Kissimmee Holidays

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Our guide on where to stay in Kissimmee

Find the best Kissimmee areas and neighborhoods for the activities you enjoy most. Learn more about Kissimmee
A wooden boardwalk leading to a gazebo over a lake, surrounded by trees with autumn leaves.

Cumbrian Lakes

While there might not be top attractions in Cumbrian Lakes, you can explore the larger area and discover places like Give Kids the World Village and Old Town.

Find hotels in Cumbrian Lakes

Kissimmee Holiday

Our pick of the best Kissimmee Hotel Deals

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is NZ$125 per night from 4 Nov to 5 Nov
NZ$125
4 Nov - 5 Nov
includes taxes & fees
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 NZ$100 per night from 1 Nov to 2 Nov
NZ$100
1 Nov - 2 Nov
includes taxes & fees
8.4/10 Very good! (5,377 reviews)
"Such a relaxing 5 night stay. Calm atmosphere, quiet, comfortable, and with an amazingly helpful staff. Will return 100%"

Reviewed on 30 Oct 2026

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 NZ$357 per night from 29 Nov to 30 Nov
NZ$357
29 Nov - 30 Nov
includes taxes & fees
Margaritaville Resort Orlando with H2O Waterpark
See all 28,778 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.

Stay near popular Kissimmee attractions

A theme park entrance with a Ferris wheel and a roller coaster.

Old Town

8.6/10 (14,011 reviews)
This retro-themed district transports you to a nostalgic era with vintage architecture. Stroll the brick-paved streets at dusk when live music and illuminated attractions create a magical atmosphere.
See properties

What to do in Kissimmee

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

NZ$59
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

NZ$48
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

NZ$347
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
See all activities in Kissimmee

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.

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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.