Kissimmee Holiday Events

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

Margaritaville Resort Orlando 19 Dec 2025

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

Promenade at Sunset Walk 14 Dec 2025

"How the Market Stole Christmas

Events Center 7 Dec 2025

Kissimmee Festival of Lights Parade & Holiday Festival

Downtown Kissimmee 13 Dec 2025

2025 Christmas Winter Festival- FTC Kissimmee

Florida Technical College - Kissimmee Campus 13 Dec 2025

Holiday Family Movie Night | Crush Yard Orlando

Crush Yard - Pickleball Bar & Lounge 12 Dec 2025

Ice Cream for Breakfast with Santa

210 S Bass Rd, Kissimmee, FL, United States, Florida 34746 7 Dec 2025

Senior’s Christmas Brunch

Oak Street Park Community Center, North Palm Avenue, Kissimmee, FL, USA 17 Dec 2025

Once Upon A Magic Market: How the Market Stole Christmas

1901 Chief Osceola Trl, Kissimmee, FL 34744-6112, United States 7 Dec 2025

Holiday Indulgence: Wine, Cheese and Seasonal Savories!

Vintage Vino 20 Dec 2025

Wills, Wine, & Winter Wishes: A Holiday Estate Planning Event

The Amador Gallery Event Venue 10 Dec 2025

The World of Music School – Christmas Spectacular 2024!

Sun On the Beach 14 Dec 2025

2nd Annual Great Gingerbread Build-Off

Chambers Park Community Center 13 Dec 2025

Ivelissa Ríos at Holiday Inn Resort Kissimmee

Holiday Inn Resort Kissimmee 12 Dec 2025

Free Picture with Santa at Susana´s Café

18 S. Orlando Ave, Kissimmee, FL, United States, Florida 34741 13 Dec 2025

Women Who Thrive on Tech - Holiday Meet & Greet

Violet's Venom Brewery 16 Dec 2025

Holiday Nights

210 S Bass Rd, Kissimmee, FL, United States, Florida 34746 20 Dec 2025

Paint and Sip Holiday Brunch

Oishi Latin Fusion 14 Dec 2025

QueenDom’s Royal Opulence Mercado

Kissimmee,orlando,florida 27 Dec 2025

Santa at the Train Depot

Pioneer Village At Shingle Creek 12 Dec 2025

Black Cake & Sorrel FL 2025

MAMMA's Banquets & Events 13 Dec 2025

Glimmer Tree Paint and Sip

1881 Restaurant & Bar 10 Dec 2025

Cookies & Cocoa Family Roller Skate🍪☕️

1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741 17 Dec 2025

Cutting Board & Candle Making Class

3038 Dyer Boulevard, Kissimmee, FL 34741 9 Dec 2025

UNO Kissimmee Kids Event - Holiday Cookie Decorating

UNO Pizzeria & Grill 16 Dec 2025

Holiday Nights

210 S Bass Rd, Kissimmee, FL, United States, Florida 34746 21 Dec 2025

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

Holiday Inn Resort Kissimmee 20 Dec 2025

Wooden Door Hanger Workshop

The Town of Kindred 15 Dec 2025

Osceola Magic vs. Noblesville Boom

Osceola Heritage Park 6 Feb 2026

Santa Sunday!

1534 W Vine St, Kissimmee, FL 34741 14 Dec 2025

CALL FOR VENDORS

3600 Reaves Rd 20 Dec 2025

The Mondayist Xmas Party Ever: Improv Holiday Party

1881 Restaurant & Bar 22 Dec 2025

Beyond & Free Spirit Experience

2145 e irlo Bronson Memorial hwy, Kissimmee, FL, United States, Florida 34744 8 Apr 2026

Osceola Magic vs. Memphis Hustle

Osceola Heritage Park 16 Dec 2025

Osceola Magic - Holiday Party + Replica Jersey Giveaway!

1875 Silver Spur Lane, Kissimmee, FL, United States, Florida 34744 16 Dec 2025

Watercolor Holiday Cards

White Rose Books & More 20 Dec 2025

Beekeepers Holiday Social

Big John's Rockin' BBQ 16 Dec 2025

Frozen Christmas Creative Together Market

7470 W Irlo Bronson Memorial Hwy 13 Dec 2025

Providence Hunters CreekToy Drive

1701 Ball Park Road 15 Dec 2025

GRINCHMAS SKATE

1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741 13 Dec 2025

Holiday Bingo & Sing Along Roller Skate

1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741 20 Dec 2025

Brunch with Santa 🎅

Metro Diner (Kissimmee) 20 Dec 2025

Free Picture with Santa at Susana´s Café

18 S. Orlando Ave, Kissimmee, FL, United States, Florida 34741 14 Dec 2025

Breakfast with Santa and the Kissimmee Woman's Club

1616 West Oak Street, 34741 13 Dec 2025

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

3274 Margaritaville Blvd 11 Dec 2025

Osceola Memory Gardens 67th Annual Holiday Remembrance Open House

1717 Old Boggy Creek Rd, Kissimmee, FL, United States, Florida 34744 18 Dec 2025

Ivelissa Rios

Holiday Inn Resort Kissimmee by The Parks 11 Dec 2025

Providence Hunter’s Creek Toy Drive

1701 Ball Park Road 15 Dec 2025

NeoCity Plug-in: Holiday Cheer

Cafe Barista NeoCity 11 Dec 2025

Osceola Magic vs. Long Island Nets

Osceola Heritage Park 17 Mar 2026

Hot Wheels Monster Trucks Live Glow-N-Fire

Osceola Heritage Park 3 May 2026

Holiday Festiball: UCF Knights vs. Florida Atlantic Owls

State Farm Field House at ESPN Wide World Of Sports Complex 22 Dec 2025

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

ESPN Wide World of Sports State Farm Field House 23 Dec 2025

Kissimmee Festival of Lights

Downtown Kissimmee 29 Nov 2025

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

Promenade at Sunset Walk 20 Nov 2025

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

Crush Yard - Pickleball Bar & Lounge 22 Dec 2025