Upper Matecumbe KeyUpper Matecumbe Key is an island in the upper Florida Keys at approximately MM 79 to MM 83.5 between Windley Key to the NE and Lower Matecumbe Key to the SW.

All of the key is within the Village of Islamorada as of November 4, 1997, when it was incorporated.

The history of the names of both this key and Lower Matecumbe Key are very confusing, as identical names have been used at different times to designate both keys. Upper Matecumbe Key is the location of the original settlement site of Islamorada. There are a number of Indian mounds and habitation sites located here.