Truman Annex Rentals in Key West

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Just steps from historic Old Town, where the Gulf meets the Atlantic, sits the premier gated community known as Truman Annex. Located by President Truman's Little White House, our home, townhouse and condo rentals can be found in the Shipyard, Presidents Walk, Foundry and Admirals Lane. The Annex is walking or biking distance to the shops, restaurants, bars, beaches and museums that make Key West so unique. Search our large selection of Truman Annex rentals below and reach out if you need assistance finding and booking the perfect rental for your stay! Please note that rentals in Truman Annex typically require a 7 night minimum stay, so please keep this in mind when searching dates for your stay.

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Displaying 1 - 12 of 27 rentals matching your search criteria
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Breezy Bungalow

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
4 Guests

When a name says it all you know you have made the perfect choice for your Key West island escape.

Pets Not AllowedWasher/DryerPoolGated Community
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Southard Getaway

Type

  • Condominium
Old Town
2 Bedrooms
1.5 Baths
5 Guests

“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer.

Pets Not AllowedWasher/DryerPoolGated Community
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Truman's Hideaway

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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Lavender Jungle

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West's most attractive, quiet, and convenient neighborhoods.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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Beach House Condo

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home. | | A beautiful 2 bedroom 2 bath ground level condo located in the gated Shipyard Condominium area of the prestigious Truman Annex community.

Pets Not AllowedWasher/DryerPoolGated Community
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Linger Longer

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests

Just imagine stepping out of the rental and stepping right into the pool!

Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath, 2-story town home, located in the President's Walk of Truman Annex.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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The Dolphin House

Type

  • House
Old Town
4 Bedrooms
3.5 Baths
8 Guests

Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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A Place In Paradise

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

Pets Not AllowedWasher/DryerPoolGated Community
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Buena Vista

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

The historic brick foundry residence is in the luxurious gated community of the Truman Annex, appropriately named after President Harry Truman.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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Key West Found

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!

Pets Not AllowedWasher/DryerPoolGated Community
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Key West Charming

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental!

Pets Not AllowedWasher/DryerPoolGated Community
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