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 25 - 36 of 70 rentals matching your search criteria
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Papa's Cottage Retreat

Type

  • House
Old Town
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.

Coral Villa

Type

  • Townhouse
Stock Island
3 Bedrooms
3 Baths
6 Guests

This charming, clean and nicely decorated vacation rental home is located in Coral Hammock, one of Key West newest communities, very close to restaurants, boating and water adventure!

Tropical Casita

Type

  • House
Old Town
1 Bedroom
2 Baths
2 Guests

If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space.

Flagler Station

Type

  • House
Mid Town
3 Bedrooms
2 Baths
6 Guests

With family in mind, this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor pool and patio space. Spend your days enjoying paradise in this spacious monthly rental. This one is a priceless gem!

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!

Flagler's Oasis

Type

  • House
Mid Town
2 Bedrooms
1 Bath
4 Guests

Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly.

Nautical Dreams

Type

  • Cottage
Old Town
2 Bedrooms
2 Baths
4 Guests

Nautical Dreams is the perfect spot for whatever you desire - parties or peace and quiet in a Key West vacation home.

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!

Conch Adventure

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Nestled in a quiet corner of the Shipyard section in the desirable Truman Annex, this 2-bedroom 1 bath downstairs condo offers peace, quiet and convenience.

A Little Slice Of Paradise

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
5 Guests

Located on the main road meandering through the secluded gated Key West Golf Club community, you’ll find A Little Slice of Paradise. Spend a month (or two) in this charming townhouse and you may never return home.

Bogey's Retreat

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes.

Key West Found

Type

  • Townhouse
Old Town
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!

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