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Florida Keys

Vacation Home Rentals

Why Choose Keys Caribbean

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Great Locations with 24/7 Service

Traveling can be stressful, but you can rest peacefully during your stay with us. Our team of agents with professional hosting experience are available 24 hours/day by phone to assist you at any time.

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Luxury Vacation Homes Available

Expect an exceptional vacation in one of our select rentals at premier Upper & Middle Keys resort communities where you’ll have exclusive access to the finest onsite amenities.

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Waterfront Homes with Docks & Pools

We manage an extensive collection of waterfront homes throughout the Upper & Middle Keys with an array of top-notch amenities including private swimming pools, boat dockage, Jacuzzi tubs, and more.

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Spacious Homes Can Host Large Families

KeysCaribbean can easily accommodate your family reunion or get-together with friends! Choose from our select rentals with up to six bedrooms or two of many neighboring properties in our rental program.

Mariner's Club Key Largo®

( Key Largo: Mile Marker 97.5 )

This upscale Key Largo vacation rental community of oceanfront condos and townhouses with up to 4 bedrooms features a variety of luxurious amenities including exclusive access to the largest freshwater swimming pool in the Florida Keys! Guests also enjoy the secondary swimming pool, heated Jacuzzi tub and Waterfall Grotto, onsite marina, tennis courts, fitness center, and game room.

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Angler's Reef Resort

( Islamorada: Mile Marker 84 )

Step into an oceanside retreat behind the gates of Angler’s Reef where classical Keys cottages are nestled against the Ocean’s edge behind 500 feet of private beachfront. Spend the afternoon sunbathing poolside or make your way to the nearby Arts District of Islamorada where vendors share their island-themed creations and locally brewed ale is served on tap.

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Village at Hawks Cay Villas

( Duck Key: Mile Marker 61 )

Discover what makes Duck Key a world-renowned vacation destination from the immaculately kept grounds to panoramic Ocean views. The Village at Hawks Cay Villas boast up to 4 bedrooms with select villas featuring private pools, Jacuzzi tubs, dockage, and more. Our guests also enjoy convenient access to top-rated activities with the Dolphin Connection, Solé Watersports, and Calm Waters Spa.

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Coral Lagoon Resort

( Marathon: Mile Marker 53 )

Immerse yourself in a limitless world of paradise at Coral Lagoon, an oceanside community of 3-bedroom homes surrounding two canal waterways that is designed to accommodate avid fishermen and their families with a stay that is as lavish as it is convenient to the surrounding waters. At our Marathon location, you’ll have convenient access to world-class charters, cruises, water sports, and more.

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Indigo Reef Resort

( Marathon: Mile Marker 53 )

It’s just steps from the backdoor to your boat at this waterfront resort community in Marathon. Our spacious 3-bedroom townhouses feature prized amenities including fully equipped kitchens, balconies overlooking the Gulf of Mexico, and complimentary dockage. Indigo Reef neighbors premier Marathon attractions including FL Keys Aquarium Encounters and Capt. Hook’s Marina & Dive Center.

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Private Home Collection

( Upper & Middle Keys )

Whether it’s a private pool or you want to keep your boat within arm’s length, you’re sure to find the property that satisfies all your wants within our extensive collection of private vacation home rentals located throughout the Upper & Middle Keys. Our homes range from waterfront one-bedroom condos to impressive seaside properties with up to six bedrooms.

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High Praise From Our Guests