Historic Downtown Kissimmee Hotels, Orlando

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24 Sept - 25 Sept
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25 Sept - 26 Sept
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26 Sept - 28 Sept
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3 Oct - 5 Oct

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53406 Cheap Hotels in Historic Downtown Kissimmee - Specials, Reviews, & Last Minute Deals

Kapp and Kappy B&B
Porch

Kapp and Kappy B&B

3.5 star property
9.8 out of 10, Exceptional, (123)
"It was perfect for us. The hosts were very friendly and accommodating. They just opened a brewery downtown that we were able to walk to, and we had a great time there as well. Overall a great B&B."
The price is NZ$332
includes taxes & fees
28 Sept - 29 Sept
Kapp and Kappy B&B
Super Boho - At Lake Toho's Water
House, 2 Bedrooms, Lake View, Lakeside | Private kitchen

Super Boho - At Lake Toho's Water

2.0 star property
The price is NZ$386
includes taxes & fees
25 Sept - 26 Sept
Super Boho - At Lake Toho's Water
Hilton Vacation Club Polynesian Isles Kissimmee
Lobby

Hilton Vacation Club Polynesian Isles Kissimmee

3.0 star property
9.8 out of 10, Exceptional, (1934)
"Very comfortable accommodations."
The price is NZ$195
includes taxes & fees
28 Sept - 29 Sept
Hilton Vacation Club Polynesian Isles Kissimmee
Pestana Orlando Suites - Lake Buena Vista
Hypo-allergenic bedding, minibar, in-room safe, individually decorated

Pestana Orlando Suites - Lake Buena Vista

4.0 star property
9.4 out of 10, Exceptional, (1792)
"Great stay"
The price is NZ$154
includes taxes & fees
2 Oct - 3 Oct
Pestana Orlando Suites - Lake Buena Vista
Rosen Shingle Creek
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (4023)
"Great resort vibes while being close to the parks and other tourist places. "
The price is NZ$159
includes taxes & fees
10 Oct - 11 Oct
Rosen Shingle Creek
Kompose Boutique Resort at Theme Parks
Suite, 1 King Bed with Sofa bed, Balcony

Kompose Boutique Resort at Theme Parks

3.0 star property
9.4 out of 10, Exceptional, (1370)
"Great place to stay"
The price is NZ$132
includes taxes & fees
5 Oct - 6 Oct
Kompose Boutique Resort at Theme Parks
Rosen Plaza on International Drive
Meeting facility

Rosen Plaza on International Drive

4.0 star property
9.2 out of 10, Wonderful, (1623)
"Hotel was great"
The price is NZ$157
includes taxes & fees
28 Sept - 29 Sept
Rosen Plaza on International Drive
Fairfield Inn By Marriott Orlando Airport
Terrace/patio

Fairfield Inn By Marriott Orlando Airport

3.5 star property
9.2 out of 10, Wonderful, (2285)
"Great stay."
The price is NZ$137
includes taxes & fees
29 Sept - 30 Sept
Fairfield Inn By Marriott Orlando Airport
Hyatt Regency Orlando
2 outdoor pools, pool cabanas (surcharge), pool umbrellas

Hyatt Regency Orlando

4.5 star property
9.2 out of 10, Wonderful, (1756)
"Great place to stay "
The price is NZ$325
includes taxes & fees
4 Oct - 5 Oct
Hyatt Regency Orlando
Hyatt Regency Grand Cypress
3 outdoor pools, open 7 AM to 10:00 PM, pool cabanas (surcharge)

Hyatt Regency Grand Cypress

4.0 star property
9.2 out of 10, Wonderful, (2263)
"Great stay, close to all attractions and very quiet."
The price is NZ$305
includes taxes & fees
4 Oct - 5 Oct
Hyatt Regency Grand Cypress
Hyatt House Orlando International Drive
Free daily buffet breakfast

Hyatt House Orlando International Drive

4.0 star property
9.2 out of 10, Wonderful, (1038)
"Beautiful room and breakfast was great"
The price is NZ$211
includes taxes & fees
13 Oct - 14 Oct
Hyatt House Orlando International Drive
Hilton Vacation Club Grand Beach Orlando
Exterior

Hilton Vacation Club Grand Beach Orlando

3.0 star property
9.4 out of 10, Exceptional, (1360)
"Great stay "
The price is NZ$215
includes taxes & fees
30 Sept - 1 Oct
Hilton Vacation Club Grand Beach Orlando
AC Hotel by Marriott Orlando Lake Buena Vista
Lobby

AC Hotel by Marriott Orlando Lake Buena Vista

3.5 star property
9.2 out of 10, Wonderful, (1488)
"Great place to stay."
The price is NZ$181
includes taxes & fees
1 Oct - 2 Oct
AC Hotel by Marriott Orlando Lake Buena Vista
Hyatt Regency Orlando International Airport
Terrace/patio

