Entertainment events in Kissimmee

Check out happening entertainment events all around Kissimmee, FL

Sunset Walk - Orlando July 4th "America 250" Celebration Starring DFALC

 Sat, 04 Jul at 04:00 pm Promenade at Sunset Walk Free

Mickey's Not So Scary Halloween Party- Book before it's too late BOO!

 Fri, 07 Aug at 04:00 pm Kissimmee , Kissimmee, FL, United States, Florida 34741

iRISE EXPO 2026

 Sat, 18 Jul at 12:00 pm 1901 Chief Osceola Trail Free

Osceola Pride

 Sun, 28 Jun at 12:00 pm 1875 Silver Spur Ln, Kissimmee, FL 34744-6105, United States

"Christmas in July" at Margaritaville Resort Orlando - July 24th!

 Fri, 24 Jul at 05:00 pm Margaritaville Resort Orlando Free

Pridefest Kissimmee

Sat, 30 May at 02:00 pm Kissimmee Lakefront Park

Alex Campos

 Sat, 30 May at 11:00 pm Silver Spurs Arena at Osceola Heritage Park

Sunset Walk Orlando - Kids' 4th of July Family Celebration

 Sat, 04 Jul at 11:00 am Promenade at Sunset Walk Free

The Magik and Mythk Festival indoor medieval fair!

 Sat, 22 Aug at 11:00 am Osceola Heritage Park

Kissimmee Juneteenth Festival

 Sat, 13 Jun at 12:00 pm Veterans Lawn at Lakefront Park Kissimmee

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

 Fri, 29 May at 11:59 pm Champion Stadium at ESPN Wide World of Sports Complex

"Bruce Springsteen" Tribute "The Boss Project" Live at The Wharf August 16

 Sun, 16 Aug at 05:00 pm 3274 Margaritaville Blvd USD 32 to 60

The Tribute to The Eagles - "The Long Run" Live at The Wharf September 13th

 Sun, 13 Sep at 05:00 pm 3274 Margaritaville Blvd USD 32 to 60

SUN Ritual

 Sat, 20 Jun at 09:30 am Sun On the Beach USD 26 to 55

Adult Playground Field Day

 Sat, 27 Jun at 12:00 pm 3705 S Poinciana Blvd USD 18 to 130

Youth Revival 2026

 Fri, 26 Jun at 03:00 pm 1904 Michigan Ave USD 109

Oddities and Curiosities Expo at Events Center at Osceola Heritage Park

 Sat, 27 Jun at 11:00 am Events Center at Osceola Heritage Park

Unidos en Alabanza

 Fri, 29 May at 07:00 pm Silver Spurs Arena

"Nightrain" The Tribute to "Guns N Roses" Live at The Wharf - June 28th

 Sun, 28 Jun at 05:00 pm 3274 Margaritaville Blvd USD 32 to 55

The Bingo Experience: Old Town - Kissimmee, FL

 Sat, 11 Jul at 03:00 pm Sun On the Beach USD 13 to 42

SCHOOLS OUT SKATE NIGHT @ SKATE REFLECTIONS

Thu, 28 May at 08:00 pm 1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741

The "Rod Stewart" Tribute Live at The Wharf - July 12th - On Sale Now

 Sun, 12 Jul at 05:00 pm 3274 Margaritaville Blvd USD 32 to 55

Kissimmee Dive-In Movie

 Sat, 06 Jun at 07:00 pm 2204 Denn John Ln, Kissimmee, FL 34744-2800, United States

Americana!: A Drag Event

 Wed, 22 Jul at 07:00 pm Old Town Tavern USD 10

The Divorce by Freida McFadden Launch Event with Signed Book (NO AUTHOR)

 Fri, 29 May at 06:30 pm Vintage Vino USD 46

Super Mario Roller Skate

Sun, 31 May at 01:30 pm 1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741

SUMMA WHITE PARTY - KISSIMMEE

 Fri, 26 Jun at 09:00 pm 1881 Restaurant & Bar USD 0 to 25

Orlando - Paint and Sip - To the Sea

 Wed, 27 May at 01:00 pm Formosa Winery Tasting House USD 47

The Bridgerton Roller Skate Soirée: The Diamond Event of the Season, hosted by Skate Reflections

Sun, 14 Jun at 06:00 pm 1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741

Hush Hush Saturdays/ Ultimate Zouk & Kompa Night

 Sat, 20 Jun at 10:00 pm FAMA RESTAURANT AND LOUNGE USD 15 to 215

UNO Kissimmee Dad and Me Detroit Style Pizza Cooking Class

 Sat, 20 Jun at 12:00 pm UNO Pizzeria & Grill USD 13 to 48

Osceola County Certified First-time Homebuyer Workshop (8-Hours)

 Tue, 16 Jun at 09:00 am 1105 Cross Prairie Pkwy Free

2026 Florida Cinderella State Finals

 Fri, 12 Jun at 05:00 am Embassy Suites by Hilton Orlando Lake Buena Vista South

Singles WEEKEND FISHING KICKBACK

 Fri, 12 Jun at 09:00 am Kissimmee Lakefront Park USD 226 to 376

Black Excellence Experience Gala and Fashion Show

 Fri, 24 Jul at 06:00 pm Kissimmee Bay Country Club

Live Music with Candice Shields

 Fri, 01 May Violet's Venom Brewery Free

Drive-thru Glow Party!

 Thu, 28 May at 08:00 pm 3286 N John Young Pkwy, Kissimmee, FL 34741

CCW Ultimate Wrestling at Sun on the Beach

 Fri, 10 Jul at 08:00 pm Sun on the Beach

Comedy on Broadway

 Fri, 15 May Violet's Venom Brewery Free

MORNING COFFEE MEET

 Thu, 05 Feb at 10:00 am Kissimmee City Chambers Park Community Center Free

THE SOUND OF REVIVAL | WORSHIP CONFERENCE

 Thu, 03 Sep at 07:30 pm Revival Place USD 98 to 162

Momentum: A Women’s Leadership Accelerator 2026

 Wed, 23 Sep at 05:30 pm The Inn at Celebration, Autograph Collection USD 425 to 525

Coastal Championship Wrestling at Sun on the Beach

 Fri, 12 Jun at 08:00 pm Sun on the Beach

Parking The Party Animals at Loco Beach Coconuts

 Fri, 29 May at 07:30 am The Stadium at the ESPN Wide World of Sports at Disney

Cashflow & Wealth Building Networking

Wed, 17 Jun at 06:30 pm B J's Restaurant #474

Talk Like a Pirate Day ! Let's Celebrate

 Sat, 19 Sep at 12:00 pm Violet's Venom Brewery Free

"Sunset Saturday Artisan Market" Every Saturday Evening starting at 6pm

 Sat, 07 Nov at 10:00 am Promenade at Sunset Walk Free

Kissimmee Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

 Thu, 28 May at 01:00 pm Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED) USD 0 to 13

Promenade Sunset Walk "Weekend Wellness Series" Saturday Mornings

 Sat, 10 Jan at 09:30 am Promenade at Sunset Walk

"Sunset Craft, Food & Drink Market" Every Thursday Evening at 6pm

 Thu, 03 Jun at 05:00 pm Promenade at Sunset Walk Free

Loco Beach Coconuts at The Party Animals

 Fri, 29 May at 07:30 am Champion Stadium

Retirement Party for Ms. Gerry Miles

 Wed, 27 May at 10:00 am 1700 Mill Slough Road, Kissimmee, FL, United States, Florida 34744