Kissimmee Hotel Guide - Historic Hotels in Kissimmee, Orlando

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Kissimmee Historic Hotels

Next weekend
In two weeks

Our top choices for Kissimmee historic hotels

*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, (143 reviews)
"The pool was great for the whole family, and everything worked and matched the listing "
United States
Robert S.
The price is €381
includes taxes & fees
13 Apr - 14 Apr
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

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, (118 reviews)
"Very comfortable stay for our day at Epcot. It was a quick, easy Uber ride to the park. The home was very clean and comfortable. The host was very nice and responsive. I will stay here again for our next Disney adventure."
United States
Sharlene G.
The price is €341
includes taxes & fees
22 Apr - 23 Apr
ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!

*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, (79 reviews)
"The house was absolutely great and perfect for our family. Its located close to Disney. We have finally found our Disney vacation spot!"
United States
Terrianne T.
The price is €371
includes taxes & fees
13 Apr - 14 Apr
*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works

Villa with a Heated Pool and Spa Near Disney!!

Villa with a Heated Pool and Spa Near Disney!!
Kissimmee
9.2 out of 10, Wonderful, (125 reviews)
"Great property for our golf group. This was our third time staying here and everything worked out very well."
United States
Eric M.
The price is €692
includes taxes & fees
29 Mar - 30 Mar
Villa with a Heated Pool and Spa Near Disney!!

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.
The price is €439
includes taxes & fees
13 Apr - 14 Apr
7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!

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)
"Everything was excellent! A wonderful family trip !"
United States
Dawn M.
The price is €717
includes taxes & fees
8 Apr - 9 Apr
Magical Adv 5 Star Villa Movie Room Arcade Pool and More

Jedi Training Camp Top Rated 5 Star Villa

Jedi Training Camp Top Rated 5 Star Villa
Windsor Hills
9.8 out of 10, Exceptional, (84 reviews)
"The first time we stayed 2 years ago was amazing very clean beautiful couldn't wait to stay again. This time was disappointing wasn't clean very well the appliances need to be fix,and cleaned found a bug in the kitchen after reaching out all we was told the bug man would be there the next week. We won't be staying again. "
United States
brad s.
The price is €681
includes taxes & fees
4 Apr - 5 Apr
Jedi Training Camp Top Rated 5 Star Villa

large 6/4 home, free pool heat, 3 miles to Disney

large 6/4 home, free pool heat, 3 miles to Disney
Windsor Hills
9.4 out of 10, Exceptional, (123 reviews)
"We loved this neighborhood and the community area/pool. The house was super spacious and lovely. The owner was responsive to communications about the gate. "
United States
Ricky S W.
large 6/4 home, free pool heat, 3 miles to Disney

2BR/2BA Getaway – 7 Miles from Orlando Parks

2BR/2BA Getaway – 7 Miles from Orlando Parks
Kissimmee
7.0 out of 10, Good, (4 reviews)
"The unit could use some additional cutlery and kitchenware- as well, the master bed mattress should be upgraded. Thanks"
Canada
Dennis E.
The price is €347
includes taxes & fees
4 Apr - 5 Apr
2BR/2BA Getaway – 7 Miles from Orlando Parks

Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
10.0 out of 10, Exceptional, (58 reviews)
"Great place to stay and explore other no-theme park areas of Orlando. "
United States
Karla
The price is €322
includes taxes & fees
2 Apr - 3 Apr
Mills Cottage by the Little Lake
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.

Top Kissimmee Hotel Reviews

Frequently asked questions

What should I expect on my historical trip to Kissimmee?
A trip to the historical sites in Kissimmee is probably first on your sightseeing list. Be sure to check out the fun-filled theme parks and entertainment choices while you're here. You can also take time at the major shopping area in this family-friendly area.
What's the best accommodation in Kissimmee to be near 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 centre and in-room kitchens. A couple of other options to soak up the local history include GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY and AMAZING 2 BEDROOM AT WESTGATE TOWN CENTER & SPA RESORT NEAR DISNEY.
How many historical hotels are located in Kissimmee?
In Kissimmee, you'll find 27479 hotels and other accommodation options bookable on Expedia, including 17 historic hotels or hotels close to historic sites.
What are the most important 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 stay in a place that has an officially recognised historic designation. A castle, a palace or even a pub or an old police station can be identified as a historic hotel as long as it's a place of special interest. Traditional architecture and period features are often preserved in the communal spaces and guestrooms of such hotels in Kissimmee, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. overall though the terms are similar. The architecture and building of a historic hotel is generally the most significant aspect. For a heritage hotel, often it's the cultural value along with how it shaped the community.
Do historic hotels in Kissimmee have modern facilities?
Hotels include modern conveniences and safety features you've come to expect, though efforts have been made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities and the popular amenities found in a hotel will be available in a historic hotel. Rest assured that when you select a historic hotel in Kissimmee, you won't find a place that's uncomfortable for guests or simply rundown.

Explore a world of travel with Expedia