Hilton Head Island to Kissimmee: Road Trip Guide & Distance

How far is Hilton Head Island from Kissimmee?

The distance from Hilton Head Island to Kissimmee is 273.2 miles (439.6 km) as the crow flies. Kissimmee is located S of Hilton Head Island. By car, the driving distance is approximately 341.4 miles, taking about 6h 52min. A direct flight would take roughly 1h 3min. Both are located in United States — Hilton Head Island in South Carolina and Kissimmee in Florida.

For a drive of this length, it's recommended to plan at least one quick rest stop to stretch your legs and grab a coffee.

Coordinates come from public place data for Hilton Head Island and Kissimmee. The driving distance is estimated from straight-line distance with a road-factor model, so confirm the route in your navigation app. Fuel, flight, bus, and train values are planning estimates and can change by date, provider, road closures, and border rules.