A couple of times, I have flown into Kissimmee (KISM), stayed at a nearby Holiday Inn and rented a car. The drive was roughly anywhere from 45 minutes to 1 hour (to the gates). At that time, the car rental rate was about the same as 2 uber's from Winter Haven, and the Holiday Inn rate was about $75 less per night than the Holiday Inn in Winter Haven. That said, one year I stayed at the Terrace Hotel in Lakeland. A very charming hotel. Just checked their room rates for SUNnFUN time. The rates have SKYROCKETED to say the least. A lot of the vendors stay at the hotel. So you meet a lot of interesting people, versus the Kissimmee area.