Kissimmee Vacations from ￥174,830

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The Latest Kissimmee Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

￥174,830
per person
Dec 23 - Dec 30
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
8.4/10 Very Good! (5,343 reviews)
Los recomiendo al 100

Reviewed on Oct 11, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

￥449,990
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

International Drive District
Save 100% on your flight
￥219,178
per person
Dec 23 - Dec 30
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9/10 Wonderful! (1,334 reviews)
It was very clean and beautiful

Reviewed on Oct 6, 2026

Seasons Florida Resort

Seasons Florida Resort

￥183,268
per person
Dec 23 - Dec 30
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9/10 Wonderful! (3,974 reviews)
The Delaney Hotel

The Delaney Hotel

South Orange
￥253,598
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.6/10 Exceptional! (1,213 reviews)

Where to stay in Kissimmee

Find the best Kissimmee areas and neighborhoods for the activities you enjoy most. Learn more about Kissimmee
A wooden boardwalk leading to a gazebo over a lake, surrounded by trees with autumn leaves.

Cumbrian Lakes

While there might not be top attractions in Cumbrian Lakes, you can explore the larger area and discover places like Give Kids the World Village and Old Town.

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Campbell

Travelers like the sporting events in Campbell, and Shingle Creek Regional Park is a top attraction you might want to visit.

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A lake with a wooden bridge and a gazebo.

Solivita

If you're looking for some top things to see and do in Solivita and surrounding area, you can visit London Island and Lake Marion.

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Crescent Lakes

While there might not be top attractions in Crescent Lakes, you can explore the larger area and discover places like Give Kids the World Village and Providence Golf Club.

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A large tree with Spanish moss, surrounded by dry grass and other vegetation.

Trafalgar Village

If you're looking for some top things to see and do in Trafalgar Village and surrounding area, you can visit Give Kids the World Village and Providence Golf Club.

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Find the Best Kissimmee Vacation Packages

Things to do in and around Kissimmee

Shopping

For shopping in Kissimmee, visit Disney Springs™, located 14.5km away, offering a vibrant atmosphere with family-friendly options. Old Town is nearby, providing entertainment and local charm. The 192 Flea Market is also in Kissimmee, perfect for unique finds and souvenirs.

Recreation

Experience the vibrant atmosphere at ESPN Wide World of Sports Complex, where you can enjoy various sports activities and events. Alternatively, unwind at Waldorf Astoria Golf Club or Hunters Creek Golf Club, both offering picturesque outdoor settings perfect for relaxation and recreation amid nature.

Adventure

Aquatica, a thrilling waterpark 14.5km from Kissimmee, boasts exhilarating slides and relaxing wave pools for family fun. Wonderworks, located 17.7km away, offers interactive arcade games in a whimsical atmosphere. For speed enthusiasts, the Orlando Kart Center, 12.9km from Kissimmee, provides an adrenaline-pumping karting experience.

Nightlife

Kissimmee's nightlife offers a vibrant atmosphere with venues like Indigo's Family Fun Center, a lively pub located 45.1km away. Enjoy a mix of romance and entertainment vibes while sipping on drinks and mingling with locals for a memorable night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Kissimmee

Kissimmee is an ideal destination for family, entertainment, and business vacations, offering a variety of attractions such as theme parks, lakes, and amusement parks. Visitors can enjoy outdoor activities, cultural experiences, and family-friendly adventures. To fully experience what Kissimmee has to offer, be sure to explore its popular points of interest and immerse yourself in the local charm.

  • Universal Orlando Resort: Experience the magic of Universal Orlando Resort, a thrilling theme park just 20.9km away from Kissimmee. With exhilarating rides, immersive attractions, and beloved characters from movies, it offers entertainment for the whole family, making it a must-visit for adventure seekers and film lovers alike.
  • Orange County Convention Center: Located 16.1km from Kissimmee, the Orange County Convention Center is a hub of culture and creativity. Hosting a variety of events, exhibitions, and conventions, this arts center showcases the vibrant arts scene and offers a unique glimpse into the local culture.
  • Kissimmee Lakefront Park: Situated within Kissimmee, Kissimmee Lakefront Park is a beautiful urban oasis perfect for families. With scenic views, walking trails, and recreational activities, it offers a relaxing outdoor experience in the heart of the city.

