Historic Downtown Kissimmee Holidays from £787

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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 £1,215, price is now £787 per person
£787
per person
7 Jun - 14 Jun
found 24 hours ago
Return flight included
London (LON) to Orlando (MCO)
8.6/10 Excellent! (1,005 reviews)
2nd stay here. Love it and staff is so nice!

Reviewed on 26 Mar 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was £2,262, price is now £1,121 per person
£1,121
per person
30 May - 6 Jun
found 11 hours ago
Return flight included
Edinburgh (EDI) to Orlando (MCO)
8.2/10 Very Good! (5,182 reviews)
I had a wonderful stay at Palazzo Hotel Orlando and would absolutely recommend it. From the moment I arrived, the staff was warm, welcoming, and attentive, making the check-in process smooth and stress-free. The rooms were clean, spacious, and well-maintained, with comfortable bedding that made it easy to relax after a long day out in Orlando. I also appreciated the quiet atmosphere—it felt like a peaceful escape while still being close to all the major attractions. The property itself was well-kept, and the amenities added to the overall experience. Whether you’re visiting for leisure or a quick getaway, this hotel offers great value for the price. Overall, a pleasant, comfortable stay with excellent service. I’d definitely come back again!

Reviewed on 29 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 £2,036, price is now £1,191 per person
£1,191
per person
7 Jun - 14 Jun
found 24 hours ago
Return flight included
London (LON) to Orlando (MCO)
9.2/10 Wonderful! (1,008 reviews)
Friendly staff. Great location. Villa was amazing

Reviewed on 28 Mar 2026

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Price was £1,368, price is now £954 per person
£954
per person
7 Jun - 14 Jun
found 24 hours ago
Return flight included
London (LON) to Orlando (MCO)
8.8/10 Excellent! (1,484 reviews)
Very nice place. The food options were lean. Surprised the bars and restaurants close so early and open so late.

Reviewed on 25 Mar 2026

Evermore Orlando Resort

Evermore Orlando Resort

4 out of 5
Save 100% on your flight
Price was £3,008, price is now £2,140 per person
£2,140
per person
9 Jun - 16 Jun
found 10 hours ago
Return flight included
London (LHR) to Orlando (MCO)
9.6/10 Exceptional! (587 reviews)
This was a beautiful resort! It was the first time I truly felt like I was in Cancun. The place is amazing, and the customer service is top-notch. The restaurants were delicious, and everything about the resort made it a great place to relax. Traveling with kids can make relaxing a little harder, but they do have plenty of activities to keep them busy, which we really appreciated. We celebrated my son’s birthday during our stay, and I was hoping they would do something small like a card or acknowledgment, but unfortunately they didn’t—that part was a bit disappointing. Overall, we loved it and would definitely come back!

Reviewed on 28 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

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 £202 per night from 12 Apr to 13 Apr
£202
12 Apr - 13 Apr
includes taxes & fees
8/10 Very Good! (9,316 reviews)
Alex was a great waiter an we checked in early. Condo was clean and property was beautiful

Reviewed on 29 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 £169 per night from 31 Mar to 1 Apr
£169
31 Mar - 1 Apr
includes taxes & fees
9.4/10 Exceptional! (4,068 reviews)
From the door man, check in and luggage clerk, everyone was amazing

Reviewed on 27 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
The price is £136 per night from 19 Apr to 20 Apr
£136
19 Apr - 20 Apr
includes taxes & fees
9.2/10 Wonderful! (5,031 reviews)
This is the only place I will stay in Orlando! We have had the best experience here. They have everything you need at the resort. Always clean and quiet. Guard shack makes you feel extra safe. Great price for the size of the rooms!

Reviewed on 29 Mar 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 53,862 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
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Family Friendly Holidays

Frequently asked questions

How much does a Historic Downtown Kissimmee travel package cost?
Starting from as little as £787, 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 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

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

£462
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

£40
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

£64
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.