A street sign reading "Welcome to Kissimmee, Florida" with a mural of horses on a building.

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Oct 9 - Oct 11
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Oct 16 - Oct 18

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Our top choices for Historic Downtown Kissimmee hotels

A covered porch with wooden chairs and a ceiling fan.

1. Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (145 reviews)
"The room was really nice and the breakfast was great."
United States
Mark
The price is NT$4,539
NT$5,152 total
includes taxes & fees
Oct 11 - Oct 12
Kapp and Kappy B&B
A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

2. Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
4.0 star property
13.8 km from Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (6,133 reviews)
"Always love staying here"
United States
Brianne
The price is NT$5,149
NT$5,793 total
includes taxes & fees
Oct 28 - Oct 29
Drury Plaza Hotel Orlando - Disney Springs Area
A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

3. 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
9.6 out of 10, Exceptional, (1,603 reviews)
"Very nice place."
United States
Nguyen
The price is NT$3,496
NT$3,968 total
includes taxes & fees
Oct 18 - Oct 19
Embassy Suites by Hilton Orlando Lake Buena Vista South
An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

4. Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
4.0 star property
14.5 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3,155 reviews)
"Great hotel in a great location for Disney"
United States
Anthony
The price is NT$3,954
NT$5,955 total
includes taxes & fees
Oct 29 - Oct 30
Wyndham Grand Orlando Resort Bonnet Creek
A hotel with a large pool, palm trees, and a waterfall feature.

5. Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite
4.5 star property
11.1 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (5,325 reviews)
"We stay here all the time and love it!"
United States
Brittany
The price is NT$6,026
NT$8,143 total
includes taxes & fees
Oct 10 - Oct 11
Caribe Royale Orlando, WorldHotels Elite
Pool

6. 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, (2,356 reviews)
"Great stay, amazing pool."
United States
Elizabeth
The price is NT$5,142
NT$7,582 total
includes taxes & fees
Oct 28 - Oct 29
Hyatt Regency Grand Cypress
A multi-story hotel with a swimming pool, outdoor seating, and a landscaped area.

7. Holiday Inn Express & Suites Orlando at SeaWorld by IHG

Holiday Inn Express & Suites Orlando at SeaWorld by IHG
2.5 star property
13.7 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (1,866 reviews)
"Excellent location and service. Great breakfast and super clean room."
United States
Roberto
The price is NT$3,095
NT$3,482 total
includes taxes & fees
Oct 11 - Oct 12
Holiday Inn Express & Suites Orlando at SeaWorld by IHG
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

8. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
7.2 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (4,015 reviews)
"Exellent place to stay!!"
United States
Antonio
The price is NT$1,480
NT$1,680 total
includes taxes & fees
Oct 21 - Oct 22
Seasons Florida Resort
A swimming pool with people in the water, including a person in a green and red inflatable ring.

9. Buena Vista Suites Orlando

Buena Vista Suites Orlando
4.0 star property
11.2 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (2,567 reviews)
"Fantastic place to stay and wonderful rooms with a family!"
United States
Jonathan
The price is NT$3,856
NT$5,163 total
includes taxes & fees
Oct 25 - Oct 26
Buena Vista Suites Orlando
A hotel room with a large bed, a desk with a chair, a television, a lamp, and a window with curtains.

10. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
23 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (5,584 reviews)
"Very clean rooms and loved the area. It was very convenient and well placed for all the places we had to travel!"
United States
Stephen
The price is NT$2,412
NT$2,714 total
includes taxes & fees
Oct 26 - Oct 27
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A breakfast area with a counter displaying hard-boiled eggs, fruits, and muffins. There are two stools and a sign reading "TOP IT BREAKFAST".

11. Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL
3.5 star property
15.3 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (4,200 reviews)
"Loved our stay!"
United States
Talore
The price is NT$2,688
NT$3,024 total
includes taxes & fees
Oct 28 - Oct 29
Tru By Hilton Orlando Convention Center Area, FL
A large hotel with multiple floors, a central courtyard, and a reflective water feature.