Best time to go to Kissimmee

None

Tips to save on your trip to Kissimmee

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Kissimmee.
  • 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.

Kissimmee Hotel Deals

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundableReserve now, pay when you stay
￥3,703
￥11,210 total
Oct 12 - Oct 13
includes taxes & fees
Kompose Boutique Resort at Theme Parks
Seasons Florida Resort

Seasons Florida Resort

4736 W Irlo Bronson Hwy Memorial Kissimmee FL
Fully refundable
￥7,223
￥8,198 total
Oct 12 - Oct 13
includes taxes & fees
Seasons Florida Resort
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL
Fully refundableReserve now, pay when you stay
￥20,422
￥31,804 total
Nov 1 - Nov 2
includes taxes & fees
Margaritaville Resort Orlando with H2O Waterpark
See all 27,163 properties in Kissimmee
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.

Stay near popular Kissimmee attractions

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.
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A golf course with sand bunkers, trees, and a flagstick.
Photo by Visit Orlando

Mystic Dunes Golf Club

7.8/10 (4,134 reviews)
This Gary Koch-designed championship course blends British links-style dunes with Carolina wetlands across dramatic 80-foot elevations. Reserve your morning tee time for optimal play conditions on both distinct nines.
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A landscape with a clear blue sky, a large body of water with lily pads, and a distant horizon.
Photo by Emily Slade

Boggy Creek Airboat Rides

7.8/10 (463 reviews)
Take the family on an outing to Boggy Creek Airboat Rides during your trip to Kissimmee. Stroll along the lakeside or attend a sporting event in the area.
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A water park with a pool, palm trees, and a statue of a horse.

Kissimmee Lakefront Park

8.4/10 (2,921 reviews)
This lakeside retreat features scenic walking paths, fishing piers, and a Monument of States along Lake Tohopekaliga. Enjoy lighthouse views or bring the family for splash pad adventures in this peaceful urban oasis.
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The Silver Spurs Arena with a clear blue sky and a few clouds.

Silver Spurs Arena

7.8/10 (3,021 reviews)
The Silver Spurs Arena showcases Kissimmee's vibrant entertainment scene through rodeos, concerts, and sporting events. Experience the celebrated Silver Spurs Rodeo, a cultural highlight held throughout the year.
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Three heraldic shields on a wall covered in ivy.

Medieval Times

8.0/10 (3,178 reviews)
Step back in time at this immersive 11th-century castle featuring knights in armor and jousting tournaments. Feast on a medieval meal without utensils while cheering for your assigned champion.
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Reunion Resort Golf Course

7.6/10 (3,040 reviews)
Experience three championship courses designed by Palmer, Watson, and Nicklaus at this prestigious Florida golf destination. Enjoy meticulously maintained fairways while savoring the resort's upscale amenities.
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Give Kids the World Village

7.8/10 (1,311 reviews)
This nonprofit resort creates magical vacations for critically ill children and their families. Families enjoy whimsical attractions, themed parties, and unlimited ice cream in a fully accessible wonderland.
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What to do in Kissimmee

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

￥5,231
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

￥20,048
per traveler
80% of travellers recommend
Universal Orlando Resort Express Passes
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

￥20,883
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
See all activities in Kissimmee

Frequently asked questions

How much does a Kissimmee vacation package cost?
You'll find cheap prices from ￥174,830 on Expedia for your Kissimmee escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Kissimmee costs.
What are the cheapest months to go to Kissimmee?
January, September and October are great times to search for cheap Kissimmee vacation 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 vacations 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 Center and seek out some lesser-known gems. Don't forget to explore cool neighborhoods 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 vacation package to Kissimmee?
Whether you'd like to check out attractions like Kissimmee Lakefront Park and Osceola Heritage Park on your Kissimmee vacation, 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 vacation 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 vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can personalize 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 vacation 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 accommodations and airfare: After you've nailed down your trip dates and duration, lock in the ideal Kissimmee vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.