Rally the corgi has sniffed out the best Christmas events for kids in Kissimmee for 2026, and here is what he found: 4 family events, 1 of them free. The magic runs from December 5 (An Osceola Christmas) through December 30, with Elf-tastic Holiday Adventure (December 12) and Pajama Jingles (December 19) along the way. We check every date on the host’s own website, and each listing links straight there. For the rest of the state, see our Florida Christmas events for kids guide.
What Rally found in Kissimmee
- 4 Christmas events for kids in Kissimmee
- 1 free event, including An Osceola Christmas
- Meet Santa: An Osceola Christmas (December 5)
- Also on the list: 1 story time and 3 craft workshops
- Season: December 5 (An Osceola Christmas) to December 30 (STEAMworks: Gingerbread Engineering)
- Every date checked on the host’s own site on Nov 10
What are you looking for?
All 4 events
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Rally’s Christmas research
Rally the corgi has 3 more Kissimmee events researched for you.
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Waiting inside
- 3 Crafts
- 1 Santa
- 1 Story time
- 1 Breakfast and treats
- 1 Free
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Free Christmas events for kids in Kissimmee
Santa visitFree
An Osceola Christmas
- When: Saturday, December 5, 2026, 10 am to 2 pm
- Where: Welcome Center & History Museum, 4155 W Vine St, Kissimmee, FL 34741 (opens in maps)
- Cost: Free admission
- Ages: Families, all ages
Expand to see the parent tip
Osceola History turns its Welcome Center and History Museum over to a family holiday day. Children can meet Santa, sit down to write him a letter, make holiday crafts and warm up with hot cocoa.
It takes place on Saturday, December 5, 2026, from 10:00 am to 2:00 pm at 4155 W Vine St in Kissimmee. Admission is free, and the page does not mention tickets or registration.
Parent tip: The four hour window means you can come and go as it suits you, so there is no need to be at the door at 10:00 am. Talk through the letter to Santa at home first, and little ones will know what they want to say when they reach the table.
- Host
- Osceola History (opens in a new tab)
- Address
- Welcome Center & History Museum, 4155 W Vine St, Kissimmee, FL 34741 (opens in maps)
- Confirmed
- On the host’s page, checked
New Kissimmee events every week
Rally researches Christmas events in Kissimmee daily and updates this page with new events. Enter your email to get a weekly update with new events in Kissimmee.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Rally’s Christmas research
Rally the corgi has 3 more Kissimmee events researched for you.
- New events every week We research new events daily and send you one email a week with the new ones we find in Kissimmee.
- Exclusive access to free events Find the free Christmas events in Kissimmee before they fill up.
- Unlock the filters Find Santa visits, free events and weekend plans in one tap.
- Rally’s Christmas Eve Express and a free advent calendar Get early access to Rally the corgi’s Christmas Eve tracker, plus a free digital advent calendar to count down to Christmas.
- One-tap add to calendar Save any event to your Google, Apple or Outlook calendar so you never miss it.
Coming up on this page
- 3 Crafts
- 1 Santa
- 1 Story time
- 1 Breakfast and treats
- 1 Free
Enter your email to get new Christmas events in Kissimmee every week.
Ticketed and paid Christmas events for kids in Kissimmee
Admission, tickets or a fee apply. Where a host has not posted a price yet, the listing says so.
Holiday crafts
Elf-tastic Holiday Adventure
- When: Saturday, December 12, 2026, 1 to 2 pm
- Where: Buenaventura Lakes Library, Multipurpose Room, 405 Buenaventura Blvd, Kissimmee, FL 34743 (opens in maps)
- Cost: No price listed on the organizer's page
- Ages: Kids and families
Expand to see the parent tip
The Buenaventura Lakes Library borrows its theme from the movie Elf for an hour of festive crafts, winter activities and games. It is set up for kids and their families to do together in the branch's multipurpose room.
The library lists it for Saturday, December 12, 2026, from 1:00 pm to 2:00 pm at the Buenaventura Lakes branch. The page gives no price and does not mention registration.
Parent tip: Crafts, games and activities are all packed into a single hour, so arrive on time to get to each of them. The description calls it a night, but the listed time is 1:00 pm, so go by the afternoon slot.
