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 76 rentals matching your search criteria
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Sunny View

Type

  • Cottage
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.

Bahamian Reed

Type

  • Townhouse
2 Bedrooms
1.5 Baths
5 Guests
Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again.

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!

Southard Square Hideaway

Type

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

Finn Key

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Recently remodeled, tastefully decorated. This rental is hard to beat!

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!

Under The Palms

Type

  • Home
2 Bedrooms
2 Baths
4 Guests
Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.

La Casita

Type

  • Home
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.

Poolside Paradise

Type

  • Home
2 Bedrooms
2 Baths
4 Guests
Spending time in the warm breezes of Key West – isn’t that why you come here? At Poolside Paradise you can enjoy outdoor living at its best!

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.

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.

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