Discover the Charm of Ann Street Gardens in Key West, FL
Cottage Rental in Key West Florida
Escape to Ann Street Gardens, an enchanting cottage nestled in the heart of Key West, FL. Immerse yourself in the tranquility of this charming vacation rental, complete with a community pool and a range of nearby activities.
Why You'll Love This Rental
Ann Street Gardens is a 479 sq. ft. one-bedroom, one-bath cottage in downtown Key West’s Old Town, set within the Ann Street Gardens compound. It sleeps up to 3 with a queen bed and a full-size sleeper sofa, and it pairs an enclosed private patio with access to a shared, heated (in season) pool and landscaped garden area reserved for residents. The property is near a beach, and includes off-street parking.
Inside, the layout includes a living area, dining space, small kitchen, and an en suite full bath. The kitchen is equipped with a stove, refrigerator, microwave, toaster, coffeemaker, and blender. Outdoor living is a major part of the stay: the brick patio includes both covered and open-air sections, outdoor seating, and a gas grill. A coin-operated washer and dryer is available on-site for the units in the compound (fee per load). Please note this is a 16+ compound; children under 16 are not allowed.
Property Highlights
Located in downtown Key West’s Old Town, Ann Street Gardens is within the Ann Street Gardens compound and is described as being a half block off Duval Street. The property is also noted as near a beach. Off-street parking is provided, which can be useful for guests who plan to leave the car parked while spending time around the downtown area.
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 12, 2026 - Oct 15, 2026 Minimum Stay: 2 Days |
$234 | $1,260 | $5,400 |
|
PMS Rate Oct 16, 2026 - Oct 25, 2026 Minimum Stay: 5 Days |
$715 | $3,850 | $11,100 |
|
PMS Rate Oct 26, 2026 - Dec 18, 2026 Minimum Stay: 2 Days |
$364 | $1,960 | $8,400 |
|
PMS Rate Dec 19, 2026 - Jan 02, 2027 Minimum Stay: 4 Days |
$650 | $3,500 | $14,925 |
|
PMS Rate Jan 03, 2027 - Jan 31, 2027 Minimum Stay: 5 Days |
$644 | $3,465 | $14,905 |
|
PMS Rate Feb 01, 2027 - Feb 28, 2027 Minimum Stay: 5 Days |
$715 | $3,850 | $16,390 |
About This Rental
Ann Street Gardens is a 16+ compound. Regretfully, NO Children under 16 allowed. There is a coin operated Washer & Dryer on the south side of the cottage for use by the units in the compound. $1.00 per load, per machine, at time of writing.
This residence has one bedroom, one full bath, a small kitchen, a living area, and a dining space. But first you'll want to open the doorway from the living room onto the delightful enclosed patio, which then opens to the main attraction-an exquisitely maintained poolside paradise. The shared, heated (in season) pool and landscaped garden area are reserved for the exclusive use of residents of the small enclave your cottage is part of. Chairs, small tables, chaise lounges, and wicker chairs around glass-top tables dot the landscape. Hidden in among the surroundings are more tables and chairs. From any spot you can observe sunshine playing through palm fronds creating a pattern of shadow and bright sparkle over the pool surface. If you look up, you're likely to spot a flock of water birds flying over. Swim, float, sit on the side, and dangle your feet in the refreshing water. Maybe relax in the sun to develop a tan. Or select the shade of a tree for your resting spot where your biggest decision might be whether to read or nap or ponder where you'll go for your next meal.
If you're in the mood for total privacy, you can enjoy the same glorious Key West weather from your enclosed brick patio, part of which is covered and part open to the sky. This area is sizable, really like another room of the cottage, almost doubling the livable square footage. Closest to the house is a small round table with lamp and two chairs under a generous overhang. A little further, in an uncovered area, is a gas grille. Antique bricks under foot and artful arrangements of plants and vases enhance the garden atmosphere. Up two stairs brings you to the second covered area with vaulted ceiling where you'll find a table suitable for serving a meal for one to four. Directly across is a cushioned wicker rocker and large rattan sideboard with six drawers. Above, a Caribbean style ceiling fan with light creates a gentle air flow and illumination for the evening hours. This is definitely the spot where you could barbeque some fresh fish and enjoy it al fresco with a glass or two of chilled wine. Or maybe go out to dinner and return to the patio to spend a few balmy hours sipping cognac under a canopy of stars.
The inside of Ann Street Gardens starts with the living area that includes a wall of glass overlooking the patio. This and other oversized windows throughout fill the cottage with lovely filtered sunlight and views of tropical greenery. The conversation setting includes a deep couch that also serves as a pull-out full bed, an ottoman that doubles as a coffee table, end tables with lamps, and an overstuffed armchair. The opposite wall holds a large flat-screen TV perfectly placed for viewing from the couch or chair. Under that is a brightly painted hutch that adds color, an artistic touch, and storage space. At the end of the room you'll find a small dining table and two chairs nicely placed beside a wall of glass that give you a congenial view as you enjoy a meal here.
Nearby a doorway opens into the bedroom with queen bed flanked by bedside tables with lamps. Above the bed, a Casablanca-type ceiling fan provides air circulation and light. The room is embellished with art work, two windows, and wall mirror that reflects the romantic scene back onto itself. A flat-screen TV is nicely positioned on an opposite wall for watching the news or latest episode of Nurse Jackie from the bed. An armoire in one corner offers plenty of space for your hanging items and four drawers for folding items. Near the rear wall is the entrance to the en suite full bath, which features colorful tile flooring, shelving, and a well-lit mirror over the sink so you can easily check on your tan lines.
The kitchen is small but perfectly functional with storage drawers, stove, refrigerator, microwave, toaster, coffeemaker, and blender. Again windows on two walls and a cloud white color scheme make this room light and airy and a pleasure to be in.
Your vacation accommodations are just the beginning-the whole of America's only Caribbean island awaits. Since Ann Street Gardens provides off-street parking, you'll find it ever so convenient to leave the car and walk or bike everywhere. For example the Historic Seaport and Boardwalk is over just one block. Follow the wooden walkway along the Key West Historic Seaport to find tall ships offering day and sunset cruises out into the Gulf of Mexico or take an all-day ferry excursion to the Dry Tortugas. If you're interested in watersports, you'll find diving, fishing, parasailing, snorkeling, and jet skiing close at hand. If you get hungry, a dozen or so restaurants of varying levels of informality ring the harbor. Maybe sit under a banyan tree filled with tiny white lights at funky Schooner Wharf while you eat a fresh Mahi sandwich, listen to local musicians, and gaze out at a harbor full of boats of all descriptions. Or for a higher vantage point, try the rooftop bar at Turtle Kraals.
From the Seaport, the world famous Duval Street with its tours, museums, shops, restaurants, and bars is only a block away. Before you walk too far, be sure to check your cell phone for sunset time so you don't miss the daily celebration at Mallory Square. And leave time to hang around for the after party as artists and street performers entertain the crowd with carnival acts, food, and drink. Maybe you've already heard about Dominique and his Flying House Cats, a feline troupe of alley cats that jumps through hoops of fire, walks tightropes, and performs other astounding circus feats.
To know what's going on from day to day, check out Historic Hideaways' informative Events page on their website. 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, which is 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
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Frequently Asked Questions
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