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 13 - 24 of 89 rentals matching your search criteria
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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.

Duval Compound

Type

  • Home
6 Bedrooms
5.5 Baths
14 Guests
With an unbeatable location, two pools and all top of the line appliances Duval Compound is a true find among vacation rental properties

Coconut Cottage

Type

  • Cottage
1 Bedroom
2 Baths
2 Guests
Private fenced outdoor space to enjoy your private plunge pool and the large outdoor space for lounging and dining.

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!

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.

The Hemingway

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
The location does not get better than this! Short bike ride to the beach and walking distance to most restaurants and shops!

Tranquility

Type

  • Cottage
1 Bedroom
1.5 Baths
4 Guests
Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental

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.

First Breath

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.

Finn Key

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat!

Bahama House

Type

  • Home
3 Bedrooms
3.5 Baths
7 Guests
Luxury rental with all the amenities you can ask for, Bahama House might just be right right vacation rental for you!

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