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.