Kissimmee Vacation Packages

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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.
Westgate Towers Resort

Westgate Towers Resort

CA $454
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
❤️

Reviewed on Sep 10, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

CA $1,496
per person
Nov 22 - Nov 29
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
The unit itself is beautiful. The bedrooms and bathrooms are gorgeous with really nice furnishings. The showers are really nice and each bedroom has an attached bathroom, which is very convenient. There were a few issues with cleanliness in the unit and the pool. We had stained washcloths in one bathroom, the sofa fabric is pilling and we found several items on the kitchen floor that hadn't been swept up. The pool filter doesn't appear to work well at all. We continually skimmed the pool but there was still dirt and leaves in the bottom of the pool that never went away. The pictures in the listing show the pool as having an attached hot tub. It does not. It also shows loungers by the pool, but there are none. I did call the front desk to advise them of this. I asked for loungers to be delivered but they will not do that as it seems it's the responsibility of the owners to provide those. They didn't have much to say about the pool not having the hot tub, even though it is advertised as having one so that was disappointing. The resort lobby is beautiful and check in was fairly easy. The resort pools and hot tubs were very nice as well. The pool bar food and drinks are expensive ($40 for a drink and hummus appetizer) and an automatic 20% gratuity is automatically added to all orders. Something to keep in mind. Overall, we had a great stay and would definitely do it again, although I would not rent this particular unit the next time.

Reviewed on Sep 14, 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

CA $543
per person
Nov 8 - Nov 13
found 14 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.4/10 Very good! (5,314 reviews)
The Delaney Hotel

The Delaney Hotel

South Orange
CA $680
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9.6/10 Exceptional! (1,202 reviews)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District
CA $1,113
per person
Oct 24 - Oct 30
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
7.8/10 Good! (580 reviews)
Room stinks To much hassle to clean your room

Reviewed on Sep 6, 2026

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.

Find hotels in Trafalgar Village

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.

*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, 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.

Ready to book your vacation to Kissimmee?

Choose your dates

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
CA $55
CA $123 total
Sep 29 - Sep 30
includes taxes & fees
9.4/10 Exceptional! (5,731 reviews)
"No microwave in rooms, no cleaning of rooms daily, needs to improve standard of rooms, washroom door opens up near entry door causing you to bump yourself always especially with kids, breakfast is limited and needs to have more variety"

Reviewed on Sep 14, 2026

Kompose Boutique Resort at Theme Parks
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

5200 West Irlo Bronson Memorial Highway Kissimmee FL
Fully refundableReserve now, pay when you stay
CA $37
CA $89 total
Sep 16 - Sep 17
includes taxes & fees
8.6/10 Excellent! (3,229 reviews)
"The rooms are clean and spacious. The staff is very kind and helpful. The breakfast is included and has outstanding options. We have been staying here for years and they only get better! 10/10!"

Reviewed on Sep 15, 2026

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL
CA $193
CA $295 total
Sep 28 - Sep 29
includes taxes & fees
8.8/10 Excellent! (3,790 reviews)
"everything was great ,everything was super clean and well maintained ,staff was very nice and helpfull ,room was beautiful and super clean , pools were clean and well maintained"

Reviewed on Sep 14, 2026

Margaritaville Resort Orlando with H2O Waterpark
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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)
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.
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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)
Tee off at one of Orlando’s premier golf clubs and enjoy the championship course, the excellent facilities and the laid-back Florida vibe.
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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)
Kissimmee Lakefront Park is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the entertainment choices in this family-friendly area.
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Three heraldic shields on a wall covered in ivy.

Medieval Times

8.0/10 (3,178 reviews)
You can get tickets for a performance at Medieval Times on your trip to Kissimmee. Make time for the shops and golf courses in this family-friendly area.
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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)
Catch an event at Silver Spurs Arena during your trip to Kissimmee. Experience the lively festivals and entertainment choices in this family-friendly area.
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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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Reunion Resort Golf Course

7.6/10 (3,040 reviews)
Enjoy a round of golf in Kissimmee at Reunion Resort Golf Course. Amble around this family-friendly area's lakeside, or seek out the local tours.
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Island H2O Live!

8.2/10 (270 reviews)
Bring the family to Island H2O Live! and have a fun-filled day at this amusement park in Four Corners. Make time for the shops and golf courses in this family-friendly area.
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What to do in Kissimmee

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $194
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

CA $38
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Andretti Indoor Karting & Games in Orlando

Andretti Indoor Karting & Games in Orlando

CA $43
per adult
88% of travellers recommend
Andretti Indoor Karting & Games in Orlando
See all activities in Kissimmee

Frequently asked questions

How much does a Kissimmee vacation package cost?
Offering great value package deals from CA $454 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.

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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.