Annie's Hideaway Condo Vacation Rental With Balcony in Key West
Condo Rental in Key West Florida
Annie's Hideaway is a 1-bedroom condo vacation rental in Key West with a covered balcony, seasonal heated pool access in Truman Annex Shipyard, and walkable access to Duval Street and Fort Zachary Taylor.
Why You'll Love This Rental
Annie's Hideaway is a 600 sq. ft. one-bedroom, one-bath condo in Key West’s downtown setting within Truman Annex’s Shipyard Condos, a gated community. The residence sleeps up to four with an Olympic queen bed and a queen sleeper sofa. Guests have access to a Shipyard pool (heated in season) and the condo includes a reserved parking space, plus beach access noted as walking distance.
Entry is through a small porch with seating, then stairs lead to the second-floor living space. A covered balcony spans the width of the condo and includes both dining and lounge areas. Inside, the living room offers TV, internet access, and ceiling fans, while the L-shaped kitchen includes a microwave and is stocked for in-home meals. The bedroom has its own TV, and a washer/dryer closet adds convenience for longer stays.
Property Highlights
The condo is located in downtown Key West within Truman Annex’s Shipyard Condos, described as a gated community. The setting provides access to landscaped grounds and connecting pathways within the complex. The listing notes proximity to Duval Street (two blocks) and indicates beach access as walking distance, with Fort Zachary Taylor beach specifically mentioned in the source description.
Rates & Availability (USD)
Live booking details are maintained by Historic Hideaways.
Availability Calendar
Use the calendar as a guide, then confirm current availability directly with the manager.
| Season | Nightly | Weekly | Monthly |
|---|---|---|---|
|
PMS Rate Oct 10, 2026 - Oct 31, 2026 Minimum Stay: 30 Days |
$150 | $1,050 | $4,500 |
|
PMS Rate Nov 01, 2026 - Dec 31, 2026 Minimum Stay: 30 Days |
$143 | $1,001 | $4,290 |
|
PMS Rate Jan 01, 2027 - Jan 30, 2027 Minimum Stay: 30 Days |
$216 | $1,512 | $6,480 |
|
PMS Rate Jan 31, 2027 - Mar 02, 2027 Minimum Stay: 30 Days |
$300 | $2,100 | $9,000 |
|
PMS Rate Mar 03, 2027 - Apr 30, 2027 Minimum Stay: 30 Days |
$216 | $1,512 | $6,480 |
|
PMS Rate May 01, 2027 - Jul 31, 2027 Minimum Stay: 30 Days |
$166 | $1,162 | $4,980 |
About This Rental
The most important vacation element is location. This one-bedroom condo fits the bill precisely located in Truman Annex’s Shipyard, a premier gated community of townhouses, condos, and parks. The Annex is rich in its own lore and amazingly close to Duval Street with all the culture and fun that it implies. Not only is there a heated (in season) pool for the exclusive use of guests in Shipyard, but there is also easy access to Fort Zachory Taylor beach and to the Truman White House. Have a car? Park it in the space reserved for your condo because you can walk or bike everywhere.
Through a white picket fence, up onto a delightful little porch with two chairs is the entrance to the condo. Once inside, you ascend polished wooden stairs to the second-floor residence. At the top of the stairs, you can see through the living room to a marvelous, covered balcony that runs the whole width of the condo. At one end is a dining area with a teak table and four chairs. At the other end, a two-section couch centers around a coffee table, an area perfect for morning coffee or afternoon cocktails. For the final tropical touch, the balcony overlooks a lush, dense, and beautiful Fishtail Palm.
Back through glass doors is the living room, which is just as you’d expect: a couch (that even converts to a queen bed w/ a deluxe mattress), two chairs, end tables with lamps, a coffee table, and a four-blade ceiling fan whirring above. The comfy and colorful couch is perfectly positioned for viewing the TV on the opposite wall. The hutch under the TV provides plenty of shelf space for books, magazines, games, etc. And of course there’s A.C., high speed internet, and cable.
In the space that leads to the kitchen is a small table with two chairs, perfect for enjoying a cup of morning coffee, maybe with a pastry from one of Key West’s French-style cafes or from Glazed Donuts. The L-shaped kitchen is striking because of the ocean blue cabinets above and below. It is well stocked with appliances, dishes, glassware, pans, silverware, etc. An area rug and large window add more color and brightness. A chicken print over the stove claims the area as part of the Conch Republic, “a sunny place for shady people.”
Adjacent are the queen bedroom with a 66" wide Olympic Queen, full bath, and washer/dryer closet. A bright shower curtain and coordinating towels provide striking accents in the bath. A few steps away, the bedroom glows with ambient light from a window. The bed is comfortable and roomy. Bedside tables with lamps provide easy access to tabletop and drawer space for travel paraphernalia, reading material, electronics that need charging, a bottle of water, or whatever. A spacious closet provides space for hanging things while a five-drawer wicker chest works for your folded things. On the chest sits a TV for viewing from the bed. Maybe a late-night movie or an episode of your favorite series. Overhead a four-blade ceiling fan circulates air and provides the finishing touch.
When you are ready to explore beyond the condo, head out through manicured landscaping and interconnecting pathways. One you pass through a wrought iron privacy gate, you are two blocks from Duval Street and its myriad of attractions: tours, museums, shopping, bars, and restaurants, many with open-air seating, some right on the water. You can have a beer with the ghost of Hemingway at Sloppy Joes Bar or the ghost of Jimmy Buffett at Margaritaville Café. To live dangerously, try petting a shark at the aquarium or having a butterfly land on your shoulder at the Butterfly and Nature Conservatory. If you’re interested in watersports, the Historic Seaport offers all kinds: diving, fishing, parasailing, snorkeling, and jet skiing to name a few. Maybe take a day trip to the Dry Tortugas National Park, seventy miles west of Key West.
Don’t miss the nightly sunset celebration at Mallory Square, where visitors and locals alike gather to applaud as the sun slips below the horizon. Afterward, stick around for the carnival-like festivities that follow. Or if leaving shore appeals, book a sunset sail on one of the tall ships. Live music, open bar, and food are included in some and while some are BYO beverage and snacks. Maybe your taste runs more towards the arts. If so, you’re in the right place for music, movies, plays, art galleries, lectures, and more. If you like beaches, your accommodations are very close to a favorite locals’ beach, Fort Zachery Taylor, where you can rent chairs, umbrellas, and snorkeling equipment. Bathrooms, showers, a snack bar, and picnic tables are also available. Or you’ll decide to skip the beach in favor of exploring the adjacent Civil War-era fort which was designated a National Historic Landmark in 1973.
The property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property. To know what's going on from day to day, check out Historic Hideaways' informative Events website page. Other information on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section) or in the print publication Paradise, available at various locations around town every Thursday.
Activities and Special Interests
This property provides access to the following activities and special interests:
Property Amenities
Featured Amenities
Property Features
Other Property Amenities
Frequently Asked Questions
Questions about this rental?
Connect directly with Historic Hideaways for current rates, availability, and local assistance.
Similar Rentals from Historic Hideaways Key West
More rentals from the same manager, prioritized by location, property type, size, and setting.