Historic Downtown Kissimmee Holidays

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Your Historic Downtown Kissimmee Holiday

With a tailor-made holiday package to Historic Downtown Kissimmee, you can spend less time planning and more time simply enjoying this interesting neighbourhood. From its shopping to its dining, there's plenty to discover here. When it's time to explore the sights, you'll find loads of top attractions nearby including Osceola Heritage Park, Kissimmee Lakefront Park and Silver Spurs Arena. Visit one, two or more during your trip to Historic Downtown Kissimmee. Expedia will help you turn your dream Historic Downtown Kissimmee holiday into reality, whatever your travel plans or budget.

Our guide on where to stay in Historic Downtown Kissimmee

Find the best Historic Downtown Kissimmee areas and neighborhoods for the activities you enjoy most. Learn more about Historic Downtown Kissimmee
International Drive showing landscape views

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

Find hotels in International Drive District

Our pick of the best Historic Downtown Kissimmee Hotel Deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
The price is AU$333 per night from 23 Mar to 24 Mar
AU$333
23 Mar - 24 Mar
includes taxes & fees
8/10 Very Good! (9,124 reviews)
A

Reviewed on 8 Mar 2026

The Grove Resort & Water Park Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
The price is AU$241 per night from 29 Mar to 30 Mar
AU$241
29 Mar - 30 Mar
includes taxes & fees
9.2/10 Wonderful! (4,797 reviews)
We were totally impressed with this resort. Tones of stuff to do and big property. My only complaint is they don't use reusable plastic cups when serving drinks. Besides that two thumbs up

Reviewed on 8 Mar 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
9500 Turkey Lake Rd Orlando FL
8.4/10 Very Good! (5,928 reviews)
Family-friendly, dog-friendly, clean, and a lot of activities avaliable on the property. The downside is that everything is an extra charge and expensive. Some staff was very friendly and helpful while others were rude and about as helpful as a poopsicle. Overall a nice stay and would consider visiting ...

Reviewed on 8 Mar 2026

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Westgate Lakes Resort & Spa Universal Studios Area
See all 53,322 properties in Historic Downtown 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.
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Frequently asked questions

How much does a Historic Downtown Kissimmee holiday package cost?
Custom build your Historic Downtown Kissimmee package from an affordable . Pick from any combination of rental cars, flights and hotels to create the trip you've been dreaming about. Don't forget to add on some activities and experiences!
How do I get a cheap travel package to Historic Downtown Kissimmee?
Bundle your hotels and flights with Expedia to save big bucks on your next trip. With more than 550 airlines and 1 000 000 properties across the world, your Historic Downtown Kissimmee holiday package can be customized exactly to suit your travel style. With all that extra money, why not throw in one or two fun tours and experiences? It's an easy way to unlock even more savings. Your dream holiday in Historic Downtown Kissimmee is much closer than you thought!
Where should I stay in Historic Downtown Kissimmee?
Stay somewhere within a stone's throw of ChampionsGate Golf Club. This fantastic attraction is in the thick of the action and on the must-do lists of many tourists.
What are the top hotels in Historic Downtown Kissimmee?
Storey Lake Ihr 2022 and 4 Bedrooms Villa - Storey Lake are two of the most sought-after properties in Historic Downtown Kissimmee. Why not check out the facilities and rates at each and then make up your mind?
How far in advance should I book my Historic Downtown Kissimmee holiday?
Get rewarded with the widest variety and the cheapest prices by booking your trip to Historic Downtown Kissimmee nice and early. Air carriers generally publish flights anywhere up to a year before departure, so secure your spot as soon as you can. Having said that, Expedia is dedicated to providing you with the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Historic Downtown Kissimmee travel package include?
That depends on what you're after. If you're travelling alone, you might decide to combine hotels and flights. Bringing the whole crew to Historic Downtown Kissimmee? A travel package that includes hotels, flights and rental cars might suit you better. Expedia gives you the freedom and flexibility to tailor-make your travel package.
What should I know before booking a Historic Downtown Kissimmee travel package?
So many places to go, so many things to do. With a package, you'll be able to tick more of them off your list. Combine your hotels, flights and rental cars and enjoy big savings.
Can I choose my airline with a Historic Downtown Kissimmee Expedia holiday package?
Yes, you're in charge. Expedia has access to more than 550 airlines globally, so you can tailor your Historic Downtown Kissimmee adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Historic Downtown Kissimmee holiday package?
If your travel plans in Historic Downtown Kissimmee have been upended, it's good to know that it is possible to amend or cancel your booking. If you made your booking less than 24 hours ago, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. For more details, visit our Customer Service Portal.

Activities

"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

AU$120
per adult
98% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
Flagler College in St. Augustine.

Historic St. Augustine Day Trip from Orlando with Hotel Pickup

AU$142
per adult
82% of travellers recommend
Historic St. Augustine Day Trip from Orlando with Hotel Pickup
Aerial view of Downtown Orlando

The ICONic City Tour of Orlando

AU$197
per adult
80% of travellers recommend
The ICONic City Tour of Orlando
See all activities in Orlando
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.