Key West Vacation Condos

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Displaying 1 - 12 of 27 rentals matching your search criteria
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Atlantic Paradise

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time. How about an evening stroll through the tropical jungle in your own backyard.

ElevatorHot TubPets Not AllowedWasher/DryerGrillPool
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Always Your Paradise

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Always Your Paradise is the perfect escape for your next trip to Key West. Conveniently located in the Shipyard Condominiums in the Truman Annex right in the heart of downtown. Enjoy the shared heated community pool or ride bikes to Ft.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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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.

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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Lazy Gecko

Type

  • Condominium
Old Town
2 Bedrooms
1.5 Baths
4 Guests

Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.

Pets Not AllowedWasher/DryerGrillMonthly Rental
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Key West Charming

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Located at the Shipyard Condominiums downtown Key West, this first floor, 2 bedroom, 1 bathroom home has been lovingly cared for by the owners.

Pets Not AllowedWasher/DryerPoolGated Community
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Southard Square Hideaway

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
4 Guests

A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

Pets AllowedPets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental
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Windchime

Type

  • Condominium
Old Town
0.5 Bedrooms
1 Bath
2 Guests

Searching for an affordable monthly vacation rental in the heart of Key West? Do you plan on spending most of your time enjoying all that Key West has to offer and seeing what if feels like to really live like a local? Then tune into Windchime!

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Conch Adventure

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Nestled in a quiet corner of the Shipyard section in the desirable Truman Annex, this 2-bedroom 1 bath downstairs condo offers peace, quiet and convenience.

Pets Not AllowedWasher/DryerPoolGated Community
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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!

Pets Not AllowedWasher/DryerPoolGated Community
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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.

Pets Not AllowedWasher/DryerPoolGated Community
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