- Host
- Osceola Library System (opens in a new tab)
- Address
- Buenaventura Lakes Library, Multipurpose Room, 405 Buenaventura Blvd, Kissimmee, FL 34743 (opens in maps)
- Confirmed
- On the host’s page, checked
New Kissimmee events every week
Rally researches Christmas events in Kissimmee daily and updates this page with new events. Enter your email to get a weekly update with new events in Kissimmee.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Holiday story time
Pajama Jingles
- When: Saturday, December 19, 2026, 10 to 11:30 am
- Where: Hart Memorial Central Library, Lillie Room, 211 E Dakin Ave, Kissimmee, FL 34741 (opens in maps)
- Cost: No price listed on the organizer's page
- Ages: Preschool, ages 0 to 5
Expand to see the parent tip
Preschoolers are invited to come to Hart Memorial Central Library in their favorite pajamas for a winter holiday story time. The morning in the Lillie Room mixes festive stories with songs.
Pajama Jingles is on Saturday, December 19, 2026, from 10:00 am to 11:30 am. The library lists it for ages 0 to 5, and the page gives no price and does not mention registration.
Parent tip: Ninety minutes is a long sit for a baby or toddler, so bring a snack for afterward and be ready to step out if yours runs out of steam. Pajamas are the dress code, which makes for an easy Saturday morning.
- Host
- Osceola Library System (opens in a new tab)
- Address
- Hart Memorial Central Library, Lillie Room, 211 E Dakin Ave, Kissimmee, FL 34741 (opens in maps)
- Confirmed
- On the host’s page, checked
New Kissimmee events every week
Rally researches Christmas events in Kissimmee daily and updates this page with new events. Enter your email to get a weekly update with new events in Kissimmee.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Holiday crafts
STEAMworks: Gingerbread Engineering
- When: Wed December 23 and Wed December 30, 2026, 4:30 to 5:30 pm (The library's page lists December 23 and shows December 30 as a further date for the same program.)
- Where: West Osceola Library, Multipurpose Room, 305 Campus St, Kissimmee, FL 34747 (opens in maps)
- Cost: No price listed on the organizer's page; registration required
- Ages: School age, 6 to 11
Expand to see the parent tip
STEAMworks is the weekly hands-on program at West Osceola Library, and this session takes gingerbread houses as its subject. School age children explore the winter tradition of gingerbread houses and the engineering it takes to put one together.
The session is on Wednesday, December 23, 2026, from 4:30 pm to 5:30 pm, and the page shows Wednesday, December 30 as a further date. It is for ages 6 to 11 and registration is required, with sign-up opening at 4:30 pm on Wednesday, November 25, 2026.
Parent tip: Registration does not open until 4:30 pm on November 25, so set a reminder for that afternoon and sign up then. It is aimed at ages 6 to 11, and preschool siblings are better served by Pajama Jingles on December 19.
- Host
- Osceola Library System (opens in a new tab)
- Address
- West Osceola Library, Multipurpose Room, 305 Campus St, Kissimmee, FL 34747 (opens in maps)
- Confirmed
- On the host’s page, checked
New Kissimmee events every week
Rally researches Christmas events in Kissimmee daily and updates this page with new events. Enter your email to get a weekly update with new events in Kissimmee.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
We check every event above on the host’s own page for the date, time and cost, plus the things parents ask about, like sign-ups and ages. Looking for a Santa train instead? Those are on our Florida Christmas train rides page.
See every event on a December calendar
Plan your December
When each Kissimmee Christmas event for kids happens
The first is An Osceola Christmas in Kissimmee on December 5; the last runs to December 30. Each bar spans an event’s dates, not every hour in them, so check the host’s page for times.
- An Osceola ChristmasKissimmee · Dec 5
- Elf-tastic Holiday AdventureKissimmee · Dec 12
- Pajama JinglesKissimmee · Dec 19
- STEAMworks: Gingerbread EngineeringKissimmee · Dec 23 to Dec 30
Looking further afield? Our Florida Christmas events for kids guide lists every event we have found in the state, and we have city guides for Orlando, Winter Garden, Maitland and Clermont. The national search sorts every event by distance from your town.
A story for the drive home
A morning with Santa or an evening of holiday stories tends to end the same way: tired kids, a long drive and one more book before bed. Our picture book follows Rally the corgi on his first train ride to see his grand-paw-rents, and every page is painted by hand. If your family is spending December missing someone, it was written for that too. For the car, print our free corgi and train coloring pages.
