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 73 - 77 of 77 rentals matching your search criteria
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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!

Papa's Cottage Retreat

Type

  • Home
1 Bedroom
1 Bath
2 Guests
As you step through the natural wooden gate onto the brick pathway, you will be embraced by this private garden oasis.

Truman's Hideaway

Type

  • Condo
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.

Lavender Jungle

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West's most attractive, quiet, and convenient neighborhoods.

Duval Sea Turtle

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle townhome within easy walking distance to everything!

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