Key West Vacation Rentals

Truman Annex Rental Condos in Key West

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 homes 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.

  • Gated Community
    Pool/Beach Towels
  • WiFi
    Bicycles
  • Pool
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22 Properties Returned
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Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

LAVENDER JUNGLE: Beautiful 2 bedroom 1 bath downstairs Shipyard condo in Truman Annex with back deck that opens to the entrance of Fort Zachary Taylor State Park, one of the nicest beaches on the island. Truman Annex, a secure gated community within Old Town Key West, is within walking distance of all the favorite hotspots on the island.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Condo
Area: Old Town

BEACH HOUSE CONDO:   A beautiful 2 bedroom 2 bath Shipyard condominium, located in the prestigious Truman Annex community. This gated community in Old Town Key West is ideal -- only 2 blocks from bars, restaurants and shopping on famous Duval Street and walking distance to all of the attractions you came here to see.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Private Home
Area: Old Town

ARTIST GARDEN:  A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of Truman Annex, a gated community within Old Town Key West. This property is in the ideal location, in walking distance to all Old Town has to offer, including the beautiful beach at Fort Zachary Taylor State Park.


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3 Bedrooms
3 Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

ALLURING PORCHES: A beautiful 2 bedroom 3 bath townhome with den, offering 3 private bedrooms with baths ensuite. Enjoy the abundant french doors that open the entire downstairs to the outdoors and give this home easy open air living. Located in the Porter Lane section of Truman Annex in walking distance of all there is to enjoy in Old Town.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

KEY WEST CHARMING: This downstairs 2 bedroom 1 bath Shipyard condo is located in prestigious Truman Annex, a gated community within Old Town Key West. Take advantage of the ideal location and convenience of walking to anything you would want to do while visiting our lovely island. Prepare to be charmed.


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3 Bedrooms
2 Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

KEY WEST CASA: Beautiful and spacious Shipyard condominium, Key West Casa is one of only a few 3 bedroom 2 bath condos. Located in the prestigous Truman Annex community just 2 blocks to infamous Duval Street and walking distance to the beach, Sunset Celebration and anything you want to do on our island paradise.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

THE HEMINGWAY: A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. Just steps away from the community pool and only 2 blocks from famous Duval Street and historic Old Town Key West. Relax on your back porch, take a dip in the pool, and check out the sights that you have heard so much about on our Island paradise.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

KEY WEST FOUND:   A striking 2 bedroom, 2.5 bath townhome located in the historic  Foundry building in Truman Annex. This 3-story townhome has all the comforts of home.  Conveniently located within walking distance of all the best of Key West -- tourist attractions, beach, Duval Street, Sunset celebration -- you will never want to leave.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Condo
Area: Old Town

CONCH CONDO: This 2 bedroom 2 bath second-floor condo features a fully-equipped kitchen, home theatre in the living room, plasma TVs in both bedrooms, soaring cathedral ceilings with ceiling fans and central air conditioning. Located in Truman Annex within walking distance of everything Key West has to offer; you have found a true Paradise.


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3 Bedrooms
4 Baths
Sleeps 8
Type of property: Private Home
Area: Old Town

EASY LIVIN': The name says it all! This lovely private 3 bedroom home with pool is located in a secluded cul-de-sac in Truman Annex, a gated community located in historic Old Town Key West. Lounge by the pool in peace and tranquility or take a short walk to Duval Street where you will find the restaurants, bars, and shopping you have heard so much about.


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4 Bedrooms
3½ Baths
Sleeps 8
Type of property: Private Home
Area: Old Town

THE DOLPHIN HOUSE: The Dolphin House Key West Vacation Rental is comprised of a bright and open main house and a lovely and bright guesthouse, with a pool and outdoor living space comfortably nestled in between. Plenty of room for friends or family gatherings.  Located in Truman Annex within walking distance of all Key West has to offer.  


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1 Bedroom
1 Bath
Sleeps 2
Type of property: Condo
Area: Old Town

CITY CAY: Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This is the place! Centrally located in Truman Annex, smart, sleek and modern with fully equipped kitchen and high-end electronics within two blocks of anything you'll want to do in our island Paradise.


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2 Bedrooms
2 Baths
Sleeps 5
Type of property: Condo
Area: Old Town

SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in secluded Truman Annex. Lots of open spaces, perfect for entertaining or keeping it low-key and intimate. Easy walking distance to all Key West has to offer.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

FINN KEY:   Beautiful 2 bedroom 1 bath downstairs condominium with all the modern conveniences located in Truman Annex, steps away from the community pool and walking distance to Fort Taylor State Park for beach and sunset views.   Just 2 blocks from Duval Street and the attractions of historic Old Town Key West.  Everything you're looking for within easy reach.


Call For Availability and Pricing
2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

SHIPYARD TREASURE: 2 bedroom 1 bath upstairs condo centrally located to all the sights and attractions of Old Town Key West including the beach at Fort Zachary Taylor State Park. Enjoy a cocktail on your balcony while watching the people stroll by and let the tropical breezes refresh your senses. ASK ABOUT OUR SPECIAL MONTHLY RATES DURING SUMMER MONTHS.


 

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