A bedtime story after seeing SantaRally Takes the Train is a five-minute rhyming picture book about a corgi’s first ride on a California train, hand-painted in watercolor. $16.99 on Amazon, ages 0 to 8.
Buy on Amazon2026 Christmas events are coming in late November
More Christmas events arrive in late November. We add them here as soon as we confirm them.
The story of Christmas in Kissimmee
Kissimmee was first called Allendale, after Major J. H. Allen, who ran the Mary Belle, the first cargo steamboat on the Kissimmee River, and it took its present name when it became a city in 1883. Christmas here centers on a free family day with Santa at the Welcome Center and History Museum, followed by holiday programs at three Osceola Library System branches.
How Kissimmee celebrates
The Christmas season for families in Kissimmee in 2026 starts on December 5, when Osceola History holds An Osceola Christmas at its Welcome Center and History Museum on West Vine Street, with Santa, holiday crafts, hot cocoa, letters to Santa and free admission. The Osceola Library System carries the rest of the month. Buenaventura Lakes Library has an Elf themed hour of crafts and games on December 12, Hart Memorial Central Library holds the Pajama Jingles story time for ages 0 to 5 on December 19, and West Osceola Library runs a gingerbread engineering session for ages 6 to 11 on December 23.
Fun facts about Christmas in Kissimmee
Kissimmee is the largest city in Osceola County and its county seat, with 79,226 residents at the 2020 census. It was incorporated in 1883, and the South Florida Railroad extended its line from Sanford to Kissimmee, which made the town on Lake Tohopekaliga a transportation hub for Central Florida. The Old Osceola County Courthouse is described as the oldest continually operating courthouse in Florida, and Shingle Creek, which runs through the city, is largely considered the headwaters of the Everglades.
Traditions today
- An Osceola Christmas: Osceola History hosts a free family day on December 5 with Santa, holiday crafts, hot cocoa and letters to Santa.
- Welcome Center and History Museum: The museum at 4155 W Vine St, listed among Kissimmee's sites of interest, is the setting for An Osceola Christmas.
- Pajama Jingles: Children aged 0 to 5 wear pajamas to Hart Memorial Central Library on December 19 for winter holiday stories and songs.
- Elf-tastic Holiday Adventure: Buenaventura Lakes Library fills an hour on December 12 with Elf inspired crafts, winter activities and games for kids and families.
- Gingerbread Engineering: West Osceola Library's weekly STEAMworks program turns to gingerbread houses on December 23 for ages 6 to 11.
A fact for kids
Kissimmee sits on a lake with a very long name, Lake Tohopekaliga, which locals shorten to Lake Toho. One of the sights listed in town is Orange World, called the World's Largest Orange.
Questions about Christmas in Kissimmee
When was Kissimmee founded?
The modern town was founded before the Civil War by the Bass, Johnson and Overstreet families. It was incorporated as a city in 1883, and that is when it took the name Kissimmee. Today it is the largest city in Osceola County and serves as the county seat.
How did Kissimmee get its name?
The area was originally named Allendale after Major J. H. Allen, who operated the Mary Belle, the first cargo steamboat on the Kissimmee River. It was renamed Kissimmee at incorporation in 1883. The origin of the word is debated, though it is generally agreed to be Native American.
What role did the railroad play in Kissimmee?
The South Florida Railroad extended the end of its line from Sanford down to Kissimmee, making the town on Lake Tohopekaliga a transportation hub for Central Florida. By 1884 the tracks continued on to Tampa. Today the city's transit hub includes an Amtrak station that is also a SunRail stop.
Why were steamboats important in early Kissimmee?
Hamilton Disston of Philadelphia based a four million acre drainage operation in the town, and his dredging and land dealings needed steamboats to move people and goods along the new waterway. The Kissimmee shipyard built most of those large steamships before railroads took over the traffic.
How big is Kissimmee?
Kissimmee had 79,226 residents at the 2020 census and covers 17.32 square miles on the northwest shore of Lake Tohopekaliga. A large stretch of unincorporated Osceola County around the city is also commonly referred to as Kissimmee, including much of the US 192 corridor.
What happens at Christmas in Kissimmee for kids?
For 2026 the confirmed events are An Osceola Christmas on December 5, Elf-tastic Holiday Adventure on December 12, the Pajama Jingles story time on December 19 and STEAMworks: Gingerbread Engineering on December 23. Between them they cover Santa, crafts, stories, songs, games and gingerbread engineering.
