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 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 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 81 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. Kissimmee Civic Center and Violet's Venom Brewery are also a couple of places to visit in the neighbourhood. 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, make sure that you visit other sights such as 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.

Top 10 Historic Downtown Kissimmee Hotels of 2026

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

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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

Historic Downtown Kissimmee

Mark

RM744 total

includes taxes & fees

25 Oct - 26 Oct

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

2. Embassy Suites by Hilton Orlando Lake Buena Vista South

8.7 km from Historic Downtown Kissimmee

Linda

RM547 total

includes taxes & fees

1 Nov - 2 Nov

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

3. Drury Plaza Hotel Orlando - Disney Springs Area

13.8 km from Historic Downtown Kissimmee

Jose

RM742 total

includes taxes & fees

30 Oct - 31 Oct

A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

4. Seasons Florida Resort

7.2 km from Historic Downtown Kissimmee

Antonio

RM226 total

includes taxes & fees

28 Oct - 29 Oct

A swimming pool with people in the water, including a person in a green and red inflatable ring.

5. Buena Vista Suites Orlando

11.2 km from Historic Downtown Kissimmee

Pamela

RM621 total

includes taxes & fees

18 Nov - 19 Nov

A multi-story hotel with a swimming pool, parking, and a landscaped area.

6. Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

14 km from Historic Downtown Kissimmee

Abi Carolina Fornino

RM381 total

includes taxes & fees

25 Oct - 26 Oct

A breakfast area with a counter displaying hard-boiled eggs, fruits, and muffins. There are two stools and a sign reading "TOP IT BREAKFAST".

7. Tru By Hilton Orlando Convention Center Area, FL

15.3 km from Historic Downtown Kissimmee

Talore

RM386 total

includes taxes & fees

28 Oct - 29 Oct

A kitchen with wooden cabinets, a microwave, a refrigerator, and two bar stools.

8. Club Sevilla

6.6 km from Historic Downtown Kissimmee

Adanise

RM255 total

includes taxes & fees

22 Oct - 23 Oct

A modern hotel with "La Quinta" signage, featuring a prominent entrance and a covered outdoor area.

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

12.7 km from Historic Downtown Kissimmee

Mark

RM389 total

includes taxes & fees

28 Oct - 29 Oct

A hotel with a central entrance, palm trees, and a clear sky.

10. Comfort Suites Maingate East

11.3 km from Historic Downtown Kissimmee

Vanessa

RM367 total

includes taxes & fees

15 Nov - 16 Nov

An outdoor seating area with green chairs and umbrellas, a fire pit, and a building with large windows in the background.

11. Hampton Inn & Suites Orlando Airport @ Gateway Village

20.4 km from Historic Downtown Kissimmee

Wakima

RM465 total

includes taxes & fees

16 Nov - 17 Nov

An aerial view of a resort with multiple swimming pools, landscaped gardens, and outdoor seating areas.

12. Rosen Shingle Creek

14.9 km from Historic Downtown Kissimmee

Dominic

RM547 total

includes taxes & fees

30 Oct - 31 Oct

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

21.1 km from Historic Downtown Kissimmee

David Arturo

RM410 total

includes taxes & fees

28 Oct - 29 Oct

An outdoor patio area with seating, a bar, and a fire feature.

14. Hyatt House Orlando Airport

20.3 km from Historic Downtown Kissimmee

Gerardo

RM547 total

includes taxes & fees

2 Nov - 3 Nov

15. Hyatt Regency Grand Cypress

14.3 km from Historic Downtown Kissimmee

Christine

RM969 total

includes taxes & fees

28 Oct - 29 Oct

A multi-story hotel with a swimming pool, outdoor seating, and a landscaped area.

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

13.7 km from Historic Downtown Kissimmee

Tyler

RM423 total

includes taxes & fees

28 Oct - 29 Oct

A modern gym with treadmills, stationary bikes, and elliptical machines.

17. Wyndham Garden Orlando Airport

18.4 km from Historic Downtown Kissimmee

Tonya

RM404 total

includes taxes & fees

26 Oct - 27 Oct

A hotel room with a large bed, a smaller bed, a desk, and a chair. There is a decorative item on the bed and a rug on the floor.

18. Palazzo Lakeside Hotel

8.5 km from Historic Downtown Kissimmee

Juan

RM243 total

includes taxes & fees

22 Oct - 23 Oct

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

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

23 km from Historic Downtown Kissimmee

Juana

RM347 total

includes taxes & fees

4 Nov - 5 Nov

A hotel with a swimming pool, palm trees, and a large building with multiple floors.

20. Caribe Royale Orlando, WorldHotels Elite

11.1 km from Historic Downtown Kissimmee

Rachel

RM974 total

includes taxes & fees

19 Nov - 20 Nov

View all properties

Compare popular hotels in Historic Downtown Kissimmee

Property	Property class	Guest rating
Kapp and Kappy B&B	3.5 star property	9.8 Exceptional 147 reviews	View
Drury Plaza Hotel Orlando - Disney Springs Area	4.0 star property	9.8 Exceptional 6,160 reviews	View
Rosen Shingle Creek	4.5 star property	9.6 Exceptional 4,988 reviews	View
Hyatt Regency Grand Cypress	4.0 star property	9.2 Wonderful 2,384 reviews	View
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance	3.0 star property	9.6 Exceptional 2,295 reviews	View

Where to stay in Historic Downtown Kissimmee

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

The entrance to the Hollywood Studios area with a large sign and distinctive architecture.

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.

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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.

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

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.

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A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.

Florida Center

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

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

Reunion

The top golf courses and fun-filled water parks 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.

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Top Historic Downtown Kissimmee Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

8/10 Good

"Wonderful staff, great amenities. Fantastic place to stay."

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

8/10 Good

"Front desk was great during check in. The room was good and kept clean. Had an issue with a maintenance employee who had to slam on brakes and come to a skidding stop in his golf cart, almost ran us over in the parking lot. No apologies at all. Very rude"

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

8/10 Good

"Friendly staff overall. The room was clean and the bed comfortable. Hot and cold breakfast was available with a decent selection to choose from. Only downside is the $20 a day for parking."

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"Couple of nights stay and the staff were very helpful getting us into our room and using the bag checknso that we could go to tue parks before and after check out. Hotel was very clean and great food options whilst in the hotel."

Hotels in Historic Downtown Kissimmee, Orlando

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Our top choices for Historic Downtown Kissimmee hotels

1. Kapp and Kappy B&B

2. Embassy Suites by Hilton Orlando Lake Buena Vista South

3. Drury Plaza Hotel Orlando - Disney Springs Area

4. Seasons Florida Resort

5. Buena Vista Suites Orlando

6. Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

7. Tru By Hilton Orlando Convention Center Area, FL

8. Club Sevilla

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

10. Comfort Suites Maingate East

11. Hampton Inn & Suites Orlando Airport @ Gateway Village

12. Rosen Shingle Creek

13. Wingate by Wyndham - Orlando International Airport

14. Hyatt House Orlando Airport

15. Hyatt Regency Grand Cypress

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

17. Wyndham Garden Orlando Airport

18. Palazzo Lakeside Hotel

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

20. Caribe Royale Orlando, WorldHotels Elite

Compare popular hotels in Historic Downtown Kissimmee

Where to stay in Historic Downtown Kissimmee

Bay Lake

International Drive District

Champions Gate

Florida Center

Reunion

Top Historic Downtown Kissimmee Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

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