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.

31 properties available

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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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.

Noona's Mansion

Private Home

$1,500^.00 - $5,878^.00 / per night

Hunting for the perfect Key West vacation home can feel like a daunting task. However, once you discover TRUMAN’S TROVE, you’ll know that you’ve struck gold! This two-story private home has been beautifully furnished and designed to the highest standard. In addition, TRUMAN’S TROVE offers an ideal location within Truman Annex, Key West’s most exclu

2026 Changes

Truman's Trove

Private Home

$475^.00 - $1,531^.00 / per night

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 - $3,449^.00 / per night

CONCH CASA GRANDE has been reborn! This majestic home recently underwent a complete renovation, turning an already stunning property into the crown jewel of Truman Annex. As the largest home in the gated community, CONCH CASA GRANDE is one of Key West’s premiere rental properties available.From the moment you set foot in this magnificent home, wit

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Conch Casa Grande

Private Home

$1,200^.00 - $4,617^.00 / per night

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

2026 Changes

Jasmine Jewel

Private Home

$600^.00 - $2,330^.00 / per night

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

2026 Changes

La Petite Penthouse

Condo

$269^.00 - $850^.00 / per night

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

2026 Changes

Banana Blossoms

Townhome

$430^.00 - $1,453^.00 / per night

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 - $2,218^.00 / per night

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

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Harborside Harmony

Condo

$400^.00 - $1,429^.00 / per night

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

Promenade to Paradise

Condo

$415^.00 - $1,546^.00 / per night

GREEN TURTLE COTTAGE will help you come out of your shell and slow down to a turtle’s pace. This 2 bedroom, 2.5 bathroom home is located in the highly sought after Truman Annex neighborhood, putting it within walking distance to Old Town's most treasured restaurants and attractions. GREEN TURTLE COTTAGE is a relaxed home that features coastal, beac

2026 Changes

Green Turtle Cottage

Private Home

$415^.00 - $1,411^.00 / per night

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

2026 Changes

Southernmost Palms

Townhome

$399^.00 - $1,060^.00 / per night

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