Winter Haven is about 50 miles southwest of Orlando and 55 miles east of Tampa on US-27 and SR-17. By car from Orlando International Airport, allow 45–60 minutes depending on traffic. Tampa International Airport is a similar distance on the other side.
Amtrak's Silver Star and Silver Meteor trains stop at Winter Haven station, making the city accessible by rail from New York, Orlando, and Tampa. The station is a short ride from the city centre. There is no meaningful local bus service, so a car or rental is essential for anything beyond the immediate downtown area.