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 31 properties available
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
Hot HOT 25
2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Jasmine Jewel
Private Home
$599.00 - $2,211.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (97)
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
2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
The Beaming Barracuda
Townhome
$333.00 - $1,090.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (46)
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
2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Harborside Harmony
Condo
$400.00 - $1,381.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (3)
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
Hot HOT 29
Noona's Mansion
Private Home
$1,500.00 - $5,707.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (275)
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
2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Garden of Emma
Private Home
$725.00 - $2,742.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (6)
GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two spacious balconies as well.Compliance with Truman Annex Community Rules & Regulations is expected of all
2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Gulfside Vistas
Condo
$430.00 - $1,549.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (264)
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.
2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Villa Bahama
Townhome
$350.00 - $1,069.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (221)
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
2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Promenade to Paradise
Condo
$415.00 - $1,497.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating Rating Rating Rating Rating 5 (160)
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
Hot HOT 150
Saltwater Harmony
Condo
$275.00 - $919.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (170)
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
2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Diamond Girl
Private Home
$850.00 - $3,199.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating 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 25
Bahamian Bamboo
Private Home Pet Friendly
$725.00 - $2,724.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (150)
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
2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
The Royal Compound
Compound Pet Friendly
$1,350.00 - $5,950.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (60)

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