Kissimmee Holidays

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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!.

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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 2.040.629 ₫ per night from 6 Jul to 7 Jul
2.040.629 ₫
2.630.297 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9.6/10 Exceptional! (424 reviews)
"First time staying here.. staff was super friendly. 10/10 recommend"

Reviewed on 28 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
8/10 Very Good! (5,100 reviews)
"Loved the stay 10/10 recommend!!!"

Reviewed on 30 Jun 2025

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Palazzo Lakeside Hotel
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
8.4/10 Very Good! (2,328 reviews)
"The room was amazing, the tub was literally next to us, which was amazing and fun."

Reviewed on 30 Jun 2025

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Vacation Village at Parkway
See all 26,706 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)

Enjoy the rides and games at Walt Disney World® Resort and find out why this is a popular theme park in Lake Buena Vista. Discover the top-notch restaurants and acclaimed theatre scene in this walkable area.

Walt Disney World® Resort
Universal Studios Florida® showing rides, a city and street scenes

Universal Orlando Resort

4.5/5(166 reviews)

Enjoy the excitement at Universal Orlando Resort and find out why this is a popular theme park in Orlando. Visit the shops and top-notch restaurants in this family-friendly area.

Universal Orlando Resort
Disney Springs™

Disney Springs™

4.5/5(322 reviews)

You can find the perfect gifts to bring home when you visit Disney Springs™, a favourite shopping spot in Lake Buena Vista. Experience the entertainment choices and acclaimed theatre scene in this family-friendly area.

Disney Springs™