Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 1 - 12 of 75 rentals matching your search criteria
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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.

Sunny View

Type

  • Cottage
Old Town
1 Bedroom
2 Baths
2 Guests

Lovely 1 bed, 2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.

A Place In Paradise

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

Shrimp Party

Type

  • Townhouse
Old Town
2 Bedrooms
2 Baths
4 Guests

Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.

Land Of Love

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
4 Guests

Your perfect escape to Key West awaits you in the Land of Love.

Southard Getaway

Type

  • Condominium
Old Town
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. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer.

Parrot Perch

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

Unbeatable location at a great price! The Parrot Perch is in the gated Shipyard Community of the prestigious Truman Annex.

Easy Livin'

Type

  • House
Old Town
3 Bedrooms
4 Baths
8 Guests

Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.

Key Lime Pie

Type

  • Cottage
Old Town
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.

Alluring Porches

Type

  • Townhouse
Old Town
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!

La Casita

Type

  • House
Old Town
2 Bedrooms
1 Bath
4 Guests

The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street.

Tropical Dreaming

Type

  • House
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido!

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