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  • Jingle Bar Hop

    Kissimmee Main Street 421 Broadway, Kissimmee, FL

    Grab your crew and jingle all the way through Downtown Kissimmee for our Jingle Bar Hop!Cocktails, mocktails & merry stops at your favorite downtown bars. Early Bird tickets only $25! Festive outfits encouraged — the more sparkle, the better!Let’s turn Broadway into a winter wonderland of cheer. Grab your tickets before they’re gone!

  • Christmas Pajama Party

    Downtown St. Cloud New York Avenue, St. Cloud, Florida

    Break out your favorite festive pj’s and come for a fun shopping night in Downtown St Cloud! Enjoy a night of festive lights, hot cocoa and holiday shopping. Sip some evening cocktails, grab a bite to eat and don’t skip dessert!

  • Greg Warmoth Reindeer Run 5k

    SeaWorld Orlando 7007 Sea World Dr., Orlando, FL, United States

    Bring the family out for the best Holiday Fun Run in the area. Run or walk the festive 3 mile route through SeaWorld to the sound of holiday bells and finish in a Runner wonderland with holiday treats for all finishers! Dash away to https://www.trackshack.com/event/236 for more information and to register PLEASE NOTE: To participate, […]

  • Breakfast with Santa and the Kissimmee Woman’s Club

    Kissimmee Woman's Club 1616 W Oak St., Kissimmee, FL

    The Kissimmee Woman’s Club invites you to a jolly good time at our Breakfast with Santa  at 1616 W Oak Street, Kissimmee, FL 34741! Bring the whole family for a morning full of Christmas cheer. Meet Santa and his elves, enjoy a delicious pancake breakfast, play Candy Bar Bingo, join in story time with children's […]

  • 2025 Winter Festival – FTC Kissimmee

    Florida Technical College 3831 West Vine St., Kissimmee, FL

    Join us for Florida Technical College's 2025 Winter Festival, a FREE event that is fun for the whole family. Enjoy holiday cheer, crafts, and a FREE photo with Santa! -Take a picture with Santa-Electronic Device Raffles*-Rumba 100.3 Broadcasting Live on Campus (with giveaways)-Free Kids Haircuts - K through 12**-Free Ice Cream**-Games-Christmas Cookies in the Show […]

    Free

  • Breakfast with Mrs. Claus

    Creative Inspiration Journey School 2030 Old Hickory Tree Rd, St. Cloud, FL

    Join us for a festive morning of holiday fun at CIJS — open to the public! Enjoy a delicious pancake breakfast and a lineup of magical activities the whole family will love: Photos with Santa and the GrinchStorytime with Mrs. ClausCookie ContestLife-Size Snow GlobeCrafts and more! Tickets go on sale soon — just $7 per […]

    $7

  • Association of Poinciana Villages Christmas Parade & Celebration

    Villages of Poinciana 625 Country Club Dr., Kissimmee, FL

    Free event. Parade from Cypress Parkway to the park, followed by a holiday celebration with kids zone, food trucks, live entertainment, vendors & crafters. Great for families — bring chairs/blanket for the parade. Since it’s midday, you may want sunscreen/hats. Check for parking early.

    Free

  • Christmas Arrives in Narcoossee

    Narcoossee School House 5028 Yukon St., St. Cloud, FL

    Join us on Saturday, December 13,  from 11 a.m. to 2 p.m. for a festive community celebration you won’t want to miss! Photos with Santa (11–2) Write a Letter to Santa Chili Cook-Off & Hot Dogs Local Vendor Market featuring crafts and baked goods

    Free

  • Christmas Market

    Hunter Arms Hotel 1029 New York Avenue, St. Cloud, FL

    The Hunter Arms Hotel is excited to bring you our 2nd Pop-Up Market.. with a Christmas twist!!-Last-minute Christmas shopping-Discover unique small businessesFree for all families to come and enjoy!

  • Harmony WinterFest Celebration

    Harmony Town Square 7254 Five Oaks Dr., St. Cloud, FL

    Join us for the WinterFest Celebration on Saturday, December 13 from 5-8pm at Harmony Town Square - a magical evening of community, cheer, and holiday fun! Tree Lighting CeremonyPhotos with SantaGingerbread House ContestTaste of Harmony local eatsLive CarolersToy Drive StationGames, crafts, vendors & more! Gingerbread House Contest Sign-Up: https://forms.office.com/r/EdVeUtaMqZ Cookie Contest Sign-Up:https://forms.office.com/r/3J9cV83CTn(Free to enter – […]

  • Soldier City Sundays Weekly Market

    Soldier City Sundays Weekly Market

    Veterans Park 1201 13th Street, St. Cloud, FL

    Join us this Sunday from 11 a.m. to 2 p.m. at Veteran’s Park for our weekly community market celebrating St. Cloud’s heritage as the Soldier City.The community is invited to shop from local vendors, enjoy live music, and grab a bite to eat. Veterans can also connect with area veterans organizations all in one place. […]

