Kissimmee Vacations from $278

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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!

The Latest Kissimmee Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Alhambra Villas

Alhambra Villas

3 out of 5
Solivita
per person
Jan 17 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (762 reviews)
It was comfortable and quiet.

Reviewed on Oct 28, 2024

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (1,005 reviews)
Very nice staff, clean room, perfect for our weekend trip

Reviewed on Oct 24, 2024

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
per person
Jan 3 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,377 reviews)
Beautiful property!!

Reviewed on Oct 28, 2024

Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
per person
Jan 3 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (1,097 reviews)
Me n my hubby loved the hot tub!!!

Reviewed on Oct 31, 2024

Fantasy Island Resort, Daytona Beach Shores

Fantasy Island Resort, Daytona Beach Shores

3.5 out of 5
Rio Mar Beaches
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (64 reviews)
We were able to check in early. Rooms were clean. They had everything that we needed in our room, such as paper towels, utensils, etc. Friendly staff. Reasonable priced.

Reviewed on Oct 22, 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

4.5/5(6 area reviews)

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

Find the Best Kissimmee Vacation Packages

Kissimmee Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
69,200
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Walt Disney World® Resort, Disneys Animal Kingdom® Theme Park and Epcot®

Ready to book your vacation to Kissimmee?

 

Choose your dates

Kissimmee Hotel Deals

Palazzo Lakeside Hotel
Palazzo Lakeside Hotel
3 out of 5
4944 W. Irlo Bronson Memorial Highway, Kissimmee, FL
The price is $83 per night from Nov 3 to Nov 4
$83
includes taxes & fees
$73 per night
Nov 3 - Nov 4
8/10 Very Good! (4,790 reviews)
"Nice hotel"

Reviewed on Oct 29, 2024

Palazzo Lakeside Hotel
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 $208 per night from Nov 27 to Nov 28
$208
includes taxes & fees
$184 per night
Nov 27 - Nov 28
8.8/10 Excellent! (3,153 reviews)
"Margaritaville is awesome. No complaints except I did find the pre-fab surroundings to be a bit limiting in terms of experience if you aren’t going to any theme parks. The resort itself is pricey but that’s to be expected! Solid stay."

Reviewed on Oct 29, 2024

Margaritaville Resort Orlando
Hilton Vacation Club Mystic Dunes Orlando
Hilton Vacation Club Mystic Dunes Orlando
7600 Mystic Dunes Lane, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is $145 per night from Nov 7 to Nov 8
$145
includes taxes & fees
$128 per night
Nov 7 - Nov 8
8.8/10 Excellent! (3,395 reviews)
"Our stay was great"

Reviewed on Oct 28, 2024

Hilton Vacation Club Mystic Dunes Orlando
See all 31,908 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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Kissimmee vacation package cost?
You’ll find cheap prices from $278 on Expedia for your Kissimmee escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Kissimmee costs.
What are the cheapest months to go to Kissimmee?
If you’re looking to score a cheap Kissimmee vacation package, consider traveling in September, October and December. You’re likely to find lower rates on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Kissimmee?
With around 3 days, you’ll have plenty of time to enjoy popular neighborhoods such as Historic Downtown Kissimmee and Bellavida during your Kissimmee vacation. Be sure to also add Skate Reflections and AMF Bowling Center to your sightseeing list. Searching for more adventures? Consider venturing outside of Kissimmee on tours and day trips.
Is it worth booking a vacation package to Kissimmee?
Whether you’d like to check out major sights such as Kissimmee Lakefront Park and Osceola Heritage Park on your Kissimmee vacation, or coming for its excellent family-friendly attractions, shopping and dining, there’s something for everyone here. With so much to experience, you’ll soon find out why so many people think Kissimmee is a good vacation destination.
How to find the best Kissimmee package deals?
Bagging a cheap Kissimmee package deal is a breeze with Expedia. After you’ve entered your destination and preferred dates under our “Packages” tab, set your maximum budget, add some filters and see what’s available. You can tailor your search by “Amenities,” “Property type,” “Guest rating” and more. Sort the results by “Price: low to high” to view the most economical Kissimmee package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Kissimmee vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can personalize your Kissimmee getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Kissimmee?
If you’ve got your Kissimmee vacation dates finalized, book as soon as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Kissimmee?

  1. Choose your travel dates: The things you’d like to do in Kissimmee and your favorite season will help you decide when to travel.
  2. Set your budget: Consider costs like flights, transportation and food when calculating how much to put aside for your trip to Kissimmee. Then, pick a hotel that matches your budget, whether that’s an affordable option or a high-end getaway.
  3. Use Expedia’s trip planning tool to explore Kissimmee: Research every part of your trip to Kissimmee with this handy planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide your trip length: Consider how much time you’d like to spend exploring Kissimmee. Plan your itinerary so you can get to all the attractions and experiences you’re interested in at a comfortable pace.
  5. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that’s left is to choose a Kissimmee vacation package that brings all your bookings together.
  6. Book any excursions or activities: Now to the fun part — organizing everything you want to see and do. Explore some of the incredible things to do in Kissimmee in Kissimmee and reserve your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Kissimmee vacation packages?
Your Kissimmee trip is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to allow you a bit more flexibility, we’ve teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

Discover the most popular places to visit in Kissimmee

Image for Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,427 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
Image for Universal Studios Florida

Universal Studios Florida

4.5/5(9,273 reviews)

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida
Image for Universal Orlando Resort

Universal Orlando Resort

4.5/5(4,155 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

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

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

$26
Per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Image for Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

$31
Per adult
86% of travellers recommend
Orlando: Museum of Illusions Admission Ticket
Image for Orlando: Chocolate Kingdom Factory Adventure Tour

Orlando: Chocolate Kingdom Factory Adventure Tour

$24
Per adult
98% of travellers recommend
Orlando: Chocolate Kingdom Factory Adventure Tour
See all activities in Kissimmee

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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.