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

Historic Downtown Kissimmee Hotels, Orlando

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Our top choices for Historic Downtown Kissimmee hotels

1. Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (147 reviews)
"An amazing experience. Freindly hosts. If we go to Orlando again we will rwbook"
United States
THOMAS
The price is NZ$214
includes taxes & fees
8 Nov - 9 Nov
Kapp and Kappy B&B

2. Club Sevilla

Club Sevilla
3.5 star property
6.6 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (1,003 reviews)
"Very nice resort"
United States
Eric
The price is NZ$114
includes taxes & fees
7 Nov - 8 Nov
Club Sevilla

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, (1,677 reviews)
"Amazing stay, really enjoyed our time and the staff was so welcoming & friendly."
United States
Mya
The price is NZ$238
includes taxes & fees
15 Nov - 16 Nov
Embassy Suites by Hilton Orlando Lake Buena Vista South

4. Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
2.0 star property
7.2 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (4,087 reviews)
"great stay"
United States
Viridiana
The price is NZ$95
includes taxes & fees
9 Nov - 10 Nov
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

5. 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, (2,028 reviews)
"Very close to airport Free airport shuttle and breakfast was a plus"
United States
cathy
The price is NZ$195
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express Orlando International Airport by IHG

6. La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport
3.0 star property
20.5 km from Historic Downtown Kissimmee
7.6 out of 10, Good, (2,946 reviews)
"Great location"
United States
Cesar
The price is NZ$96
includes taxes & fees
23 Nov - 24 Nov
La Quinta Inn & Suites by Wyndham Orlando Airport

7. 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, (2,395 reviews)
"Great hotel!"
United States
Christine
The price is NZ$360
includes taxes & fees
28 Nov - 29 Nov
Hyatt Regency Grand Cypress

8. 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, (3,783 reviews)
"It’s always a blast staying here."
United States
Michelle Elis Onofre
The price is NZ$126
includes taxes & fees
30 Nov - 1 Dec
SPOT X Hotel Orlando/Intl Dr by The Red Collection

9. Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
14.9 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (4,976 reviews)
"Great staff, location, resort was amazing"
United States
Dominic
The price is NZ$222
includes taxes & fees
24 Nov - 25 Nov
Rosen Shingle Creek

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, (5,720 reviews)
"Great location, breakfast, clean, and very nice and helpful staff!"
United States
Robert
The price is NZ$152
includes taxes & fees
24 Nov - 25 Nov
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

11. Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
18.4 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (4,244 reviews)
"Excellent staff, dining options and clean property with convenient location."
United States
Linette
The price is NZ$176
includes taxes & fees
16 Nov - 17 Nov
Wyndham Garden Orlando Airport

12. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
8.5 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (5,378 reviews)
"Great stay"
United States
Juan
The price is NZ$88
includes taxes & fees
22 Nov - 23 Nov
Palazzo Lakeside Hotel

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, (4,362 reviews)
"Great stay."
United States
Diana
The price is NZ$158
includes taxes & fees
16 Nov - 17 Nov
Wingate by Wyndham - Orlando International Airport

14. 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, (2,931 reviews)
"Clean room, friendly staff, and great breakfast options"
United States
Imran
The price is NZ$219
includes taxes & fees
22 Nov - 23 Nov
Hampton Inn & Suites Orlando Airport @ Gateway Village

15. Comfort Suites Maingate East

Comfort Suites Maingate East
3.0 star property
11.3 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (2,604 reviews)
"We loved our stay at the Kenmore, the hotel is beautiful and so close to the beach"
Canada
Maria
The price is NZ$160
includes taxes & fees
6 Dec - 7 Dec
Comfort Suites Maingate East

16. 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, (6,377 reviews)
"Excellent place to stay!!"
United States
Theresa
The price is NZ$120
includes taxes & fees
10 Nov - 11 Nov
Kompose Boutique Resort at Theme Parks

17. 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, (1,915 reviews)
"Great place to stay!"
United States
Maria
The price is NZ$195
includes taxes & fees
11 Nov - 12 Nov
Holiday Inn Express & Suites Orlando at SeaWorld by IHG

18. 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, (4,214 reviews)
"It was an incredible place and plenty of food and room"
United States
Jacqueline
The price is NZ$169
includes taxes & fees
25 Nov - 26 Nov
Tru By Hilton Orlando Convention Center Area, FL

19. Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista
3.5 star property
13.7 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (6,279 reviews)
"Awesome place to stay"
United States
Yotuel
The price is NZ$122
includes taxes & fees
16 Nov - 17 Nov
Rosen Inn Lake Buena Vista

20. Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport
3.0 star property
20.4 km from Historic Downtown Kissimmee
8.2 out of 10, Very good, (6,209 reviews)
"Very nice and close to the airport"
United States
Donald
The price is NZ$155
includes taxes & fees
30 Nov - 1 Dec
Ramada by Wyndham Suites Orlando Airport
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.

Compare popular hotels in Historic Downtown Kissimmee

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A two-story house with a porch, surrounded by lush greenery and hanging moss.
Kapp and Kappy B&B
3.5 star property
9.8
Exceptional
147 reviews
View
A kitchen with wooden cabinets, a microwave, a refrigerator, and two bar stools.
Club Sevilla
3.5 star property
9.0
Wonderful
1,003 reviews
View
A spacious lobby with a reception desk, seating area, and a decorative flower arrangement.
Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
9.6
Exceptional
1,677 reviews
View
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
2.0 star property
9.0
Wonderful
4,087 reviews
View
A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.
Kompose Boutique Resort at Theme Parks
3.0 star property
9.4
Exceptional
6,377 reviews
View

Our guide on where to stay in Historic Downtown Kissimmee

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

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.

