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.

Displaying 1 - 12 of 26 rentals matching your search criteria
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A Siesta Bay

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Here is your perfect opportunity to stay in one of the most popular complexes of Key West, the Truman Annex!

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.

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!

Easy Livin'

Type

  • House
Old Town
3 Bedrooms
4 Baths
8 Guests

Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.

Finn Key

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Recently remodeled, tastefully decorated. This rental is hard to beat!

Shipyard Treasure

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Finding a perfect property for your family vacation is easier said than done, but this contemporary condo at Truman Annex might just be the one.

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.

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.

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 Barefoot Retreat

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community. This two-bedroom, one bath, second floor condo will feel like your own tropical home the minute you walk through the door.

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.

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