Key West Vacation Rentals with Pools

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Displaying 61 - 72 of 72 rentals matching your search criteria
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Key Lime Pie

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Key Lime Pie is the private cottage that perfectly encompasses the “Key West vibe” that you’re looking for. The minute you walk in to see the bright, sunny walls and local artwork, you know you are somewhere special.

A Siesta Bay

Type

  • Condo
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!

Breezy Bungalow

Type

  • Townhouse
2 Bedrooms
2.5 Baths
4 Guests
Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you!

Tropical Casita

Type

  • Home
1 Bedroom
2 Baths
2 Guests
If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space.

City Cay

Type

  • Condo
1 Bedroom
1 Bath
2 Guests
Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This understated Truman Annex Condo is the place!

Beach House Condo

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

Artist Garden

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
This spacious home with a large outside deck is tucked away on a quiet lane of Truman Annex, yet only a short walk to all attractions.

Conch Condo

Type

  • Condo
2 Bedrooms
2 Baths
5 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, second floor condo in Truman Annex.

Alluring Porches

Type

  • Townhouse
3 Bedrooms
3 Baths
6 Guests
Feel the tropical allure of this spacious home in the center-of-it-all community of the historic Truman Annex!

Lighthouse Villa

Type

  • Home
3 Bedrooms
4.5 Baths
8 Guests
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.

President's Walk

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
It wasn't that long ago that President Truman took casual walks in this same location- now it's your turn! President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind.

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