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Kissimmee Holidays

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Where to stay in Kissimmee

Find the best Kissimmee areas for the activities you enjoy most. Learn more about Kissimmee
Learn more about Kissimmee
A golf course with bunkers, water hazards, and a large lake.

Reunion

Reunion delivers the ultimate resort experience with championship golf courses, luxurious holiday homes, and water parks just minutes from Orlando's famous theme parks. Three legendary courses designed by Palmer, Nicklaus, and Watson provide perfect fairways for golf enthusiasts. The Mediterranean-style community offers pristine pools and upscale amenities throughout. Families appreciate the water park with slides and lazy rivers. Active travellers enjoy tennis facilities and spa treatments between theme park visits. Though limited in local dining and shopping options, the gated community provides a peaceful retreat from Orlando's tourist bustle.

A street sign reading "Welcome to Kissimmee, Florida" with a mural of horses on a building.

Historic Downtown Kissimmee

Historic City centre Kissimmee charms visitors with preserved Victorian architecture along Broadway Street. The 1890s Osceola County Courthouse stands proudly with its distinctive red brick and clock tower. Seasonal street festivals and farmers markets bring this cultural hub to life throughout the year. Stroll along the waterfront paths of Lake Tohopekaliga or explore the quirky Monument of States. Local shops offer everything from cowboy memorabilia to Florida-themed crafts. The area's Cuban cafes and Southern comfort food restaurants perfectly complement its small-town atmosphere.

An aerial view of a residential area with numerous houses, roads, and several lakes.

Windsor Hills

Windsor Hills offers families a perfect retreat just minutes from Disney's Animal Kingdom and other Orlando attractions. This welcoming area features Mediterranean-style holiday homes with resort amenities like community pools and game rooms. Wide, palm-lined streets create a peaceful atmosphere after busy theme park days. The area primarily serves as a comfortable base for exploring Central Florida's famous destinations. Most homes include private pools and themed decor for extended family stays. While dining and shopping options are limited within the area, everything you need is just a short drive away.

A sunset over a marshy landscape with a wooden pier extending into the water.

Orange Lake

Orange Lake combines resort luxury with prime access to Orlando's world-famous attractions. This Four Corners area centers around Orange Lake Resort, where championship golf courses and sprawling pool complexes create a holiday paradise. Walt Disney World is just minutes away, making this an ideal home base for theme park adventures. Families love the balance of on-site recreation and nearby entertainment options. Holiday villas with full kitchens offer space to relax after busy days. Resort shuttles make reaching major attractions simple, though rental cars provide the most flexibility for exploring beyond the area.

A lakeside town with a prominent white building, lush greenery, and a distant city skyline.

Lake Berkley

While Lake Berkley may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Medieval Times and Give Kids the World Village.

Discover the most popular places to visit in Kissimmee

A theme park entrance with a Ferris wheel and a roller coaster.

Old Town

8.6/10 (14,011 reviews)
This retro-themed district transports you to a nostalgic era with vintage architecture. Stroll the brick-paved streets at dusk when live music and illuminated attractions create a magical atmosphere.

What to do in Kissimmee

Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

€158
per adult
88% of travellers recommend
Walt Disney World® Resort Theme Park Tickets
See all activities in Kissimmee

Kissimmee Hotel Deals

Exterior

Hampton Inn Kissimmee North

Hampton Inn Kissimmee North
2.5 star property
5.6 km from Kissimmee
9.6 out of 10, Exceptional, (763 reviews)
"Greetings in the morning & the excellent continental breakfast"
The price is €97
includes taxes & fees
2 Aug - 3 Aug
Hampton Inn Kissimmee North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Kissimmee

Frequently Asked Questions

How much does a Kissimmee holiday package cost?

You'll find cheap prices on Expedia for your Kissimmee escape. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Kissimmee costs.

What are the cheapest months to go to Kissimmee?

January, September and October are great times to search for cheap Kissimmee holiday packages. Choosing to travel in less busy periods means you can typically find better prices on flights and hotels.

How many days is enough for Kissimmee?

