Historic Downtown Kissimmee Holidays from £760

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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 Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was £1,135, price is now £760 per person
£760
per person
29 Aug - 5 Sept
found 1 day ago
Return flight included
London (LON) to Orlando (MCO)
8.4/10 Very good! (6,584 reviews)
Our room wasn’t ready until 2 pm. I felt they were trying to influence us to take an older non-renovated room. The Water Park entrance is not free and the entrance is a bit hidden. The onsite amenities are excellent including the restaurant/bar. The Concierge was very helpful and responsive to our text messages. Overall it was worth the price but minor things to be aware of.

Reviewed on 27 Jun 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was £2,540, price is now £1,727 per person
£1,727
per person
1 Aug - 8 Aug
found 6 hours ago
Return flight included
Edinburgh (EDI) to Orlando (MCO)
9.2/10 Wonderful! (1,006 reviews)
Es excelente este hotel, me encantó su limpieza,atención y muy buena ubicación lo volvería a repetir

Reviewed on 23 Jun 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was £1,232, price is now £892 per person
£892
per person
4 Sept - 11 Sept
found 6 hours ago
Return direct flight included
Edinburgh (EDI) to Orlando (MCO)
7.8/10 Good! (518 reviews)
It was okay. They charged me with $250 as security deposit which I didn’t get back yet.

Reviewed on 16 Jun 2026

WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Price was £1,156, price is now £844 per person
£844
per person
29 Jul - 5 Aug
found 1 day ago
Return flight included
London (LON) to Orlando (MCO)
8.4/10 Very good! (4,075 reviews)
We stayed at this resort two weekends in the last 8 weeks. The first time our 3 bedroom was outdated and dryer did not work. This last time great remodeled Disney decor beautiful and well equipped.

Reviewed on 11 May 2026

Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

4 out of 5
Price was £1,346, price is now £998 per person
£998
per person
1 Sept - 8 Sept
found 5 hours ago
Return flight included
London (LHR) to Orlando (MCO)
9/10 Wonderful! (1,189 reviews)
Great place to stay.

Reviewed on 5 May 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
A theme park with a large rock formation, Old-Town sign, and various food and restaurant signs.

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

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 £144 per night from 14 Jul to 15 Jul
£144
14 Jul - 15 Jul
includes taxes & fees
9.4/10 Exceptional! (4,251 reviews)
"Overall an excellent experience with the convenience of being near the gate for my flight."

Reviewed on 27 Jun 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 £115 per night from 26 Jul to 27 Jul
£115
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (5,920 reviews)
"It was beautiful and very clean. Be aware there are daily parking fees."

Reviewed on 27 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 refundableReserve now, pay when you stay
The price is £76 per night from 12 Jul to 13 Jul
£76
12 Jul - 13 Jul
includes taxes & fees
8.6/10 Excellent! (6,933 reviews)
"Perfect location!"

Reviewed on 26 Jun 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 52,249 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 £760, 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

8.4/5 (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 lively festivals in this family-friendly area.
See properties

Things to do

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

£450
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

£39
per traveller
86% 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

£63
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. Flight-inclusive packages are ATOL protected.