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 31 rentals matching your search criteria
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Bowe Conch House

Type

  • Cottage
3 Bedrooms
2 Baths
6 Guests
BOWE CONCH HOUSE (monthly rental): The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised in Key West, for more than 4 generations.

Key Lime Pie

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Private cottage that has all the amenities you would require for your stay, private pool, outdoor space for lounging, grill and dining. One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town.

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.

True Paradise

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Located in one of the most sought out neighborhoods "The Meadows" this lovely condo has everything you need to enjoy your time in Key West.

Poolside Paradise

Type

  • Home
2 Bedrooms
2 Baths
4 Guests
It is all about outdoor living at this beautiful private home with large covered living space overlooking your private 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.

Flagler Station

Type

  • Home
3 Bedrooms
2 Baths
8 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.

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.

Coral Breeze

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
Perfect view from your screened porch to watch golfers play the first hole on the Rees Jones designed Key West Golf Course.

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.

Treetop Paradise

2 Bedrooms
2 Baths
6 Guests
Small quiet compound with a pool an off street parking, walking distance to great restaurants, shopping and entertainment.

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.

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