Vacation Rentals
Find your new favorite place to stay
Angler’s Reef Resort
Islamorada: Mile Marker 84 Oceanside
Relax in a charming island-style retreat with private beach access and serene surroundings.
Learn MoreCoral Lagoon Resort
Marathon: Mile Marker 53 Oceanside
Unwind in a tranquil marina-side haven featuring elegant villas and modern comforts.
Learn MorePrivate Home Collection
Upper & Middle Florida Keys
Indulge in the privacy and comfort of exquisite homes tailored for your perfect vacation.
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MarathonKey colony beach
The Heart of the Florida Keys
Duck KeyThe Crown Jewl of the Keys
IslamoradaThe Sportifishing Capital of the World
Key LargoThe Diving Capital of the World
Select a rental collection to learn more
Mariner’s Club Key Largo®
Key Largo: Mile Marker 97.5 Oceanside
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.
Learn MoreAngler’s Reef Resort
Islamorada: Mile Marker 84 Oceanside
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.
Learn MoreVillage at Hawks Cay Villas
Duck Key: Mile Marker 61 Oceanside
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.
Learn MoreCoral Lagoon Resort
Marathon: Mile Marker 53 Oceanside
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 Gulfside
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.
Learn MorePrivate Home Collection
Upper & Middle Florida 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.
Learn MoreThe Florida Keys are one of the most visually breathtaking and captivating destinations in the world. The world-famous island chain is perfect for all travelers, with endless adventures and opportunities to make lifetime memories.
From the thrill of fishing and boating to the joy of snorkeling and beach-combing, the islands boast an abundance of activities to enjoy. Whether you want a quiet getaway or a luxurious and extravagant experience, the Florida Keys have it all.
At KeysCaribbean, we specialize in offering vacation rentals in the Florida Keys that provide stunning views and exceptional amenities. Our collection of homes includes seaside cottages with pools, opulent villas with boat dockage, and more incredible rental properties. Many of our fabulous homes, including pet-friendly properties, also boast exclusive access to upscale resort amenities.
Depending on the type of experience you’re looking for, we also offer traditional residences in secluded neighborhoods. Our Florida Keys vacation home rentals come with an array of features, like private pools, kayaks, or putting courses. Regardless of what you seek in a Florida Keys getaway, KeysCaribbean is sure to have what you’re looking for.
We also offer flexible length-of-stay options for travelers seeking short- or long-term stays. With a wide range of homes to choose from, it is simple to find the ideal rental that matches your preferences and budget.
You can be confident that your dream vacation awaits you in the Florida Keys! To begin your search, you can filter by island location or browse our resort locations and Private Homes below.
The Florida Keys are one of the most visually breathtaking and captivating destinations in the world. The world-famous island chain is perfect for all travelers, with endless adventures and opportunities to make lifetime memories.
From the thrill of fishing and boating to the joy of snorkeling and beach-combing, the islands boast an abundance of activities to enjoy. Whether you want a quiet getaway or a luxurious and extravagant experience, the Florida Keys have it all.
At KeysCaribbean, we specialize in offering vacation rentals in the Florida Keys that provide stunning views and exceptional amenities. Our collection of homes includes seaside cottages with pools, opulent villas with boat dockage, and more incredible rental properties. Many of our fabulous homes, including pet-friendly properties, also boast exclusive access to upscale resort amenities.