Where can children see Santa in Kissimmee?
Santa appears at An Osceola Christmas, held at the Welcome Center and History Museum, 4155 W Vine St, on Saturday, December 5, 2026, from 10:00 am to 2:00 pm. Children can also write letters to Santa, make holiday crafts and have hot cocoa while they are there.
Who organizes Christmas events for kids in Kissimmee?
Osceola History, the county's historical society, runs An Osceola Christmas at its Welcome Center and History Museum. The Osceola Library System runs the other three programs at its Buenaventura Lakes, Hart Memorial Central and West Osceola branches, each with a named staff organizer on its event page.
Which Kissimmee Christmas events are free?
An Osceola Christmas on December 5, 2026 states that admission is free. The three library programs do not show a price on their pages. STEAMworks: Gingerbread Engineering is the only one that requires registration, which opens at 4:30 pm on November 25, 2026.
What is Shingle Creek in Kissimmee?
Shingle Creek runs through the city and is largely considered the headwaters of the Everglades. It has a canoe and kayak trail that starts at Steffe Landing on US 192 and ends in Lake Tohopekaliga, and a regional bicycle trail is planned along it toward Orlando.
Sources
- Kissimmee, Florida, Wikipedia
- An Osceola Christmas, Osceola History
- Elf-tastic Holiday Adventure, Osceola Library System
- Pajama Jingles, Osceola Library System
- STEAMworks: Gingerbread Engineering, Osceola Library System
Keep the Christmas magic going: track Rally the corgi on Christmas Eve, print free Christmas coloring pages, learn how to say Merry Christmas in 100+ languages, find train museums to visit with kids, or browse Christmas events in every Florida city.
Kissimmee Christmas events for kids: questions parents ask
What are the best Christmas events for kids in Kissimmee to start with?
Begin with An Osceola Christmas at the Welcome Center and History Museum on Saturday, December 5, 2026. It runs from 10:00 am to 2:00 pm and puts Santa, crafts, hot cocoa and letters to Santa in one place. After that, the Osceola Library System has holiday programs on December 12, 19 and 23.
Are there free Christmas events for kids in Kissimmee?
Yes. An Osceola Christmas on December 5, 2026 advertises free admission. The three Osceola Library System programs, Elf-tastic Holiday Adventure, Pajama Jingles and STEAMworks: Gingerbread Engineering, do not list a price on their pages, so check with the branch if you want that confirmed.
Where can kids meet Santa in Kissimmee?
Santa is at An Osceola Christmas on Saturday, December 5, 2026, from 10:00 am to 2:00 pm at the Welcome Center and History Museum, 4155 W Vine St. Children can also write letters to Santa there. It is the only Kissimmee event confirmed here that lists a Santa visit.
Are there holiday story times for little ones in Kissimmee?
Pajama Jingles at Hart Memorial Central Library is made for them. On Saturday, December 19, 2026, from 10:00 am to 11:30 am, children aged 0 to 5 come in pajamas for winter holiday stories and songs in the Lillie Room. No holiday light displays or stage shows are confirmed here.
Which Kissimmee Christmas events need tickets or sign-up?
Only STEAMworks: Gingerbread Engineering at West Osceola Library on December 23, 2026 states that registration is required, and sign-up opens at 4:30 pm on November 25. An Osceola Christmas, Elf-tastic Holiday Adventure and Pajama Jingles mention no tickets or registration on their pages.
Which Kissimmee library branches have Christmas programs for kids?
Three Osceola Library System branches do. Buenaventura Lakes Library holds Elf-tastic Holiday Adventure on December 12, 2026. Hart Memorial Central Library has Pajama Jingles on December 19 for ages 0 to 5. West Osceola Library runs STEAMworks: Gingerbread Engineering on December 23 for ages 6 to 11.
Are there Christmas train rides for kids near Kissimmee?
Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Florida Christmas train rides guide. This Kissimmee guide covers Santa visits, story times, light shows and other events off the rails.
How do you confirm these events?
We list an event only after we find this season’s date on the host’s own website or an official city or tourism calendar. We last checked every listing on November 10, 2026. Hosts change details, so always confirm on the host’s page before you go.
Event names belong to their hosts. Rally Takes the Train is a family picture book and is not affiliated with, sponsored by or endorsed by any host listed here. Confirm dates, times and prices on each host’s own site before you go.