A pathway through a park with Spanish moss hanging from trees and a body of water in the background.

Kissimmee Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Kissimmee Vacation

Lock in a custom vacation package to Kissimmee and get ready for your next big adventure. Consider basing yourself in the neighborhood of Historic Downtown Kissimmee, which is great for shopping and dining, for a true taste of this unique city. Ready to explore? Gatorland®, Osceola Heritage Park and Give Kids the World Village are some of the top-rated places to visit during your trip to Kissimmee. Stop daydreaming and start doing. Explore the wide range of options on Expedia today and finally put your Kissimmee vacation plans in motion!

Top Kissimmee vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A hotel with a central pool area, multiple swimming pools, and a waterfront location.
    Jan 9 - Jan 15

    Westgate Town Center Resort + Flight

    Kissimmee
    6 nights
    4.0 star property
    8.4/10 - Very good (2,081 reviews)
    "The new rooms are good"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,122
    CA $590
    per traveller
    found 1 day ago
    Westgate Town Center Resort
  • A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a clear sky.
    Dec 18 - Dec 23

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • Nonstop MCO - YHM • Nonstop
    Save 100% on your flight
    CA $2,415
    CA $1,358
    per traveller
    found 19 hours ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • A deck with lounge chairs and tables overlooking a beach with palm trees and ocean waves.
    Jan 24 - Jan 28

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    4 nights
    4.0 star property
    8.6/10 - Excellent (578 reviews)
    "The beaches across the street. The pools are nice however I had a room right next to the pool and they play music up until 9:00pm at night. So if you just trying to rest that will not happen. The music just kept playing all day long."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    Save 100% on your flight
    CA $1,703
    CA $966
    per traveller
    found 1 day ago
    Westgate Cocoa Beach Resort
  • An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.
    Jan 15 - Jan 21

    Meliá Orlando Celebration + Flight

    Celebration
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,646 reviews)
    Roundtrip • Toronto (YTO) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,659
    CA $974
    per traveller
    found 1 day ago
    Meliá Orlando Celebration
  • A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.
    Jan 31 - Feb 5

    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort + Flight

    Kissimmee
    5 nights
    2.0 star property
    9.0/10 - Wonderful (4,109 reviews)
    "My bueno"
    Reviewed November 9, 2026
    Roundtrip • Halifax (YHZ) - Orlando (MCO)
    YHZ - MCO • Nonstop MCO - YHZ • Nonstop
    CA $1,524
    CA $946
    per traveller
    found 1 day ago
    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

Where to stay in Kissimmee

Find the best Kissimmee areas and neighborhoods 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 vacation 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 Downtown 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 vacation 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 vacation 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. Vacation 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

When in Lake Berkley, you can plan a visit to Medieval Times and Give Kids the World Village, some noteworthy sights in the nearby area.

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)
Enjoy the excitement at Old Town and see why people love this theme park in Kissimmee. Check out the shops and top-notch restaurants in this family-friendly area.
See properties

What to do in Kissimmee

Universal Orlando Resort Theme Park Tickets (US & Canada)

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $222
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
See all activities in Kissimmee

Kissimmee Hotel Deals

A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
18.2 km from Kissimmee
9.4 out of 10, Exceptional, (6,434 reviews)
"The room was so clean and the beds are huge and comfortable."
The price is CA $33
CA $100 total
includes taxes & fees
Nov 17 - Nov 18
Kompose Boutique Resort at Theme Parks
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

Find out more about Kissimmee

Things to do in and around Kissimmee

Kissimmee, Florida, offers a delightful mix of family-friendly activities, entertainment options, and business-themed attractions. Visitors can enjoy golf vacations, explore nearby theme and amusement parks, and indulge in shopping at local malls and centres. With a variety of day trips available, Kissimmee is an ideal destination for those seeking adventure and relaxation in a vibrant setting.

