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 49 - 59 of 59 rentals matching your search criteria
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Bayview Harbor

Type

  • Condo
2 Bedrooms
1 Bath
5 Guests
Enjoy your morning coffee, afternoon cocktail or freshly grilled fresh catch on the outside patio when taking a break from exploring Key West!

Coral Villa

Type

  • Townhouse
3 Bedrooms
3 Baths
8 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!

Verandah

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out.

Island Wind

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
Located in a quiet community of Windward Park, only a short walk to Duval Street, with a large shared pool, Island Wind is a true gem in between our rentals

Welcome to a tropical sun drenched oasis in the heart of Old Town Key West.

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!

Key West Ginger Whole House

Type

  • Cottage
2 Bedrooms
2 Baths
6 Guests
Located right around the corner from Banana Cafe and Duval Street ,but still offering plenty of privacy, this cozy cottage with fully fenced yard makes a perfect rental for a small family or few friends trying to make the best of Key West!

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.

William's Loft

Type

  • Cottage
2 Bedrooms
1 Bath
3 Guests
Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops.

Coral Casita

Type

  • Townhouse
3 Bedrooms
3 Baths
8 Guests
Ideal for a family vacation or group of friends looking for a rental on a budget. Located very close to some great Key West restaurants this property is a steal!

Easy Livin'

Type

  • Home
3 Bedrooms
4 Baths
8 Guests
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.

The name says it all!

Casa Grande

Type

  • Home
5 Bedrooms
5.5 Baths
12 Guests
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!

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