Chokoloskee is an unincorporated community and census-designated place (CDP) located at the edge of the Ten Thousand Islands in Collier County, Florida, United States. The population was 345 at the 2020 census, down from 359 at the 2010 census. It is part of the Naples–Marco Island Metropolitan Statistical Area.

The Ten Thousand Islands are a chain of islands and mangrove islets off the coast of southwest Florida, between Cape Romano and the mouth of the Lostmans River. Some of the islands are high spots on a submergent coastline. Others were produced by mangroves growing on oyster bars. Despite the name, the islets in the chain only number in the hundreds.