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 52 rentals matching your search criteria
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Cayo Hueso Sunshine

Type

  • Home
2 Bedrooms
3 Baths
6 Guests
French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool.

Treetop Paradise

2 Bedrooms
2 Baths
6 Guests
Small quiet compound with a pool an off street parking, walking distance to great restaurants, shopping and entertainment.

Ibis

Type

  • Cottage
1 Bedroom
1 Bath
2 Guests
Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.

Artist Garden

Type

  • Home
2 Bedrooms
2.5 Baths
6 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 events.

Lighthouse Villa

Type

  • Home
3 Bedrooms
4.5 Baths
8 Guests
In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point.

Coral Garden

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
For those looking for a cozy little getaway on a budget - Coral Garden is the asnwer!

Bogey's Retreat

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes.

Southard Square Hideaway

Type

  • Condo
1 Bedroom
1 Bath
4 Guests
Quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

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!

4 Palms

Type

  • Condo
2 Bedrooms
2 Baths
6 Guests
Key West is all about the beach and the ocean! Located right by Smathers Beach, this tastefully decorated rental might just be the answer!

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!

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