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 73 - 84 of 86 rentals matching your search criteria
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A Barefoot Retreat

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Looking for the perfect home away from home? No need to look any further!

Step into this fantastic condo and the first thing you'll want to do is take off your shoes; feels just like home.

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.

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.

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

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!

President's Walk

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
Large outside deck invites you to just unwind after a long day of exploring with a good book and a glass of wine or enjoy it with friends grilling your fresh catch

Sunset Celebration

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Beautiful, recently updated 2 bedroom apartment located in a popular community of Truman Annex, only a short bike ride to Fort Zachary Taylor Beach

Key West Casa

Type

  • Townhouse
3 Bedrooms
2 Baths
6 Guests
This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants.

Wind Swept

Type

  • Townhouse
2 Bedrooms
1.5 Baths
6 Guests
Screened porches up and down for you to enjoy the the extra living space in this lovely townhome.

Bahamian Reed

Type

  • Townhouse
2 Bedrooms
1.5 Baths
5 Guests
Look No Further!! Bahamian Reed is a vacation rental home that you will come back to again and again

2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West.

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