Historic Downtown Kissimmee Holidays

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Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was €2,153, price is now €1,067 per person
€1,067
per person
2 Jun - 9 Jun
found 1 day ago
Return direct flight included
Riga (RIX) to Orlando (MCO)
8.2/10 Very Good! (5,182 reviews)
Clean hotel, kid/ family friendly, staff 💯, different menu at breakfast each day

Reviewed on 18 Mar 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was €2,581, price is now €1,651 per person
€1,651
per person
2 Jun - 9 Jun
found 1 day ago
Return direct flight included
Riga (RIX) to Orlando (MCO)
9.2/10 Wonderful! (1,008 reviews)
Loved it here. House was perfect. Resort great

Reviewed on 17 Mar 2026

Evermore Orlando Resort

Evermore Orlando Resort

4 out of 5
Save 100% on your flight
Price was €3,723, price is now €2,788 per person
€2,788
per person
2 Jun - 9 Jun
found 1 day ago
Return direct flight included
Riga (RIX) to Orlando (MCO)
9.6/10 Exceptional! (587 reviews)
Stayed in a 4 bedroom flat with views of the magic kingdom fireworks. Thrilled with everything about this resort!

Reviewed on 18 Mar 2026

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was €1,428, price is now €1,085 per person
€1,085
per person
2 Jun - 9 Jun
found 1 day ago
Return direct flight included
Riga (RIX) to Orlando (MCO)
9/10 Wonderful! (3,493 reviews)
Check in was efficient and friendly. Clean room. Quiet area.

Reviewed on 20 Mar 2026

Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Price was €1,414, price is now €1,137 per person
€1,137
per person
2 Jun - 9 Jun
found 1 day ago
Return direct flight included
Riga (RIX) to Orlando (MCO)
8.6/10 Excellent! (1,600 reviews)
Staff were friendly, accommodating, and helpful during our stay. Our rooms were clean and spacious. We loved the pool area and hot tub. The Hotel was very clean and inviting. We enjoyed are stay here and would recommend.

Reviewed on 19 Mar 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
International Drive showing landscape views

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

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 €222 per night from 19 Apr to 20 Apr
€222
19 Apr - 20 Apr
includes taxes & fees
8/10 Very Good! (9,198 reviews)
Great place - stayed here a bunch of times, but they do not have a spa.

Reviewed on 20 Mar 2026

The Grove Resort & Water Park 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 €207 per night from 30 Mar to 31 Mar
€207
30 Mar - 31 Mar
includes taxes & fees
9.4/10 Exceptional! (4,054 reviews)
Great amenities convenient

Reviewed on 19 Mar 2026

Hyatt Regency Orlando International Airport
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 €124 per night from 19 Apr to 20 Apr
€124
19 Apr - 20 Apr
includes taxes & fees
9.2/10 Wonderful! (4,921 reviews)
This was our second stay at the hotel. The set-up with the two rooms was very convenient as we traveled with our toddler. It was clean and lots of amenities on site. The restaurants onsite have decent food but it’s centrally located to other food places.

Reviewed on 20 Mar 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 53,322 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 €1,067. 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

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

€512
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

€46
per traveller
84% of travellers recommend
Aquatica Orlando
"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
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.