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*

  • Find the right fit

    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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

CA $836
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.4/10 Very good! (5,343 reviews)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight
CA $1,905
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight
CA $1,097
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.4/10 Very good! (7,160 reviews)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

Save 100% on your flight
CA $931
per person
Jan 1 - Jan 8
found 20 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very good! (2,082 reviews)
Me gustó mucho el lugar y la atención de los trabajadores es espectacular lo volvería a repetir para pasar las vacaciones

Reviewed on Oct 13, 2026

Westgate Towers Resort

Westgate Towers Resort

Save 100% on your flight
CA $920
per person
Jan 1 - Jan 8
found 20 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.6/10 Excellent! (1,004 reviews)
I felt like a VIP here. The price was incredible. The room was clean and cool. The staff was very friendly. Super easy drive to and from Magic Kingdom. Highly recommend.

Reviewed on Oct 12, 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
Default Image

Campbell

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

Find hotels in Campbell
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.

Find hotels in Solivita
Default Image

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.

Find hotels in Crescent Lakes
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

Seasons Florida Resort

Seasons Florida Resort

4736 W Irlo Bronson Hwy Memorial Kissimmee FL
Fully refundableReserve now, pay when you stay
CA $57
CA $65 total
Oct 18 - Oct 19
includes taxes & fees
Seasons Florida Resort
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 $43
CA $112 total
Oct 21 - Oct 22
includes taxes & fees
9.4/10 Exceptional! (6,055 reviews)
"Great experience.Love this hotel"

Reviewed on Oct 13, 2026

Kompose Boutique Resort at Theme Parks
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL
CA $184
CA $287 total
Nov 1 - Nov 2
includes taxes & fees
Margaritaville Resort Orlando with H2O Waterpark
See all 28,563 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

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.
See properties
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.
See properties
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.
See properties
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.
See properties
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.
See properties
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.
See properties

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.
See properties

Give Kids the World Village

7.8/10 (1,311 reviews)
Bring the kids to Give Kids the World Village and have a fun-filled day at this theme park in Kissimmee. Amble around this family-friendly area's lakeside or experience its entertainment choices.
See properties

What to do in Kissimmee

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $196
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
WonderWorks All Access After Dark

WonderWorks All Access After Dark

CA $39
per traveller
90% of travellers recommend
WonderWorks All Access After Dark
See all activities in Kissimmee

Frequently asked questions

How much does a Kissimmee vacation package cost?
Offering great value package deals from CA $836 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.

Explore a world of travel with Expedia

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