0 Bedrooms for 1 Guest
Price $10 - $1000+

666 Islamorada Vacation Rentals & Short Term Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Islamorada vacation rentals from 7 rental sites including HomeAway, Booking.com, TripAdvisor, and more, ranging from $25 to $1785 a night. 

    Information about Islamorada

    About Islamorada

    Islamorada, Florida is a beach town located in the Florida Keys south of the Florida mainland. It’s known as the “Sport Fishing Capital of the World” and is also very popular for scuba diving, snorkeling, and other ocean activities. Come for the beach and stay for the friendly locals and relaxing atmosphere.

    Things to do in Islamorada

    Islamorada is a very popular spot in the Florida Keys and you’ll never be bored. It is known as the “Sport Fishing Capital of the World” for a reason - the fishing here is excellent. If you want to go fishing, but don’t have your own boat, check out fishing charter companies in the area, such as A Pirates Choice Deep Sea Fishing Charters. There are also charters available at Robbie’s Marina, where you can purchase buckets of bait to feed the tarpon off the marina dock. You can also rent kayaking, snorkeling and scuba gear there. Scuba diving has become huge in Islamorada with wide variety of shallow coral reefs, mini walls and shipwrecks. Some of the best diving areas include The Eagle Shipwreck, Davis Reef, Alligator Reef and Crocker Wall, among others. When in Islamorada, check out the 11-acre Indian Key Historic State Park and view the remains of a shipwreck salvage community from the 1830s. There are also several hundred yards of well-maintained trails that line the interior of the island. Experience one of the world’s largest collections of historic dive equipment and trace 3,000 years of diving at the Florida Keys History of Diving Museum.

    Another one of Islamorada’s top attractions is Theater of the Sea, the second oldest marine mammal facility in the world, where you can view dolphin and sea lion shows and even get in the water and swim with them. For beer lovers, there are two great island breweries in Islamorada to check out: head to Florida Keys Brewing Company and the Islamorada Beer Company Brewery to sample the beers and enjoy the friendly environment. There are many small beaches to check out in Islamorada including Anne’s Beach, Sea Oats Beach and Kite Beach, which are all great for relaxing and taking in the beautiful sunsets.

    Day trips from Islamorada

    There are some great day trips you can take from Islamorada despite its location in the secluded Florida Keys. For a quick trip, just a 15-minute drive from Islamorada is Key Largo, one of the most popular areas in the Florida Keys. You can easily spend a day in Key Largo, which is one of the most popular scuba diving cities in the world. There are many fun classes and instruction courses to take in Key Largo and the sites that you’ll dive in mostly fall in the 25-40-foot depth range in warm water that doesn’t have currents that could bother you. The Molasses Reef is a great place to dive in Key Largo, where you’ll see great wildlife with different types of fish and maybe even turtles in the sandy area. Enjoy a unique experience swimming with dolphins at Dolphins Plus, and check out more great boat and fishing tours out on the water. You can also get out of the keys and take a 1.5-hour drive north to Miami, Florida, one of the most popular tourist destinations in the country. Once you’re there, you can experience great beaches in Miami as well as the cultural vibrance of Florida with salsa dancing, delicious restaurants throughout the city, and art like the famous Wynwood Walls. You can also visit Zoo Miami or you can catch a concert or Miami Heat basketball game at the American Airlines Arena.

    Islamorada Accommodations

    There are great vacation rentals throughout the Florida Keys, and Islamorada is no exception. You can’t really go wrong on choosing where to stay, considering that mostly everything is on the water. The Overseas Highway is what runs through the keys and anything off of that will put you in a good spot for your vacation in Islamorada.

    Transportation in Islamorada

    You’ll definitely need a car in order to get around whether you drive down from the Florida mainland or you rent one at the airport. There is also Islamorada Taxi to help get you around if you don’t feel like driving. Consider renting a bike and riding it around the flat, scenic beach areas!

    Vacation Rentals in Islamorada

    Find the best Islamorada vacation rentals with Tripping.com. Choose from 637 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $1785 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 425 of homes in Islamorada offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 274 rentals with pool or jacuzzi, or relax with the family in one of the 595 homes with cable TV.

    For all those dog lovers and cat lovers, Islamorada offers 142 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

    Search properties from 7 rental sites in Islamorada where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 312 HomeAway rentals, 150 Booking.com short term rentals and 125 TripAdvisor vacation rentals.