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Kissimmee ( (listen) kih-SIM-ee) is the largest city and county seat of Osceola County, Florida, United States. As of the 2020 census, the population was 79,226. It is a Principal City of the Orlando-Kissimmee-Sanford, Florida, Metropolitan Statistical Area, which had a 2010 population of 2,234,411. == History == This area was originally named Allendale, after Confederate Major J. H. Allen who operated the first cargo steamboat along the Kissimmee River—the Mary Belle. It was renamed Kissimmee when incorporated as a city in 1883.