Historic Downtown Kissimmee Holidays from £870

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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 Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was £1,205, price is now £870 per person
£870
per person
15 Jul - 22 Jul
found 1 day ago
Return direct flight included
London (LHR) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Our favorite place to stay at when we are in Orlando

Reviewed on 28 Apr 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 £2,369, price is now £1,440 per person
£1,440
per person
17 Jun - 24 Jun
found 1 day ago
Return flight included
Edinburgh (EDI) to Orlando (MCO)
9.2/10 Wonderful! (1,004 reviews)
Great property thoroughly enjoyed our stay

Reviewed on 13 May 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was £1,662, price is now £1,066 per person
£1,066
per person
17 Jun - 24 Jun
found 1 day ago
Return flight included
Edinburgh (EDI) to Orlando (MCO)
8.4/10 Very Good! (6,342 reviews)
Overall, the room was nice and spacious and included a small kitchen area with a nice large balcony overlooking a pond. There were many pools on property were available to use with lifejackets for children. The biggest disappointment was that the waterpark that is advertised all over this website is not included in the resort fee. This is not disclosed anywhere on the website or in communications prior to arriving to the hotel. When we went to use the waterpark, there were several guests, complaining and berating the attendants because they assumed it was included . Ultimately after downloading their app, we had to pay $18.75 per person to use the waterpark for the day which closes very early at 6PM. It’s unfortunate because this property is quite nice, particularly for the price, but the deception of the waterpark soured my image of the resort.

Reviewed on 13 May 2026

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was £1,622, price is now £1,151 per person
£1,151
per person
13 Jun - 20 Jun
found 4 hours ago
Return flight included
Edinburgh (EDI) to Orlando (MCO)
9.2/10 Wonderful! (1,353 reviews)
Nice location, clean roomsp

Reviewed on 12 May 2026

Accessible 3Bd Condo Close to Disney @ Storey Lake Orlando 208 3180

Accessible 3Bd Condo Close to Disney @ Storey Lake Orlando 208 3180

4.5 out of 5
Price was £1,878, price is now £1,352 per person
£1,352
per person
27 Jun - 4 Jul
found 3 hours ago
Return flight included
London (LHR) to Orlando (MCO)
10/10 Exceptional! (3 reviews)
I had a great stay here for four nights. The place was clean, comfortable, and exactly as described in the listing. Check-in was smooth and the host was responsive and helpful throughout the stay. The location was convenient and made it easy to get around. I would definitely recommend this place to others and would be happy to stay here again in the future.

Reviewed on 10 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 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 £124 per night from 2 Jun to 3 Jun
£124
2 Jun - 3 Jun
includes taxes & fees
9.2/10 Wonderful! (5,456 reviews)
We had such a great time on our trip. The room was clean and spacious, and the tub was amazing! There were several pools to choose from and mini golf, and we had a great time, even in spite of some cloudy and rainy conditions. We will definitely be back!

Reviewed on 14 May 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/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 £174 per night from 25 May to 26 May
£174
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,147 reviews)
Bed was comfortable

Reviewed on 12 May 2026

Hyatt Regency Orlando International Airport
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 £178 per night from 21 May to 22 May
£178
21 May - 22 May
includes taxes & fees
8/10 Very Good! (9,892 reviews)
Elevator not working, slides and lazy river not open. Disappointing all around

Reviewed on 13 May 2026

The Grove Resort & Water Park Orlando
See all 53,142 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 £870, 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 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 entertainment choices 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

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

£447
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

£39
per traveller
84% of travellers recommend
Aquatica Orlando
Florida: 90 Minute Everglades Cruise

Florida: 90 Minute Everglades Cruise

£41
per adult
100% of travellers recommend
Florida: 90 Minute Everglades Cruise
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.