Truman Annex Key West Rentals

Welcome to Last Key Realty, your source for the best vacation rentals in the Truman Annex on Key West Island, Florida. Our properties are handpicked and offer the perfect blend of luxury and comfort for your vacation.

Our Truman Annex Key West rentals range from cozy condos to spacious homes with private pools, providing accommodations for couples, families, and groups. Each property is beautifully decorated and furnished, offering all the amenities you need to feel at home during your stay.

Our rentals are located in the heart of the Truman Annex. This historic and picturesque neighborhood is just steps away from Key West's famous attractions, including Duval Street, Mallory Square, and the Ernest Hemingway Home and Museum. You'll also have easy access to the island's beautiful beaches, watersports, and other outdoor activities.

At Last Key Realty, we pride ourselves on our exceptional customer service. Our team is available 24/7 to assist you with any needs or questions that may arise during your stay. We want your Truman Annex Key West rental experience to be unforgettable. We're committed to ensuring you have everything you need to enjoy your vacation.

Book your Truman Annex Key West rental today and plan your dream vacation in paradise. Contact us for more information or browse our properties online. We look forward to welcoming you to Key West!


You can also search our rentals near Duval Street or search any of our Key West Condo Rentals or Key West Home Rentals.

Properties Available 33 properties available
THE COZY STARFISH is a newly furnished and decorated first floor condo located in the Truman Annex, a private gated community situated in the heart of the island. Despite being only steps away from all that Old Town Key West has to offer, THE COZY STARFISH is a peaceful retreat within a private gated community that offers access to a large, shared
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The Cozy Starfish
Condo
$290.00 - $1,135.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (9)
THE BEAMING BARRACUDA is a freshly renovated townhome located within Truman Annex, Key West's most exclusive gated community. You’ll be within walking distance to all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to its excellent location, THE BEAMING BARRACUDA provides an open living area and outdoor co
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The Beaming Barracuda
Townhome
$333.00 - $1,299.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (42)
Located in Truman Annex, a gated community with some of the most impressive homes in Key West, this exceptional home stands out from all the rest. NOONA'S MANSION is nestled in a quiet cul-de-sac facing the ocean on a beautifully landscaped piece of property. This impressive home features six spacious bedrooms, a fully equipped kitchen, a stunning
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Noona's Mansion
Private Home
$1,500.00 - $6,681.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (273)
Tranquility. Peace. Relaxation. You’ll find these traits are in abundance at GARDEN OF EMMA. The open and airy interior of this exquisite Key West home will keep your group connected and present, while being the perfect complement to the tranquil, tropical exterior. The spacious backyard is your very own private oasis, complete with a lagoon-style
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Garden of Emma
Private Home
$736.00 - $3,222.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (4)
Located in the Truman Annex, a gated community with some of the most impressive homes in Key West, this meticulously furnished estate occupies an entire block, making it the largest single property in the Annex. Formerly referred to as "Plantation Tropicale," with three dwellings, two kitchens (one indoor, one outdoor), a very large pool and enoug
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The Royal Compound
Compound Pet Friendly
$1,500.00 - $6,757.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (59)
LA PETITE PENTHOUSE is a jewel-like second-story condo in the Shipyard at the Truman Annex, a gated community located in the very heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have all of the peace and quiet that comes with a gated community.THE LIVING A
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La Petite Penthouse
Condo
$269.00 - $1,087.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (185)
If you’ve recently heard the Siren’s call beckoning you to Key West, it might be because you were drawn by the SIREN’S SERENADE luxurious interior, lush private backyard, and dream-like location. The moment you enter the gate, you’ll meet the Siren posed in her tropical garden. You’ll come around the lavish and very private pool area to enter this
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Siren's Serenade
Private Home
$999.00 - $3,933.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
COLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking distance of all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to a prime location, COLORS OF THE
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Colors of the Keys
Townhome
$350.00 - $1,408.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (62)
There’s no better way to escape the hustle and bustle of reality than by sneaking off to Key West for a taste of the island life. ELEGANT ESCAPE offers first-class accommodations in a beautiful tropical setting. From the open layout and soaring ceilings of the main house to the enticing private pool and unique guest cottage, ELEGANT ESCAPE has ever
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Elegant Escape
Private Home
$850.00 - $3,402.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (13)
When you think of Key West, you think of spending relaxing days with your toes in the sand under the palm trees, and fun-filled nights walking through the Streets of Old Town on your way to catch the sunset at Mallory Square. Experience these kinds of days (and nights) at SOUTHERNMOST PALMS, a beautifully renovated townhome, located at The Foundry
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Southernmost Palms
Townhome
$399.00 - $1,321.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (102)
SALTWATER HARMONY is a cozy and beautifully furnished first-floor condo in the Shipyard at the Truman Annex, an exclusive gated community located in the heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all of Key West's major attractions, and yet you'll have all of the peace and quiet that comes with a gated co
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Saltwater Harmony
Condo
$290.00 - $1,103.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (167)
Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a two-story private home that not only transcends island living at its finest but also offers an ideal location for e
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Jasmine Jewel
Private Home
$675.00 - $2,773.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (94)

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