Oak Street Community Park

Pickleball players in Kissimmee, FL will find 4 free, publicly accessible outdoor courts at Oak Street Community Park on Hill Street. The courts are in good condition, though visitors should be aware there are no permanent pickleball lines, and nets are not provided — plan to bring your own. The park operates Monday through Thursday from 9:00 AM to 8:00 PM and Friday from 9:00 AM to 6:00 PM, with organized play noted on Tuesday, Thursday, and Friday mornings. Rated 4.5 across 186 reviews, players note the park is generally well-maintained and kept clean throughout the day. Its multi-sport setting and kid-friendly amenities, including restrooms, make it a practical stop for families fitting pickleball into a broader park visit.