Find hotels in Historic Downtown Kissimmee, Orlando from ₩100,757

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 8 - Nov 9
Tomorrow
Nov 9 - Nov 10
Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23

Filter by

Guest rating
Guest rating
Star rating

Discover 52,920 Historic Downtown Kissimmee hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Porch
Kapp and Kappy B&B

Kapp and Kappy B&B

3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (124)
"Only B&B in Kissimmee. Owners were excellent. Enjoyed talking to them each morning over a great breakfast. Would definitely go back. "
United States
John
The price is ₩233,368
₩264,873 total
includes taxes & fees
Nov 20 - Nov 21
Kapp and Kappy B&B
House, 2 Bedrooms, Lake View, Lakeside | Private kitchen
Super Boho - At Lake Toho's Water

Super Boho - At Lake Toho's Water

2.0 star property
Historic Downtown Kissimmee
The price is ₩166,587
₩393,657 total
includes taxes & fees
Dec 9 - Dec 10
Super Boho - At Lake Toho's Water
Terrace/patio
The Delaney Hotel

The Delaney Hotel

3.5 star property
26 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (1005)
"All around wonderful stay"
United States
Caleb
The Delaney Hotel
6 outdoor pools, free cabanas, pool umbrellas
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4.0 star property
12.8 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (3881)
"Nice place to stay for family. "
United States
Niketan Chhaganbhai
The price is ₩133,270
₩149,928 total
includes taxes & fees
Dec 1 - Dec 2
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Aerial view
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4.0 star property
25.2 km from Historic Downtown Kissimmee
8.0 out of 10, Very Good, (8701)
"Great stay"
United States
Breanna
The price is ₩241,113
₩337,012 total
includes taxes & fees
Nov 30 - Dec 1
The Grove Resort & Water Park Orlando
Premium bedding, in-room safe, desk, blackout drapes
Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport

3.0 star property
20.5 km from Historic Downtown Kissimmee
8.2 out of 10, Very Good, (5052)
"Great stay!"
Canada
Sherry
The price is ₩116,757
₩131,351 total
includes taxes & fees
Nov 24 - Nov 25
Ramada by Wyndham Suites Orlando Airport
Front of property - evening/night
SPOT X Hotel Orlando/Intl Dr by The Red Collection

SPOT X Hotel Orlando/Intl Dr by The Red Collection

3.0 star property
13.3 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (2844)
"Nice location, nice rooms, clean and comfortable"
United States
LIBARDO
The price is ₩93,508
₩131,484 total
includes taxes & fees
Nov 30 - Dec 1
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Outdoor pool, pool umbrellas, sun loungers
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3.0 star property
18.3 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (1721)
"The best place to stay in 🏝️🏝️"
United States
ywar
The price is ₩90,746
₩102,998 total
includes taxes & fees
Nov 12 - Nov 13
Kompose Boutique Resort at Theme Parks
Pillowtop beds, in-room safe, desk, blackout drapes
Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport

3.0 star property
21.1 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3671)
"Great room good facilities"
United Kingdom
gerwyn
The price is ₩124,940
₩140,561 total
includes taxes & fees
Nov 11 - Nov 12
Wingate by Wyndham - Orlando International Airport
5 outdoor pools, pool umbrellas, sun loungers
Summer Bay Orlando by Exploria Resorts

Summer Bay Orlando by Exploria Resorts

3.5 star property
25.6 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (2069)
"We loved our stay here. "
Canada
Andrew
The price is ₩151,243
₩216,540 total
includes taxes & fees
Nov 16 - Nov 17
Summer Bay Orlando by Exploria Resorts
Property amenity
Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

2.5 star property
25.6 km from Historic Downtown Kissimmee
8.4 out of 10, Very Good, (1006)
"Everything was great! "
United States
Laquania
The price is ₩137,361
₩152,471 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Exterior
Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL

3.0 star property
20.6 km from Historic Downtown Kissimmee
7.8 out of 10, Good, (4183)
"Staff was friendly and welcoming and rooms were clean"
United States
Terrence
The price is ₩101,049
₩113,681 total
includes taxes & fees
Dec 9 - Dec 10
Country Inn & Suites by Radisson, Orlando Airport, FL
3 outdoor pools, open 7 AM to 10:00 PM, cabanas (surcharge)
Hyatt Regency Grand Cypress

Hyatt Regency Grand Cypress

4.0 star property
14.3 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (2275)
"Great stay!"
United States
Rachana
The price is ₩232,345
₩343,586 total
includes taxes & fees
Nov 14 - Nov 15
Hyatt Regency Grand Cypress
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

4.5 star property
14.9 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (4147)
" Everything was beautiful we will be going back for another stay!!"
United States
Marcelle
The price is ₩162,495
₩182,807 total
includes taxes & fees
Nov 23 - Nov 24
Rosen Shingle Creek
View from room
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

3.5 star property
13.7 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (5536)
"Amazing stay "
United States
Elsy
The price is ₩115,720
₩130,187 total
includes taxes & fees
Nov 10 - Nov 11
Rosen Inn Lake Buena Vista
Outdoor pool
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4.0 star property
21.1 km from Historic Downtown Kissimmee
8.4 out of 10, Very Good, (6834)
"Great stay "
United States
Anthony
The price is ₩142,593
₩160,418 total
includes taxes & fees
Nov 17 - Nov 18
DoubleTree by Hilton at the Entrance to Universal Orlando
Front of property - evening/night
Rosen Inn International

Rosen Inn International

3.0 star property
18.8 km from Historic Downtown Kissimmee
8.4 out of 10, Very Good, (5862)
"Great location"
United States
Phylis Annette
The price is ₩116,889
₩131,502 total
includes taxes & fees
Nov 10 - Nov 11
Rosen Inn International
Lobby lounge
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

3.0 star property
14.1 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (1845)
"Nice hotel "
United States
Miguel
The price is ₩112,519
₩126,583 total
includes taxes & fees
Dec 1 - Dec 2
Aloft Orlando Lake Buena Vista
Sport court
Caribe Royale Orlando

Caribe Royale Orlando

4.5 star property
11 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (4457)
"Great stay "
United States
Tracey
The price is ₩203,119
₩290,986 total
includes taxes & fees
Nov 25 - Nov 26
Caribe Royale Orlando
Property grounds
Seasons Florida Resort

Seasons Florida Resort

2.0 star property
7.2 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3216)
"Clean, nice pool, friendly staff. "
Canada
Mihai Adrian
The price is ₩88,773
₩100,757 total
includes taxes & fees
Nov 10 - Nov 11
Seasons Florida Resort
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.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

Top Historic Downtown Kissimmee Hotel Reviews

Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"Nice place to stay! Great restaurants and service! "
Cynthia 1-night trip
Posted 1 day ago
Walt Disney World Dolphin

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 81 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.