Middle Keys vacation rentals
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Top-rated vacation rentals in Middle Keys
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middle Keys vacation rentals
Private vacation rentals in Middle Keys
Condo in Key Colony Beach
4.96 out of 5 average rating, 177 reviewsOceanfront Sunrise Condo Private Beach Heated Pool
Home in Marathon
4.95 out of 5 average rating, 129 reviewsOceanfront Tiny Villa in the Heart of the FL Keys
Townhouse in Key West
4.88 out of 5 average rating, 176 reviews*Sparkling new kitchen* 3 bedroom/3 bath home.
Villa in Marathon
4.89 out of 5 average rating, 157 reviewsNew Aqua Lodge 2Beds 1 Bath with Full Kitchens
Home in Cudjoe Key
4.9 out of 5 average rating, 104 reviewsSunrise Beach Escape
Cottage in Islamorada
4.84 out of 5 average rating, 133 reviews1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Cottage in Cudjoe Key
4.9 out of 5 average rating, 136 reviewsATLANTIS...Ocean Front Cottage Retreat!
Tiny home in Key Largo
4.98 out of 5 average rating, 170 reviewsThe Oasis in key largo with your own private beach
Middle Keys beach vacation rentals
Home in Marathon
4.97 out of 5 average rating, 36 reviewsThe Gulf Cottage at Marathon Key
Condo in Key West
4.94 out of 5 average rating, 33 reviewsCondo de Paradise/Salt Water Pool/Boat Dock
Tiny home in Key Largo
4.99 out of 5 average rating, 72 reviewsOceanfront Lookout Point w/two Kayaks & Deck
Home in Upper Sugarloaf Key
4.88 out of 5 average rating, 50 reviewsBungalows at Sugarloaf Beach - The Lighthouse
Home in Key Largo
5.0 out of 5 average rating, 54 reviewsThe Paradise 2
Condo in Key West
4.93 out of 5 average rating, 45 reviewsBright Condo in Paradise
Home in Marathon
4.97 out of 5 average rating, 35 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Home in Marathon
5.0 out of 5 average rating, 18 reviewsHorizon
House rentals in Middle Keys
Home in Islamorada
4.96 out of 5 average rating, 168 reviewsFlakey's
Home in Marathon
4.91 out of 5 average rating, 160 reviewsBeachfront Villa - Florida Keys
Home in Cudjoe Key
4.97 out of 5 average rating, 126 reviewsCudjoe Key Home with a View
Home in Key Largo
4.9 out of 5 average rating, 354 reviewsYour Keys Getaway!
Home in Key Colony Beach
4.96 out of 5 average rating, 137 reviewsBeautiful open plan remodeled home in Key Colony
Home in Marathon
4.99 out of 5 average rating, 109 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Home in Marathon
5.0 out of 5 average rating, 16 reviewsFlorida Keys Oceanside Utopia
Home in Key West
4.98 out of 5 average rating, 51 reviewsGone Coastal
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