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Islamorada vacation rentals

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Popular amenities for Islamorada vacation rentals

Stay near Islamorada's top sights

The Spa at Cheeca Lodge9 locals recommend
Robbie's165 locals recommend
Theater of the Sea140 locals recommend
Anne's Beach46 locals recommend
Lazy Days Restaurant76 locals recommend
Lorelei Restaurant & Cabana Bar73 locals recommend

Quick stats about vacation rentals in Islamorada

  • Total rentals

    840 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    6.8K reviews

  • Family-friendly rentals

    590 properties are a good fit for families

  • Pet-friendly rentals

    370 properties allow pets

  • Rentals with a pool

    640 properties have a pool

Your guide to Islamorada

All About Islamorada

Islamorada’s beaches make for a great retreat, but the area is also known for its water sports. Whether you’re an angler looking to go tarpon fishing, an adventurer hoping to go dolphin spotting, or a boater who wants to cruise the backwaters before heading back to the Islamorada Marina’s protected dockage, there’s a getaway with your name on it. Known as the Village of Islands, Islamorada comprises five islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and Indian Key. Approximately halfway between Miami and Key West in the Florida Keys, it’s about 10 miles south of Tavernier, 16 miles south of Key Largo, and 81 miles north of Key West.


The best time to stay in a vacation rental in Islamorada

Summertime in the Keys and the living is easy — but scorching hot. High temperatures are in the upper 80s to 90s Fahrenheit, while lows hover around the mid-70s. Along with the warm weather comes humidity, which can often feel oppressive, so opt for lightweight, comfortable clothing. Hurricane season runs from June through November, so keep an eye on the forecast, since there is only one road in and out of the Keys, and you’ll want to plan ahead if conditions get extreme. Spring and fall may be the more comfortable times of year to visit, when it’s between the upper 60s and 80s. But winters are also lovely in the mid-60s to upper 70s — and with less rain.


Top things to do in Islamorada

Founders Park

This 45-acre park is the most popular of the village’s parks, especially because of its shallow beach on the bay side. In addition to tiki huts, picnic tables, volleyball courts, and a playground, there’s also an Olympic-size pool, walking trails, a driving range, and courts for basketball, tennis, and pickleball.

Windley Key Fossil Reef Geological State Park

Walk along the eight-foot-high walls of the former quarry, formed of Key Largo limestone (fossilized coral). The land was once owned by the Florida East Railroad, a company that helped build the Overseas Railroad in the early 20th century, connecting the mainland to Key West — but it was eventually damaged by hurricanes and shut down.

Alligator Reef Lighthouse

The namesake for the 136-foot-tall lighthouse, built in 1873, is not the reptile, but rather the USS Alligator, whose remains are deep underwater. Nowadays, the area is known for its reef with 500 sea life species, including barracudas and spiny lobsters.

Frequently Asked Questions

  • How is the weather in Islamorada?

    Islamorada has a tropical climate with warm temperatures year-round. In the summer, temperatures can reach 90°F (32°C), while winters are mild, with highs around 75°F (24°C). Rain is common from May to October, with September being the wettest month.

  • What are some of the best things to do in Islamorada?

    Popular activities in Islamorada include snorkeling and scuba diving at the Alligator Reef, fishing in the clear blue waters, and exploring the Indian Key Historic State Park. Visitors also frequently enjoy paddle boarding, biking, and kayaking.

  • What is the best time of year to visit Islamorada?

    The most popular time to visit Islamorada is from December to April when the weather is mild and dry. During this period, the island often hosts various events such as the Island Fest in April, which features art, food, and music.

  • What are the best places to stay in Islamorada?

    Popular areas to stay in Islamorada include the centrally-located Islamorada Village, which has easy access to restaurants and shops. The quieter Lower Matecumbe Key is also frequently suggested for its beautiful beaches and easy access to Anne's Beach.

  • What are the best places to visit in Islamorada?

    Popular places to visit in Islamorada include the History of Diving Museum, Anne's Beach, Theater of the Sea, and the Rain Barrel Sculpture Gallery. Visitors often explore Lignumvitae Key Botanical State Park and Indian Key Historic State Park as well.

  • What are some hiking trails in Islamorada?

    While Islamorada is more famous for its water activities, it also has some enjoyable walking trails. The Windley Key Fossil Reef Geological State Park has several short trails that feature unique geological formations and the Indian Key Historic State Park has a walking path with interpretive signs about local history.

  • What are some family activities to do in Islamorada?

    Families in Islamorada often enjoy exploring the Theater of the Sea, the History of Diving Museum, and the Windley Key Fossil Reef Geological State Park. A visit to the Dolphin Research Center or the Florida Keys Wild Bird Rehabilitation Center can also be a rewarding experience for children and adults alike.

  • What are some of the best day trip ideas in Islamorada?

    Day trips from Islamorada often involve visiting the nearby Key Largo or Marathon islands, both perfect for snorkeling and wildlife watching. The vibrant city of Miami is just 1.5 hours (130 km) away and exploring the Everglades National Park is also a feasible day trip.

  • What types of vacation rentals are available in Islamorada?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Islamorada. From over 310 house rentals to over 90 condo rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Islamorada?

    Yes! Work meets play with ease at over 460 vacation rentals in Islamorada featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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