Events in May in Kissimmee

• Sat, 02 May, 2026 - 07:30 PM

  Hot Wheels Monster Trucks Live Glow-N-Fire at Silver Spurs Arena at Osceola Heritage Park

  Silver Spurs Arena at Osceola Heritage Park

  13+ Interested
• Sat, 02 May Onwards

  Hot Wheels Monster Trucks Live Glow-N-Fire

  Silver Spurs Arena at Osceola Heritage Park
• Tue, 05 May, 2026 - 03:00 PM

  "Cinco de Mayo" Street Party and Celebration - Promenade at Sunset Walk

  Promenade at Sunset Walk

  Free
• Sat, 30 May, 2026 - 07:00 PM

  Alex Campos y Ingrid Rosario: Unidos en Alabanza

  Silver Spurs Arena At OHP
• Sat, 30 May, 2026 - 11:00 PM

  Alex Campos

  Silver Spurs Arena at Osceola Heritage Park
• Sat, 30 May, 2026 - 12:00 AM

  Unidos En Alabanza

  Osceola Heritage Park / Silver Spurs Arena

  8+ Interested
• Sat, 23 May, 2026 - 09:00 AM

  Kissimmee Collectorfest 2026 - Spring

  Osceola Heritage Park

  792+ Interested
• Sun, 24 May, 2026 - 05:00 PM

  "Bon Jovi" Tribute "Slippery When Wet" Live at The Wharf May 24th

  3274 Margaritaville Blvd

  USD 32
• Sun, 10 May, 2026 - 10:00 AM

  Krush Brau Park Mother’s Day Brunch & Moms Market

  2198 4 Winds Blvd

  USD 25
• Fri, 29 May, 2026 - 07:00 PM

  Unidos en Alabanza

  Silver Spurs Arena
• Fri, 29 May, 2026 - 11:59 PM

  Party Animals at Loco Beach Coconuts at Champion Stadium at ESPN Wide World of Sports Complex

  Champion Stadium at ESPN Wide World of Sports Complex
• Sat, 02 May, 2026 - 12:00 PM

  Maifest Spring Celebration Celebrate the Joy of Spring — the Bavarian Way!

  2198 4 Winds Blvd

  USD 8
• Sun, 24 May, 2026 - 07:00 PM

  Orlando City B vs. Inter Miami CF II

  Osceola County Stadium at Osceola Heritage Park
• Sat, 23 May, 2026 - 08:00 AM

  FUJI BJJ Orlando Spring Championship

  Kissimmee Middle School

  11+ Interested
• On Demand

  Orlando City B vs. Crown Legacy FC

  Osceola County Stadium At Osceola Heritage Park