Kissimmee Holidays
Tailor Made Florida Holidays
Experiences that promise to melt your worries away
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Experience a Kissimmee holiday
Only a stone’s throw from Orlando and its amusement parks is the charming city of Kissimmee. The city is home to a fantastic array of things to see and do, from adrenaline-inducing activities that’ll keep the whole family entertained to more relaxing experiences that promise to melt your worries away.
Whatever you choose to do on your Kissimmee holiday, your evenings will be spent being wined and dined in the excellent local eateries and bars before laying down your weary head at one of the city’s luxurious hotels.
Location
Kissimmee Weather
Average temperature (°C) and average rainfall (days)
Jan
16.3 5
Feb
16.9 5
Mar
19.5 6
Apr
21.9 5
May
24.8 7
June
26.8 13
July
27.7 15
Aug
27.8 12
Sept
26.8 6
Oct
23.6 7
Nov
19.4 4
Dec
16.6 5
Hotels in Kissimmee
Bohemian Hotel Celebration
This cultured hotel overlooks the beautiful Lake Rianhard, less than a mile from the prestigious Celebration Golf Club and a few miles more from the world famous Walt Disney Resort.
Reunion Resort
Stay at the Reunion Resort, a destination where you won’t be bored for a second! This fantastic hotel has a vast selection of sports activities and even has it’s own water park making it the ideal choice of location if you’re looking for a fun-filled trip for all the family.
Start planning your tailor made Florida holiday
From iconic fly-drive holidays to luxury destinations off the beaten path.
Call our experts on 0800 669 6409 or click the link below to speak with a travel expert.
Things to do on Kissimmee holidays
History
Osceola County Welcome Center and History Museum
Discover Osceola County’s rich history at this interactive welcome centre and museum. It showcases the four different habitats found in Osceola County – the swamplands, oak hammock, pine flatwoods and the lakefront. Each of the dioramas is so distinct yet they all work together to support the diverse ecosystem of the area. After exploring the museum’s exhibits, head outside and put your newly learned knowledge into practice at the nearby Shingle Creek.
Museum of Military History
Orange County Regional History Center
A superb showcase of Floridian history and culture, highlighting the first peoples to populate the state, the arrival of European settlers, the 19th century Seminole Wars, and the birth of modern tourism. Be prepared to be amazed at just how much there is to learn!
Orlando Museum of Art
Founded in 1924, the museum is one of Central Florida’s leading sources of cultural history, and features both permanent and travelling exhibitions aimed at connecting people with art and new ideas.
Wild Florida
Enjoy a slice of the REAL Florida as you head out into the countryside south of Kissimmee and discover the many delights of Wild Florida on Cypress Lake in Kenansville. Take one of their airboat rides, check out the Wild Gator Park and variety of animal encounters, and don’t miss the new drive-through Safari Park, with a mix of local and exotic animals.
Wild Willy’s Airboat Tours
Get up close and personal with the inhabitants of Lake Tohopekaliga on this hour-long airboat exploration. Along the way, there’ll be ample opportunity to spot gators and turtles, eagles and perhaps even a few deer. Alternatively, if it’s the alligators you’re looking to see, opt for the Gator Experience, where you can meet and even have your picture taken with the area’s apex predator! Afterwards, head to the snack bar and chow down on some gator bites and fries.
Boggy Creek Airboat Rides




Explore the great outdoors
Shingle Creek Paddling Trail
The Everglades are arguably the most well-known freshwater wetlands in the world, and it’s in Kissimmee that you’ll find Shingle Creek, the northernmost headquarters of this watershed. The state-designated paddling trail travels from Osceola County’s Shingle Creek Regional Park, all the way to Lake Tohopekaliga, or Lake Toho as it’s more commonly known. As you paddle along the stream you’ll pass scenic views, early pioneer buildings and even the site of a battle during the Second Seminole War.
Orlando Tree Trek
Wekiva Island
Just north of Orlando, revel in this large slice of nature on the crystal-clear Wekiva River, where you can hire kayaks and paddle-boards and explore this pristine wilderness, then kick back in their rustic bar, or enjoy your own private riverfront cabana.
Sports
ESPN Wide World of Sports® Complex
Those with a competitive side will love this sports complex, which comprises 220 acres of state-of-the-art facilities and hosts over 170 events every year. The complex welcomes amateurs and professionals, so all can experience the world-class equipment. The complex is a must-see if you’re a fan of baseball.
Whether you’re an amateur athlete or an armchair fan, there’s a whole host of events at the ESPN Wide World of Sports Complex for you to discover.
Orange Lake Resort – Legend’s Walk Golf Course
Spread across an impressive 1,581 yards, this walking course offers golfers spectacular views as they progress through their game. Holes vary greatly in length – from 85 yards up to 222 yards, so tackling this course is no easy feat. Luckily for newbies, Arnold Palmer and Palmer Course Design Company created the rolling fairways and pristine greens to be accessible (and yet a challenge) to all skill levels and ages.
Omni Orlando Resort at Champions Gate
Orlando City Soccer
The arrival of Major League Soccer in Orlando in 2015 has give the city a whole new purple-coloured passion as Orlando City SC has brought the beautiful game to The City Beautiful from March to October each year at 25,000-seat Exploria Stadium.
Orlando Magic Basketball
Get a taste of the big sports action with the NBA’s Orlando Magic, one of Florida’s handful of major league teams, with games at the impressive Amway Center from October to May.




Dinner shows & unique experiences
Medieval Times Dinner and Tournament
Capone’s Dinner & Show
Florida Orange World
With special soil and a climate that’s unique to the Indian River, this area of Florida produces some of the finest citrus fruits. Florida Orange World is the world’s largest, and perhaps only specialist orange store, where you’ll find thin-skinned high-quality oranges, as well as fruit baskets, candies and knick-knacks.
Sleuths Mystery Dinner Shows
Solve a murder mystery as you dine, and be royally entertained by the Sleuths comedy players on famous International Drive, with a series of different shows to choose from and a delicious meal, with drinks, to keep the whole family happy.
ICON Park
Take a ride on the 400ft Wheel at ICON Park, visit Madame Tussauds Orlando and SeaLife Orlando Aquarium, try the Orlando StarFlyer (the world’s tallest swing ride), plus an arcade and a great range of dining opportunities, including Ole Red by Blake Shelton.
WonderWorks
All the family will enjoy this hugely interactive fun house of games, wacky challenges and rides, plus laser tag, ropes course and nightly entertainment of the Outta Control Magic Comedy Dinner Show.
Theme Parks
Walt Disney World
Check out the 47 square miles, of fantasy, thrills and magic of Disney’s four essential theme parks – the Magic Kingdom, EPCOT, Disney’s Hollywood Studios and Disney’s Animal Kingdom – plus two water parks, four golf courses, sports center and the shopping-dining-entertainment hub of Disney Springs.
Universal Orlando
Be ready to ‘ride the movies’ in high style, including the likes of Harry Potter, the Marvel super-heroes, Jason Bourne, Dr Suess, The Simpsons, Men in Black, Transformers and much, much more as you discover Universal’s two full theme parks (Universal Studios and Islands of Adventure), plus the Volcano Bay water park and CityWalk nightlife district.
SeaWorld Parks
Take a big step into marine nature with the expansive SeaWorld theme park, which boasts some of the best roller-coasters in Florida as well as a variety of captivating animal exhibits, then thrill to their Aquatica water park and chill out in style – with the chance to swim with dolphins – at the unique Discovery Cove.