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 93 rentals matching your search criteria
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Tranquility

Type

  • Cottage
1 Bedroom
1.5 Baths
4 Guests
Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental

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.

Conch Republic Retreat

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space.

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!

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.

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.

La Casita

2 Bedrooms
1 Bath
4 Guests
LOCATION YOU CAN NOT BEAT! Located right in the heart of Old Town yet on a quiet lane, only steps to Duval Street, Blue Heaven and many other restaurants and little boutiques!

The Dolphin House

Type

  • Home
4 Bedrooms
3.5 Baths
8 Guests
Wonderful for larger groups or family get togethers, The Dolphin House offers a roomy vacation home in one of Key West's most desirable locations, Truman Annex.

Coral Palm

Type

  • Townhouse
3 Bedrooms
3 Baths
8 Guests
Completely remodeled, renovated and freshly painted 3 bedroom, 3 bath, 2 level Key West townhome is about to be your home away from home!

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.

Mermaid's Dream

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Ocean views from your wrap around balcony and the Olympic sized pool await you at this beautiful home.

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