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  • 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 […]

    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 […]

    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 […]

  • 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 […]

  • 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 […]

  • 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 […]

  • 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 […]

  • 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 […]

    $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, […]

  • 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 […]

  • Holiday Lights Cruise

    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 […]

  • Operation Save Christmas: A Live Radio Play and Day Cruise

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

    Join the Old Florida River Boat Company for a unique Holiday Fundraiser Cruise aboard The Lillie!Enjoy a relaxing scenic cruise on the beautiful East Lake Toho while being entertained by […]

  • Surfing Santas of Cocoa Beach

    Cocoa Beach 2 Minutemen Causeway, Cocoa Beach, FL

    Surfing Santas 2025 is on Christmas Eve, 7:30 a.m. Where: End of Minutemen Causeway, in front of Coconuts on the Beach Hundreds of Surfing Santas will hit the waves, and […]

    Free

  • Exotic Cars & Coffee

    Old Town 5770 W Irlo Bronson Memorial Hwy, Kissimmee, FL

    Join us for some coffee and car talk. The term “exotic” is used in marketing by automakers to mean “unusual or expensive,” but we like to think it means “the […]

  • New Year’s Eve Celebration at Old Town

    Old Town 5770 W Irlo Bronson Memorial Hwy, Kissimmee, FL

    End 2025 with a bang at a New Year's Eve Celebration presented by Old Town and Fun Spot.Bring the family for Live Music & Entertainment featuring the band DRAW 4 […]

  • Rockin’ the Cloud – New Year’s Eve

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

    St. Cloud’s biggest New Year’s Eve celebration returns. Rockin’ the Cloud takes place Wednesday, December 31, from 7 p.m. to 1 a.m. in Historic Downtown St. Cloud. We are excited […]

  • Three Kings Day 2026

    Old Town 5770 W Irlo Bronson Memorial Hwy, Kissimmee, FL

    The Feast of the Three Kings is an intricate part of Latin Folklore. Traditionally, this day is very important, especially for children, for it is on this eve that they […]

    Free

  • Walking tour of Mt. Peace Cemetery

    Woman's Club of St. Cloud 1014 Massachusetts Ave, St. Cloud, FL

    Walking tour of Mt. Peace Cemetery on E 10th Street. Purchase tickets at the St. Cloud Heritage Museum Thursday, Friday, or Saturday 11 a.m.-3 p.m.  For more information, call Cede […]

    $15
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