Find luxury hotels in Historic Downtown Kissimmee, Orlando

Start date: Check-in selected.
To Date
End date: Check-out

Check availability on Historic Downtown Kissimmee Luxury Hotels

Tonight
Dec 7 - Dec 8
Tomorrow
Dec 8 - Dec 9
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Top Historic Downtown Kissimmee Luxury Hotels

Indoor pool, 4 outdoor pools
Disney's Coronado Springs Resort

Disney's Coronado Springs Resort

4.0 star property
Bay Lake
9.0 out of 10, Wonderful, (1004)
"Very clean property, friendly staff and good food options"
United States
Manasa
$301 nightly
The price is $339
Jan 4 - Jan 5, 2026
Total with taxes and fees
Disney's Coronado Springs Resort
Front of property
Gaylord Palms Resort & Convention Center

Gaylord Palms Resort & Convention Center

4.0 star property
Kissimmee
9.2 out of 10, Wonderful, (1304)
"Everything was good, we enjoyed our stay. "
United States
Cassandra
$368 nightly
The price is $417
Dec 8 - Dec 9
Total with taxes and fees
Gaylord Palms Resort & Convention Center
Lobby
Renaissance Orlando Resort – Disney Springs® Area

Renaissance Orlando Resort – Disney Springs® Area

4.0 star property
Lake Buena Vista
8.6 out of 10, Excellent, (622)
"Clean room, room was available for early check in, nice stay for 3 days "
United States
kayla
$124 nightly
The price is $139
Jan 5 - Jan 6, 2026
Total with taxes and fees
Renaissance Orlando Resort – Disney Springs® Area
2 outdoor pools
Disney's Contemporary Resort

Disney's Contemporary Resort

4.5 star property
Bay Lake
8.4 out of 10, Very Good, (1001)
"We enjoyed the stay and proximity to Magic Kingdom "
United States
Anonymous traveler
$510 nightly
The price is $573
Jan 5 - Jan 6, 2026
Total with taxes and fees
Disney's Contemporary Resort
Free daily buffet breakfast
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1341)
"Room, Breakfast, location AAAA+ "
United States
Ahmed Gabriel
$116 nightly
The price is $131
Dec 11 - Dec 12
Total with taxes and fees
Hyatt House Orlando International Drive
Exterior
Universal's Helios Grand Hotel, a Loews Hotel

Universal's Helios Grand Hotel, a Loews Hotel

4.0 star property
Orlando
9.6 out of 10, Exceptional, (84)
"Beautiful propery"
United States
Heather
$572 nightly
The price is $644
Jan 7 - Jan 8, 2026
Total with taxes and fees
Universal's Helios Grand Hotel, a Loews Hotel
3 outdoor pools, open 6:00 AM to 11:00 PM, cabanas (surcharge)
Walt Disney World Dolphin

Walt Disney World Dolphin

4.0 star property
Bay Lake
8.8 out of 10, Excellent, (3979)
"Great place to stay"
United States
Steven
$290 nightly
The price is $327
Dec 16 - Dec 17
Total with taxes and fees
Walt Disney World Dolphin
Outdoor pool, cabanas (surcharge), pool umbrellas
Signia by Hilton Orlando - An Official Walt Disney World® Hotel

Signia by Hilton Orlando - An Official Walt Disney World® Hotel

4.0 star property
Orlando
8.8 out of 10, Excellent, (1002)
"Room was spotless and comfortable. Breakfast was excellent, especially the made-to-order omelettes. The shuttle service to all the parks was convenient and reliable. I’d highly recommend staying here to anyone visiting the parks."
United States
Jonathan
$211 nightly
The price is $237
Dec 14 - Dec 15
Total with taxes and fees
Signia by Hilton Orlando - An Official Walt Disney World® Hotel
Interior
Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl

4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1741)
"Amazing accommodations "
Canada
Marina
$365 nightly
The price is $415
Dec 8 - Dec 9
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl
View from property
Walt Disney World Swan Reserve

Walt Disney World Swan Reserve

4.0 star property
Bay Lake
9.2 out of 10, Wonderful, (893)
"The room was nice and the staff was excellent "
United States
John
$395 nightly
The price is $445
Dec 16 - Dec 17
Total with taxes and fees
Walt Disney World Swan Reserve
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.
View all properties

Top Historic Downtown Kissimmee Hotel Reviews

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"The room was very clean and the staff were very courteous."
Steven 3-night trip
Posted 12 hours ago
Rosen Inn Lake Buena Vista

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Historic Downtown Kissimmee?
Let Expedia help you arrange your flight to Kissimmee, FL (ISM-Kissimmee Gateway) airport or Orlando Intl. Airport (MCO) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to get what you want to make your stay special. If you want an upscale hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Historic Downtown Kissimmee has to offer. While you're visiting, you might want to think about enjoying the entertainment and festivals, which Historic Downtown Kissimmee is known for.
What's there to see and do in Historic Downtown Kissimmee?
Enjoy Historic Downtown Kissimmee and visit Lake Tohopekaliga, Kissimmee Civic Center, and Violet's Venom Brewery. If you have spare time during your trip, you might want to make a stop at Monument of States and Bataan-Corregidor Memorial.

Explore a world of travel with Expedia