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 36 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.

Flagler Station

Type

  • Home
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 space and pool to spend your days enjoying.

Wind Swept

Type

  • Townhouse
2 Bedrooms
1.5 Baths
6 Guests
Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. All that and much more awaits you at Windswept!

Lazy Gecko

Type

  • Condo
2 Bedrooms
1.5 Baths
4 Guests
Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.

La Casita

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.

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.

Shrimp Party

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.

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.

Coral Villa

Type

  • Townhouse
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!

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.

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