  • Cookies and Cocoa with Santa – Special Sunday Cruise

    Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FL

    All aboard for a magical afternoon of holiday fun on the Lillie! Join us for our Cookies & Cocoa with Santa Cruise, the perfect family-friendly Christmas adventure on the water. Guests will enjoy warm cocoa and fresh cookies while playing holiday games, creating festive crafts, listening to story time with Santa, and taking pictures with […]

  • Kissimmee Senior Christmas Brunch

    Oak Street Park Community Center 717 N Palm Ave, Kissimmee, FL

    Celebrate the holidays with friends, family, and neighbors at our free Senior Christmas Brunch! Guests aged 55 and above are invited to enjoy a complimentary holiday meal, music, and festive activities in a warm and welcoming atmosphere. This special holiday event is the perfect way to connect with loved ones, share in the season’s joy, […]

    Free

  • Kissimmee Senior Christmas Brunch

    Oak Street Park Community Center 717 N Palm Ave, Kissimmee, FL

    Celebrate the holidays with friends, family, and neighbors at our free Senior Christmas Brunch! Guests aged 55 and above are invited to enjoy a complimentary holiday meal, music, and festive activities in a warm and welcoming atmosphere. This special holiday event is the perfect way to connect with loved ones, share in the season’s joy, […]

    Free

  • Wednesday Free Movie Matinee – Featured Film: The Family Man

    St Cloud Community Center 3101 17th St, St. Cloud, FL

    Join us for a Free Movie Matinee at the Community Center on Wednesday, December 17th, at 12:30 p.m. This month's featured movie: The Family Man This 18+ event is perfect for a mid-week break. Location: Community Center, 3101 17th St. For more info, call 407-957-4243.

  • Knockout Christmas Classic

    Knockout Christmas Classic

    Osceola Heritage Park

    Knockout Christmas Classic is the toughest in-season wrestling tournament in the Southeast, bringing in teams from all over the country! Featuring the best high school boys, girls and youth in the country. This year we have added D1. Wrestling fans will not want to miss this event! Children under the age of 6 are free. […]

  • Holiday Lights Cruise Featuring the Super Freak Duo

    Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FL

    Hop aboard the beautifully restored “Lillie” for a magical Holiday Lights Tour on the water! Enjoy a festive evening surrounded by sparkling holiday lights, cheerful décor, and the joyful spirit of the season as we cruise into a cozy holiday night. Featuring live music from local favorites Super Freak Duo, this cruise delivers the perfect […]

  • Commissioner Brandon Arrington’s Party with Santa

    Valencia College Poinciana Campus 3255 Pleasant Hill Road, Kissimmee, FL

    Get ready for a holiday night your kids will not forget. Join Commissioner Brandon Arrington, Osceola County District 3, for Party With Santa on Friday, December 19, 2025, from 5–7 p.m. at Valencia College – Poinciana Campus, 3255 Pleasant Hill Road, Kissimmee, FL 34746. Photos with Santa (bring your own camera)Face painting, balloon artist and […]

  • Knockout Christmas Classic

    Knockout Christmas Classic

    Osceola Heritage Park

    Knockout Christmas Classic is the toughest in-season wrestling tournament in the Southeast, bringing in teams from all over the country! Featuring the best high school boys, girls and youth in the country. This year we have added D1. Wrestling fans will not want to miss this event! Children under the age of 6 are free. […]

  • Breakfast with Santa

    St Cloud Community Center 3101 17th St, St. Cloud, FL

    Annual event for kids. Each child gets breakfast, goodie bag, a book and a visit with Santa Claus. Live music by Denny GeeDoor prizes and elves Contact Linda Lokken for tickets407-569-7688

    $15

  • Breakfast with Santa in Pajamas

    Chambers Park Community Center 2380 N. Smith St, Kissimmee, FL

    Join us for our 21st annual Breakfast with Santa! This year, come cozy in your favorite pajamas for a festive and magical morning. Families will enjoy a free breakfast spread, meet Santa, take holiday photos, and celebrate the season together. Don’t miss this heartwarming event that has been creating memories for two decades.

  • Ugly Sweater Wine Walk in the Cloud

    Downtown St. Cloud New York Avenue, St. Cloud, Florida

    Grab your friends and your ugliest Christmas sweater for December’s wine walk in the Cloud! Get your tickets on the Eventbrite link below. Returning wine walkers buy your tix on site and bring your reusable plastic glass back with you to save five dollars off! https://www.eventbrite.com/e/wine-walk-in-the-cloud-tickets-1076743742519?aff=erelpanelorg

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