Orlando Hotel Guide. Hotels in Historic Downtown Kissimmee, Orlando, United States of America

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Our top choices for Historic Downtown Kissimmee hotels

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 €169
includes taxes & fees
29 Dec - 30 Dec
Kapp and Kappy B&B

Super Boho - At Lake Toho's Water

Super Boho - At Lake Toho's Water
2.0 star property
Historic Downtown Kissimmee
The price is €221
includes taxes & fees
13 Jan - 14 Jan 2026
Super Boho - At Lake Toho's Water

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
9.2 out of 10, Wonderful, (5096)
"Great location nice breakfast and front desk people is amazing "
United States
Orlando
The price is €102
includes taxes & fees
4 Jan - 5 Jan 2026
Home2 Suites by Hilton Orlando at Flamingo Crossings

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, (2956)
"Clean room, close to Disney and good breakfast at a reasonable price"
United States
pamela
The price is €85
includes taxes & fees
5 Jan - 6 Jan 2026
SPOT X Hotel Orlando/Intl Dr by The Red Collection

The Delaney Hotel

The Delaney Hotel
3.5 star property
26 km from Historic Downtown Kissimmee
9.6 out of 10, Exceptional, (1039)
"Everything about the Delaney Hotel was absolutely amazing!!!!"
United States
Tara
The Delaney Hotel

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, (1975)
"Great location, good, staff, and rooms "
Canada
Jobin
The price is €130
includes taxes & fees
6 Jan - 7 Jan 2026
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
25.3 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (4073)
"Clean hotel, very spacious and the staff was very friendly even in a very late check in "
United States
Ana
The price is €126
includes taxes & fees
12 Jan - 13 Jan 2026
Hilton Vacation Club Aqua Sol Orlando West

Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
13.6 km from Historic Downtown Kissimmee
8.6 out of 10, Excellent, (1574)
"was a very nice stay"
United States
Taylor Elaine
The price is €121
includes taxes & fees
4 Jan - 5 Jan 2026
Meliá Orlando Celebration

Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando
3.0 star property
11.7 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (1440)
"This vacation club offer lot of amenities to the guests as well the place is amazing "
United States
Juliano
The price is €126
includes taxes & fees
12 Jan - 13 Jan 2026
Hilton Vacation Club Grand Beach Orlando

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
23 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (2147)
"Great room and stay!"
United States
christopher michael
The price is €128
includes taxes & fees
13 Jan - 14 Jan 2026
Homewood Suites by Hilton Orlando at Flamingo Crossings

Days Inn by Wyndham Orlando Conv. Center/International Dr

Days Inn by Wyndham Orlando Conv. Center/International Dr
2.0 star property
15.3 km from Historic Downtown Kissimmee
8.0 out of 10, Very good, (2516)
"Great place "
United States
Julio
The price is €77
includes taxes & fees
21 Dec - 22 Dec
Days Inn by Wyndham Orlando Conv. Center/International Dr

Wyndham Lake Buena Vista – Disney Springs® Area

Wyndham Lake Buena Vista – Disney Springs® Area
4.0 star property
13.7 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (2795)
"Great location and consistent service, we’ve stayed many times. "
United States
Tracy
The price is €139
includes taxes & fees
4 Jan - 5 Jan 2026
Wyndham Lake Buena Vista – Disney Springs® Area

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
22 km from Historic Downtown Kissimmee
9.0 out of 10, Wonderful, (452)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is €83
includes taxes & fees
4 Jan - 5 Jan 2026
Spark by Hilton Orlando near Universal

Comfort Suites Near Universal Orlando Resort

Comfort Suites Near Universal Orlando Resort
2.5 star property
21.4 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (1098)
"Great stay "
United States
BRIAN
The price is €105
includes taxes & fees
6 Jan - 7 Jan 2026
Comfort Suites Near Universal Orlando Resort

Element Orlando Universal Blvd.

Element Orlando Universal Blvd.
3.0 star property
17.8 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (1951)
"The room and staff were awesome!!!"
United States
danyell
The price is €89
includes taxes & fees
4 Jan - 5 Jan 2026
Element Orlando Universal Blvd.

Spectrum Resort Villas Orlando and Waterparks

Spectrum Resort Villas Orlando and Waterparks
4.0 star property
Reunion, 18.7 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (838)
"Great location for a family vacation"
United States
Deanne
The price is €419
includes taxes & fees
4 Jan - 5 Jan 2026
Spectrum Resort Villas Orlando and Waterparks

The Vietta Hotel

The Vietta Hotel
2.0 star property
8.4 km from Historic Downtown Kissimmee
7.4 out of 10, Good, (1005)
"Great staff beautiful view clean room "
United States
Navita
The Vietta Hotel

Bryan’s Spanish Cove

Bryan’s Spanish Cove
3.0 star property
12.1 km from Historic Downtown Kissimmee
9.4 out of 10, Exceptional, (1000)
"Amazing resort, very relaxing by the lake. We will be returning. It felt clean and well appointed. I loved the balcony and free coffee/hot chocolate machine in the lobby."
United Kingdom
Patricia
The price is €161
includes taxes & fees
11 Jan - 12 Jan 2026
Bryan’s Spanish Cove

Hilton Vacation Club Grande Villas Orlando

Hilton Vacation Club Grande Villas Orlando
3.5 star property
14.3 km from Historic Downtown Kissimmee
9.2 out of 10, Wonderful, (2906)
"Rooms were huge, great stay! "
United States
Robert
The price is €116
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Vacation Club Grande Villas Orlando

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
14.1 km from Historic Downtown Kissimmee
8.8 out of 10, Excellent, (1909)
"Great stay"
United States
Gerard
The price is €79
includes taxes & fees
23 Dec - 24 Dec
Aloft Orlando Lake Buena Vista
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.

Where to stay in Historic Downtown Kissimmee

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

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.

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.

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.

Florida Center

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

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

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 79 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.

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