Kissimmee Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
per person
Jul. 27 - Aug. 3
just found
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.8/10 Excellent! (1,894 reviews)
Fantastic and affordable !!!

Reviewed on Jun. 21, 2024

Aladdin Motel By OYO Merritt Island

Aladdin Motel By OYO Merritt Island

2.5 out of 5
per person
Jul. 27 - Aug. 3
just found
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
7.6/10 Good! (35 reviews)
Bathroom was very clean

Reviewed on Jun. 6, 2024

Where to stay in Kissimmee

Find the best Kissimmee areas and neighborhoods for the activities you enjoy most. Learn more about Kissimmee
Default Image

Windsor Hills

If you're looking for some top things to see and do in Windsor Hills and surrounding area, you can visit Mystic Dunes Golf Club and Island H2O Live!.

Find hotel + flight trips in Windsor Hills

Kissimmee Hotel Deals

Palazzo Lakeside Hotel
Palazzo Lakeside Hotel
3 out of 5
4944 W. Irlo Bronson Memorial Highway, Kissimmee, FL
The price is CA $61 per night from Jul. 16 to Jul. 17
CA $61
CA $110 total
includes taxes & fees
Jul 16 - Jul 17
7.8/10 Good! (4,134 reviews)
"Second time staying at this property and it meets my expectations. Very helpful and kind staff. Conveniently located around restaurants, retail, grocery stores, and theme parks"

Reviewed on Jun. 20, 2024

Palazzo Lakeside Hotel
Hilton Vacation Club Mystic Dunes Orlando
Hilton Vacation Club Mystic Dunes Orlando
3.5 out of 5
7600 Mystic Dunes Lane, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Jul. 9 to Jul. 10
CA $119
CA $182 total
includes taxes & fees
Jul 9 - Jul 10
8.8/10 Excellent! (3,220 reviews)
"Staff at the main building were not really friendly . “A new girl” was very rude the day we checked in. The atmosphere was nice and people were friendly around the resort . We did have a cockroach in our room. Otherwise it was an okay stay."

Reviewed on Jun. 21, 2024

Hilton Vacation Club Mystic Dunes Orlando
Margaritaville Resort Orlando
Margaritaville Resort Orlando
4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Jun. 26 to Jun. 27
CA $195
CA $284 total
includes taxes & fees
Jun 26 - Jun 27
8.8/10 Excellent! (3,036 reviews)
"Would definitely come back !"

Reviewed on Jun. 19, 2024

Margaritaville Resort Orlando
See all 32,348 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

Frequently asked questions

How much does a Kissimmee vacation package cost?
The cheapest Kissimmee vacation package is CA $594, so your dream vacation can become a reality — without it costing a fortune. Bundle flights, hotels and car rentals to create a package that matches your travel style.
How do I get a cheap travel package to Kissimmee?
Just think of all the amazing things you could do in Kissimmee with a pile of extra cash in your pocket. Watch your savings stack up when you combine your flights, hotels and extras into a Kissimmee vacation package. You have plenty of choice when you book your trip with Expedia too. In fact, you can take your pick of over 550 airlines and 1,000,000 hotel options worldwide. Whether you’re heading off with the whole family or adventuring alone, planning a getaway to Kissimmee is better with a package.
Where should I stay in Kissimmee?
With loads to discover in Kissimmee, it’d be handy for you to secure a room in a hotel close to its attractions. ChampionsGate Golf Club, Old Town and Mystic Dunes Golf Club are some fascinating ones to put on your itinerary.
What are the top hotels in Kissimmee?
Travelers visiting Kissimmee often make a booking at The Grove Resort & Water Park Orlando or Ramada By Wyndham Kissimmee Gateway. You’ll find them in Windsor Hills. Another great neighborhood is Bellavida. Red Lion Hotel Orlando Lake Buena Vista South and Palazzo Lakeside Hotel are well-liked options in this area.
How far in advance should I book my Kissimmee vacation?
It all depends on the air carrier, but you can generally compare international flights on Expedia up to 12 months in advance. While it’s advisable to book ahead of time, lucky customers will occasionally find a cheaper flight just weeks before the date of departure.
What does an Expedia Kissimmee travel package include?
With Expedia, you can select a combination of car rentals, flights and hotels to create your ideal Kissimmee package. Once you’ve made your booking, you can add on fun stuff like sightseeing tours and activities. Remember, the more you bundle, the bigger the savings!
What should I know before booking a Kissimmee travel package?
You’ll score great savings when you combine your flights, hotels and rental cars into a travel package. Not only that, booking everything in one spot just makes things easier. So why waste your time or money? Whether you’re putting together a ritzy romantic getaway or an affordable family break, check out our vacation packages today.
Can I choose my airline with a Kissimmee Expedia vacation package?
You sure can. Expedia has access to more than 550 airline partners worldwide, so pick the carrier that fits your needs.
If I'm not able to travel, can I cancel my Kissimmee vacation package?
You can. We understand that things don’t always go to plan, so we’re here to help if you need to make changes to your Kissimmee vacation package. It may be possible to change or cancel your itinerary for free if you’ve booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Other vacations you might like

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