The city of Osceola is said to be named after a Seminole Indian chief who led his tribe in the Second Seminole War in Florida. In 1839 William Edrington bartered with the original occupants, an Indian tribe, for the site, and renamed it Plum Point. In 1838 the town was incorporated and renamed Osceola. Osceola was the home of Kemmons Wilson, founder of Holiday Inn, and Francis Smith, who later married as Dale Evans to Roy Rogers.