visitors. At the corner of Southard and Whitehead (the first and last bar on Highway 1), it's right on your way back to the Shipyard.

To know what's going on from day to day, check out Historic Hideaways' informative Events page on our website. Other information on the current music scene, movies, plays, gallery openings, and charitable events include milezerokeywest.com and Paradise, which comes out every Thursday.

Activities and Special Interests

This property provides access to the following activities and special interests: