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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.

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Historic Hideaways
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Rates from
$143 / night
Additional fees may apply
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Rental overview

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.

Good fit for
Honeymooners
Sleeps Up to 4 Sleeping setup includes 1 Olympic queen bed and 1 queen sleeper sofa.
Shipyard Pool Access Guests have access to the Shipyard pool, heated in season.
Full-Width Balcony Covered balcony spans the condo and includes dining and seating areas.
Washer/Dryer In Unit A washer/dryer closet is included inside the condo.
Reserved Parking Includes a reserved parking space for the condo.
At a glance

Property Highlights

City / DowntownLocation Setting
Near a BeachBeach Access
1 BedroomBedrooms
1 Full BathroomBathrooms
Sleeps 4Guest Capacity
600 sq. ft.Living Space
PoolPool
Internet AccessInternet
TelevisionTelevision
YesWasher / Dryer
Key West Florida
Location & nearby Explore the Area

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.

Plan your stay

Rates & Availability (USD)

Rates from
$143 per night
30-day minimum stay
Check current rates & availability

Live booking details are maintained by Historic Hideaways.

Check Availability

Availability Calendar

Use the calendar as a guide, then confirm current availability directly with the manager.

Available Booked
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
PMS Rate
Aug 01, 2027 - Sep 30, 2027
Minimum Stay: 30 Days
$150 $1,050 $4,500
About this rental

About This Rental

Annie's Hideaway is a second-floor condo at Shipyard Condos in Truman Annex, a gated community in downtown Key West. With one bedroom and one full bathroom, it accommodates up to four guests using an Olympic queen bed plus a queen sleeper sofa in the living area. The condo is approximately 600 square feet and includes central air conditioning, internet access, televisions, and ceiling fans.

The entry begins at a small porch with seating, then a staircase leads to the main living level. A covered balcony runs the full width of the condo and is arranged with a dining table for four as well as a separate seating area. Inside, the living room is set up for relaxing with TV viewing and includes the pull-out sofa for additional sleeping space.

A small table for two sits near the kitchen, and the L-shaped kitchen includes a microwave and is equipped for preparing meals. The bedroom includes its own TV and storage, and the full bath is adjacent. A washer/dryer is located in a closet within the unit.

On-site amenities include a pool for Shipyard guests (heated in season) and a reserved parking space for the condo. The property notes beach access as walking distance, and the surrounding Truman Annex area includes interconnecting pathways and landscaped grounds. The property is limited to residential accommodations; special events, parties, and functions are not permitted.

Summer & Fall Discounts. Book Now!

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.
Things to enjoy

Activities and Special Interests

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

Beach
Biking
Boating
Catamaran
Fishing
Deep Sea Fishing
Golfing
Honeymoon
State National Parks
Ocean
Sailing
Scuba Diving
Theatre
Wind Surfing
Kayaking
Canoeing
Fly Fishing
Surfing
What's included

Property Amenities

Featured Amenities

Internet Access
Pool
Television
Washer/Dryer

Property Features

Ceiling Fan(s)
Microwave
Parking

Other Property Amenities

Bed Size 1st/Master: Olympic Queen
Beds Pull-out: Queen Sleeper
Number of Baths: 1 Full
Square Footage, Est.: 600
DVD Player(s)
Patio
Air Conditioned: Central
Bldg. Complex Name: Shipyard Condos
Beach Distance: Walking
Helpful details

Frequently Asked Questions

Annie's Hideaway is located in Key West, Florida.

Annie's Hideaway accommodates up to 4 guests.

1 Bedroom and 1 Full Bathroom.

The listed beach access for Annie's Hideaway is Near a Beach.

Yes. The property lists Pool.

The property lists a 30-night minimum stay.
Local management

Professionally Managed By

Historic Hideaways
In business since 1996
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Questions about this rental?

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Property reference
#187968 · Annie's Hideaway
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