Historic Downtown Kissimmee Vacation Packages
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Top Holiday Package Deals in Historic Downtown Kissimmee
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
CA $1,388
per person
Dec 7 - Dec 12
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
Check in was a breeze. I admire Vstays and how effortless they with booking and accommodating my needs.
Reviewed on Sep 19, 2026
The Delaney Hotel
South Orange
CA $2,117
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Orlando (MCO)
9.6/10 Exceptional! (1,202 reviews)
We were upgraded to a King suite! I loved how spacious the space was; the shower was a decent size. I loved the cleanliness of the overall hotel. The bed was an actual king size and very comfortable.
Reviewed on Sep 20, 2026
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
CA $838
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (580 reviews)
Room stinks
To much hassle to clean your room
Reviewed on Sep 6, 2026
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
Bay Lake
3 out of top 10 points of interest in this area
Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.
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.
Florida Center
2 out of top 10 points of interest in this area
While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.
Champions Gate
Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.
Reunion
The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.
Historic Downtown Kissimmee Hotel Deals
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
CA $306
CA $345 total
Sep 21 - Sep 22
includes taxes & fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
CA $191
CA $215 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (6,783 reviews)
"A little slow on the shuttle, but for the most part, it was amazing. I loved it. I will definitely be coming back."
Reviewed on Sep 19, 2026
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
CA $134
CA $151 total
Oct 11 - Oct 12
includes taxes & fees
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 Historic Downtown Kissimmee vacation package cost?
Custom build your Historic Downtown Kissimmee package from an affordable CA $652. 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 vacation 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 vacation 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 vacation?
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 vacation!
What does an Expedia Historic Downtown Kissimmee travel package include?
That depends on what you're after. If you're traveling 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 vacation 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 vacation 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.
Stay near popular Historic Downtown Kissimmee attractions
Kissimmee Lakefront Park
8.4/10 (2,921 reviews)
Kissimmee Lakefront Park is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the entertainment choices in this family-friendly area.
Osceola County Clerk of the Court
8.8/10 (9 reviews)
After visiting Osceola County Clerk of the Court, make a plan to see the other sights and activities in Kissimmee. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
Kissimmee Civic Center
7.2/10 (22 reviews)
Kissimmee Civic Center is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Discover the entertainment choices and shops in this family-friendly area.
Monument of States
7.6/10 (17 reviews)
Learn about the local history of Kissimmee with a stop at Monument of States. Amble around this family-friendly area's lakeside or experience its lively festivals.
Bataan-Corregidor Memorial
8.2/10 (12 reviews)
You can find out about the history of Kissimmee when you stop by Bataan-Corregidor Memorial. Stroll along the lakeside or experience the lively festivals in this family-friendly area.
Violet's Venom Brewery
You can take time to visit Violet's Venom Brewery during your travels to Kissimmee. While you're in the area, find time to visit its shops.
First United Methodist Church
6.4/10 (21 reviews)
After visiting First United Methodist Church, make a plan to see the other sights and activities in Kissimmee. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Things to do
Universal Orlando Resort Theme Park Tickets (US & Canada)
CA $194
per adult
86% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
CA $118
per adult
94% of travellers recommend
Orlando: Polynesian Fire Luau with Dinner and Live Show
CA $103
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.