Kissimmee to Winter Haven: Road Trip Guide & Distance

How far is Kissimmee from Winter Haven?

The distance from Kissimmee to Winter Haven is 27.4 miles (44.1 km) as the crow flies. Winter Haven is located SW of Kissimmee. By car, the driving distance is approximately 35.6 miles, taking about 43min. A direct flight would take roughly 33min. Both are located in United States.

This is a very short trip, perfect for a quick morning drive or an easy commute. Since you'll be heading mostly West, pack a good pair of sunglasses if you plan to drive during the late afternoon to avoid the harsh sun glare. Given the short distance, driving or taking a train is often faster and more convenient than dealing with airport security and flight boarding times.

Coordinates come from public place data for Kissimmee and Winter Haven. 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.