Kissimmee Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,274 reviews)
The outlooks of the property is good however the facilities are too old. No room cleaning services makes me so upsets.

Reviewed on Jul. 14, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Very family friendly. I stayed with my kids, partner and mom and we loved that it was clean , safe and the staff was approachable

Reviewed on Jul. 14, 2025

ette hotel

ette hotel

5 out of 5
per person
Oct 2 - Oct 7
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
very friendly helpful staff. nice area with many restaurants and grocery stores around. clean rooms. elegant hotel

Reviewed on Jul. 4, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 25
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,060 reviews)
This property is great! So many amenities that you do not need to leave the property! Pools were beautiful, food options plenty ! The property was spotless. The only issue is the parking at night, big issue.

Reviewed on Jul. 14, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
7.8/10 Good! (1,649 reviews)
It took a very long time for them to come see about why the microwave wasn’t working in the room along with the remote control

Reviewed on Jul. 13, 2025

Where to stay in Kissimmee

Find the best Kissimmee areas and neighborhoods for the activities you enjoy most. Learn more about Kissimmee
Reunion which includes golf and landscape views as well as a small group of people

Reunion

1 out of top 10 points of interest in this area

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Find hotels in Reunion

Ready to book your vacation to Kissimmee?

 

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Kissimmee Hotel Deals

Kompose Boutique Resort at Theme Parks
Kompose Boutique Resort at Theme Parks
4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Aug 10 to Aug 11
CA $107
CA $138 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (606 reviews)
"Family friendly, excellent condition."

Reviewed on Jul. 12, 2025

Kompose Boutique Resort at Theme Parks
Vacation Village at Parkway
Vacation Village at Parkway
3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Aug 3 to Aug 4
CA $92
CA $127 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (2,460 reviews)
"A very familiar place with the comfort of preparing your meals and close to restaurants and supermarkets."

Reviewed on Jul. 11, 2025

Vacation Village at Parkway
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Holiday Inn Club Vacations at Orange Lake Resort by IHG
4 out of 5
8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundable
The price is CA $136 per night from Aug 4 to Aug 5
CA $136
CA $213 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,169 reviews)
"Love this place"

Reviewed on Jul. 14, 2025

Holiday Inn Club Vacations at Orange Lake Resort by IHG
See all 26,749 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

Discover the most popular places to visit in Kissimmee

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(226 reviews)

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida

Universal Studios Florida

4.5/5(988 reviews)

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando which includes street scenes, a city and rides

Universal Orlando Resort

4.5/5(399 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

What to do in Kissimmee

2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

CA $74
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $108
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Explore the Wonderful World of the Oz Books in a way that you have never seen before...

Wizard of OZ Museum tour

CA $41
per adult
100% of travellers recommend
Wizard of OZ Museum tour
See all activities in Kissimmee

Frequently asked questions

How much does a Kissimmee vacation package cost?
Offering great value package deals from CA $623 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.