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Dec 17 - Dec 18
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Dec 18 - Dec 19
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Dec 19 - Dec 21
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Dec 26 - Dec 28

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Our top choices for Historic Downtown Kissimmee hotels

House, 2 Bedrooms, Lake View, Lakeside | Private kitchen
Super Boho - At Lake Toho's Water

Super Boho - At Lake Toho's Water

Super Boho - At Lake Toho's Water
2.0 star property
Historic Downtown Kissimmee
The price is NT$3,118
NT$7,948 total
includes taxes & fees
Dec 19 - Dec 20
Super Boho - At Lake Toho's Water
Porch
Kapp and Kappy B&B

Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (125)
"Friendly host. Felt like home. "
Canada
Gordon
The price is NT$5,030
NT$5,709 total
includes taxes & fees
Jan 1 - 2026/1/2
Kapp and Kappy B&B
Property grounds
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
7.2 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3291)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is NT$1,984
NT$2,252 total
includes taxes & fees
Jan 4 - 2026/1/5
Seasons Florida Resort
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
14.9 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (4355)
"Great resort "
United States
Camille
The price is NT$3,502
NT$3,940 total
includes taxes & fees
Dec 21 - Dec 22
Rosen Shingle Creek
Exterior
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG
3.5 star property
18.5 km from Historic Downtown Kissimmee
8.4 out of 10, Very Good, (1051)
"Great hotel"
United States
Steven
The price is NT$2,236
NT$3,164 total
includes taxes & fees
Jan 4 - 2026/1/5
Holiday Inn Resort Kissimmee by the Parks by IHG
Free daily buffet breakfast
La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North
3.0 star property
20.5 km from Historic Downtown Kissimmee
7.4 out of 10, Good, (864)
"nice and clean staff was great also"
United States
sumatran
The price is NT$2,696
NT$3,033 total
includes taxes & fees
Jan 5 - 2026/1/6
La Quinta Inn & Suites by Wyndham Orlando Airport North
Free daily buffet breakfast
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
19.2 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (1372)
"The staff was really friendly and the property was nice and cozy "
United States
curtis
The price is NT$3,716
NT$4,181 total
includes taxes & fees
Jan 4 - 2026/1/5
Hyatt House Orlando International Drive
Outdoor pool
DoubleTree by Hilton at the Entrance to Universal Orlando

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, (6914)
"Wonderful stay. Great location!"
United States
Charmaine
The price is NT$3,332
NT$3,748 total
includes taxes & fees
Jan 18 - 2026/1/19
DoubleTree by Hilton at the Entrance to Universal Orlando
Outdoor pool, pool umbrellas, sun loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
19.4 km from Historic Downtown Kissimmee
7.4 out of 10, Good, (3925)
"The bar and pool were great"
United States
Melissa
The price is NT$2,051
NT$2,946 total
includes taxes & fees
Dec 21 - Dec 22
Wyndham I-Drive Avanti Resort & Conference Center
In-room safe, laptop workspace, blackout drapes, iron/ironing board
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
8.5 km from Historic Downtown Kissimmee
8.2 out of 10, Very Good, (5145)
"Beautiful place to stay."
United States
Mohammad
The price is NT$930
NT$2,127 total
includes taxes & fees
Dec 21 - Dec 22
Palazzo Lakeside Hotel
Exterior
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway
3.0 star property
18.2 km from Historic Downtown Kissimmee
8.0 out of 10, Very Good, (3927)
"Always great to stay there "
United States
Giandre
The price is NT$1,587
NT$2,445 total
includes taxes & fees
Jan 4 - 2026/1/5
Ramada by Wyndham Kissimmee Gateway
Lobby lounge
Aloft Orlando Lake Buena Vista

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, (1911)
"Great stay"
United States
Gerard
The price is NT$2,583
NT$2,905 total
includes taxes & fees
Dec 21 - Dec 22
Aloft Orlando Lake Buena Vista
Lobby
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
18.9 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (700)
"Clean rooms, friendly staff, delicious breakfast "
United States
Katherin
The price is NT$2,383
NT$2,680 total
includes taxes & fees
Jan 7 - 2026/1/8
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Exterior
Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
3.0 star property
20.4 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (2457)
"Great location to airport and food choices. "
United States
Aliza
The price is NT$3,177
NT$3,574 total
includes taxes & fees
Dec 23 - Dec 24
Hampton Inn & Suites Orlando Airport @ Gateway Village
Exterior
Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
19.1 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (1941)
"The room was clean and the staff was welcoming and friendly!"
United States
Otthoniel
The price is NT$3,052
NT$3,433 total
includes taxes & fees
Dec 24 - Dec 25
Cambria Hotel Orlando Airport
Outdoor pool, pool umbrellas, sun loungers
Kompose Boutique Resort at Theme Parks

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, (1995)
"Great stay! Beautiful hotel with amazing rooms and an awesome location."
United States
Andrew
The price is NT$1,923
NT$3,433 total
includes taxes & fees
Jan 7 - 2026/1/8
Kompose Boutique Resort at Theme Parks
Lobby
Hyatt House Orlando Airport

Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
20.3 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (2802)
"Great location, friendly staff, great breakfast"
United States
Gabriel
The price is NT$3,590
NT$4,039 total
includes taxes & fees
Dec 24 - Dec 25
Hyatt House Orlando Airport
Exterior
Caribe Royale Orlando

Caribe Royale Orlando

Caribe Royale Orlando
4.5 star property
11 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (4513)
"Excellent hotel I will be booking again"
United States
Wilshaundra
The price is NT$5,008
NT$6,980 total
includes taxes & fees
Dec 19 - Dec 20
Caribe Royale Orlando
Lobby
Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
12.9 km from Historic Downtown Kissimmee
8.4 out of 10, Very Good, (3566)
"Love staying here friendly staff and well kept property. "
United States
Carlos
The price is NT$2,142
NT$3,472 total
includes taxes & fees
Jan 14 - 2026/1/15
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Business center
Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
22 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (440)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is NT$2,749
NT$3,093 total
includes taxes & fees
Jan 4 - 2026/1/5
Spark by Hilton Orlando near Universal
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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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.

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.

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.

Top Historic Downtown Kissimmee Hotel Reviews

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Clean room. Comfy bed. Good shower water pressure. Enough space. Near everything. "
Michael 8-night trip
Posted 7 hours ago
Rosen Inn Lake Buena Vista

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 79 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.

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