Truman Annex Rentals in Key West

You are here

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.

Share Results
Displaying 1 - 12 of 30 rentals matching your search criteria
Map View
List View
Add Favorite

Finn Key

Type

  • Condo
Old Town
2 Bedrooms
1 Bath
4 Guests
Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat!

Daily - Weekly / PoolGated Community
View Details
Add Favorite

Conch Condo

Type

  • Condo
Old Town
2 Bedrooms
2 Baths
4 Guests
Perfect rental for a small family or couple of friends, close proximity to the pool and beach, Conch Condo makes one of the most desirable vacation rentals

A two-bedroom, two-bath condo in Truman Annex.

Daily - Weekly / PoolGated Community
View Details
Add Favorite

Bayview Harbor

Type

  • Condo
Old Town
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!

Daily - Weekly / PoolGrillGated Community
View Details
Add Favorite

Truman's Hideaway

Type

  • Condo
Old Town
2 Bedrooms
2 Baths
5 Guests
Enjoy breathtaking sunsets with a glass of wine from your own private porch

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.

Daily - Weekly / PoolGrillGated Community
View Details
Add Favorite

Key West Casa

Type

  • Townhouse
Old Town
3 Bedrooms
2 Baths
6 Guests
This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants.

Daily - Weekly / PoolGrillGated Community
View Details
Add Favorite

Captains Wheel

Type

  • Townhouse
Old Town
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!

Daily - Weekly / PoolGated Communitypets not allowed
View Details
Add Favorite

President's Walk

Type

  • Townhouse
Old Town
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

Daily - Weekly / PoolGrillGated Community
View Details
Add Favorite

Easy Livin'

Type

  • Home
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.

The name says it all!

Daily - Weekly / PoolGrillGated Community
View Details
Add Favorite

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! Just relax and enjoy your vacation!

Daily - Weekly / PoolGrillGated Community
View Details
Add Favorite

Alluring Porches

Type

  • Townhouse
Old Town
3 Bedrooms
3 Baths
6 Guests
Beautifully decorated and spacious home in the community of Truman Annex is awaiting for you!

Daily - Weekly / PoolGated Community
View Details
Add Favorite

Bahamian Reed

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests
Look No Further!! Bahamian Reed is a vacation rental home that you will come back to again and again

2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West.

Daily - Weekly / PoolGated Community
Explore All Specials
View Details

Pages