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  • (305) 294-7358
Key West Time
May 28th
10:46am · 87°F

Key West Poolside Loft ~ Monthly Rental

2BR 2BA ~ Monthly Rental
Sleeps 4

You know that adage … “An unexpected turn can lead to hidden treasures.”  Well if there were ever a place that meets that description, this 2BR 2BA Key West Poolside Loft is the one. Like a secret island hideout, there’s no way you’d find this place until you’re shown the way.

Cleverly tucked away in the exclusive gated community of Key West Truman Annex, here you’re in an island cottage style condo, with a loft and private deck. Peek over your deck railing and you can see that you’re only steps away from the sparkling shared pool below. Sit back and relax, you're at the perfect point of view to keep an eye on family members who are swimming.

The Key West Poolside Loft is nestled inside the exclusive location of the Truman Annex neighborhood, Key West’s premier gated community. No matter where you walk in the neighborhood, you’ll enjoy manicured gardens lined with white picket fences, pastel colored cottages, and lush tropical gardens. When you step outside the gates, the most desired destinations on the island are a short walk or bike ride away.

When you’re ready for one of the most gorgeous beaches in the country, head west and you’re less than a 10 minute walk to Fort Zachary Taylor Historic State Park Beach. Enjoy not only the natural beauty of the beach and the turquoise sea, but also the profound Pre-Civil War Fort that’s built right up to the southern coastline of the island.

On the way to the beach, you’ll discover you have immediate access to the Key West Truman Waterfront Park offering something for everyone in the family. It features an outstanding water splash pad that is wildly popular with the kids. It also holds the impressive Key West Amphitheater, an outdoor live music venue complete with a sound stage surrounded by sloping picnic greens.  

Location and convenience means so much when you’re on vacation, and when you’re ready for some downtown time, it’s a lovely stroll down the lane, through the Truman Annex gates, to all the restaurants, shopping, bars, museums, and attractions of historic Old Town Key West. If you walk a few blocks northeast, you can stop into the Green Parrot Bar for an afternoon cocktail and some live music, or Jimmy Buffett’s Margaritaville for a cheeseburger… in paradise, of course. Head in the opposite direction and you can spend the day admiring the wildlife at the Key West Butterfly Conservatory. This is the perfect location to park your car and forget about it. Welcome to Key West Poolside Loft, your southernmost home-away-from-home.

Interior layout:

The entrance to this condominium is on the ground level. Step inside the front entrance to a friendly vestibule space welcomes you with a gallery wall filled whimsical island art that will get you in the Key West spirit. It's an easy walk up the staircase the main living and dining area. You are upstairs in a townhouse condo, but you'll feel like you're in a classic Key West cottage. An airy vaulted ceiling and perfectly weathered wood floors create an authentic and spacious great room to kick back and unwind. Two huge single-pan glass doors frame the tropical landscaping beyond and invite the Key West sunshine to flood the space with natural light.

Furnishings are stylish and comfortable. The living area includes a soft leather sofa and two upholstered armchairs surrounding a glass-topped coffee table. There’s a lamp on the side table and a floor lamp next to the sofa, so there’s plenty of light to read by in the evenings. Or if you prefer, the flatscreen HDTV is ideal for catching up on your favorite TV show or hosting a movie night.

Next to the living area is a circular glass-top dining table with seating for four. This space is decorated by artistic wall sconces and is the perfect spot to serve some fresh banana pancakes in the morning. A peninsula bar with seating for two leads into the open kitchen. Bright white cabinets surround the full suite of white appliances— including a refrigerator, electric range, dishwasher, and microwave. 

Key West Poolside Loft includes two peaceful sleeping spaces. The first is on the main floor, near the living area, while the second is a lofted space that’s partially closed off to the main area below. In the primary bedroom suite, a luxe king-size bed is draped in high-quality linens and sits underneath a cooling ceiling fan. On either side of the bed is a starfish lamp that’s perfect for late-night reading. This room also includes a spacious chest of drawers and flatscreen television. In the en-suite bathroom, there’s a step-in, glass-enclosed shower with multiple showerheads. There’s also another full bathroom that’s accessible from the hallway.

Next is the lofted sleeping space— a unique, cozy, treehouse-like spot that kids of all ages will love. To get up to the loft, you must climb a sturdy ladder that’s located in the center of the living space. In the loft, there are two comfortable, twin-size beds that are made up with colorful, island-inspired bedspreads. There’s also a custom, upholstered window seat that can become another space for sleeping. This space includes an armchair, a mirror, reading lamps, a flatscreen television, and a sunny window. Fabric dividers on the railings add a bit more privacy to this open space. 

