Islamorada 1 villa complex near canal

Islamorada Vacation Rentals

Islamorada, sometimes known as ‘Islas Moradas’, is a popular village in the Florida Keys famed for its sport fishing. Made up of 6 islands, Islamorada is nestled between the Everglades National Park and the Florida Strait, many head to this destination for its incredible sea views, coral reefs ripe for exploration, and its small coastal town atmosphere.

While away the hours lounging on one of Islamorada’s postcard-perfect beaches, or explore its amazing cultural gems, such as the tropical forest within the Lignumvitae Key Botanical State Park, the Theatre of the Sea, or the more unusual Toilet Seat Cut.

Our Islamorada vacation rentals are the perfect homes from which to explore the area. These luxurious homes come with a plethora of fabulous facilities, such as access to communal pools and pet-friendly features. Several of our Islamorada vacation rentals are wheelchair accessible and are within easy reach of the finest beaches and attractions in the area.

A wooden jetty into the water at sunset

Things to do

  • A view of a Florida Keys beach near Islamorada
    Discover the Florida Keys beaches
    Soak up the stunning Key West's Smathers, Islamorada and Bahia Honda State Park beaches. Go sunbathing, swimming, and snorkeling, and discover hidden coves and vibrant coral reefs.

  • A pelican poses by the water at Robbie's Marina Islamorada
    Take a trip to Robbie's Marina
    Feed the resident tarpon at Robbie's Marina, an iconic Florida Keys attraction. You can also rent kayaks, go on a snorkeling tour, or dine at waterfront restaurants.

  • Sportfishing in Florida Keys
    Go Sportfishing
    Experience world-class sportfishing in the "Sportfishing Capital of the World." Charter a boat and head out to catch tarpon, mahi-mahi, marlin, and other prized fish.

  • A diver in the waters off Florida Keys
    Snorkeling & Diving
    Explore the vibrant underwater world of the Florida Keys by snorkeling or diving. Encounter colorful coral reefs, shipwrecks, and diverse marine life in the crystal-clear waters.

  • A dolphin rides a wave off Florida
    Visit Theater of the Sea
    Visit Theater of the Sea, a marine mammal park where you can swim with dolphins, sea lions, and even sharks. It's a fun and educational experience for all ages.

  • An artist's palette
    Explore the Art Galleries
    Explore the local art scene in Islamorada by visiting the numerous art galleries and studios. You'll find a diverse range of artistic styles and creations.

  • Kayaker at sunset off Islamorada in the Florida Keys
    Go Paddleboarding & Kayaking
    Take in the mangrove-lined channels and scenic waterways of Islamorada, by paddleboarding or kayaking. Rentals and guided tours are available - for hassle-free exploration.

  • Fresh seafood in Florida
    Savor the Tiki Bars & Seafood
    Enjoy the laid-back island vibe at tiki bars and seafood restaurants. Try fresh catches like conch fritters, stone crab, and key lime pie while sipping tropical cocktails.

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

A chef prepares food for guests in one of our Spectrum vacation rentals

Enhance your stay with Travel Extras

A vacation experience with Top Villas is all about indulging in life's little luxuries, and, to elevate your Islamorada vacation rentals, we offer an exclusive range of incredible Travel Extras to enhance every aspect of your trip. One of our most sought-after Travel Extras is a private in-home chef, who will be on hand throughout your stay to design and create beautiful dishes to your taste, whether you're after a romantic meal for two or a family feast.

What makes our private chefs, and all of our Travel Extras special, is the personal touch from the moment that you book to the end of your Islamorada vacation, offering a truly customized service.

With a range of stunning extras including spa treatments, local tours and attraction tickets, airport transfers, grocery deliveries, and so much more, our Travel Extras provide you with anything and everything you could wish for in your Islamorada vacation rentals, creating a stress-free stay, where the only thing you need to do is create magical memories.

Oceanfront beach house rentals in Islamorada - Islamorada 0 large luxury villa by the sea

Oceanfront beach house rentals in Islamorada

There are plenty of amazing beaches dotted across the six islands that make up the village of Islamorada. The destination is renowned for prime fishing spots, exciting snorkeling excursions, and beautiful coral reefs. Why not get as close as possible to the lively beach atmosphere with one of our beach house rentals?

Our beachfront villas offer clean, stylish designs and well-furnished interiors. With access to fantastic amenities and a private beach area, these vacation rentals cater to everything you might want out of an Islamorada getaway.

Islamorada beach house rentals with resort amenities

When staying in one of our oceanfront Islamorada Resort vacation rentals, you'll be impressed not only by the direct beach access, but by the welcome array of resort amenities too. From its ocean-view pool, private marina with flats fishing boat hire to its 24-hour gym, outdoor fitness classes and pickleball courts, this Islamorada resort boasts everything you need to enjoy an active vacation. You'll also find paddle boards available to cast off from the resort beach, on-site spa services and a popular ocean-view resort bar. Our beachfront resort vacation rentals promise all the comfort of a 5-star hotel with the added freedom and space of your own oceanfront vacation rental.

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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A golden retriever dog takes in the ocean view from the bow of a speed boat

Pet-friendly vacation rentals in Islamorada

If you can't bear the thought of leaving your dog behind as you embark on your Florida Keys vacation, then you don't have to - thanks to our selection of pet-friendly vacation rentals in Islamorada. All promising first-class ocean views, our selection of 4-bedroom vacation homes promise plenty of style and substance, alongside a welcome array of resort amenities.

With private outdoor space to enjoy in the comfort of your vacation rental, your pooch will easily be able to soak up a memorable Florida Keys vacation.

Away from your pet-friendly vacation home in Islamorada, you'll find a host of nearby dog-friendly activities to keep your furry friend's tail wagging. From dog-friendly beaches, scenic parks and trails to a host of dog-friendly restaurants and boat tours, as well as kayaking as paddle boarding opportunities, there's every excuse to enjoy a 'pawfect' pet-friendly vacation in Islamorada.

Communal outdoor pool in Islamorada Florida Keys

Islamorada vacation rentals with pool

When looking to stay on the Florida Keys, our collection of Islamorada vacation rentals promise the perfect dose of oceanfront escapism and luxury - take our vacation homes with pool access for example. Refresh and revitalize the senses with a dip in one of the outdoor resort pools or jacuzzi of our exclusive Islamorada Resort. Overlooking the beach, with a host of additional on-site amenities including a resort beach, scenic tiki bar, gym and resort marina, this beautiful Florida Keys West makes it easy to soak up a relaxing pool break with your partner, family and friends.

Our larger Islamorada vacation rentals go one step further, by offering guests the luxury and privacy of their own sprawling private pool and boat dock. Whichever Islamorada vacation rental with pool you're looking to soak up, you will find a fantastic collection with Top Villas.