Historic Downtown Kissimmee Holidays from £597
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Your Historic Downtown Kissimmee Holiday
From its shopping to its dining, there's a lot to love about Historic Downtown Kissimmee. Book a Historic Downtown Kissimmee holiday package and prepare to experience the delights of this neighbourhood. Kick off your trip to Historic Downtown Kissimmee with a visit to nearby attractions such as Osceola Heritage Park, Silver Spurs Arena and 192 Flea Market. Whatever your travel plans or budget, booking a perfect Historic Downtown Kissimmee holiday is quick and easy with Expedia.
Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
£597
per person
3 Nov - 10 Nov
found 14 hours ago
Return flight included
London (LON) to Orlando (MCO)
8.2/10 Very good! (2,045 reviews)
Staff was knocking on our neighbors window and door which woke up my child and family at 3am
In the morning , called front desk no help at all
Reviewed on 27 Sept 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
£1,185
per person
29 Nov - 6 Dec
found 23 hours ago
Return direct flight included
London (LHR) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms.
The staff at the main building were so helpful with our packages and printing documents for us.
Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort.
Overall, a great selection and would start again!
Reviewed on 25 Sept 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
Bay Lake
3 out of top 10 points of interest in this area
Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.
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
2 out of top 10 points of interest in this area
If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.
Champions Gate
Ample dining options and top 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.
Downtown Orlando
One of the most popular neighborhoods in Florida, this bustling area is full of art galleries, shops, bars and restaurants.
Top hotels in Historic Downtown Kissimmee
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
£186
12 Oct - 13 Oct
includes taxes & fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
£116
18 Oct - 19 Oct
includes taxes & fees
9.2/10 Wonderful! (6,871 reviews)
"Check in process was a mess. Hotel room was clean and neat."
Reviewed on 27 Sept 2026
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
£82
18 Oct - 19 Oct
includes taxes & fees
9/10 Wonderful! (5,048 reviews)
"Todo fue excelente"
Reviewed on 27 Sept 2026
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 travel package cost?
Starting from as little as £597, you can create your own Historic Downtown Kissimmee package. Simply combine hotels, flights and car rentals and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Historic Downtown Kissimmee travel package?
Plans can change unexpectedly, so yes, you can. You may be able to amend or cancel your Historic Downtown Kissimmee travel package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make the necessary changes, but your car rental company, hotel or airline may impose a charge. Want more information? Check out our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Historic Downtown Kissimmee?
Booking a Historic Downtown Kissimmee travel package with Expedia is a smart way to save. We have access to more than 550 air carriers and 1,000,000 hotels globally. With such a broad range to pick from, you'll have no difficulty pulling together your ideal adventure.
Does Expedia offer Book Now, Pay Later Historic Downtown Kissimmee holidays?
Expedia has partnered with online lender Klarna to make booking your next getaway easier on the purse strings. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find something that falls within your budget. Browse these flexible payment options:
- Pay monthly holidays: Klarna has easy monthly payment plans that work for all budgets, so you can take that well-earned holiday now.
- Pay in instalments holidays: If you want to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: Pressing the "book now" button is easier with this option. Just put down a small deposit on your holiday and then start packing your suitcase.
Where should I stay in Historic Downtown Kissimmee?
We recommend staying within walking distance of ChampionsGate Golf Club, one of this area's top attractions. It's the ideal spot for those eager to check out the local sights.
What are the top hotels in Historic Downtown Kissimmee?
Get your trip off to a fantastic start by booking a stay at Magic Moment Resort and Kids Club. It's one of most popular hotels in Historic Downtown Kissimmee. Another leading option is Red Lion Hotel Orlando Lake Buena Vista South.
How far in advance should I book my Historic Downtown Kissimmee holiday?
While prices change frequently, we generally advise booking your holiday as soon as possible. Most international fares can be found on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you might still be lucky. Low prices to Historic Downtown Kissimmee occasionally appear just weeks before departure.
What does an Expedia Historic Downtown Kissimmee travel package include?
Expedia has all you need to arrange your Historic Downtown Kissimmee escape, but what your package looks like is up to you. Select from any combination of hotels, rental cars and flights. Looking for some activities to keep you entertained? Once you've made your booking, you can add them too. Whatever your style, there's a deal to suit your needs.
What should I know before booking a Historic Downtown Kissimmee travel package?
Our prices are already low. However, you'll pick up an even better deal if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and a terrific range of choice.
Can I choose my airline with a Historic Downtown Kissimmee Expedia travel package?
Expedia offers access to more than 550 airline partners globally, so you definitely can. Simply select the carrier you want and craft your ideal Historic Downtown Kissimmee holiday.
Stay near popular Historic Downtown Kissimmee attractions
Kissimmee Lakefront Park
8.4/10 (2,921 reviews)
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 Civic Center
7.2/10 (22 reviews)
Kissimmee Civic Center is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Discover the entertainment choices and shops in this family-friendly area.
Osceola County Clerk of the Court
8.8/10 (9 reviews)
After visiting Osceola County Clerk of the Court, make a plan to see the other sights and activities in Kissimmee. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
Bataan-Corregidor Memorial
8.2/10 (12 reviews)
You can find out about the history of Kissimmee with a trip to Bataan-Corregidor Memorial. Stroll along the lakeside or experience the lively festivals in this family-friendly area.
Violet's Venom Brewery
You can take time to visit Violet's Venom Brewery during your travels to Kissimmee. While you're in the area, find time to visit its shops.
First United Methodist Church
6.4/10 (21 reviews)
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 visit its top-notch restaurants.
Monument of States
7.6/10 (17 reviews)
Learn about the local history of Kissimmee when you take a trip to Monument of States. Amble around this family-friendly area's lakeside or experience its lively festivals.
Things to do
90 Minute Open Jump at a Trampoline Park in Kissimmee
£17
per adult
Old Town Kissimmee: Ferris Wheel, Mortem Manor, and Meal
£11
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.