Islamorada Waterfront Villa 1 by the water with boat in foreground

Florida Keys Vacation Rentals

Sun-soaked luxury in the Sunshine State; that’s what defines the Florida Keys. This band of islands has an average daily temperature of 77 F (25 C), plentiful beaches, and jaw-droppingly beautiful natural spaces, so it’s no surprise that it has become the place to see and be seen for some winter sun. The Florida Keys cover a vast area, including Key West, Islamorada, and Key Lago. The region offers a plethora of fantastic attractions, from relaxing on the beach to shopping and diving North America’s only living coral barrier reef.

Find and book fabulous Florida Keys vacation rentals, in stunning locations around this popular destination. From beachfront villas to pet-friendly homes, whatever you’re looking for, we’ve got you covered. Our Florida Keys vacation rentals are perfect for breaks with the family in the Sunshine State, with luxurious villa facilities and easy access to the beaches and attractions of the Florida Keys right on the doorstep.

Straight road over the water in the Florida Keys

Things to do

  • View of the pristine beaches in the Florida Keys
    Soak up the Florida Keys beaches
    Relax and indulge in the beaches of the Florida Keys, catering to all interests. Enjoy Bahia Honda State Park, Smathers Beach, Higgs Beach, Fort Zachary Taylor State Park Beach, and Sombrero Beach - to name a few!

  • Aerial view of the laidback coastal city of Key West
    Explore Key West
    Experience Key West's laid-back vibe, historic sites, and vibrant nightlife. Discover the iconic Ernest Hemingway Home, enjoy sunset celebrations at Mallory Square, and shop and dine along lively Duval Street.

  • A diver explores the underworld paradise in the Florida Keys
    Snorkeling & Diving
    Dive or snorkel into Florida Keys' underwater paradise, home to the only living coral barrier reef in the continental U.S. Explore renowned spots like John Pennekamp Coral Reef State Park and the Sombrero Reef.

  • View of the Dry Tortugas National Park
    Visit Dry Tortugas National Park
    Reachable by boat or seaplane from Key West, this remote island paradise showcases Fort Jefferson, a massive 19th-century coastal fortress. Set against a backdrop of crystal-clear waters, the scenic Park promises a unique day out!

  • A row of fishing rods stand ready and primed for a great day of fishing on the Florida Keys
    Renowned as a fishing destination, the Florida Keys offer opportunities for deep-sea and flats fishing. Both seasoned anglers and beginners can find exciting charters to suit!

  • View of a couple of exploring the Bahia Honda State Park
    Explore the Bahia Honda State Park
    Located in the Lower Keys, Bahia Honda State Park offers stunning beaches and plenty of wildlife spotting opportunities, with clear waters and nature trails leading to scenic viewpoints.

  • A friendly dolphin in Florida Keys
    Visit the Dolphin Research Center
    Explore the nonprofit Dolphin Research Center in Marathon, dedicated to marine mammal research and education. Engage and swim with dolphins, and interact with sea lions.

  • A huge delicious slice of Key Lime pie, served in Key West
    Tuck into some Key Lime Pie
    Don't miss the famous Key lime pie when in the Florida Keys. Savor this sweet and tangy treat at various restaurants and bakeries across the islands.

Luxury Vacation Rentals

A curated portfolio of the best vacation homes and villas in the world’s top destinations

Travel Planners

Experienced vacation rental and villa experts to help you find the perfect home

Concierge & Support

Enjoy 5-star hotel concierge services and dedicated local support with every stay

Private chef seasoning a BBQ feast

Optimize your vacation with Travel Extras

When on vacation in the Florida Keys, you may be looking to make your stay extra special, as well as convenient. Our dedicated Travel Extras invite you to make your vacation as effortless as can be, with a host of optional hotel concierge-style services.

From car hire and airport transportation to private chef hire, baby equipment hire, grocery shopping, welcome hampers, fishing charters and more, our Travel Extras help to make the world your oyster, this vacation. Make your stay extra memorable and explore our Travel Extras today.

Beachfront rentals in Florida Keys - Islamorada 0 luxury villa with private pool and sea view

Beautiful beachfront rentals in Florida Keys

Florida Keys offers one of the most stunning destinations in the state to head for pristine, untouched beaches. Located between the Atlantic Ocean and Gulf of Mexico, here you can even see the line where the two oceans clash together. Take it all in from your stunning beachfront rental in the Florida Keys, where you’ll be able to gaze out over the ocean from your bedroom window, wander down to one of the world’s most stunning beaches within moments, and depending where you stay, have easy access to a huge variety of thrilling seaside activities, such as boating, diving and snorkeling.

Oceanfront vacation rentals in Islamorada with pool access

Nothing quite says Florida Keys vacation, like our scenic beachfront vacation rentals with pool access in Islamorada. Embracing a laid-back, tropical ambiance, Islamorada is famous for its world-class sportfishing and incidentally, fresh seafood cuisine, alongside its beautiful coral reefs. Kick back with a cocktail on the beach, or soak up the resort pools and tempting water-based activities. Our scenic oceanfront vacation homes come in all sizes and configurations, opening the doors to romantic couple breaks, family and group stays and guests needing accessible, wheelchair-friendly accommodation. Explore our incredible Florida Keys beachfront rentals today!

Book with Confidence

With over 100,000 happy guests every year, you can book your next stay with us with total confidence.

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Islamorada Premium Villa 1 - Ocean Views inside shot of living room with couch, chair and balcony with sea view

Florida Keys pet-friendly rentals

Enjoy the beauty of the Sunshine State with your faithful companion in our Florida Keys pet-friendly rentals. These lovely homes are perfect for families and four-legged friends, with easy access to walks and places to run and frolic. Our range of pet-friendly homes in the Florida Keys are close to the region's beautiful beaches, many of which are dog friendly, and have wonderful facilities inside, including private pools. We also offer fantastic wheelchair-accessible homes that are pet-friendly - inviting the whole family to come and stay.

For families vacationing with pets, our larger, pet-friendly Florida Keys rentals are ideal. All benefiting from spacious layouts and private outdoor space, they provide a stylish yet functional base from which to unwind and enjoy the Florida Keys. Our largest 4-bedroom luxury vacation rentals are perfectly-suited for groups of 8 to 10 - perfect for hosting unforgettable reunions!