Kissimmee holidays come in many shapes and sizes, but to get a true feel for this place, we'd suggest 3 days is about right. With this timeframe, you can visit top attractions like Capone's Dinner Show and Osceola Performing Arts Centre and seek out some lesser-known gems. Don't forget to explore cool neighbourhoods such as Historic Downtown Kissimmee and Bellavida either. If you plan wisely, you may even be able to take a day trip from Kissimmee too.

Is it worth booking a holiday package to Kissimmee?

Whether you'd like to check out attractions like Kissimmee Lakefront Park and Osceola Heritage Park on your Kissimmee holiday, or coming for its great family-friendly attractions, shopping and dining, there's something for everyone here. With so much to do, you'll soon discover why so many families think Kissimmee is a good holiday destination.

How to find the best Kissimmee package deals?

Begin your search for a Kissimmee package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Kissimmee package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Kissimmee adventure underway.

Is it cheaper to book a Kissimmee holiday as a package?

An Expedia holiday package could land you considerable savings when compared to booking flights and accommodation separately. Better still, you can personalise your Kissimmee getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.

When to book a holiday package to Kissimmee?

If you're planning an impromptu Kissimmee trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.

How to plan a trip to Kissimmee?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to escape to Kissimmee.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will likely be the largest expense during your trip to Kissimmee.
  3. Determine how many days away: Start by making a list of all the attractions you'd like to get to in Kissimmee. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your accommodation and airfare: After you've nailed down your trip dates and duration, lock in the ideal Kissimmee holiday package for you.

Book with confidence

Things to do in and around Kissimmee

Kissimmee is an ideal destination for families and those seeking entertainment or business-themed holidays. Visitors can enjoy a variety of activities, including outdoor adventures, sun-soaked pursuits, and engaging miniature golf. The area boasts numerous resorts and vibrant shopping centres, making it a perfect blend of relaxation and excitement for all ages.

Shopping

Disney Springs™ is a delightful shopping area located 14.5km from Kissimmee, offering a vibrant atmosphere perfect for families. Orlando Vineland Premium Outlets, 12.9km away, provides a fantastic mix of entertainment and shopping. For a local experience, visit the 192 Flea Market in Kissimmee, brimming with unique finds.

Recreation

Mystic Dunes Golf Club offers a tranquil golfing experience amidst lush landscapes, perfect for relaxation and sport. For sports enthusiasts, the ESPN Wide World of Sports Complex boasts thrilling events, while Medieval Times presents an enchanting blend of entertainment and culture, ideal for family outings.

Adventure

Experience thrilling water slides and wave pools at Aquatica, only 14.5km from Kissimmee. Enjoy adrenaline-fueled karting at Kissimmee Go-Karts right within the area. Don’t miss Disney's Typhoon Lagoon Water Park, also 14.5km away, where adventure meets family fun in a tropical paradise.

Nightlife

Kissimmee's nightlife offers vibrant entertainment, ideal for a fun evening. For a lively atmosphere, visit Indigo's Family Fun Center, a charming pub located 45.1km away, where you can enjoy romance and enjoy the entertainment vibes with friends and fellow travellers.

Find the best attractions in and around Kissimmee

Kissimmee, Florida, offers a delightful blend of family-friendly attractions, entertainment, and cultural experiences, making it an ideal destination for all types of travellers. Visitors can explore renowned theme parks, enjoy the serene lakes, and indulge in the excitement of amusement parks. Whether you're seeking outdoor adventures or engaging cultural encounters, Kissimmee provides a vibrant atmosphere that caters to families and leisure seekers alike.

  • Universal Orlando Resort: Experience the thrill of this renowned theme park, just 20.9km from Kissimmee. With immersive attractions and entertainment options, it’s a fantastic destination for families seeking adventure and fun.
  • Orange County Convention Center: Located 16.1km away, this arts centre is a hub of culture, hosting a variety of events and exhibitions. Immerse yourself in the vibrant art scene and enjoy the creative atmosphere.
  • Osceola Heritage Park: Situated within Kissimmee, this urban park offers a delightful blend of family-friendly activities and outdoor spaces. Enjoy the city vibes while exploring nature and engaging in community events.

Tips to save on your trip to Kissimmee

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically August to September and November) for more affordable package holidays to Kissimmee.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.