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 25 - 36 of 43 rentals matching your search criteria
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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.

Lazy Gecko

Type

  • Condo
2 Bedrooms
1.5 Baths
4 Guests
Beautifully recently remodeled 2 bed/1.5 bath condo located just 4 blocks to Duval Street and the Historic Seaport.

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.

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.

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.

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.

Linger Longer

Type

  • Townhouse
2 Bedrooms
1.5 Baths
5 Guests
Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation!

Ibis

Type

  • Cottage
1 Bedroom
1 Bath
2 Guests
Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.

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

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.

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.

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