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Holiday Gift Market
Kissimmee Christian Church 415 N Main Street, Kissimmee, FLThe Women's Ministry of Kissimmee Christian Church will present the Holiday Gift Market on Thursday, December 4, from 5 to 8 p.m. at Kissimmee Christian Church, 415 N. Main Street, Kissimmee, FL 34744. Join us for an evening of shopping and fun, and get into the holiday spirit! This is the perfect chance to find […]
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St. Cloud 2025 Holiday Events
Downtown St. Cloud New York Avenue, St. Cloud, FloridaDowntown St Cloud is full of festivities this holiday season. Shop, dine & enjoy the downtown community this season. We hope this little list of dates helps in the busy season and stay tuned as we continue to post more about specific upcoming events.
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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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KUA Movie in the Park: Home Alone 2
Kissimmee Lakefront ParkKick off the holiday season with a magical night at Movie in the Park! Join us at Kissimmee Lakefront Park on December 5 for a festive screening of Home Alone 2, featuring family-friendly fun, including free crafts, inflatables, a photo booth with Santa, and holiday-themed crafts.To add to the spirit of giving, bring a canned […]
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Annual Tree Lighting Winter Wonderland Ceremony
St. Cloud City Hall 1300 9th St, St. Cloud, FLCelebrate the season at the Annual Tree Lighting - Winter Wonderland Ceremony on Friday, December 5, from 6 p.m. to 9 p.m. at St. Cloud City Hall, 1300 9th Street. Enjoy an evening filled with musical performances, crafts, letters to the North Pole, visits with Santa, carnival games, snowslide, inflatables, and more festive fun for […]
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Oh, What Fun! Run 5k
Lake Nona Town Center 13630 Sachs Avenue, Orlando, FLGet ready to dash through the sunshine for the Oh, What Fun! Run 5k at Lake Nona Town Center on December 6 at 7:30 a.m.! Lace up your running shoes, dress in your best holiday and celebrate the season with a fun-filled run. Whether you're sprinting, jogging, or walking with friends and family, it's a […]
$45 -
St. Cloud Holiday Festival
Downtown St. Cloud New York Avenue, St. Cloud, FloridaGet ready for a full day of festive fun in the heart of St. Cloud! This year’s Holiday Festival brings together local crafters and artists, live performances, an exciting Kids Zone the whole family will love, fabulous food trucks, and MUCH more. Don’t miss your chance to grab photos with Santa, enjoy delicious festival food, […]
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2025 St. Cloud Christmas Parade presented by Orlando Health – St. Cloud Hospital
Downtown St. Cloud New York Avenue, St. Cloud, FloridaThe Annual Christmas parade, presented by Orlando Health St. Cloud Hospital and the City of Saint Cloud, is brought to you by Experience Kissimmee. This year's theme for the Christmas parade is "The Magic of Christmas." The St. Cloud Christmas parade is a family-friendly event, featuring festivities for all ages. This locally televised event will […]
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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 Marketplace - an extravagant array of holiday décor, themed trees, stunning vignettes, and baskets galore, all available for purchase.
$25 -
Christmas Carols & Ugly Sweaters – Holiday Lights Cruise
Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FLGrab your most wonderfully tacky holiday sweater and join us aboard the Lillie for a festive Christmas Carols & Ugly Sweater Cruise! Set sail at 5 p.m. for an evening of merry music, twinkling lights, and plenty of holiday cheer on the water. Sing along to your favorite Christmas carols, show off your ugliest (and […]
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Sons of the American Legion Poker Tournament
American Legion Post 80 1019 Pennsylvania Avenue, St. Cloud, FLPoker tournament to raise money for Christmas gifts for families in need this holiday season! Pre-register for an additional $5000 in chips! Pre-registration requires pre-payment!
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Holiday Golf Cart Parade
Old Town 5770 W Irlo Bronson Memorial Hwy, Kissimmee, FLJoin us right before our weekly Car Cruise as residents from Sherwood Forest RV Resort present their personal golf carts in all of their Holiday glory! Golf carts will begin arriving at 6:30pm and will parade down Old Town’s MainStreet before our Car Cruise at 8:30pm.
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St. Cloud Holiday Festival
Downtown St. Cloud New York Avenue, St. Cloud, FloridaGet ready for a full day of festive fun in the heart of St. Cloud! This year’s Holiday Festival brings together local crafters and artists, live performances, an exciting Kids Zone the whole family will love, fabulous food trucks, and MUCH more. Don’t miss your chance to grab photos with Santa, enjoy delicious festival food, […]
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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 in classic Old Florida charm.Only $24.99 per person and $10 for bottomless mimosas.The Lillie is an authentic sternwheeler, lovingly restored and named after the historic […]
$24.99 -
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 Marketplace - an extravagant array of holiday décor, themed trees, stunning vignettes, and baskets galore, all available for purchase.
$25 -
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 deliver letters to Santa …and more! Admission: $5 (Kids 2 & under are free!)
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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! 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!
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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 evening cocktails, grab a bite to eat and don’t skip dessert!
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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 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, […]
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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 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 […]
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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 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 […]
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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 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, 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 for the parade. Since it’s midday, you may want sunscreen/hats. Check for parking early.
Free
24 events found.
