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Muffins and Mimosas – Special Sunday Cruise
Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FLHop aboard the beautifully restored “Lillie” for a serene Sunday morning on the water! Enjoy a delightful selection of fresh muffins, sparkling mimosas, and gentle morning breezes as we cruise […]
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2025 Holiday Home Tour & Magical Marketplace
Celebration Celebration, FLEnjoy a self-guided tour through beautifully decorated homes throughout Celebration as you soak in the sights, sounds, and spirit of the season. Your ticket also includes access to the Magical […]
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Santa at the Train Depot
Pioneer Village at Shingle Creek 2491 Babb Rd, Kissimmee, FLSanta is coming to Pioneer Village! Celebrate the season with us at this festive holiday event featuring: Christmas carolers, local vendors, delicious food, crafts & pioneer games, a chance to […]
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Kissimmee Makers Market – Friday Nights
KMS Makers Market 413 Broadway, Kissimmee, FLKissimmee Main Street has invited the Grinch to the Friday night Makers Market the month of December. Join us for games, crafts, vendors, and a weekly “Kids Ugly Sweater” contest.
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Jingle Bar Hop
Kissimmee Main Street 421 Broadway, Kissimmee, FLGrab 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! […]
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Christmas Pajama Party
Downtown St. Cloud New York Avenue, St. Cloud, FloridaBreak 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 […]
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Greg Warmoth Reindeer Run 5k
SeaWorld Orlando 7007 Sea World Dr., Orlando, FL, United StatesBring 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 […]
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Breakfast with Santa and the Kissimmee Woman’s Club
Kissimmee Woman's Club 1616 W Oak St., Kissimmee, FLThe 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 […]
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2025 Winter Festival – FTC Kissimmee
Florida Technical College 3831 West Vine St., Kissimmee, FLJoin 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 […]
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Breakfast with Mrs. Claus
Creative Inspiration Journey School 2030 Old Hickory Tree Rd, St. Cloud, FLJoin 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 […]
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Association of Poinciana Villages Christmas Parade & Celebration
Villages of Poinciana 625 Country Club Dr., Kissimmee, FLFree 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 […]
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Christmas Arrives in Narcoossee
Narcoossee School House 5028 Yukon St., St. Cloud, FLJoin 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 […]
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Christmas Market
Hunter Arms Hotel 1029 New York Avenue, St. Cloud, FLThe 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!
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Harmony WinterFest Celebration
Harmony Town Square 7254 Five Oaks Dr., St. Cloud, FLJoin 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 […]
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Soldier City Sundays Weekly Market
Veterans Park 1201 13th Street, St. Cloud, FLJoin 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 […]
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Cookies and Cocoa with Santa – Special Sunday Cruise
Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FLAll 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. […]
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Kissimmee Senior Christmas Brunch
Oak Street Park Community Center 717 N Palm Ave, Kissimmee, FLCelebrate 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 […]
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Kissimmee Senior Christmas Brunch
Oak Street Park Community Center 717 N Palm Ave, Kissimmee, FLCelebrate 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 […]
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Wednesday Free Movie Matinee – Featured Film: The Family Man
St Cloud Community Center 3101 17th St, St. Cloud, FLJoin 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 […]
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Knockout Christmas Classic
Osceola Heritage ParkKnockout 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 […]
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Kissimmee Makers Market – Friday Nights
KMS Makers Market 413 Broadway, Kissimmee, FLKissimmee Main Street has invited the Grinch to the Friday night Makers Market the month of December. Join us for games, crafts, vendors, and a weekly “Kids Ugly Sweater” contest.
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Holiday Lights Cruise Featuring the Super Freak Duo
Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FLHop 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 […]
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Commissioner Brandon Arrington’s Party with Santa
Valencia College Poinciana Campus 3255 Pleasant Hill Road, Kissimmee, FLGet 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 […]
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Knockout Christmas Classic
Osceola Heritage ParkKnockout 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 […]
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