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 13 - 24 of 65 rentals matching your search criteria
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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.

Beach House Condo

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

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.

Finn Key

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat!

Paradise Place

Type

  • Condo
1 Bedroom
1 Bath
4 Guests
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach

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!

Nautical Dreams

Type

  • Cottage
2 Bedrooms
2 Baths
6 Guests
In a small gated community this perfect cottage with a large private deck to allow all the privacy you would need to grill, dine and lounge.

Emma's Escape

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

First Breath

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.

A Place In Paradise

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

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