A street sign reading "Welcome to Kissimmee, Florida" with a mural of horses on a building.

Historic Downtown Kissimmee Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Historic Downtown Kissimmee Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 7 - Jan 12

    Westgate Town Center Resort + Flight

    Kissimmee
    5 nights
    4.0 star property
    8.2/10 - Very good (2,067 reviews)
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • 1 stop
    CA $1,073
    CA $597
    per traveller
    found 21 hours ago
    Westgate Town Center Resort
  • Jan 17 - Jan 23

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    6 nights
    4.0 star property
    8.6/10 - Excellent (577 reviews)
    "Great place!"
    Reviewed November 2, 2026
    Roundtrip • Montreal (YUL) - Orlando (MCO)
    YUL - MCO • Nonstop MCO - YUL • Nonstop
    CA $2,512
    CA $1,359
    per traveller
    found 1 day ago
    Westgate Cocoa Beach Resort
  • Jan 21 - Jan 25

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Halifax (YHZ) - Orlando (MCO)
    YHZ - MCO • 1 stop MCO - YHZ • Nonstop
    Save 100% on your flight
    CA $1,991
    CA $1,159
    per traveller
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • Jan 6 - Jan 11

    Ocean Landings Resort and Racquet + Flight

    Cocoa Beach
    5 nights
    2.5 star property
    7.2/10 - Good (52 reviews)
    "This is an older property but very clean and well maintained. The two ocean front buildings are under a major renovation but there is still access to the beach. We would stay again."
    Reviewed October 30, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    Save 100% on your flight
    CA $1,629
    CA $1,017
    per traveller
    found 1 day ago
    Ocean Landings Resort and Racquet
  • Jan 6 - Jan 11

    The Resort on Cocoa Beach + Flight

    Cocoa Beach
    5 nights
    3.5 star property
    9.4/10 - Exceptional (684 reviews)
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    Save 100% on your flight
    CA $1,984
    CA $1,258
    per traveller
    found 1 day ago
    The Resort on Cocoa Beach

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
Learn more about Historic Downtown Kissimmee

Bay Lake

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

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.

Discover the most popular places to visit in Historic Downtown Kissimmee

What to do near Historic Downtown Kissimmee

Historic Downtown Kissimmee Hotel Deals

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 $597. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.