Search Hotels in Historic Downtown Kissimmee, Orlando

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
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Historic Downtown Kissimmee, Orlando

Porch
Kapp and Kappy B&B
Kapp and Kappy B&B
3.5 star property
9.8 out of 10, Exceptional, (124)
"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."
United States
Gregory
The price is ₹12,908
₹14,651 total
includes taxes & fees
24 Nov - 25 Nov
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
The price is ₹8,873
₹22,370 total
includes taxes & fees
11 Nov - 12 Nov
Super Boho - At Lake Toho's Water
Terrace/patio
The Delaney Hotel
The Delaney Hotel
3.5 star property
9.6 out of 10, Exceptional, (1004)
"All around wonderful stay"
United States
Caleb
The price is ₹13,275
₹14,936 total
includes taxes & fees
24 Nov - 25 Nov
The Delaney Hotel
Water park
Ramada by Wyndham Hotel & Water Park
Ramada by Wyndham Hotel & Water Park
3.0 star property
7.2 out of 10, Good, (1508)
"Excellent staff and service "
United States
MARITZA
The price is ₹2,811
₹5,684 total
includes taxes & fees
28 Oct - 29 Oct
Ramada by Wyndham Hotel & Water Park
Aerial view
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4.0 star property
8.0 out of 10, Very good, (8659)
"I loved the room and hotel. Wonderful place to stay. "
United States
Barbara
The price is ₹14,495
₹20,261 total
includes taxes & fees
16 Nov - 17 Nov
The Grove Resort & Water Park Orlando
Premium bedding, in-room safe, desk, blackout curtains
Ramada by Wyndham Suites Orlando Airport
Ramada by Wyndham Suites Orlando Airport
3.0 star property
8.2 out of 10, Very good, (4987)
"Very nice stay"
United States
Donald
The price is ₹7,019
₹7,897 total
includes taxes & fees
24 Nov - 25 Nov
Ramada by Wyndham Suites Orlando Airport
Suite, 1 King Bed with Sofa bed, Balcony | 1 bedroom, premium bedding, minibar, in-room safe
Kompose Boutique Resort at Theme Parks
Kompose Boutique Resort at Theme Parks
3.0 star property
9.4 out of 10, Exceptional, (1611)
"Great place to stay"
United States
Maribel
The price is ₹5,364
₹6,088 total
includes taxes & fees
19 Nov - 20 Nov
Kompose Boutique Resort at Theme Parks
Pillow-top beds, in-room safe, desk, blackout curtains
Wingate by Wyndham - Orlando International Airport
Wingate by Wyndham - Orlando International Airport
3.0 star property
8.8 out of 10, Excellent, (3698)
"Great service amazing breakfast at great price "
United States
Janelle
The price is ₹7,274
₹8,183 total
includes taxes & fees
28 Oct - 29 Oct
Wingate by Wyndham - Orlando International 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
8.6 out of 10, Excellent, (2843)
"Exelente hotel nos encanto "
United States
Carmen
The price is ₹5,266
₹7,504 total
includes taxes & fees
23 Nov - 24 Nov
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Exterior
Country Inn & Suites by Radisson, Orlando Airport, FL
Country Inn & Suites by Radisson, Orlando Airport, FL
3.0 star property
7.8 out of 10, Good, (4139)
"Beautiful hotel"
United States
Malikah S
The price is ₹6,048
₹6,804 total
includes taxes & fees
10 Nov - 11 Nov
Country Inn & Suites by Radisson, Orlando Airport, FL
7 outdoor pools, pool cabanas (surcharge), pool umbrellas
Westgate Lakes Resort & Spa Universal Studios Area
Westgate Lakes Resort & Spa Universal Studios Area
4.0 star property
8.2 out of 10, Very good, (5443)
"Great place to stay"
United States
Brooke ann
The price is ₹8,581
₹12,222 total
includes taxes & fees
26 Oct - 27 Oct
Westgate Lakes Resort & Spa Universal Studios Area
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
8.4 out of 10, Very good, (984)
"The breakfast was good and the fresh cinnamon buns was also excellent. "
United States
Rena
The price is ₹7,819
₹8,679 total
includes taxes & fees
27 Oct - 28 Oct
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
3 outdoor pools, open 7 AM to 10:00 PM, pool cabanas (surcharge)
Hyatt Regency Grand Cypress
Hyatt Regency Grand Cypress
4.0 star property
9.2 out of 10, Wonderful, (2267)
"Great stay!"
United States
Rachana
The price is ₹13,968
₹20,656 total
includes taxes & fees
14 Nov - 15 Nov
Hyatt Regency Grand Cypress
Outdoor pool
DoubleTree by Hilton at the Entrance to Universal Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando
4.0 star property
8.4 out of 10, Very good, (6829)
"Great stay"
United States
Bianca
The price is ₹8,573
₹9,644 total
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton at the Entrance to Universal Orlando
View from room
Rosen Inn Lake Buena Vista
Rosen Inn Lake Buena Vista
3.5 star property
8.6 out of 10, Excellent, (5510)
"Great hotel!"
Canada
Amanda
The price is ₹5,983
₹6,731 total
includes taxes & fees
24 Nov - 25 Nov
Rosen Inn Lake Buena Vista
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek
Rosen Shingle Creek
4.5 star property
9.4 out of 10, Exceptional, (4101)
"Always a great experience when we stay here. "
United States
Marla
The price is ₹8,099
₹9,112 total
includes taxes & fees
18 Nov - 19 Nov
Rosen Shingle Creek
Front of property – evening/night
Rosen Inn International
Rosen Inn International
3.0 star property
8.4 out of 10, Very good, (5850)
"Great value and convenient location. "
United States
Amanda
The price is ₹6,324
₹7,115 total
includes taxes & fees
12 Nov - 13 Nov
Rosen Inn International
Sports court
Caribe Royale Orlando
Caribe Royale Orlando
4.5 star property
9.2 out of 10, Wonderful, (4445)
"Loved our 3 night stay. The staff are friendly, room was very clean and the food was great."
United States
Brianna
The price is ₹13,090
₹18,482 total
includes taxes & fees
2 Nov - 3 Nov
Caribe Royale Orlando
Property grounds
Seasons Florida Resort
Seasons Florida Resort
2.0 star property
8.8 out of 10, Excellent, (3200)
"Great place to stay. "
United States
Bernadette
The price is ₹4,697
₹5,332 total
includes taxes & fees
4 Nov - 5 Nov
Seasons Florida Resort
Outdoor pool, pool loungers
Wyndham Garden Orlando Airport
Wyndham Garden Orlando Airport
3.0 star property
9.0 out of 10, Wonderful, (3908)
"Wonderful Hotel, would stay here about! "
United States
Gregory
The price is ₹8,153
₹9,172 total
includes taxes & fees
24 Nov - 25 Nov
Wyndham Garden Orlando Airport
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Where to stay in Historic Downtown Kissimmee

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

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 showing interior views and rides 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® featuring night scenes, a city 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.

Champions Gate

Ample dining options and top 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

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

10/10 Excellent
"Staff at the front was accommodating and friendly "
Nathalie 2-night trip
Posted 2 days ago
Wyndham I-Drive Avanti Resort & Conference Center

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 80 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 Violet's Venom Brewery, Monument of States and Bataan-Corregidor Memorial. While you're out sightseeing in Kissimmee, make sure that you visit other sights such as 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.