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Dec 25 - Dec 26
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Our top choices for Historic Downtown Kissimmee hotels

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 ₩258,813
₩293,734 total
includes taxes & fees
Dec 29 - Dec 30
Kapp and Kappy B&B
House, 2 Bedrooms, Lake View, Lakeside | Living room
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 ₩204,197
₩438,921 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Super Boho - At Lake Toho's Water
Terrace/patio
The Delaney Hotel

The Delaney Hotel

The Delaney Hotel
3.5 star property
26 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (1037)
"Everything about the Delaney Hotel was absolutely amazing!!!!"
United States
Tara
The Delaney Hotel
Exterior
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
22.9 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (1981)
"Great location, good, staff, and rooms "
Canada
Jobin
The price is ₩224,913
₩253,027 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Exterior
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
22.9 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (5118)
"Great location nice breakfast and front desk people is amazing "
United States
Orlando
The price is ₩156,522
₩176,089 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Home2 Suites by Hilton Orlando at Flamingo Crossings
Exterior
Days Inn by Wyndham Orlando Conv. Center/International Dr

Days Inn by Wyndham Orlando Conv. Center/International Dr

Days Inn by Wyndham Orlando Conv. Center/International Dr
2.0 star property
15.3 km from Historic Downtown Kissimmee
8.2 out of 10, Very Good, (2519)
"Great place "
United States
Julio
The price is ₩114,335
₩128,626 total
includes taxes & fees
Dec 25 - Dec 26
Days Inn by Wyndham Orlando Conv. Center/International Dr
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, (469)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is ₩131,234
₩147,639 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Spark by Hilton Orlando near Universal
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
23 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (2157)
"Great room and stay!"
United States
christopher michael
The price is ₩192,922
₩217,038 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Homewood Suites by Hilton Orlando at Flamingo Crossings
Exterior
Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando
3.0 star property
11.7 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (1451)
"The place was amazing."
United States
Kasheia
The price is ₩157,343
₩218,634 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hilton Vacation Club Grand Beach Orlando
2 outdoor pools, pool umbrellas, sun loungers
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
25.3 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (4080)
"Clean hotel, very spacious and the staff was very friendly even in a very late check in "
United States
Ana
The price is ₩157,217
₩218,493 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Hilton Vacation Club Aqua Sol Orlando West
Front of property
Wyndham Lake Buena Vista – Disney Springs® Area

Wyndham Lake Buena Vista – Disney Springs® Area

Wyndham Lake Buena Vista – Disney Springs® Area
4.0 star property
13.7 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (2789)
"Well kept hotel, friendly staff"
United States
Sean
The price is ₩160,990
₩241,042 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wyndham Lake Buena Vista – Disney Springs® Area
Property grounds
SPOT X Hotel Orlando/Intl Dr by The Red Collection

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, (2970)
"Clean room, close to Disney and good breakfast at a reasonable price"
United States
pamela
The price is ₩100,679
₩139,882 total
includes taxes & fees
Jan 7 - Jan 8, 2026
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Outdoor wedding area
Meliá Orlando Celebration

Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
13.6 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (1573)
"was a very nice stay"
United States
Taylor Elaine
The price is ₩137,611
₩209,931 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Meliá Orlando Celebration
Outdoor pool
Element Orlando Universal Blvd.

Element Orlando Universal Blvd.

Element Orlando Universal Blvd.
3.0 star property
17.8 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (1962)
"The room and staff were awesome!!!"
United States
danyell
The price is ₩137,093
₩154,230 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Element Orlando Universal Blvd.
Reception
The Vietta Hotel

The Vietta Hotel

The Vietta Hotel
2.0 star property
8.4 km from Historic Downtown Kissimmee
7.4 out of 10, Good, (1001)
"Great staff beautiful view clean room "
United States
Navita
The Vietta Hotel
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, (1917)
"Great stay"
United States
Gerard
The price is ₩146,489
₩164,800 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Aloft Orlando Lake Buena Vista
Outdoor pool, a heated pool, pool umbrellas, sun loungers
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, (3579)
"Great place to stay "
United States
Nathaniel
The price is ₩100,619
₩163,136 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Exterior
Candlewood Suites Orlando - Lake Buena Vista by IHG

Candlewood Suites Orlando - Lake Buena Vista by IHG

Candlewood Suites Orlando - Lake Buena Vista by IHG
2.5 star property
14.5 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (2309)
"Check in was easy and the room was nice and clean"
United States
Arthur
The price is ₩103,578
₩133,172 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Candlewood Suites Orlando - Lake Buena Vista by IHG
Terrace/patio
Hilton Vacation Club Grande Villas Orlando

Hilton Vacation Club Grande Villas Orlando

Hilton Vacation Club Grande Villas Orlando
3.5 star property
14.3 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (2913)
"Rooms were huge, great stay! "
United States
Robert
The price is ₩149,671
₩201,674 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Vacation Club Grande Villas Orlando
Aerial view
The Grove Resort & Water Park Orlando

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, (8828)
"It was a great place to stay."
United States
Katherine Mercedes Cruz
The price is ₩250,068
₩362,894 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Grove Resort & Water Park 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.
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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.

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.

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.

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

CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

10/10 Excellent
"Swimming pool was cleaned and enjoyable. Staff were very friendly and warming. I really loved this place. My kids enjoyed every single thing. "
Marianna 1-night trip
Posted 11 hours ago
CoCo Key Hotel and Water Resort 

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.