Find hotels in Historic Downtown Kissimmee, Orlando from ￥8,197

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

Filter by

Guest rating
Guest rating
Star rating

Discover 53,531 Historic Downtown Kissimmee hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

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 ￥25,521
￥28,966 total
includes taxes & fees
Oct 6 - Oct 7
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
Super Boho - At Lake Toho's Water
The Delaney Hotel
Terrace/patio

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1025)
"great restaurant and even better rooms!"
The Delaney Hotel
The Grove Resort & Water Park Orlando
Aerial view

The Grove Resort & Water Park Orlando

4.0 star property
8.0 out of 10, Very Good, (8624)
"Great place to stay!!!"
The price is ￥25,113
￥34,940 total
includes taxes & fees
Oct 1 - Oct 2
The Grove Resort & Water Park Orlando
Ramada by Wyndham Hotel & Water Park
Water park

Ramada by Wyndham Hotel & Water Park

3.0 star property
7.2 out of 10, Good, (1490)
"Excellent place for familys"
The price is ￥5,350
￥10,290 total
includes taxes & fees
Oct 14 - Oct 15
Ramada by Wyndham Hotel & Water Park
Ramada by Wyndham Suites Orlando Airport
Premium bedding, in-room safe, desk, blackout drapes

Ramada by Wyndham Suites Orlando Airport

3.0 star property
8.2 out of 10, Very Good, (4916)
"Awesome hotel!"
The price is ￥11,167
￥12,563 total
includes taxes & fees
Oct 1 - Oct 2
Ramada by Wyndham Suites Orlando Airport
Wingate by Wyndham - Orlando International Airport
Pillowtop beds, in-room safe, desk, blackout drapes

Wingate by Wyndham - Orlando International Airport

3.0 star property
8.8 out of 10, Excellent, (3667)
"My stay was very comfortable, I enjoyed the continental breakfast very much."
The price is ￥12,071
￥13,579 total
includes taxes & fees
Oct 1 - Oct 2
Wingate by Wyndham - Orlando International Airport
Kompose Boutique Resort at Theme Parks
Suite, 1 King Bed with Sofa bed, Balcony | 1 bedroom, premium bedding, minibar, in-room safe

Kompose Boutique Resort at Theme Parks

3.0 star property
9.4 out of 10, Exceptional, (1415)
"Great place to stay"
The price is ￥9,206
￥12,249 total
includes taxes & fees
Oct 1 - Oct 2
Kompose Boutique Resort at Theme Parks
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Front of property - evening/night

SPOT X Hotel Orlando/Intl Dr by The Red Collection

3.0 star property
8.6 out of 10, Excellent, (2786)
"Great property to stay with family while visiting the parks"
The price is ￥8,907
￥12,694 total
includes taxes & fees
Oct 14 - Oct 15
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Hyatt Regency Grand Cypress
3 outdoor pools, open 7 AM to 10:00 PM, cabanas (surcharge)

Hyatt Regency Grand Cypress

4.0 star property
9.2 out of 10, Wonderful, (2269)
"Great stay, close to all attractions and very quiet."
The price is ￥23,330
￥34,604 total
includes taxes & fees
Oct 13 - Oct 14
Hyatt Regency Grand Cypress
Rosen Inn International
Front of property - evening/night

Rosen Inn International

3.0 star property
8.4 out of 10, Very Good, (5820)
"Will stay here again!"
The price is ￥12,556
￥14,126 total
includes taxes & fees
Oct 2 - Oct 3
Rosen Inn International
DoubleTree by Hilton at the Entrance to Universal Orlando
Outdoor pool

DoubleTree by Hilton at the Entrance to Universal Orlando

4.0 star property
8.4 out of 10, Very Good, (6716)
"It was an amazing stay! "
The price is ￥15,031
￥16,910 total
includes taxes & fees
Oct 30 - Oct 31
DoubleTree by Hilton at the Entrance to Universal Orlando
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Property amenity