Shopping

Discover Disney Springs™, a vibrant shopping area located 14.5km from Kissimmee, offering a mix of dining and entertainment. In the heart of Kissimmee, Old Town provides a charming shopping mall experience with family-friendly vibes. If you're up for a drive, visit Oak Ridge Gun Range, situated 20.9km away.

Recreation

At Mystic Dunes Golf Club, enjoy a round of golf amidst beautiful landscapes, perfect for relaxation and outdoor activity. Meanwhile, the ESPN Wide World of Sports Complex offers thrilling sports vibes just 16.1km away, while Medieval Times combines culture and entertainment for a memorable family experience in Kissimmee.

Adventure

Experience thrilling water slides and lazy rivers at Aquatica, located 14.5km from Kissimmee. Enjoy family fun at Wonderworks' arcadeAdventureZone, 17.7km away, or feel the adrenaline rush at Kissimmee Go-Karts, right in the heart of the city. Adventure awaits you.

Nightlife

Kissimmee's nightlife features Indigo's Family Fun Center, a vibrant drinking pub 45.1km away, offering a mix of entertainment and romantic vibes. Enjoy a lively atmosphere with friends or a loved one while sipping on craft cocktails and enjoying the evening's energy.

Find the best attractions in and around Kissimmee

Kissimmee, Florida, is an ideal destination for families and entertainment seekers, offering a variety of attractions that cater to outdoor enthusiasts and culture lovers alike. Visitors can explore exciting theme parks, amusement parks, and picturesque lakes, making it perfect for both business and leisure vacations. Whether you're seeking thrilling adventures or cultural experiences, Kissimmee provides an enjoyable getaway for everyone.

  • Universal Orlando Resort: Experience the thrill of world-class attractions and immersive themed lands, perfect for families and entertainment seekers. From exhilarating rides to enchanting shows, it’s a must-visit destination just 20.9km from Kissimmee.
  • Orange County Convention Center: Embrace the vibrant cultural scene at this arts centre located 16.1km away. With various events, exhibitions, and conventions, it showcases the artistic spirit of the region and is an exciting hub for art enthusiasts.
  • Kissimmee Lakefront Park: Enjoy a serene escape in this urban park situated in the heart of Kissimmee. Ideal for families and outdoor lovers, it offers scenic views, walking trails, and recreational activities along the picturesque lake.

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.

Frequently Asked Questions

How much does a Kissimmee vacation package cost?

Offering great value package deals from CA $590 on Expedia, you'll be surprised at how little a vacation to Kissimmee costs! Our packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Kissimmee?

January, September and October are great times to look for cheap Kissimmee vacation packages. Travelling in quieter months means you'll typically find better prices on hotels and flights.

How many days is enough for Kissimmee?

We'd recommend booking a Kissimmee vacation for a minimum of 3 days. This will allow you time to tick off major attractions including Kissimmee Lakefront Park and Osceola Heritage Park, and check out neighbourhoods like Historic Downtown Kissimmee and Bellavida. You could even fit in one or two day trips beyond Kissimmee.

Is it worth booking a vacation package to Kissimmee?

Well known for its family-friendly attractions, shopping and dining, a Kissimmee vacation has something for everyone. Be sure to visit major sights like Kissimmee Lakefront Park and Osceola Heritage Park, and consider renting some wheels for day trips to explore even more.

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 "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Kissimmee package deal right away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Kissimmee getaway off to a flying start.

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

Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still get the flexibility to create a customized Kissimmee vacation by choosing your preferred type of stay, airline and car class.

When to book a vacation package to Kissimmee?

If you've got your Kissimmee vacation dates confirmed, book early to score some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for quick escapes.

How to plan a trip to Kissimmee?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Kissimmee.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to activities and airfares. Your hotel will probably be the largest expense during your trip to Kissimmee.
  3. Decide how long to go away for: Now that you're more familiar with Kissimmee, you can figure out the perfect length of your vacation. Put together a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Kissimmee vacation package that brings all your bookings together.

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