12. 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, (2,271 reviews)
"A great place to stay!"
United States
Camille
The price is NT$2,742
NT$3,085 total
includes taxes & fees
Oct 29 - Oct 30
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A modern restaurant with multiple dining tables and chairs, a bar area, and a television mounted on the wall.

13. 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, (4,277 reviews)
"Great place to overnight before a flight."
United States
Sheri
The price is NT$2,726
NT$3,067 total
includes taxes & fees
Oct 13 - Oct 14
Wingate by Wyndham - Orlando International Airport
An aerial view of a resort with multiple swimming pools, landscaped gardens, and outdoor seating areas.

14. Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
14.9 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (4,958 reviews)
"Nice clean rooms, the resort had everything."
United States
Maria
The price is NT$3,801
NT$4,276 total
includes taxes & fees
Oct 18 - Oct 19
Rosen Shingle Creek
A modern hotel with "La Quinta" signage, featuring a prominent entrance and a covered outdoor area.

15. La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
3.0 star property
12.7 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3,166 reviews)
"Place was great. Would stay there again"
United States
Mercedes
The price is NT$2,841
NT$3,196 total
includes taxes & fees
Oct 20 - Oct 21
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

16. 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
9.4 out of 10, Exceptional, (6,123 reviews)
"Nice hotel to stay"
United States
Kevin
The price is NT$3,111
NT$3,500 total
includes taxes & fees
Oct 25 - Oct 26
Home2 Suites by Hilton Orlando at Flamingo Crossings
A modern lobby with a checkered carpet, seating area, and a reception desk.

17. Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Express Orlando International Airport by IHG
2.5 star property
19 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (2,043 reviews)
"Wonderful stay! The staff were very accommodating and made us feel so comfortable. The breakfast was absolutely delicious and offered a great variety."
United States
Lorellie
The price is NT$3,095
NT$3,482 total
includes taxes & fees
Oct 12 - Oct 13
Holiday Inn Express Orlando International Airport by IHG
A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

18. 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, (6,010 reviews)
"Amazing stay"
United States
Nicolas
The price is NT$829
NT$2,352 total
includes taxes & fees
Oct 13 - Oct 14
Kompose Boutique Resort at Theme Parks
An outdoor patio area with seating, a bar, and a fire feature.

19. 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, (2,886 reviews)
"Great staff, good breakfast and excellent location."
United States
Gerardo
The price is NT$3,769
NT$4,240 total
includes taxes & fees
Nov 3 - Nov 4
Hyatt House Orlando Airport
A spacious lobby with a high ceiling, seating areas, and a bar.

20. Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites
3.0 star property
19.3 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (5,771 reviews)
"Great stay!"
United States
Jorge
The price is NT$4,503
NT$5,066 total
includes taxes & fees
Nov 2 - Nov 3
Universal's Endless Summer Resort - Dockside Inn and Suites
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
The entrance to the Hollywood Studios area with a large sign and distinctive architecture.
Photo by Gary Burke
Open Photo by Gary Burke

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.

A large Ferris wheel with blue lights, surrounded by a cityscape with illuminated buildings and a tall green tower.

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.

A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.
Photo by Peter Sutton
Open Photo by Peter Sutton

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

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.

A golf course with bunkers, water hazards, and a large lake.

Reunion

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Top Historic Downtown Kissimmee Hotel Reviews

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Great stay!"
Stephanie 5-night trip
Posted 2 hours ago
Universal's Endless Summer Resort - Dockside Inn and Suites

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 Kissimmee Civic Center 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. Kissimmee Civic Center and Violet's Venom Brewery are also a couple of places to visit in the neighborhood. A few places to visit in the area around Historic Downtown Kissimmee include Monument of States, Bataan-Corregidor Memorial, and Brinson Park. While you're out sightseeing in Kissimmee, be sure to visit other sights like Big Toho Marina or Bob Makinson Aquatic Center.
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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