Entertainment events in Kissimmee

• Fri, 06 Feb, 2026 - 08:00 PM

  Lebrón Brothers in Kissimmee

  Fonda Dulce Jesus Mio
• Sat, 21 Feb, 2026 - 01:00 PM

  BLACK HISTORY CELEBRATION

  Kissimmee City Chambers Park Community Center

  Free
• Sat, 21 Feb, 2026 - 10:00 PM

  Aniversario... Lucha bajo las estrellas

  Downtown Kissmmee

  26+ Interested
• Thu, 12 Feb, 2026 - 07:30 PM

  Kel Pérez - Crowd Work Therapy.

  FAMA GASTROBAR

  USD 23
• Sat, 21 Feb, 2026 - 07:00 PM

  AW's ANIVERSARIO Lucha bajo las estrellas

  Plaza Espinosa

  15+ Interested
• Tue, 17 Feb, 2026 - 05:00 PM

  Promenade - Sunset Walk Fat Tuesday/Mardi Gras Street Party! February 17th

  Promenade at Sunset Walk

  Free
• Fri, 06 Mar, 2026 - 05:30 PM

  City of Kissimmee Movie in the Park (Pending)

  Kissimmee Lakefront Park
• Sat, 28 Feb, 2026 - 07:00 PM

  LANDFALL at Cypress Cove Nudist Resort

  Cypress Cove Nudist Resort

  11+ Interested
• Sat, 25 Apr, 2026 - 05:00 PM

  Playboy Pool Party

  4122 Reaves Rd

  USD 34
• Wed, 11 Mar, 2026 - 11:00 PM

  Parking Wisconsin Herd at Osceola Magic

  Silver Spurs Arena at Osceola Heritage Park
• Thu, 26 Mar, 2026 - 05:00 PM

  "The Cars" Tribute - "Carpool" in Concert - March 26th - On Sale Now

  3274 Margaritaville Blvd

  USD 32
• Fri, 29 May, 2026 - 07:30 AM

  Parking The Party Animals at Loco Beach Coconuts

  The Stadium at the ESPN Wide World of Sports at Disney
• Thu, 26 Feb, 2026 - 12:00 AM

  Parking Cleveland Charge at Osceola Magic

  Silver Spurs Arena at Osceola Heritage Park
• Fri, 30 Jan, 2026 - 10:00 AM

  Fresh Produce Day - Pleasant Hill

  Orlando Family Physicians by InnovaCare Health

  Free
• Mon, 06 Apr, 2026 - 04:20 PM

  Kissimmee Youth Hip Hop Dance Crew

  Oak St Community Center