Hyatt Regency Orlando International Airport

4.0 star property
9.4 out of 10, Exceptional, (3624)
"Well located at the airport, very convenient, food was great. "
The price is NZ$309
includes taxes & fees
28 Sept - 29 Sept
Hyatt Regency Orlando International Airport
Caribe Royale Orlando
Sports court

Caribe Royale Orlando

4.5 star property
9.2 out of 10, Wonderful, (4432)
"Great place to stay"
The price is NZ$398
includes taxes & fees
28 Sept - 29 Sept
Caribe Royale Orlando
Buena Vista Suites Orlando
Lobby

Buena Vista Suites Orlando

4.0 star property
9.2 out of 10, Wonderful, (1896)
"Clean room , staff very nice "
The price is NZ$271
includes taxes & fees
28 Sept - 29 Sept
Buena Vista Suites Orlando
Rosen Centre Hotel
Outdoor pool, open 6:00 AM to midnight, pool umbrellas, pool loungers

Rosen Centre Hotel

4.0 star property
9.0 out of 10, Wonderful, (3956)
"Perfect stay close to the parks."
The price is NZ$150
includes taxes & fees
11 Oct - 12 Oct
Rosen Centre Hotel
Hilton Vacation Club Mystic Dunes Orlando
4 outdoor pools, pool cabanas (surcharge), pool umbrellas

Hilton Vacation Club Mystic Dunes Orlando

4.0 star property
9.0 out of 10, Wonderful, (4357)
"Staff is super friendly, clean environment."
The price is NZ$254
includes taxes & fees
8 Oct - 9 Oct
Hilton Vacation Club Mystic Dunes Orlando
Tru By Hilton Orlando Convention Center Area, FL
Exterior

Tru By Hilton Orlando Convention Center Area, FL

3.5 star property
9.0 out of 10, Wonderful, (3338)
"It was a great stay!"
The price is NZ$162
includes taxes & fees
30 Sept - 1 Oct
Tru By Hilton Orlando Convention Center Area, FL
Holiday Inn Orlando - Disney Springs® Area by IHG
Outdoor pool, pool umbrellas, pool loungers

Holiday Inn Orlando - Disney Springs® Area by IHG

3.5 star property
9.0 out of 10, Wonderful, (1387)
"We have stayed here numerous times over the years and it has always been one of our favorite places to stay. I highly recommend this hotel!"
The price is NZ$237
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Orlando - Disney Springs® Area by IHG
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.
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Our guide on where to stay in Historic Downtown Kissimmee

Find the best Historic Downtown Kissimmee areas for the activities you enjoy most.

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.

Magic Kingdom® Theme Park featuring rides and interior views as well as a couple
Photo by ©Disney
Open Photo by ©Disney

Bay Lake

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.

Universal Studios Florida® which includes a city, night scenes and signage

Florida Center

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

Downtown Orlando

One of the most popular neighborhoods in Florida, this bustling area is full of art galleries, shops, bars and restaurants.

Windsor Hills

While there might not be top attractions in Windsor Hills, you can explore the larger area and discover places like Mystic Dunes Golf Club and Island H2O Live!.

Top Historic Downtown Kissimmee Hotel Reviews

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Staff Resa was very courteous"
Eric 1-night trip
Posted 2 days ago
Rosen Inn Lake Buena Vista

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What is Historic Downtown Kissimmee like?

Historic Downtown Kissimmee is a neighbourhood that people enjoy for its major shopping area. Make sure that you visit Osceola County Clerk of the Court and Lake Tohopekaliga as part of your Historic Downtown Kissimmee travel plans.

Where is the best place to stay in Historic Downtown Kissimmee?

Based on Expedia customer reviews, Kapp and Kappy B&B is the highest ranked property in Historic Downtown Kissimmee. This B&B offers free breakfast and free parking.

How many hotels will I be able to find in the Historic Downtown Kissimmee area?

If you're searching for places to stay in Kissimmee, Expedia has something to meet your needs with 85 Historic Downtown Kissimmee hotels and other accommodation options to choose from.

If I need to cancel my hotel reservation in Historic Downtown Kissimmee, will I receive a refund?

Yes! The majority of hotel bookings are fully refundable if cancelled before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of booking. Put your dates in and click on "Search", then filter by "fully refundable" to get the top deals on offer in Historic Downtown Kissimmee.

What is there to do around this Kissimmee neighbourhood?

Spend some time exploring the natural setting of Historic Downtown Kissimmee with a visit to Kissimmee Lakefront Park and Lake Tohopekaliga. Osceola County Clerk of the Court and Kissimmee Civic Center are also a couple of places to visit in the neighbourhood. A few places to visit in the area around Historic Downtown Kissimmee include Monument of States, Bataan-Corregidor Memorial and Brinson Park. While you're out sightseeing in Kissimmee, make sure that you visit other sights such as Big Toho Marina or Bob Makinson Aquatic Center.

How can I get around Historic Downtown Kissimmee and the greater Kissimmee area?

To venture out of town, take a train from Kissimmee Station.