Historic Downtown Kissimmee Holidays from £586

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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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
per person
25 Oct - 1 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very Good! (5,163 reviews)
Excelente lugar, cómodo, buena ubicacion, buen desayuno. Lo recomiendo al 100 %

Reviewed on 13 Aug 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
per person
4 Oct - 11 Oct
found 1 day ago
Return flight included
London (LON) to Orlando (MCO)
8.8/10 Excellent! (1,013 reviews)
It was a very comfortable place to stay. Well equipped for everything you need and it feels you’re home. The location is in the center from the theme parks, shopping and restaurants. Everything comes easy on this place and area. We stayed 6 nights and we slept well and good

Reviewed on 14 Aug 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Save 100% on your flight
per person
29 Sept - 5 Oct
found 1 hour ago
Return flight included
London (LHR) to Orlando (MCO)
9/10 Wonderful! (1,001 reviews)
Beds were very comfortable. There were tons of food options around the area

Reviewed on 8 Aug 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
25 Oct - 1 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very Good! (5,177 reviews)
i loved the spacious room i disliked the cleanliness of the bathroom, the hot tub was really filthy i personally had to clean it. several times before using it. Always had a hard time finding a parking spot, we were not told about shuttles taking us to our room or car in case we parked far.

Reviewed on 13 Aug 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
per person
4 Oct - 11 Oct
found 1 day ago
Return flight included
London (LON) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Excellent, loved the location and atmosphere, also the free parking was a nice bonus

Reviewed on 10 Aug 2025

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
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International Drive District

1 out of top 10 points of interest in this area

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

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 refundableReserve now, pay when you stay
The price is £77 per night from 10 Sept to 11 Sept
£77
10 Sept - 11 Sept
includes taxes & fees
8.4/10 Very Good! (6,558 reviews)
"The room was great, pool was fantastic and the staff were all super helpful, we will stay again!"

Reviewed on 14 Aug 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is £56 per night from 28 Aug to 29 Aug
£56
28 Aug - 29 Aug
includes taxes & fees
8.4/10 Very Good! (4,778 reviews)
"Price was very reasonable"

Reviewed on 11 Aug 2025

Rosen Inn at Pointe Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is £72 per night from 4 Sept to 5 Sept
£72
4 Sept - 5 Sept
includes taxes & fees
8.8/10 Excellent! (2,851 reviews)
"Second stay at this resort - beautiful property in which we could feel safe. The pools are beautiful, making you really enjoy your vacation. Really enjoyed the aqua-aerobics offered daily!"

Reviewed on 14 Aug 2025

Marriott's Grande Vista
See all 52,497 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Historic Downtown Kissimmee travel package cost?
Starting from as little as £586, 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.

Popular places to visit

Kissimmee Lakefront Park

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

Monument of States

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 entertainment choices.

Monument of States

Things to do

Florida: 90 Minute Everglades Cruise

Florida: 90 Minute Everglades Cruise

£37
per adult
100% of travellers recommend
Florida: 90 Minute Everglades Cruise
1 Hour Pontoon Adventures

Kissimmee: Florida Everglades Pontoon Boat Tour

£30
per adult
100% of travellers recommend
Kissimmee: Florida Everglades Pontoon Boat Tour
Deluxe Fully Electric Trike with extra large seat and backrest. No pedaling required. Seniors welcome. Ages 14 and up.

Experience Wild Florida Nature Up Close on Electric Trike (2 hrs)

£44
per adult
100% of travellers recommend
Experience Wild Florida Nature Up Close on Electric Trike (2 hrs)
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. Flight-inclusive packages are ATOL protected.