Search for Cheap Deals on
5 Star Hotels in Historic Downtown Kissimmee

Check Last Minute Historic Downtown Kissimmee Hotel Deals

Tonight Jun 13 - Jun 14This weekend Jun 13 - Jun 15

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!

Featured 5 Star Historic Downtown Kissimmee Hotels

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
5 out of 5
Fully refundableReserve now, pay when you stay
  • 24 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury resort in Orlando. Enjoy 2 outdoor pools, a full-service spa, and 12 restaurants. Our guests praise the helpful staff in our reviews. ...
Get rates
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Conrad Orlando
5 out of 5
Fully refundableReserve now, pay when you stay
  • 29 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury hotel in Orlando. Enjoy a full-service spa, 5 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. ...
Get rates
Conrad Orlando
The Ritz-Carlton Orlando, Grande Lakes
5 out of 5
Fully refundableReserve now, pay when you stay
  • 21 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury hotel in Orlando. Enjoy a full-service spa, 7 restaurants, and a golf course. Our guests praise the helpful staff and the property ...
Get rates
The Ritz-Carlton Orlando, Grande Lakes
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
5 out of 5
Fully refundableReserve now, pay when you stay
  • 30 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury resort in Lake Buena Vista. Enjoy 3 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff in our ...
Get rates
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Reunion Resort & Golf Club
5 out of 5
  • 31 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury aparthotel in Kissimmee. Enjoy 11 outdoor pools, 7 restaurants, and a golf course. Our guests praise the helpful staff in our reviews. ...
Get rates
Reunion Resort & Golf Club
Encore Resort and Water Park At Reunion by Rentyl
5 out of 5
  • 31 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury resort in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Get rates
Encore Resort and Water Park At Reunion by Rentyl
ette hotel
5 out of 5
Fully refundableReserve now, pay when you stay
  • 32 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury hotel in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Get rates
ette hotel
Splendid 5Bd Close to Disney at Storey Lake 4251
5 out of 5
  • 11 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury vacation home in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Old Town and Disney Springs™ are ...
Get rates
Splendid 5Bd Close to Disney at Storey Lake 4251
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
5 out of 5
  • 10 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury vacation home in Kissimmee. Enjoy free parking, private pools, and free water park access. Popular attractions Old Town and Disney ...
Get rates
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
5 out of 5
  • 41 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury vacation home in Davenport. Enjoy free parking, private pools, and free water park access. Popular attractions Reunion Resort Golf ...
Get rates
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
The Bear's Den Resort Orlando
5 out of 5
  • 33 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury vacation home in Kissimmee. Enjoy free WiFi, free parking, and a golf course. Popular attractions ESPN Wide World of Sports Complex ...
Get rates
The Bear's Den Resort Orlando
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
5 out of 5
  • 15 min drive from Kissimmee Lakefront Park
Stay at this 5-star luxury villa in Kissimmee. Enjoy free WiFi, free parking, and free water park access. Popular attractions Old Town and Disney Springs™ are ...
Get rates
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
Don't see what you're looking for?
See all available properties in Historic Downtown Kissimmee
View all properties
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.