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 13 - 24 of 30 rentals matching your search criteria
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Conch Adventure

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Come enjoy one of Key West's most desirable rental complexes, Truman Annex. Conveniently located just couple blocks to the beach, Duval Street and Mallory Square, makes this the ideal rental for a small family or couple of friends

Key West Charming

Type

  • Condo
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

  • Home
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.

The name says it all!

Captains Wheel

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer!

Siesta Bay

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Here is your perfect opportunity to enjoy your stay in one of the most popular complexes of Key West, Truman Annex!

Lavender Jungle

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
This gorgeous apartment is located in one of Key West's most attractive, quiet, and convenient neighborhoods, Truman Annex, close to many attractions and also Fort Zachary Taylor Beach

Bayview Harbor

Type

  • Condo
2 Bedrooms
1 Bath
5 Guests
Enjoy your morning coffee, afternoon cocktail or freshly grilled fresh catch on the outside patio when taking a break from exploring Key West!

Parrot Perch

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
Unbeatable location! Only a block to famous Green Parrot bar yet in a secluded, quiet community of Truman Annex

President's Walk

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
Large outside deck invites you to just unwind after a long day of exploring with a good book and a glass of wine or enjoy it with friends grilling your fresh catch

Southard Getaway

Type

  • Condo
2 Bedrooms
1.5 Baths
5 Guests
Amazingly Perfect!!! That is how one of our guests reviewed Southard Getaway! This amazingly perfect rental can be yours as well!

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