Key West Vacation Rentals with Pools

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Displaying 1 - 12 of 72 rentals matching your search criteria
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Sunset Celebration

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Be one of the first to stay in this totally updated vacation home in the popular gated community of the Truman Annex. This 2-bedroom 1 bath second floor Shipyard condo has new floors, fresh paint, all new furnishings, artwork, linens and towels.

Southard Getaway

Type

  • Condo
2 Bedrooms
1.5 Baths
5 Guests
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree.

Paradise Place

Type

  • Condo
1 Bedroom
1 Bath
4 Guests
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach

Casa de Rosalie

Type

  • Home
3 Bedrooms
2 Baths
8 Guests
Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.

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!

Sundown Refuge

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

Ecco Domani

Type

  • Home
3 Bedrooms
2.5 Baths
6 Guests
Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool.

Papaya Place

Type

  • Condo
2 Bedrooms
2 Baths
6 Guests
Atlantic Ocean is just at your reach when staying at Papaya Place! You can almost hear the waves of the ocean!

Atlantic Paradise

Type

  • Condo
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?

William's Loft

Type

  • Cottage
2 Bedrooms
1 Bath
3 Guests
This perfect spot offers plenty of private outdoor space within walking distance of great restaurants and shops.

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