Holiday events in Kissimmee

Check out happening holiday events all around Kissimmee, FL

Margaritaville Resort Orlando Holiday Celebration 2026. Friday Dec. 19th!

 Fri, 19 Dec at 06:00 pm Margaritaville Resort Orlando Free

Kissimmee Festival of Lights Parade & Holiday Festival

 Sat, 13 Dec at 04:00 pm Downtown Kissimmee

Sunset Walk & Osceola County Sheriff's Office Santa's Toy Drive & Car Show

 Sun, 14 Dec at 11:00 am Promenade at Sunset Walk Free

2025 Christmas Winter Festival- FTC Kissimmee

 Sat, 13 Dec at 10:00 am Florida Technical College - Kissimmee Campus Free

Senior’s Christmas Brunch

 Wed, 17 Dec at 10:00 am Oak Street Park Community Center, North Palm Avenue, Kissimmee, FL, USA Free

Holiday Nights

 Sun, 21 Dec at 06:00 pm 210 S Bass Rd, Kissimmee, FL, United States, Florida 34746

Holiday Family Movie Night | Crush Yard Orlando

 Fri, 12 Dec at 06:00 pm Crush Yard - Pickleball Bar & Lounge Free

The World of Music School – Christmas Spectacular 2024!

 Sun, 14 Dec at 11:30 am Sun On the Beach Free

Holiday Indulgence: Wine, Cheese and Seasonal Savories!

 Sat, 20 Dec at 06:00 pm Vintage Vino

2nd Annual Great Gingerbread Build-Off

 Sun, 14 Dec at 01:00 pm Hart Memorial Central Library

Ivelissa Ríos at Holiday Inn Resort Kissimmee

 Fri, 12 Dec at 08:00 pm Holiday Inn Resort Kissimmee

Black Cake & Sorrel FL 2025

 Sat, 13 Dec at 07:00 pm MAMMA's Banquets & Events USD 23

QueenDom’s Royal Opulence Mercado

Sat, 27 Dec at 10:00 am Kissimmee,orlando,florida

Holiday Nights

 Sat, 20 Dec at 06:00 pm 210 S Bass Rd, Kissimmee, FL, United States, Florida 34746

Santa at the Train Depot

 Fri, 12 Dec at 04:00 pm Pioneer Village At Shingle Creek

Free Picture with Santa at Susana´s Café

 Sat, 13 Dec at 11:00 am 18 S. Orlando Ave, Kissimmee, FL, United States, Florida 34741

Cookies & Cocoa Family Roller Skate🍪☕️

 Wed, 17 Dec at 06:30 pm 1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741

NeoCity Plug-in: Holiday Cheer

 Thu, 11 Dec at 08:30 am Cafe Barista NeoCity Free

CALL FOR VENDORS

 Sat, 20 Dec at 10:00 am 3600 Reaves Rd Free

UNO Kissimmee Kids Event - Holiday Cookie Decorating

 Tue, 16 Dec at 04:00 pm UNO Pizzeria & Grill Free

SR Family - Ni Santos Ni Perfectos at Holiday Inn Resort Kissimmee

 Sat, 20 Dec Holiday Inn Resort Kissimmee

Osceola Magic vs. Noblesville Boom

 Fri, 06 Feb at 07:00 pm Osceola Heritage Park

The Mondayist Xmas Party Ever: Improv Holiday Party

 Mon, 22 Dec at 07:00 pm 1881 Restaurant & Bar USD 13

Wooden Door Hanger Workshop

Mon, 15 Dec at 08:30 pm The Town of Kindred

Santa Sunday!

 Sun, 14 Dec at 12:00 pm 1534 W Vine St, Kissimmee, FL 34741

Osceola Magic - Holiday Party + Replica Jersey Giveaway!

 Tue, 16 Dec at 07:00 pm 1875 Silver Spur Lane, Kissimmee, FL, United States, Florida 34744

Ugly Sweater Themed Mid Month Party

 Tue, 16 Dec at 05:00 pm 850 W. Osceola Pkwy, Kissimmee, FL 34741

Frozen Christmas Creative Together Market

 Sat, 13 Dec at 12:00 pm 7470 W Irlo Bronson Memorial Hwy USD 0 to 13

Beyond & Free Spirit Experience

 Wed, 08 Apr at 12:00 am 2145 e irlo Bronson Memorial hwy, Kissimmee, FL, United States, Florida 34744

Beekeepers Holiday Social

 Tue, 16 Dec at 06:30 pm Big John's Rockin' BBQ

Watercolor Holiday Cards

 Sat, 20 Dec at 11:00 am White Rose Books & More USD 38

Providence Hunters CreekToy Drive

Mon, 15 Dec at 03:00 pm 1701 Ball Park Road

Women Who Thrive on Tech - Holiday Meet & Greet

 Tue, 16 Dec at 06:30 pm Violet's Venom Brewery Free

GRINCHMAS SKATE

 Sat, 13 Dec at 01:30 pm 1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741

Holiday Bingo & Sing Along Roller Skate

 Sat, 20 Dec at 10:00 am 1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741

Paint and Sip Holiday Brunch

 Sun, 14 Dec at 11:00 am Oishi Latin Fusion USD 59

Breakfast with Santa and the Kissimmee Woman's Club

 Sat, 13 Dec at 08:00 am 1616 West Oak Street, 34741

"Elvis: The Blue Christmas Show" The Tribute to Elvis - December 11th

 Thu, 11 Dec at 05:00 pm 3274 Margaritaville Blvd USD 32 to 55

Brunch with Santa 🎅

 Sat, 20 Dec at 12:00 pm Metro Diner (Kissimmee)

Free Picture with Santa at Susana´s Café

 Sun, 14 Dec at 11:00 am 18 S. Orlando Ave, Kissimmee, FL, United States, Florida 34741

Osceola Magic vs. Memphis Hustle

 Tue, 16 Dec at 07:00 pm Osceola Heritage Park

Osceola Memory Gardens 67th Annual Holiday Remembrance Open House

 Thu, 18 Dec at 04:00 pm 1717 Old Boggy Creek Rd, Kissimmee, FL, United States, Florida 34744

Ivelissa Rios

 Thu, 11 Dec at 07:00 pm Holiday Inn Resort Kissimmee by The Parks

Providence Hunter’s Creek Toy Drive

 Mon, 15 Dec at 03:00 pm 1701 Ball Park Road

Osceola Magic vs. Long Island Nets

 Tue, 17 Mar at 07:00 pm Osceola Heritage Park

Holiday Festiball: UCF Knights vs. Florida Atlantic Owls

 Mon, 22 Dec at 07:00 pm State Farm Field House at ESPN Wide World Of Sports Complex

Holiday Festiball at ESPN Wide World of Sports State Farm Field House

 Tue, 23 Dec at 12:00 am ESPN Wide World of Sports State Farm Field House

Kissimmee Festival of Lights

 Sat, 29 Nov at 12:00 am Downtown Kissimmee

"Holinights" Holiday Celebration at Promenade Sunset Walk - Public Welcome

 Thu, 20 Nov at 06:30 pm Promenade at Sunset Walk Free

Winter Pickleball Kids Camp | 12/22-1/2 | Orlando, FL

 Mon, 22 Dec at 10:00 am Crush Yard - Pickleball Bar & Lounge USD 90 to 598