A pathway through a park with Spanish moss hanging from trees and a body of water in the background.

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Check availability on Kissimmee Historic Hotels

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

Our top choices for Kissimmee historic hotels

Smart TV, DVD player, foosball, books

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Kissimmee
9.6 out of 10, Exceptional, (151 reviews)
"Amir was very responsive. The house was clean and well stocked! Great trip to Florida!"
United States
Anne B.
The price is AED 611
AED 1,673 total
includes taxes & fees
8 Jul - 9 Jul
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Smart TV, video games, DVD player, foosball

*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works

*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works
kissimmee
9.4 out of 10, Exceptional, (81 reviews)
"We had a great time staying in this vacation rental!"
United States
Amanda S.
The price is AED 665
AED 1,741 total
includes taxes & fees
19 Jul - 20 Jul
*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works
Smart TV, Netflix, DVD player, books

Remodeled 3/2 condo minutes to Parks, shopping and entertainment

Remodeled 3/2 condo minutes to Parks, shopping and entertainment
Royal Palm Bay
9.4 out of 10, Exceptional, (44 reviews)
"The location was perfect for our needs and true to it's online description."
United States
Angie S.
The price is AED 327
AED 941 total
includes taxes & fees
6 Jul - 7 Jul
Remodeled 3/2 condo minutes to Parks, shopping and entertainment
Sport court

7 BDRM, Private Pool/HotTub, Heat Included, Games

7 BDRM, Private Pool/HotTub, Heat Included, Games
Kissimmee
9.0 out of 10, Wonderful, (63 reviews)
"Host was very welcoming. The house was very spacious and comfortable and the neighborhood was great. The pool and hot tub were perfect. Host was very responsive to questions /concerns. "
United States
Michele P.
The price is AED 701
AED 1,892 total
includes taxes & fees
19 Jul - 20 Jul
7 BDRM, Private Pool/HotTub, Heat Included, Games
Outdoor pool, a heated pool

The Adventure Villa - South Facing Pool with Jets - Min. to Disney - Game Room

The Adventure Villa - South Facing Pool with Jets - Min. to Disney - Game Room
Kissimmee
9.8 out of 10, Exceptional, (241 reviews)
"We absolutely loved our stay at The Adventure Villa! The place was spacious and clean, and perfect for our family. We couldn’t recommend this home enough, and look forward to visiting again in the future. "
United States
Megan R.
The price is AED 446
AED 1,764 total
includes taxes & fees
12 Jul - 13 Jul
The Adventure Villa - South Facing Pool with Jets - Min. to Disney - Game Room
A heated pool

#2780 Priv Spa Pool 2 Masters Disney Universal.

#2780 Priv Spa Pool 2 Masters Disney Universal.
Kissimmee
8.6 out of 10, Excellent, (8 reviews)
"This home was our base camp for Disney World. Family of 8. Location was great. Comfortable beds. 3.5 baths were a convenience. Pack and play crib and high chair..Clean. Livingroom seating was minimal with one small, hard couch that seated three adults. Gas BBQ is an additional cost. Nice home."
United States
corinne n.
#2780 Priv Spa Pool 2 Masters Disney Universal.
Outdoor pool, a heated pool

Luxury Windsor Hills Villa 5BR/5BA 5 Min to Disney Free Resort Amenities

Luxury Windsor Hills Villa 5BR/5BA 5 Min to Disney Free Resort Amenities
Windsor Hills
9.4 out of 10, Exceptional, (100 reviews)
"Recommend very good place "
United States
Furkat R.
Luxury Windsor Hills Villa 5BR/5BA 5 Min to Disney Free Resort Amenities
4 bedrooms, memory foam beds, desk, iron/ironing board

ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!

ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
Kissimmee
9.6 out of 10, Exceptional, (127 reviews)
"Everything was amazing & perfect for our girls trip to Disney! Everything was so close to the property, and the property was bigger than i even expected! "
United States
Payton T.
ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
Pool

Jedi Training Camp Top Rated 5 Star Villa

Jedi Training Camp Top Rated 5 Star Villa
Windsor Hills
9.8 out of 10, Exceptional, (92 reviews)
"We had a great time at your place. It was clean, had everything we needed in it and it was a close drive to the parks we went to. Thank you again "
United States
DANIELLE N.
Jedi Training Camp Top Rated 5 Star Villa
Pool

Magical Adv 5 Star Villa Movie Room Arcade Pool and More

Magical Adv 5 Star Villa Movie Room Arcade Pool and More
Windsor Hills
9.2 out of 10, Wonderful, (16 reviews)
"Everything was excellent! A wonderful family trip !"
United States
Dawn M.
The price is AED 1,286
AED 2,881 total
includes taxes & fees
11 Jul - 12 Jul
Magical Adv 5 Star Villa Movie Room Arcade Pool and More
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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Top Kissimmee Hotel Reviews

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"I loved my stay the only thing I will say is the room floor could have been cleaned better. But otherwise everything was amazing"
Anjelene 8-night trip
Posted 11 hours ago
Hilton Vacation Club Mystic Dunes Orlando

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Frequently asked questions

What should I expect on my historical trip to Kissimmee?
A trip to the sights with historical relevance in Kissimmee is probably first on your sightseeing itinerary. Be sure to check out the fun-filled theme parks and lively festivals while you're here. You can also take time at the popular shops in this family-friendly area.
What's the best place to stay in Kissimmee that's close to historical sites?
Based on our travel expertise, AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY is a top resort on Expedia for those interested in history, and it features a fitness center and in-room kitchens. A couple of other options near historic sites include GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY and Two-Bedroom Villa at WESTGATE VACATION VILLAS Resort just One Mile from DISNEY.
How many historical hotels will I find in Kissimmee?
In Kissimmee, there are 26892 hotel accommodations bookable on Expedia, including 17 hotels designated as historic or close to historic sites.
What are the must-see historical places and other sights to visit in Kissimmee?
Top places to visit include Walt Disney World® Resort, Disney's Animal Kingdom® Theme Park, and Old Town. Additionally, in the area you'll find Disney Springs™ and ESPN Wide World of Sports Complex.
What is a historic hotel like in Kissimmee?
Guests who choose a historic hotel can spend a night or two in a building that has an officially recognized historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be turned into a historic hotel as long as it has special significance. Traditional architecture and period features are typically found in the guestrooms or communal spaces of these historic hotels in Kissimmee, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, while "historic hotel" is a term often used in the U.S. overall though the terms are similar. The architecture and actual building of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value along with how it influenced the community.
Do historic hotels in Kissimmee have modern facilities?
Hotels include modern conveniences and safety features you expect to find, though efforts have been made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, free WiFi, and the usual amenities found in most hotels should be available at a historic hotel. When you book a historic hotel in Kissimmee, don't worry that you'll find yourself staying at a place that's uncomfortable for guests or simply rundown.