2026 Compare Cities Overview:
Kissimmee, FL vs Winter Park, FL

Are people in Winter Park older or younger than people in Kissimmee?
- The Median Age in Winter Park is 10.0 years older than in Kissimmee.

Are housing costs cheaper in Winter Park or Kissimmee?
- Winter Park housing costs are 42.9% more expensive than Kissimmee housing costs.

Which city has a longer commute, Winter Park or Kissimmee?
- The average commute for residents of Winter Park is 5.2 minutes shorter than it is for residents of Kissimmee.

Things to do in Kissimmee?
Kissimmee, Florida is a vibrant city located in the Southeast United States. Home to attractions such as Gatorland and Disney World, visitors can enjoy outdoor activities and nature when visiting Kissimmee. There are also plenty of museums, galleries, and performance venues such as Old Town and the Osceola Center for the Arts. For entertainment, visitors can explore downtown shopping districts and restaurants along with movie theaters and live music clubs. Whether you're looking for a peaceful retreat or an exciting night out, Kissimmee has something for everyone!

Things to do in Winter Park?
Winter Park, FL is nestled between Orlando & Sanford offering magnificent mansions combined with vibrant street scenes fulls fabulous restaurants and boutique stores. Visitors here can enjoy swan boats cruising across Lake Virginia or find tranquility at Leu Gardens which offers breathtaking views no matter which season you visit during!