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 23 rentals matching your search criteria
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Amelia Home

Type

  • Home
2 Bedrooms
2.5 Baths
6 Guests
After a long day cool off in the private pool, enjoy cold Margarita on the covered porch and cook up some fresh catch on the grill! Welcome to your dream vacation home!

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!

Casa de Rosalie

3 Bedrooms
2 Baths
8 Guests
Private home that accommodates 8 guests to enjoy the large outdoor dining area while viewing your private pool in your fenced yard.

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.

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.

Hidden Treasure

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Private outdoor kitchen to able to enjoy cooking your favorite dish while enjoying the large outdoor space.

Tropical Casita

Type

  • Home
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.

Conch Corner

Type

  • Home
3 Bedrooms
3 Baths
6 Guests
Private conch home in a quiet neighborhood but still within walking distance to all of the Key West sites.

A Suite Paradise

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
Private home with large covered outdoor living area overlooking your private pool w/waterfall.

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.

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