Hotels in Historic Downtown Kissimmee, Orlando

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Top 10 Hotels in Historic Downtown Kissimmee, Orlando

Porch
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 RM513
RM583 total
includes taxes & fees
11 Dec - 12 Dec
Kapp and Kappy B&B
Private kitchen
Super Boho - At Lake Toho's Water

Super Boho - At Lake Toho's Water

2.0 star property
Historic Downtown Kissimmee
The price is RM281
RM898 total
includes taxes & fees
1 Dec - 2 Dec
Super Boho - At Lake Toho's Water
Terrace/patio
The Delaney Hotel

The Delaney Hotel

3.5 star property
26 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (1010)
"Really nice and clean space in the middle of Orlando. Will stay here for future Orlando vacations."
United States
Alex
The Delaney Hotel
6 outdoor pools, free pool cabanas, pool umbrellas
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4.0 star property
12.8 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (4018)
"Nice place to stay for family. "
United States
Niketan Chhaganbhai
The price is RM436
RM490 total
includes taxes & fees
16 Dec - 17 Dec
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Aerial view
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4.0 star property
25.2 km from Historic Downtown Kissimmee
8.0 out of 10, Very good, (8815)
"Great stay"
United States
Breanna
The price is RM454
RM738 total
includes taxes & fees
1 Dec - 2 Dec
The Grove Resort & Water Park Orlando
Premium bedding, in-room safe, desk, blackout curtains
Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport

3.0 star property
20.5 km from Historic Downtown Kissimmee
8.2 out of 10, Very good, (5156)
"Great place to stay close to airport "
United States
Rebekah
The price is RM369
RM415 total
includes taxes & fees
1 Dec - 2 Dec
Ramada by Wyndham Suites Orlando Airport
Outdoor pool, pool umbrellas, pool loungers
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, (1868)
"Great stay."
United States
Jasmin
The price is RM156
RM342 total
includes taxes & fees
2 Dec - 3 Dec
Kompose Boutique Resort at Theme Parks
Property amenity
Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

2.5 star property
25.6 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (1050)
"Great room great breakfast"
United States
Kelly
The price is RM393
RM437 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Property grounds
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, (2927)
"One of the best hotel!"
United States
Li
The price is RM257
RM364 total
includes taxes & fees
8 Dec - 9 Dec
SPOT X Hotel Orlando/Intl Dr by The Red Collection
5 outdoor pools, pool umbrellas, pool loungers
Summer Bay Orlando by Exploria Resorts

Summer Bay Orlando by Exploria Resorts

3.5 star property
25.6 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (2062)
"The staff are very friendly and the resort is gorgeous! "
United States
Katherina
The price is RM405
RM587 total
includes taxes & fees
10 Dec - 11 Dec
Summer Bay Orlando by Exploria Resorts
Pillow-top beds, in-room safe, desk, blackout curtains
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, (3742)
"Good room, good breakfast and convenient to the airport."
United States
Mark
The price is RM348
RM391 total
includes taxes & fees
1 Dec - 2 Dec
Wingate by Wyndham - Orlando International Airport
7 outdoor pools, pool cabanas (surcharge), pool umbrellas
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4.0 star property
16.5 km from Historic Downtown Kissimmee
8.2 out of 10, Very good, (5543)
"Great staff and resort"
United States
Parker
The price is RM404
RM575 total
includes taxes & fees
3 Dec - 4 Dec
Westgate Lakes Resort & Spa Universal Studios Area
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

4.5 star property
14.9 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (4321)
"Great resort "
United States
Camille
The price is RM460
RM517 total
includes taxes & fees
14 Dec - 15 Dec
Rosen Shingle Creek
3 outdoor pools, open 7 AM to 10:00 PM, pool cabanas (surcharge)
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, (2296)
"Rooms were a nice size and clean, we enjoyed the property grounds and overall atmosphere of the hotel."
United States
Casey
The price is RM666
RM981 total
includes taxes & fees
14 Dec - 15 Dec
Hyatt Regency Grand Cypress
Outdoor pool
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4.0 star property
21.1 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (6931)
"Great stay "
United States
Anthony
The price is RM369
RM416 total
includes taxes & fees
15 Dec - 16 Dec
DoubleTree by Hilton at the Entrance to Universal Orlando
Outdoor pool, free pool cabanas, pool umbrellas
Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG

Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG

3.0 star property
13.4 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (1690)
"Good place to stay "
United States
Arturo
The price is RM327
RM368 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG
Exterior
Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL

3.0 star property
20.6 km from Historic Downtown Kissimmee
7.8 out of 10, Good, (4280)
"We had a great stay. The room, breakfast, and staff were great. "
United States
Jeidyn
The price is RM302
RM339 total
includes taxes & fees
16 Dec - 17 Dec
Country Inn & Suites by Radisson, Orlando Airport, FL
Exterior
Caribe Royale Orlando

Caribe Royale Orlando

4.5 star property
11 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (4521)
"Hotel was very clean, staff was super friendly, a lot of food options!"
United States
Justin
The price is RM740
RM1,009 total
includes taxes & fees
1 Dec - 2 Dec
Caribe Royale Orlando
Front of property – evening/night
Rosen Inn International

Rosen Inn International

3.0 star property
18.8 km from Historic Downtown Kissimmee
8.4 out of 10, Very good, (5924)
"Close to all attractions "
United States
JoAnn
The price is RM307
RM346 total
includes taxes & fees
1 Dec - 2 Dec
Rosen Inn International
Outdoor pool, pool loungers
Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport

3.0 star property
18.5 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (3999)
"Would stay again! "
United States
Matthew
The price is RM301
RM338 total
includes taxes & fees
15 Dec - 16 Dec
Wyndham Garden 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.
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Where to stay in Historic Downtown Kissimmee

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

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® Theme Park featuring rides and interior views as well as a couple
Photo by ©Disney
Open Photo by ©Disney

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.

Downtown Orlando

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

Universal Studios Florida® featuring night scenes, a city and signage

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.

Top Historic Downtown Kissimmee Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"The Grove is a great resort for families! Multiple Pools, Water park and Arcade all onsite. Marketplace has everything you need if you forgot something for your stay. We lucked up and got upgraded to a 3 bed 2 bath room which was bigger than an apartment and super clean!"
Steven 2-night trip
Posted 9 hours ago
The Grove Resort & Water Park Orlando

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Frequently asked questions

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 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 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. Osceola County Clerk of the Court and Kissimmee Civic Center are also a couple of places to visit in the neighbourhood. 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, make sure that you visit other sights such as 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.