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 dream of waking up to expansive water views and island breezes, and walking out your front door right onto the streets of Old Town Key West in the center of it all - PROMENADE TO PARADISE is everything you are looking for. With a spacious layout, relaxed island-style furnishings, a semi-private gated pool, and three private balconies all you
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Promenade to Paradise
Condo
$415.00 - $1,651.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (54)
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
$600.00 - $2,696.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (36)
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
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Diamond Girl
Private Home
$850.00 - $3,926.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (4)
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
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Grand Key Oasis
Compound
$876.00 - $3,926.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 8 guests
Rating 5 (3)
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.
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Villa Bahama
Townhome
$350.00 - $1,263.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (96)
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 - $3,387.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
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 - $1,089.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (72)
BLUE HERON'S COVE is a beautifully decorated villa in the Porter Court Complex at the Truman Annex, Old Town Key West's most desirable gated community. You'll be close to all of the Key West's best restaurants and attractions, including Mallory Square and Fort Zachary Taylor State Park. Smoking is not permitted in any Last Key Realty home. In addit
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Blue Heron's Cove
Townhome
$325.00 - $1,601.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (40)
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
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Banana Blossoms
Townhome
$430.00 - $1,736.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (33)
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 - $6,728.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (24)
A trip to Key West is like a breath of fresh air! The sounds of rustling palm trees, the scent of fragrant flowers and the smell of salt air are the rejuvenation that only the tropics can provide. This home is a breath of Key West fresh air, or BRISA FRESCA, a timeless, beach-inspired home that seems to be straight out of the pages of Coastal Livin
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Brisa Fresca
Private Home
$860.00 - $2,532.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (98)
SEA CAPTAIN'S HAVEN is an immaculately furnished villa at the Porter Court Complex in Truman Annex, Key West's most desirable gated community, right in the middle of Old Town. At SEA CAPTAIN'S HAVEN, you'll be close to all of Key West's best restaurants and attractions, including Mallory Square and Fort Zachary Taylor State Park.THE LIVING AREA...S
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Sea Captain's Haven
Townhome
$315.00 - $1,353.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (22)

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