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!
2 Bedrooms
1.5 Baths
4 Guests
Located above the world-renowned Wyland Gallery of Key West. Wyland Penthouse offers a fantastic front row seat overlooking the famous Duval Street from your private outdoor balcony.
Daily - Weekly / Washer/Dryer
2 Bedrooms
2.5 Baths
4 Guests
Beautifully restored private cottage located in Old Town Key West.
30 Day RentalWasher/DryerPets Allowed
3 Bedrooms
2 Baths
8 Guests
Private home that accommodates 8 guests to enjoy the large outdoor dining area while viewing your private pool in your fenced yard.
30 Day RentalPoolGrillWasher/DryerPets Allowed
5 Bedrooms
5.5 Baths
12 Guests
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!
Daily - Weekly / PoolGrillWasher/Dryer
2 Bedrooms
1 Bath
4 Guests
Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental!
Daily - Weekly / PoolWasher/DryerGated Community
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!
30 Day RentalGrillWasher/Dryer
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.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2 Baths
5 Guests
View passing ships and sunsets from your own deck or balcony in the Truman Annex’s most prestigious building
Daily - Weekly / PoolGrillWasher/DryerGated Community
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!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityPets Allowed
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.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2 Baths
4 Guests
Small quiet compound with a pool an off street parking, walking distance to great restaurants, shopping and entertainment.
30 Day RentalPoolGrillWasher/DryerPets Allowed
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.
Daily - Weekly / PoolGrillWasher/DryerGated Community
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