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 (1,005 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 $1,291
    CA $678
    per traveller
    found 1 day ago
    Westgate Towers Resort
  • Terrace/patio
    Aug 11 - Aug 22

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    11 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 • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • 1 stop MCO - YHM • 1 stop
    CA $3,029
    CA $1,264
    per traveller
    found 1 day ago
    Westgate Palace Hotel / Universal / I-Drive
  • Water park
    Aug 11 - Aug 22

    Westgate Town Center Resort + Flight

    Kissimmee
    11 nights
    4.0 star property
    8.2/10 - Very good (1,749 reviews)
    "Es super increíble me encantó"
    Reviewed May 31, 2026
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • 1 stop MCO - YHM • 1 stop
    CA $1,952
    CA $954
    per traveller
    found 1 day ago
    Westgate Town Center Resort
  • Aerial view
    Aug 7 - Aug 14

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    7 nights
    4.0 star property
    8.2/10 - Very good (1,948 reviews)
    "This was a amazing resort with so many amenities and the Mexican restaurant was great and the ice cream was yummy - rooms are clean and it is very family friendly"
    Reviewed May 27, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $1,462
    CA $748
    per traveller
    found 1 day ago
    Westgate Vacation Villas Resort
  • Water park
    Aug 11 - Aug 22

    Westgate Lakes Resort & Spa Universal Studios Area + Flight

    Orlando
    11 nights
    4.0 star property
    8.4/10 - Very good (6,458 reviews)
    "It was upsetting that we were booked into an accessible room because I informed them I had a walker and ground floor would be easier. I'm having hip surgery and lowered cabinets and sinks are impossible as bending over is very difficult. They did move us but not until we had already gone to the 1st room. It was exhausting having to walk to 2 separate rooms. Not a good way to start out our stay, I just wanted to leave I was so exhausted. But would still be charged as we had already checked..."
    Reviewed May 30, 2026
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • 1 stop MCO - YHM • 1 stop
    CA $2,055
    CA $1,086
    per traveller
    found 1 day ago
    Westgate Lakes Resort & Spa Universal Studios Area

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 3 to Jun 4
CA $206
CA $231 total
Jun 3 - Jun 4
includes taxes & fees
9.2/10 Wonderful! (5,620 reviews)
"Check in time, if it can be faster would perfect"

Reviewed on May 31, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 CA $233 per night from Jun 8 to Jun 9
CA $233
CA $338 total
Jun 8 - Jun 9
includes taxes & fees
8/10 Very Good! (10,016 reviews)
"Overall great place to stay. Rooms were very clean, and staff is friendly."

Reviewed on May 31, 2026

The Grove Resort & Water Park Orlando
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 Jun 7 to Jun 8
CA $207
CA $233 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (6,877 reviews)
"Excellent!"

Reviewed on May 31, 2026

Universal's Cabana Bay Beach Resort
See all 53,320 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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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.