Porch and Grounds:

Chances are, at this Truman Annex vacation rental, you may find that you spend most of your time at this home-away-from home outside on the sun-kissed private porch. This home is perfectly situated next to the swimming pool, allowing you to gaze out at the pool area from your patio. A poolside dining table is place for alfresco dining. Or maybe it will become your favorite spot for sipping a morning cup of Cuban coffee and perusing the Key West Citizen, the island’s daily newspaper. There are also a few rocking chairs for when you want to slip off your flip flops and sip a frosty margarita in the shade. 

When it’s time for a dip, or you want to practice your backstroke, the swimming pool, kept private for the Shipyard complex, is right outside your door. The pool scene is surrounded by lush landscaping, comfortable chaise lounge chairs, large umbrellas, and a shady cabana with Caribbean-inspired vibes. 

Bedding Summary:

  • Primary Suite Downstairs: King-size bed
  • Loft: Two twin-size beds and a window-seat/bed

Amenities: Central air conditioning, a full-size washer and dryer, 3 HDTVs— one in the living area, and one in each sleeping space, a fully-equipped kitchen, and Wi-Fi. This home is a second-floor garden loft with a private back porch with pool views. There’s a heated resort-style shared swimming pool, manicured tropical landscaping, and a fully fenced, gated neighborhood. All linens and towels are provided. Interim housekeeping service is available upon request.

Activities: At Key West Poolside Loft, you’re steps away from nearly everything. If you love music, it's a short walk to the Key West Amphitheater, where wonderful music acts are feature on the green, where the entire family can gather and enjoy. It’s an easy walk to lively Duval Street, eclectic shopping, mouth-watering dining, exciting nightlife, and charming coffee shops. You’re also a ten-minute walk away from the sandy beaches and historic Civil War Fort at Fort Zachary Taylor State Park, the Truman Waterfront Park, and the Splash Pad. This location allows for easy planning of all local activities, including dining, fishing, paddle boarding, kayaking, trolley tours, the Conch Tour train, Sunset Celebrations, museums, and the theater. 

Area: The Truman Annex neighborhood offers a picture-perfect backdrop to your Key West getaway. Manicured landscaping, luscious hibiscus, gorgeous Bougainvillea flowers, sparkling water fountains, and swaying palm trees are all surrounded by sherbet-colored homes and crisp white picket fences. You’ll want to stroll or bike through this community often. The perfect place for families with awesome activities including the Key West Amphitheater, the Truman Waterfront Park, the Key West kids Splashpad, and Fort Zachary Taylor Beach Park, and Pre-Civil War Fort.

Parking: This Key West condo includes a free, private parking spot located close to the front door. Parking is very limited in Old Town Key West, so if you do bring a car, you can park it here safely and forget about it. Almost everything is accessible via walking or bike riding from here.

Restrictions: Key West Poolside Loft is a smoke-free home. Any guest under 25 years old must be accompanied by a guardian or be part of a family group. This is a quiet, gated residential community that does not allow loud parties.


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special rates available



Sept 1- Sept 30

Monthly $4700

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Dates Monthly
May 1, 2024 - May 31, 2024 $4850
Jun 1, 2024 - Jun 30, 2024 $4850
Jul 1, 2024 - Jul 31, 2024 $4850
Aug 1, 2024 - Aug 31, 2024 $4850
Sep 1, 2024 - Sep 30, 2024 $4850
Oct 1, 2024 - Oct 31, 2024 $4850
Nov 1, 2024 - Nov 30, 2024 $4850
Dec 1, 2024 - Dec 31, 2024 $5950
Jan 1, 2025 - Jan 31, 2025 $8800
Feb 1, 2025 - Feb 28, 2025 $9200
Mar 1, 2025 - Mar 31, 2025 $9200
Apr 1, 2025 - Apr 30, 2025 $5950
May 1, 2025 - May 31, 2025 $4950
Jun 1, 2025 - Jun 30, 2025 $4950
Jul 1, 2025 - Jul 31, 2025 $4950
Aug 1, 2025 - Aug 31, 2025 $4950
Sep 1, 2025 - Sep 30, 2025 $4950
Oct 1, 2025 - Oct 31, 2025 $4950
Nov 1, 2025 - Nov 30, 2025 $4950
Dec 1, 2025 - Dec 31, 2025 $5950

Additional Notes:

  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter.
  • Future Dates not listed, please call 305-294-7358 for pricing.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

Bedding Summary:

  • Master Suite: King-size bed
  • Sleeping Loft: Two twin-size beds and a window-seat/bed
Dec 05, 2023,
Always a pleasure…love the condo…back in April. Never disappointed with VHKW or the condo❤️

May 09, 2023,
Very helpful and enjoyed stopping in the office to talk to them. The place we stayed was clean and well maintained. I will definitely be using them in the future.

Dec 05, 2022,
Couldn’t be happier with the condo and VHKW. Such an amazing experience we already booked for 2023. Staff is first class. Thank you for answering all our questions and addressing concerns in a professional and timely manner.

Feb 01, 2022,
Easy to book! Fulfilled all things advertised

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