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Luxury vacation rentals in Islamorada

With its idyllic beaches and laid-back luxurious vibe, Islamorada is a vacationer’s dream. Just an hour south of Miami, it couldn’t be easier to travel to but feels like a world away from it all. Encompassing six of the stunning Florida Keys, Islamorada is hailed for its world-class fishing, fantastic dining and upscale seaside atmosphere.

Located in the brand new ‘Islands of Islamorada’ community, our Islamorada vacation rentals range from luxurious waterfront villas to gracious hotel suites, all nestled along miles of private shoreline. Each villa spans more than 3,000 square feet and includes four spacious bedrooms, a fully-equipped kitchen, waterfront balconies, an elevator and a 2-car garage.

Spend your days enjoying everything the resort has to offer, or head out and explore the many local attractions. Watch a dolphin show at the Theater of the Sea, see historic exhibits at the Diving Museum, or check out Islamorada’s fantastic shops, art galleries, restaurants and bars.

Where is Islamorada?

Islamorada is a seaside resort town in Monroe County, Florida Keys. It’s located directly in the middle of Miami and Key West together with Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key. Recently named one of the most beautiful destinations in America, this scenic stretch of coastline is around 80 miles from Miami via US-1 S.

Enjoy the perfect Islamorada vacation

No matter the time of year, a vacation in Islamorada will never disappoint. Ideal for couples and families alike, the region offers endless activities, incredible views and plenty of stylish oceanfront accommodation.

Head out and you’ll find so many things to do nearby. Located in the exclusive Islands of Islamorada community, each home offers access to the resort’s excellent amenities including resort pools, a swanky marina and a private white-sand beach.

Make the most of beach activities like snorkeling, paddleboarding, kayaking, sailing and kiteboarding. And should you crave a bigger adventure, the resort’s on-site concierge can coordinate trips for off-shore diving, fishing, sailing and jet skiing.

For fitness, you can work up a sweat at the tennis courts, fitness classes or 24-hour gym, before cooling off at the resort's two oceanfront pools which are perfectly positioned for sea views. For a little extra pampering, the team can arrange private spa services in the comfort of your vacation rental or by the beach.

The Islands marina provides dockage space for those who want to bring their own vessel, or you can hire a fishing boat for the duration of your stay. Enjoy waterfront drinks and beachside cocktails at the Ocean House bar, available at leisure, almost any time of day.

With its scenic waterfront outdoor space, Islands of Islamorada is the perfect spot for weddings and special celebrations. The resort’s concierge team can connect you with the best local caterers, wedding planners, photographers and more to make your perfect event come to life.

A choice of Islamorada vacation rentals

Need some inspiration to help you find the perfect vacation rental? Whether you’re looking for a stylish hotel suite or a huge 3-storey beach house, Top Villas has something to suit you. Browse through our Islamorada vacation rentals to find that special something you’re looking for.

Villas & cottages on the beach

From large beachfront houses to stylish cottage rentals, our Islamorada vacation homes are available in a range of styles and sizes. Our biggest homes include three-storey waterfront villas complete with four bedrooms, full kitchens, living and dining spaces and three outdoor waterfront lounge areas.

Family friendly vacation rentals

Choose one of our family friendly rentals in Islamorada and you can bring your little ones on vacation with you. Kids will love this fun beach-based destination, and all of the local facilities are family friendly too. If you’re not sure which of our vacation rentals are child friendly, just ask!

Romantic hotel suites

For something cosier, we offer one-bedroom suites directly on the beach. Open, airy and light, these rentals blend seamlessly with the awe-inspiring beachside setting. Perfect for honeymoons or romantic stays, guests can drive, boat or land by seaplane right outside this unique island resort.

When to visit Islamorada

Summer, fall, winter or spring - there is always so much going on in Islamorada. December through May is the peak season in Islamorada when the region is at its busiest and best. If you want to avoid the crowds, October and November are great times to visit. Look out for special offers and last-minute deals by joining our mailing list.

How to book a stay

Need help finding the perfect vacation rentals in Islamorada? Contact our friendly team of experts today and they’ll be able to provide you with insider tips on the best rental for your trip.

When you book your stay with us you’ll be allocated a dedicated personal guest experience manager who can take care of everything, from arranging car hire, to booking incredible experiences. Once you arrive, your locally-based concierge will assist you throughout your stay.

Reviews of our vacation rentals

You can read reviews of our happy customers’ stays on this page.

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