Islamorada Vacation Rentals: Condo and House Rentals

Islamorada consists of four islands in the Upper Florida Keys south and west of Key Largo, encompassing Plantation Key, Windley Key, Upper Matecumbe Key and Lower Matecumbe plus the offshore islands of Indian Key and Lignumvitae Key. These are all great destinations for Islamorada vacation rentals.

Known as the “Village of Islands”, Islamorada is also often called the “sport fishing capital of the world.” Aqua blue waters, shallow reefs, abundant coral and wildlife make Islamorada any water sport lover’s paradise. Visitors can easily pursue all watersport recreational activities including snorkeling and scuba diving the reef and wrecks, kayaking and windsurfing, power boating and sailing. Perhaps the world’s highest density of professional offshore charter boats can be found here where backcountry sport fishing and saltwater fly fishing were pioneered.

Beyond fishing and water sports, Islamorada offers visitors tranquil, white sand beaches and a variety of diversions such as waterfront dining, an active nightlife and music scene, and attractions with historical interest. The only way to experience these activities to their full extent is through the use of Islamorada vacation rentals.

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TRAVEL TIMESIslamorada vacation rentals

Islamorada to Key West: 1.75 hours
Islamorada to Big Pine Key: 1.25 hours
Islamorada to Marathon: 35 minutes
Islamorada to Key Largo: 25 minutes
Islamorada to Miami International Airport: 2.25 hours
Islamorada to Ft. Lauderdale International Airport: 2.5 hours


Islamorada’s average temperature ranges between 79 and 90 degrees in July and August, the two warmest months, and 62 to 75 degrees in January, the coolest month of the year.

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On The WaterAttractionsRecreationDiningShoppingEntertainment


  • Anne’s Beach MM 73.5 Islamorada , FL 33036
  • Founders Park, Pool & Skate Park, 87000 Overseas Hwy Mile Marker 87 Islamorada , FL 33037
  • Library Beach – Library Beach is a small beach on the gulfside directly behind the Monroe County Public Library in Islamorada. It is a wonderful spot for small children, with a playground, plenty of grassy area, and a protected waterway.





Visitors can only access Indian Key Historic State Park by canoe or kayak. The park was the botanical vision of doctor and horticulturalist Henry Perrine (1838). The park survived attack from Indians in 1840 and the destruction of Hurricane Wilma, and remains a rare cultural landscape. U.S. 1 Mile Marker 85.5, Islamorada, Florida 33036, Phone (305) 664-2540

Lignumvitae Key Botanical State Park is a virgin tropical hardwood hammock, once common in the Florida Upper Keys. In 1919, a wealthy Miami chemist, William J. Matheson, bought the island and built a caretaker’s home, windmill and cistern. Today, these structures serve as visitor and education centers. Accessible only by private Offshore Island – MM 78.5 Oceanside, Islamorada, Florida 33036 Phone (305) 664-2540

Windley Key Fossil Reef Geological State Park is formed of Key Largo limestone and fossilized coral. Originally land sold to the Florida East Coast Railroad, which used the stone to build Henry Flagler’s Overseas Railroad in the early 1900s, the park now features eight-foot-high quarry walls of the ancient coral. Visitors can walk the walls and learn about the quarry and its operation- an important part of Florida’s 20th century history. Picnic tables are available. Visitor center open Thursday through Monday, 8:00 a.m.-5:00 p.m., features educational exhibits about the history of this site. Located at Mile Marker 85.5 on Windley Key near Islamorada, Phone (305) 664-2540

The Florida Keys History of Diving Museum is dedicated to collecting, preserving, displaying and interpreting artifacts, antiques, books, documents, photographs and oral history relative to diving history. The museum tells the international story of man’s attempts to explore, understand and venture under the sea. Mile Marker 83, Upper Matecumbe Key, Florida Keys Phone (305)664-9737

Theater of the Sea
Phone: 305-664-2431
5 Oceanside
Islamorada, FL 33036
Marine Mammal Adventure Park. Eco tours, swim with Dolphins, Sea Lions, and Sting Rays, plus other programs in beautifully landscaped setting. Reservations required for swims.

Robbie’s Marina is the place where you can watch and feed wild Tarpon; it is also the hub for most of Islamorada’s marine activities. From here you can embark on popular tours, rent a kayak or go on a jet ski tour, hire a Backcountry or Patch Reef Fishing Guide, or Rent-A-Boat and chart your own course. 77522 Overseas Highway Islamorada, FL 33036.

See additional resources on local attractions in Islamorada at the Florida Keys’ official tourism website.

See “Things to do” at the Islamorada Official Chamber of Commerce website.





  • There are no public golf courses in Islamorada, however the golf courses of Marathon are about a 45-minute drive south. Key West’s course is just under a two-hour drive south.
  • There are a number of hard tennis courts available at Founders Park
  • Islamorada Tennis Club is a private tennis facility situated at 76800 Overseas Hwy, Islamorada, FL 33036. There are 6 private tennis courts present at this tennis location. The tennis courts are lighted.

The Rain Barrel is an artist village, home to the studios and galleries of many artists. Although there are only 10 resident artists, more than 100 artists are represented here. Not only are their works on display but visitors get a first-hand look at exactly how art is created. These are working studios. See pottery, jewelry, stained glass and more being designed right before your eyes. In the a maze of little shops, you’ll find specialty foods such as mango ketchup and lime marinade, artists working in their studios, a sculpture gallery, tropical gardens, and a vegetarian cafe. You can’t miss the rows of colorful fish-shaped mailboxes as you enter the village. Located at Mile Marker 86.7, the village is open 9 a.m. to 5 p.m. every day and is home to the Islamorada Rain Barrel Art Show usually held in March. 86700 Overseas Hwy, Islamorada, FL 33036, Phone (305) 852-3084.

The Banyan Tree Nursery & Gift Shop has around the world for gift ideas and antiques. 81197 Overseas Hwy, MM 81.2, Islamorada, FL 33036, Phone (305) 664-3433.

For additional shopping resources, visit Islamorada’s Chamber of Commerce website.

See a directory of Islamorada shopping suggestions at the Florida Keys official tourism website.

See customer reviews for Key Largo shopping in Yelp


  • See our Business Directory for information on supermarkets, drugstores, healthcare, marine supplies, government, law enforcement, veterinarians, and other Keys resources you may want to visit during your stay.

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