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, (145 reviews)
"The room was really nice and the breakfast was great."
United States
Mark
The price is NZ$289
includes taxes & fees
20 Oct - 21 Oct
Kapp and Kappy B&B

2. 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, (1,596 reviews)
"Rooms were clean and breakfast was good."
United States
Cassandra
The price is NZ$182
includes taxes & fees
18 Oct - 19 Oct
Embassy Suites by Hilton Orlando Lake Buena Vista South

3. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
7.2 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (4,014 reviews)
"Exellent place to stay!!"
United States
Antonio
The price is NZ$100
includes taxes & fees
19 Oct - 20 Oct
Seasons Florida Resort

4. Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
14.9 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (4,957 reviews)
"Nice clean rooms, the resort had everything."
United States
Maria
The price is NZ$208
includes taxes & fees
17 Oct - 18 Oct
Rosen Shingle Creek

5. 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, (6,140 reviews)
"Very peaceful and convinient stay, close to where we where headed and not loud environment"
United States
Odett
The price is NZ$126
includes taxes & fees
27 Oct - 28 Oct
Rosen Inn Lake Buena Vista

6. 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, (4,193 reviews)
"Great stay will definitely stay again"
United States
Ian Robinson
The price is NZ$177
includes taxes & fees
11 Oct - 12 Oct
Wyndham Garden Orlando Airport

7. 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, (3,720 reviews)
"We loved this hotel Central to everything we needed and the staff were awesome Highly recommend"
Canada
Lisa
The price is NZ$148
includes taxes & fees
27 Oct - 28 Oct
SPOT X Hotel Orlando/Intl Dr by The Red Collection

8. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
8.5 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (5,349 reviews)
"Great stay for a great price"
United States
Joel
The price is NZ$115
includes taxes & fees
11 Oct - 12 Oct
Palazzo Lakeside Hotel

9. 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, (1,861 reviews)
"Excellent location and service. Great breakfast and super clean room."
United States
Roberto
The price is NZ$197
includes taxes & fees
18 Oct - 19 Oct
Holiday Inn Express & Suites Orlando at SeaWorld by IHG

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, (5,593 reviews)
"Clean room awesome breakfast i would absolutely stay here again"
United States
Deidra
The price is NZ$151
includes taxes & fees
26 Oct - 27 Oct
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

11. Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
9.2 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3,785 reviews)
"Great location close to everything. The place was easy to get to and the check in was super easy."
United States
JORGE
The price is NZ$135
includes taxes & fees
8 Nov - 9 Nov
Radisson Hotel Orlando Lake Buena Vista South

12. 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, (6,130 reviews)
"Always love staying here"
United States
Brianne
The price is NZ$323
includes taxes & fees
30 Oct - 31 Oct
Drury Plaza Hotel Orlando - Disney Springs Area

13. 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, (2,279 reviews)
"A great place to stay!"
United States
Camille
The price is NZ$172
includes taxes & fees
29 Oct - 30 Oct
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

14. 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, (4,273 reviews)
"Great place to overnight before a flight."
United States
Sheri
The price is NZ$179
includes taxes & fees
26 Oct - 27 Oct
Wingate by Wyndham - Orlando International Airport

15. 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, (6,002 reviews)
"Amazing stay"
United States
Nicolas
The price is NZ$126
includes taxes & fees
12 Oct - 13 Oct
Kompose Boutique Resort at Theme Parks

16. 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 NZ$332
includes taxes & fees
30 Oct - 31 Oct
Wyndham Grand Orlando Resort Bonnet Creek

17. SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
3.0 star property
14 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (3,639 reviews)
"Great place to stay!"
United States
Fabiola
The price is NZ$174
includes taxes & fees
4 Nov - 5 Nov
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

18. Rosen Inn International

Rosen Inn International
3.0 star property
18.8 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (6,383 reviews)
"Close to Universal and restaurant on site."
United States
Bob
The price is NZ$110
includes taxes & fees
10 Oct - 11 Oct
Rosen Inn International

19. 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, (2,896 reviews)
"So close to restaurants and the airport"
United States
Karen
The price is NZ$195
includes taxes & fees
19 Oct - 20 Oct
Hampton Inn & Suites Orlando Airport @ Gateway Village

20. 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, (2,041 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 NZ$195
includes taxes & fees
12 Oct - 13 Oct
Holiday Inn Express Orlando International Airport by IHG
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.

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.

Downtown Orlando

One of the most popular neighborhoods in Florida, this bustling area is full of art galleries, shops, bars and restaurants.

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 3.5-star 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 3.5-star 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 3.5-star 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 3.5-star 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 program—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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