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Check availability on Kissimmee Historic Hotels

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, (144 reviews)
"The host was great, the pool and spa were warm and great. The house was clean and had good amenities! Will definitely keep in mind for future visits "
United States
Sarah H.
The price is AED 523
AED 1,559 total
includes taxes & fees
26 May - 27 May
*Tinkerbells Castle 1* 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.
Remodeled 3/2 condo minutes to Parks, shopping and entertainment
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, (122 reviews)
"Everything was perfect"
United States
Natasha B.
The price is AED 485
AED 1,441 total
includes taxes & fees
2 Jun - 3 Jun
ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
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)
"The location was great and very clean. Would stay there again!"
United States
Bryan H.
The price is AED 551
AED 1,597 total
includes taxes & fees
25 May - 26 May
*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works
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, (99 reviews)
"Recommend very good place "
United States
Furkat R.
The price is AED 731
AED 2,285 total
includes taxes & fees
16 Jun - 17 Jun
Luxury Windsor Hills Villa 5BR/5BA 5 Min to Disney Free Resort Amenities
Sport court

7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!

7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!
Kissimmee
9.0 out of 10, Wonderful, (63 reviews)
"Property was well kept and it was a quiet safe neighborhood with a beautiful pool."
United States
Amanda D.
7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!
Outdoor pool, a heated pool

Free Water Park-Walk to Clubhouse-6BR Disney Home-Sleeps 15-Private Pool & Spa

Free Water Park-Walk to Clubhouse-6BR Disney Home-Sleeps 15-Private Pool & Spa
Windsor Hills
9.4 out of 10, Exceptional, (211 reviews)
"The host was very responsive, welcoming and kind! We were repeat customers as we had such a great vacation the last time we stayed at their home. "
United States
Kaycee S.
The price is AED 843
AED 2,203 total
includes taxes & fees
12 Jun - 13 Jun
Free Water Park-Walk to Clubhouse-6BR Disney Home-Sleeps 15-Private Pool & Spa
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, (15 reviews)
"Great vacation home. Kitchen was well stocked. Home was clean and spacious. Property manager was quick on communication. Thank you! "
United States
Thomas L.
The price is AED 1,730
AED 3,447 total
includes taxes & fees
18 Jun - 19 Jun
Magical Adv 5 Star Villa Movie Room Arcade Pool and More
Outdoor pool, a heated pool

Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
10.0 out of 10, Exceptional, (61 reviews)
"Beautiful grounds and awesome amenities."
United States
Serenity C.
The price is AED 576
AED 1,328 total
includes taxes & fees
25 May - 26 May
Mills Cottage by the Little Lake
Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (98 reviews)
"Very nice accommodations. Great stay!!"
United States
John G.
The price is AED 364
AED 1,032 total
includes taxes & fees
2 Jun - 3 Jun
Eastpark. Pet friendly! Lake Nona
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

Seasons Florida Resort

Seasons Florida Resort

10/10 Excellent
"When we arrived I wasn’t sure but the the staff was great, the place was clean and there was always someone around if needed. Though there are not a lot of amenities you cannot expect that for the cost. The pool was clean, rooms clean, no complaints."
Samantha 3-night trip
Posted less than an hour ago
Seasons Florida Resort

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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 entertainment choices 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 27518 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 Orange County Convention Center.
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.