Historic Downtown Kissimmee Vacation Packages

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Price found within the past 48 hours. Click for updated prices.
  • Restaurant
    Aug 7 - Aug 14

    Westgate Towers Resort + Flight

    Kissimmee
    7 nights
    3.5 star property
    8.6/10 - Excellent (1,009 reviews)
    "The room was clean staff was nice.i was good for the weekend stay really enjoyed it."
    Reviewed May 24, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $1,333
    CA $718
    per traveller
    found 1 day ago
    Westgate Towers Resort
  • Terrace/patio
    Jul 1 - Jul 8

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    7 nights
    4.0 star property
    8.8/10 - Excellent (1,257 reviews)
    "It was a very nice clean property just a bit smaller unit size than what we’re used to!"
    Reviewed May 25, 2026
    Roundtrip • Halifax (YHZ) - Orlando (MCO)
    YHZ - MCO • 1 stop MCO - YHZ • 1 stop
    CA $2,755
    CA $1,308
    per traveller
    found 0 hours ago
    Westgate Palace Hotel / Universal / I-Drive
  • Water park
    Aug 7 - Aug 14

    Westgate Town Center Resort + Flight

    Kissimmee
    7 nights
    4.0 star property
    8.2/10 - Very good (1,737 reviews)
    "Great for families. Only complain is that the water park opens from 11am-6pm, therefore if you gonto the water park you pretty much have to spend the hottest part of the day there. I wish they would open earlier or close later so I would not have to be in the sun when it is the hottest."
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $1,384
    CA $746
    per traveller
    found 1 day ago
    Westgate Town Center Resort
  • Aerial view
    Aug 17 - Aug 24

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    7 nights
    4.0 star property
    9.2/10 - Wonderful (1,003 reviews)
    "Everything was excellent, except the pool definitely needed maintenance and cleaning."
    Reviewed May 26, 2026
    Roundtrip • Halifax (YHZ) - Orlando (MCO)
    YHZ - MCO • 2 stops MCO - YHZ • 2 stops
    CA $3,098
    CA $1,719
    per traveller
    found 18 hours ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • Aerial view
    Aug 2 - Aug 8

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    6 nights
    4.0 star property
    8.2/10 - Very good (1,943 reviews)
    "i didn’t like it was faults advertising the water park in the facility was not included as it stated in the discrimination i payed over 200 a night and that was the only reason why i wanted to stay at this hotel and that was not included. i would not rent this plays out again for that price it’s way over priced"
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,535
    CA $930
    per traveller
    found 1 day ago
    Westgate Vacation Villas Resort

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 District

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

Historic Downtown Kissimmee Hotel Deals

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
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Jun 1 to Jun 2
CA $206
CA $231 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (5,584 reviews)
"Our stay was amazing just not long enough. We will definitely stay there again in the future."

Reviewed on May 26, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $295 per night from May 31 to Jun 1
CA $295
CA $332 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (4,176 reviews)
"The hotel is extremely convenient for people needing a place near the airport. Rooms are modern and large, and the hotel is located directly in the airport. Was easy to get food and the pool is quite nice."

Reviewed on May 25, 2026

Hyatt Regency Orlando International Airport
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from May 31 to Jun 1
CA $207
CA $233 total
May 31 - Jun 1
includes taxes & fees
9/10 Wonderful! (6,867 reviews)
"Todo super bueno lo mejor de todo el la entrada al parque de agua volcano queda dentro del hotel, las piscinas del hotel super buenas y en excelentes condiciones ,las habitaciones están en buen estado lo que recomendaría las luz del baño que las arreglen por lo menos en mi habitación 6646 , por lo ..."

Reviewed on May 25, 2026

Universal's Cabana Bay Beach Resort
See all 53,244 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 vacation 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 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.

Discover the most popular places to visit in Historic Downtown Kissimmee

Kissimmee Lakefront Park Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad

Kissimmee Lakefront Park

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.

Kissimmee Lakefront Park

First United Methodist Church

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.

First United Methodist Church

Things to do

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $221
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
Aquatica Orlando

Aquatica Orlando

CA $72
per traveller
84% of travellers recommend
Aquatica Orlando
Florida: 90 Minute Everglades Cruise

Florida: 90 Minute Everglades Cruise

CA $75
per adult
100% of travellers recommend
Florida: 90 Minute Everglades Cruise
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.