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

2.5 star property
8.4 out of 10, Very Good, (956)
"Had a great experience this weekend at the hotel and the free breakfast was good and very convenient for the family and kids. "
The price is ￥12,148
￥13,484 total
includes taxes & fees
Oct 7 - Oct 8
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Rosen Inn Lake Buena Vista
View from room

Rosen Inn Lake Buena Vista

3.5 star property
8.6 out of 10, Excellent, (5449)
"Clean rooms very nice staff always a great stay."
The price is ￥9,436
￥10,616 total
includes taxes & fees
Oct 7 - Oct 8
Rosen Inn Lake Buena Vista
Country Inn & Suites by Radisson, Orlando Airport, FL
Exterior

Country Inn & Suites by Radisson, Orlando Airport, FL

3.0 star property
7.8 out of 10, Good, (4082)
"Great location and amazing staff. "
The price is ￥11,106
￥12,494 total
includes taxes & fees
Oct 28 - Oct 29
Country Inn & Suites by Radisson, Orlando Airport, FL
Rosen Shingle Creek
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (4040)
"Great resort vibes while being close to the parks and other tourist places. "
The price is ￥13,421
￥15,100 total
includes taxes & fees
Oct 10 - Oct 11
Rosen Shingle Creek
Caribe Royale Orlando
Sport court

Caribe Royale Orlando

4.5 star property
9.2 out of 10, Wonderful, (4454)
"Great place to stay"
The price is ￥26,599
￥36,277 total
includes taxes & fees
Oct 2 - Oct 3
Caribe Royale Orlando
Seasons Florida Resort
Property grounds

Seasons Florida Resort

2.0 star property
8.8 out of 10, Excellent, (3168)
"Great place to stay. "
The price is ￥7,223
￥8,197 total
includes taxes & fees
Oct 8 - Oct 9
Seasons Florida Resort
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Exterior

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 star property
7.0 out of 10, Good, (4229)
"Perfect for families. The water park inside the hotel was amazing! "
The price is ￥9,510
￥21,565 total
includes taxes & fees
Oct 2 - Oct 3
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Hyatt Regency Orlando
2 outdoor pools, cabanas (surcharge), pool umbrellas

Hyatt Regency Orlando

4.5 star property
9.2 out of 10, Wonderful, (1774)
"Great place to stay "
The price is ￥17,720
￥28,159 total
includes taxes & fees
Oct 2 - Oct 3
Hyatt Regency Orlando
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.
View all properties

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
Learn more about Historic Downtown Kissimmee
International Drive showing landscape views

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® Park showing rides and interior views as well as a couple
Photo by ©Disney
Open Photo by ©Disney

Bay Lake

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.

Universal Studios Orlando featuring signage, a city and night scenes

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

Downtown Orlando

Downtown Orlando

Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation.

Windsor Hills

If you're looking for some top things to see and do in Windsor Hills and surrounding area, you can visit Mystic Dunes Golf Club and Island H2O Live!.

Top Historic Downtown Kissimmee Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Very nice clean complex. Only negative was $25 per night parking charge which would put me off booking again. "
CAROLE 9-night trip
Posted 9 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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 neighborhood that people enjoy for its major shopping area. Be sure to check out 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 find in Historic Downtown Kissimmee?

If you're searching for places to stay in Kissimmee, Expedia has something to meet your needs with 84 Historic Downtown Kissimmee hotels and other accommodations to choose from.

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

Yes! You'll find that most hotel bookings are refundable if you cancel before the hotel’s cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and receive a refund within 24 hours of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to get the best deals available in Historic Downtown Kissimmee.

Where can I learn more about changing or cancelling my trip to Historic Downtown Kissimmee?

For more details about picking new dates or cancelling your trip to Historic Downtown Kissimmee, click here.

What is there to do around this Kissimmee neighborhood?

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 neighborhood. A few places to visit in the area around Historic Downtown Kissimmee include Violet's Venom Brewery, Monument of States, and Bataan-Corregidor Memorial. While you're out sightseeing in Kissimmee, be sure to visit other sights like Brinson Park or Big Toho Marina.

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

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