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.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was CA $1,357, price is now CA $809 per person
CA $809
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (524 reviews)
Super clean

Reviewed on Jul 5, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $2,112, price is now CA $968 per person
CA $968
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,275 reviews)
Super clean and easy access

Reviewed on Jul 6, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,475, price is now CA $832 per person
CA $832
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very good! (6,621 reviews)
The property was emasculate, my family enjoyed our stay there and we will most definitely be staying in the future.

Reviewed on Jul 5, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,543, price is now CA $920 per person
CA $920
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
8.2/10 Very good! (1,977 reviews)
Terrible check in; very busy since was a Independence day but horrible experience with the rooms.

Reviewed on Jul 5, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,981, price is now CA $1,795 per person
CA $1,795
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,006 reviews)
Excellent location

Reviewed on Jul 2, 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.

Find hotels in Cumbrian Lakes

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

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is CA $60 per night from Jul 8 to Jul 9
CA $60
CA $131 total
Jul 8 - Jul 9
includes taxes & fees
9.4/10 Exceptional! (4,713 reviews)
"Excelente"

Reviewed on Jul 6, 2026

Kompose Boutique Resort at Theme Parks
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

3 out of 5
5711 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundable
The price is CA $72 per night from Jul 13 to Jul 14
CA $72
CA $123 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very good! (2,788 reviews)
"The only thing about this hotel is the breakfast! Hotel is very old not an update in sight! Charge resort fees and is not a resort!"

Reviewed on Jul 5, 2026

Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Aug 2 to Aug 3
CA $215
CA $321 total
Aug 2 - Aug 3
includes taxes & fees
8.8/10 Excellent! (3,640 reviews)
"The best time and the best facility!"

Reviewed on Jul 6, 2026

Margaritaville Resort Orlando with H2O Waterpark
See all 26,900 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.
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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)
Bring your family to Old Town and enjoy the excitement of 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

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $239
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 $43
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Aquatica Orlando

Aquatica Orlando

CA $82
per traveller
86% of travellers recommend
Aquatica Orlando
See all activities in Kissimmee

Frequently asked questions

How much does a Kissimmee vacation package cost?
Offering great value package deals from CA $809 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.