A healthy annual crop of pineapples made Upper Matecumbe Key the largest producer of the fruit in the United States in the early 1900s. Upper Matecumbe Key was one of the first of the Upper Keys to be permanently settled and was the original settlement site of Islamorada. Today, the island welcomes visitors and is an ideal place for fishing and water sports. Visitors frequent Upper Matecumbe vacation rentals while staying in the Upper Florida Keys. The island is located between Mile Markers 79 and 83.5.
Welcome to Keys Cottage, a delightful haven nestled in the heart of Downtown Islamorada. This enchanting three-bedroom, two-bath residence exudes charm and offers an abun...
Fabulous top floor location with spectacular ocean views! This spacious condo has tile floors throughout and a lovely open terrace to enjoy the ocean view and breezes. ...
Highly sought after live aboard boat slip available in Islamorada. Located adjacent to the iconic Lorelei Restaurant & Cabana Bar, this boat slip is 45ft long and 20.7ft...
Bay Hammock Retreat. Recently remodeled with modern coastal inspiration and inviting outdoor spaces. Three bedrooms and two bathrooms with pool, garage and boat slip. One...
Discover the essence of elegance at 'Southern Paradise,' a coastal masterpiece nestled along the Atlantic Ocean. Located at Mile Marker 83, this property offers direct 'O...