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 32 properties available
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
Hot HOT 222
Siren's Serenade
Private Home
$999.00 - $3,728.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
HARBORSIDE HARMONY is the epitome of luxurious waterfront living! With scenic views of the Gulf from the living area and private balcony, coupled with a spacious layout and island-style furnishings, this gorgeous condo is the ideal place to call home during your Key West vacation. Best of all, HARBORSIDE HARMONY is located in the exclusive gated co
Hot HOT 228
Harborside Harmony
Condo
$440.00 - $1,607.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (3)
Seals & Crofts said it best: ‘Diamond Girl, you sure do shine.’ Formerly known as Seventh Heaven, DIAMOND GIRL is a stunning two-story private home that epitomizes island living, with its’ distinct exterior eyebrow design, ample indoor and outdoor living space, and comfortable accommodations. Once here you’ll quickly realize this peaceful oasis
Hot HOT 233
Diamond Girl
Private Home
$850.00 - $3,751.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (24)
BAHAMIAN BAMBOO has been painstakingly decorated and furnished in a sophisticated yet distinctive Bahamian style. Your lifestyle in this home will be very Bahamian as well, with large French doors that open up to provide seamless tropical indoor/outdoor living. The pool is just steps away from the living room sectional or the outdoor dining area. Y
Hot HOT 216
Bahamian Bamboo
Private Home Pet Friendly
$820.00 - $3,124.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (150)
SERENITY ON SOUTHARD is a beautifully renovated 1 bedroom second floor condo with a full kitchen and washer and dryer. This condo is located in the Truman Annex, a gated community located in the heart of the island - just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have a peaceful retreat withi
Hot HOT 221
Serenity on Southard
Condo
$251.00 - $1,002.00 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating 5 (42)
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
Hot HOT 221
Garden of Emma
Private Home
$800.00 - $3,055.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (4)
When exploring Old Town Key West it is typical to stumble upon a surprise tropical bloom that reminds you of the magic of the island you have found yourself on. At the right time of year when enjoying the private garden of this townhouse, you may look up into the trees and spot a bunch of bananas smiling down on you. BANANA BLOSSOMS surprises you w
Hot HOT 258
Banana Blossoms
Townhome
$466.00 - $1,688.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (84)
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
Hot HOT 227
The Cozy Starfish
Condo
$290.00 - $1,069.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (9)
The vacation opportunity of a lifetime awaits at GRAND KEY OASIS. This breathtaking one-of-a-kind property is the epitome of luxurious island living, featuring two separate homes connected by a covered pavilion that overlooks the exceptional backyard and resort-style private pool. The interior design of this compound will leave you marveling at the
Hot HOT 236
Grand Key Oasis
Compound
$985.00 - $3,751.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (10)
The sound of steel drums, the warm breeze off the water, the palm trees rustling in the sky… the essence of the Caribbean awaits in Key West for your next private vacation. This classic island townhome is located within Truman Annex, Key West's most exclusive gated community. From the Tommy Bahama furnishings and island inspired décor to the tropic
Hot HOT 257
Caribbean Charm
Townhome
$350.00 - $1,238.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (66)
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
Hot HOT 227
Colors of the Keys
Townhome
$350.00 - $1,331.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (62)
VILLA BAHAMA is located at The Foundry in the Truman Annex, Key West's most exclusive gated community. You'll be just around the block from Mallory Square, Duval Street and all the attractions Key West has to offer, yet you'll benefit from the peace and quiet that the Truman Annex is known for. Smoking is not permitted in any Last Key Realty home.
Hot HOT 224
Villa Bahama
Townhome
$350.00 - $1,228.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (220)

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