Kissimmee Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Where to stay in Kissimmee

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

While there might not be top attractions in Windsor Hills, you can explore the larger area and discover places like Mystic Dunes Golf Club and Island H2O Live!.

Find hotels in Windsor Hills

Top hotels in Kissimmee

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 S$169 per night from 17 Jun to 18 Jun
S$169
17 Jun - 18 Jun
includes taxes & fees
9.6/10 Exceptional! (281 reviews)
"Everything was fine, except they have very strong fragrance in the hotel lobby. They did say many people like and many people didn't like. There are many people like me are sensitive to those artificial fragrances. Please stop that thank you."

Reviewed on 13 Jun, 2025

Kompose Boutique Resort at Theme Parks
Palazzo Lakeside Hotel
Palazzo Lakeside Hotel
3 out of 5
4944 W. Irlo Bronson Memorial Highway, Kissimmee, FL
The price is S$178 per night from 29 Jun to 30 Jun
S$178
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (5,030 reviews)
"Staff was friendly and rooms were clean. Not luxurious but nice"

Reviewed on 12 Jun, 2025

Palazzo Lakeside Hotel
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 S$296 per night from 16 Jun to 17 Jun
S$296
16 Jun - 17 Jun
includes taxes & fees
8.8/10 Excellent! (3,378 reviews)
"Very relaxing getaway!"

Reviewed on 12 Jun, 2025

Margaritaville Resort Orlando with H2O Waterpark
See all 26,619 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.

Frequently asked questions

How much does a Kissimmee holiday package cost?
You’ll find cheap prices on Expedia for your Kissimmee escape. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Kissimmee costs.
What are the cheapest months to go to Kissimmee?
January, September and October are great times to search for cheap Kissimmee holiday packages. Choosing to travel in less busy periods means you can typically find better prices on flights and hotels.
How many days is enough for Kissimmee?
Kissimmee holidays come in many shapes and sizes, but to get a true feel for this place, we’d suggest 3 days is about right. With this timeframe, you can visit top attractions like Capone’s Dinner Show and Osceola Performing Arts Centre and seek out some lesser-known gems. Don’t forget to explore cool neighbourhoods such as Historic Downtown Kissimmee and Bellavida either. If you plan wisely, you may even be able to take a day trip from Kissimmee too.
Is it worth booking a holiday package to Kissimmee?
Whether you’d like to check out attractions like Kissimmee Lakefront Park and Osceola Heritage Park on your Kissimmee holiday, or coming for its great family-friendly attractions, shopping and dining, there’s something for everyone here. With so much to do, you’ll soon discover why so many families think Kissimmee is a good holiday destination.
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 “Popular locations” and “Property type,” to fine-tune the results to your exact needs. You can also sort by “Package discount” and browse offers that come with unbeatable savings. If you don’t find the perfect Kissimmee package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Kissimmee adventure underway.
Is it cheaper to book a Kissimmee holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking flights and accommodation separately. Better still, you can personalise 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 holiday package to Kissimmee?
If you’re planning an impromptu Kissimmee trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Kissimmee?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to escape to Kissimmee.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will likely be the largest expense during your trip to Kissimmee.
  3. Determine how many days away: Start by making a list of all the attractions you’d like to get to in Kissimmee. Then, estimate how long you’ll need at each, including any travel time.
  4. Combine your accommodation and airfare: After you’ve nailed down your trip dates and duration, lock in the ideal Kissimmee holiday package for you.

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(63 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(273 reviews)

Exhilarating rides and world class film sets are brought together to create this outstanding world-renowned theme park.

Universal Studios Florida
Universal Studios Florida® featuring rides, street scenes and a city

Universal Orlando Resort

4.5/5(166 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

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$98
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction and Meal Combo Offers

S$19
per adult
80% of travellers recommend
Old Town Kissimmee: Attraction and Meal Combo Offers
Indoor Karting

Andretti Indoor Karting & Games in Orlando

S$40
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
See all activities in Kissimmee

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.