Kissimmee Holiday Events

The Happiest Market: Holly Jolly Market

Island H2O Water Park 22 Nov 2025

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

Margaritaville Resort Orlando 19 Dec 2025

Trivia & Paint Night

3038 Dyer Boulevard, Kissimmee, FL 34741 21 Nov 2025

Holiday Holiday Pie and WIne

Vintage Vino 29 Nov 2025

Senior’s Christmas Brunch

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

Black Friday at White Rose Books & More

White Rose Books & More 28 Nov 2025

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

Holiday Inn Resort Kissimmee 20 Dec 2025

Small Business Saturday - Author Signing and BEST DEAL OF THE YEAR

White Rose Books & More 29 Nov 2025

Ice Cream for Breakfast with Santa

210 S Bass Rd, Kissimmee, FL, United States, Florida 34746 6 Dec 2025

Frozen Christmas Creative Together Market

7470 W Irlo Bronson Memorial Hwy 13 Dec 2025

Ivelissa Rios

Holiday Inn Resort Kissimmee by The Parks 11 Dec 2025

Thanksgiving Networking Collective

Loa's Suites 24 Nov 2025

Kissimmee Festival of Lights Parade & Holiday Festival

Downtown Kissimmee 13 Dec 2025

Beyond & Free Spirit Experience

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

2025 MADD Central Florida Holiday Victim Tribute

Fun Spot America Theme Parks - Kissimmee 15 Nov 2025

Ivelissa Ríos at Holiday Inn Resort Kissimmee

Holiday Inn Resort Kissimmee 12 Dec 2025

D2 Thanksgiving Meal Distribution

Archie Gordon Memorial Park 19 Nov 2025

Holiday Nights

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

Holiday Gift Market

415 N Main St, Kissimmee, FL, United States, Florida 34744 4 Dec 2025

The Marketplace of Magic- Holiday's at the Parks

Gaylord Palms Resort & Convention Center 16 Nov 2025

Breakfast with Santa and the Kissimmee Woman's Club

1616 West Oak Street, 34741 13 Dec 2025

Ice Cream for Breakfast with Santa

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

Holiday Nights

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

Grow & Gather

Achieve Wellness 19 Nov 2025

Black Cake & Sorrel FL 2025

MAMMA's Banquets & Events 13 Dec 2025

Santa at the Train Depot

Pioneer Village At Shingle Creek 12 Dec 2025

Christmas Social and TOY DRIVE - FREE EVENT

Sajoma Latin Fusion 5 Dec 2025

2025 Christmas Winter Festival- FTC Kissimmee

Florida Technical College - Kissimmee Campus 13 Dec 2025

Osceola Magic - Holiday Party + Replica Jersey Giveaway!

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

Kids Class Thanksgiving Special ONLY $25!!

3038 Dyer Boulevard, Kissimmee, FL 34741 25 Nov 2025

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

Promenade at Sunset Walk 14 Dec 2025

Cyber Monday - BEST DEAL OF THE YEAR ONLINE

White Rose Books & More 1 Dec 2025

2nd Annual Great Gingerbread Build-Off

Chambers Park Community Center 13 Dec 2025

Osceola Magic vs. Noblesville Boom

Osceola Heritage Park 6 Feb 2026

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

3274 Margaritaville Blvd 11 Dec 2025

Osceola Magic vs. Memphis Hustle

Osceola Heritage Park 16 Dec 2025

Hot Wheels Monster Trucks Live Glow-N-Fire

Osceola Heritage Park 3 May 2026

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