Pickleball Courts in Kissimmee, FL

Playing pickleball in Kissimmee

We list 11 pickleball venues in Kissimmee, FL. The 9 that publish a court count add up to 51 courts, so the real total is higher — we don't estimate the 2 we haven't confirmed. The largest single site is Oak Street Park Pickleball Courts with 16 courts, followed by Crush Yard Orlando Pickleball (10) and Cypress Cove Nudist Resort Pickleball (10).

On access, 1 is free public court, 3 are pay-to-play and 7 are membership clubs. The biggest free option is Oak Street Park Pickleball Courts at 16 courts.

2 venues have courts under a roof (1 of which runs both indoor and outdoor), and 9 are outdoor-only.

Where to start

• Oak Street Park Pickleball Courts — Free to play — 16 courts, no membership.
• Crush Yard Orlando Pickleball — Indoor play when the weather turns — 10 courts inside.
• Cypress Cove Nudist Resort Pickleball — One of the biggest sites in Kissimmee — 10 courts, so open play rarely stalls.

What we've confirmed

9 of 11 have a confirmed court count, 1 publish hours and 2 publish pricing. 2 of these listings have been confirmed first-party against the venue's own website or Google Business Profile; the rest are sourced leads we're still working through. Most recent check in Kissimmee: 2026-07-12.