Historic Downtown Kissimmee Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Terrace/patio
    Jul 12 - Jul 19

    The Delaney Hotel + Flight

    South Orange
    7 nights
    3.5 star property
    9.6/10 - Exceptional (1,120 reviews)
    "Clean atmosphere, smells good, great bar, and friendly staff."
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Orlando (MCO)
    DUB - MCO • Direct MCO - DUB • Direct
    €1,604
    €1,079
    per traveller
    found 1 day ago
    The Delaney Hotel
  • Terrace/patio
    Aug 10 - Aug 31

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    21 nights
    4.0 star property
    9.0/10 - Wonderful (1,261 reviews)
    "Clean"
    Reviewed June 2, 2026
    Return • Dublin (DUB) - Orlando (MCO)
    DUB - MCO • 1 stop MCO - DUB • 1 stop
    €3,828
    €1,487
    per traveller
    found 1 day ago
    Westgate Palace Hotel / Universal / I-Drive
  • Outdoor pool
    Aug 10 - Aug 31

    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight

    International Drive District
    21 nights
    3.0 star property
    7.8/10 - Good (506 reviews)
    "Most of the staff was very helpful. Our rooms were clean and well kept. We were close to the parks."
    Reviewed June 7, 2026
    Return • Dublin (DUB) - Orlando (MCO)
    DUB - MCO • 1 stop MCO - DUB • 1 stop
    Save 100% on your flight
    €2,739
    €1,429
    per traveller
    found 1 day ago
    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
  • Outdoor pool
    Aug 10 - Aug 31

    Element by Marriott Orlando Universal Blvd. + Flight

    International Drive District
    21 nights
    3.0 star property
    9.2/10 - Wonderful (2,240 reviews)
    "I enjoy my stay at element. Room was neat and clean. Well supply. Staff were friendly and kind. Breakfast was good. I will stay there again. Location is quiet and close to restaurants and parks."
    Reviewed June 10, 2026
    Return • Dublin (DUB) - Orlando (MCO)
    DUB - MCO • 1 stop MCO - DUB • 1 stop
    Save 100% on your flight
    €2,263
    €1,225
    per traveller
    found 1 day ago
    Element by Marriott Orlando Universal Blvd.
  • Lounge
    Aug 10 - Aug 31

    Landing Townhomes Davenport + Flight

    Davenport
    21 nights
    4.0 star property
    8.6/10 - Excellent (17 reviews)
    "The apartment is big and it was clean. I appreciated the constant communication with the landlord. They made everything easier. I definitely recommend this place, since is close to most touristy places."
    Reviewed May 27, 2026
    Return • Dublin (DUB) - Orlando (MCO)
    DUB - MCO • 1 stop MCO - DUB • 1 stop
    Save 100% on your flight
    €2,348
    €1,610
    per traveller
    found 1 day ago
    Landing Townhomes Davenport

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

Top hotels in Historic Downtown Kissimmee

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 €175 per night from 14 Jun to 15 Jun
€175
14 Jun - 15 Jun
includes taxes & fees
9.2/10 Wonderful! (5,737 reviews)
"Our family enjoyed the spacious rooms and beautiful pool giving us a quiet and relaxing stop before continuing on our trip."

Reviewed on 9 Jun 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Fully refundable
The price is €104 per night from 6 Jul to 7 Jul
€104
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (6,986 reviews)
"Room was nice and big and clean."

Reviewed on 8 Jun 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
The price is €242 per night from 14 Jun to 15 Jun
€242
14 Jun - 15 Jun
includes taxes & fees
8/10 Very Good! (10,160 reviews)
"Check-in was at 4:00 pm. When my family and I got there at 4:00 pm our room was not ready. They said we would receive a text message when our room was ready. At about 4:15 pm, I spoke to another employee and she was able to get us a room that was ready. The room was very spacious and modern. Very ..."

Reviewed on 10 Jun 2026

The Grove Resort & Water Park Orlando
See all 52,363 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.

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.

Popular places to visit

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 lively festivals in this family-friendly area.

Kissimmee Lakefront Park

Bataan-Corregidor Memorial

You can find out about the history of Kissimmee with a trip to Bataan-Corregidor Memorial. Stroll along the lakeside or experience the entertainment choices in this family-friendly area.

Bataan-Corregidor Memorial

Things to do

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

Drawn to Life presented by Cirque du Soleil and Disney

€73
per adult
96% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
Florida: 90 Minute Everglades Cruise

Florida: 90 Minute Everglades Cruise

€47
per adult
100% of travellers recommend
Florida: 90 Minute Everglades Cruise
Flagler College in St. Augustine.

Historic St. Augustine Day Trip from Orlando with Hotel Pickup

€82
per adult
84% of travellers recommend
Historic St. Augustine Day Trip from Orlando with Hotel Pickup
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.