Key West Vacation Rentals with Pools

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Displaying 37 - 48 of 72 rentals matching your search criteria
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Nautical Dreams

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Nautical Dreams is the perfect spot for whatever you desire - parties or peace and quiet in a Key West vacation home.

Emma's Escape

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

Conch Republic Retreat

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890.

Perfect Pineapple

Type

  • Home
2 Bedrooms
1 Bath
4 Guests
Sit along side your private pool for morning coffee or your evening glass of wine.

Conch Wind

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
CONCH WIND - Stop searching, Conch Wind is the rental home in Key West you have been hunting for!

Key West Casa

Type

  • Townhouse
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.

Conch Adventure

Type

  • Condo
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.

Shipyard Treasure

Type

  • Condo
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.

A Barefoot Retreat

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Looking for the perfect home away from home? No need to look any further!

No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community.

Key West Found

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!

Coral Villa

Type

  • Townhouse
3 Bedrooms
3 Baths
6 Guests
This charming, clean and nicely decorated vacation rental home is located in Coral Hammock, one of Key West newest communities, very close to restaurants, boating and water adventure!

Linger Longer

Type

  • Townhouse
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!

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