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.

Florida Center

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

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.

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.

Top Historic Downtown Kissimmee Hotel Reviews

Recent Reviews in Historic Downtown Kissimmee

Frequently asked questions

What other neighbourhoods are similar to Historic Downtown Kissimmee?
While Historic Downtown Kissimmee truly offers a unique blend of history, local shops, and Lake Toho access, for travellers seeking a similar blend of local character, convenience, and a relaxed atmosphere, Celebration and the Old Town area of Kissimmee are excellent alternatives.

Celebration, a master-planned community just a short drive from Historic Downtown Kissimmee, offers a charming, pedestrian-friendly village centre. Its main street, Market Street, is lined with shops, restaurants, and cafes, all built in a distinct architectural style. The community is designed around a central lake, providing pleasant walking paths and a tranquil setting.

Couples looking for a peaceful and picturesque escape will particularly enjoy Celebration. It's an ideal spot for leisurely strolls, enjoying a meal overlooking the water, and experiencing a thoughtfully designed residential area with a strong sense of community. The focus here is on quality of life and a relaxed pace, offering a nice contrast to the nearby theme parks.

Old Town, located on Highway 192, provides a different but equally engaging experience with a focus on classic American fun. This entertainment district features brick-paved streets, classic car cruises on Friday and Saturday nights, and a variety of shops, eateries, and amusement rides. It has a lively, nostalgic feel, reminiscent of a traditional fairground.

Families, especially those with younger children or teenagers, will find Old Town particularly appealing. The area offers plenty of entertainment options, from carnival games and rides to live music, ensuring there's always something to do.
What are the best hotels in Historic Downtown Kissimmee that travellers recommend?
For an exceptional stay in Historic Downtown Kissimmee, travellers consistently recommend Kapp and Kappy B&B.

This bed and breakfast, with an outstanding 9.8 rating, is highly praised by guests for its excellent and free full breakfast. Guests also frequently comment on the spotless rooms, ensuring a comfortable and clean stay. The B&B is conveniently located near several points of interest, including Kissimmee Civic Centre, Monument of States, and Kissimmee Lakefront Park, all within 0.8 km. Early check-in is available, adding to the convenience.
What hotels in Historic Downtown Kissimmee offer free breakfast?
For a hotel in Historic Downtown Kissimmee that offers free breakfast, consider the Kapp and Kappy B&B.

The Kapp and Kappy B&B, with an exceptional 9.8 rating, provides a complimentary full breakfast to all guests. This highly-rated bed and breakfast is praised for its spotless rooms and offers free WiFi and free self-parking, including space for RVs, buses, and trucks. Its convenient location places it close to the Bataan-Corregidor Memorial, just 1.0 km away, and the Monument of States, 0.8 km distant.
What are the top pet-friendly hotels in Historic Downtown Kissimmee?
For a top pet-friendly hotel in Historic Downtown Kissimmee, the Kapp and Kappy B&B is an excellent choice.

This bed and breakfast, with an outstanding 9.8 rating, warmly welcomes both dogs and cats. Guests frequently mention the excellent breakfast and the spotless rooms. The B&B also provides food and water bowls for your pets, ensuring they are well looked after. It is conveniently located near the Kissimmee Civic Centre, Monument of States, and Kissimmee Lakefront Park, all within 0.8 km.
What are the best hotels in Historic Downtown Kissimmee near Kissimmee Lakefront Park?
For a highly-rated hotel in Historic Downtown Kissimmee near Kissimmee Lakefront Park, consider the Kapp and Kappy B&B.

This bed and breakfast has an exceptional rating of 9.8 and is located just 0.8 kilometres from Kissimmee Lakefront Park. Guests consistently praise the excellent breakfast, which is provided free of charge, and the spotless rooms. Free WiFi and complimentary self-parking are also available, adding to the convenience. The Kapp and Kappy B&B is also a short distance from the Kissimmee Civic Centre and the Monument of States.
When is the best time to go to Historic Downtown Kissimmee?
The best time to visit Historic Downtown Kissimmee is during the cooler, drier months from November to April.

During this period, the weather is generally pleasant, with lower humidity and comfortable temperatures, making it ideal for exploring the downtown area and enjoying outdoor activities. These months typically avoid the heat and humidity of the summer, as well as the higher chance of rain and tropical storms.

Families planning a trip during school holidays will find April particularly good, as the weather is consistently warm but not excessively hot, great for visiting nearby attractions and enjoying the downtown's lakeside park.

Couples looking for a peaceful getaway might prefer November or early December.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline − this is often within 24 to 48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our 'Fully refundable property' filter during your search to find the right Historic Downtown Kissimmee hotel for you.
How can I save on a hotel booking in Historic Downtown Kissimmee with Expedia?
One Key™—Expedia's free travel rewards programme—gives you instant access to discounts with Member Prices on Historic Downtown Kissimmee hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Historic Downtown Kissimmee?
Hotel prices in Historic Downtown Kissimmee often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates and sort search results by 'Price: low to high' for our cheapest rates.

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