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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 ₩252,161
₩286,184 total
includes taxes & fees
Dec 29 - Dec 30
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

Super Boho - At Lake Toho's Water
2.0 star property
Historic Downtown Kissimmee
The price is ₩142,724
₩363,831 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Super Boho - At Lake Toho's Water
Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers
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, (5126)
"Rooms were spacious and clean, breakfast was so good and different items each day. "
United States
Juan Jesus
The price is ₩164,320
₩184,859 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Home2 Suites by Hilton Orlando at Flamingo Crossings
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, (2975)
"Great place to stay"
United States
Jany
The price is ₩103,929
₩142,855 total
includes taxes & fees
Jan 11 - Jan 12, 2026
SPOT X Hotel Orlando/Intl Dr by The Red Collection
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, (1041)
"Everything about the Delaney Hotel was absolutely amazing!!!!"
United States
Tara
The Delaney Hotel
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
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, (1977)
"Great location, good, staff, and rooms "
Canada
Jobin
The price is ₩206,157
₩231,926 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
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, (2526)
"Enjoyed staying here and very convenient "
United States
Rachael
The price is ₩101,651
₩114,357 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Days Inn by Wyndham Orlando Conv. Center/International Dr
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, (1450)
"The place was amazing."
United States
Kasheia
The price is ₩153,299
₩213,015 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hilton Vacation Club Grand Beach Orlando
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, (496)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is ₩124,199
₩139,724 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Spark by Hilton Orlando near Universal
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, (1969)
"The room and staff were awesome!!!"
United States
danyell
The price is ₩128,668
₩144,751 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Element Orlando Universal Blvd.
Exterior
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, (4071)
"Excellent Hotel, comfort room and area pool, recommend and select in other moment to visit Orlando. "
United States
Ramon Gilberto Ayala
The price is ₩153,176
₩212,877 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Hilton Vacation Club Aqua Sol Orlando West
Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)
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, (1580)
"was a very nice stay"
United States
Taylor Elaine
The price is ₩134,074
₩204,535 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Meliá Orlando Celebration
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, (2164)
"Very nice hotel, great amenities and friendly staff."
United States
Latasha
The price is ₩187,964
₩211,461 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Homewood Suites by Hilton Orlando at Flamingo Crossings
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, (2797)
"Very conveniently located to Disney Springs, clean rooms and grounds, and very friendly service."
United States
Todd
The price is ₩156,852
₩234,845 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wyndham Lake Buena Vista – Disney Springs® Area
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, (1922)
"Good place to stay "
United States
victor
The price is ₩112,449
₩126,504 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Aloft Orlando Lake Buena Vista
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, (3590)
"Very convenient and liked the hotel"
United States
Melanie
The price is ₩95,150
₩155,700 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Outdoor pool, sun loungers, lifeguards on site
Spectrum Resort Villas Orlando and Waterparks

Spectrum Resort Villas Orlando and Waterparks

Spectrum Resort Villas Orlando and Waterparks
4.0 star property
Reunion, 18.7 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (849)
"Great location for a family vacation"
United States
Deanne
The price is ₩373,390
₩754,334 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Spectrum Resort Villas Orlando and Waterparks
2 outdoor pools, a heated pool, cabanas (surcharge)
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, (2898)
"Rooms were huge, great stay! "
United States
Robert
The price is ₩145,824
₩196,490 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Vacation Club Grande Villas Orlando
Lobby
Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
8.7 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (1256)
"Clean Room, Daily Room Service & Awesome breakfast. Enjoyed staying here with family."
United States
Prashant
The price is ₩223,428
₩253,590 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Embassy Suites by Hilton Orlando Lake Buena Vista South
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, (1403)
"Good location, good breakfast "
United States
Andrea
The price is ₩170,116
₩191,380 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hyatt House Orlando International Drive
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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Very clean room and very friendly staff alongside a wonderful dining experience. Will definitely be staying here again! "
Aureo 6-night trip
Posted 11 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando

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.