Search Historic Hotels in Kissimmee

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Kissimmee Historic Hotels

Our top choices for Kissimmee historic hotels

Smart TV, DVD player, table football, 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, (138 reviews)
"The pool was great for the whole family, and everything worked and matched the listing "
United States
Robert S.
The price is £330
includes taxes & fees
23 Feb - 24 Feb
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
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, (116 reviews)
"Family friendly. Clean apartment. Host was very responsive and friendly. Highly recommend for family functions. Very close to WDW attractions ."
United States
Maria M.
The price is £311
includes taxes & fees
25 Feb - 26 Feb
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, (84 reviews)
"The house was exactly as described. The kids loved the theater room"
United States
Samantha S.
The price is £614
includes taxes & fees
17 Feb - 18 Feb
Jedi Training Camp Top Rated 5 Star Villa
A heated pool

🌴 Relax & Recharge Near Disney – Top-Floor 3BR Condo at Windsor Palms 🌴

🌴 Relax & Recharge Near Disney – Top-Floor 3BR Condo at Windsor Palms 🌴
Kissimmee
9.8 out of 10, Exceptional, (19 reviews)
"I really enjoyed the Disney theme at the place"
United States
Anonymous traveller
The price is £234
includes taxes & fees
4 Mar - 5 Mar
🌴 Relax & Recharge Near Disney – Top-Floor 3BR Condo at Windsor Palms 🌴
Smart TV, video games, DVD player, table football

*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, (77 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 £335
includes taxes & fees
6 Mar - 7 Mar
*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works
Outdoor pool, a heated pool

"2 Miles to Disney, 2 min walk to Clubhouse, Big private pool, Free Water Park!"

"2 Miles to Disney, 2 min walk to Clubhouse, Big private pool, Free Water Park!"
Windsor Hills
9.2 out of 10, Wonderful, (197 reviews)
"Very nice location, great house with plenty of room. The grandchildren loved the playroom. Master bedroom was very spacious. "
United States
Trish P.
The price is £395
includes taxes & fees
23 Feb - 24 Feb
"2 Miles to Disney, 2 min walk to Clubhouse, Big private pool, Free Water Park!"
Outdoor pool, a heated pool

Luxury 6BR, Theater, Game Rooms, Pool–Min to Disney/Universal Epic Universe!

Luxury 6BR, Theater, Game Rooms, Pool–Min to Disney/Universal Epic Universe!
Reunion
9.2 out of 10, Wonderful, (79 reviews)
"It was awesome location. Lot of space to relax. Kids absolutely loved it Best vacation spot for us with a mix of kids from 3 months to 16 yo"
United States
Rebecca L.
The price is £482
includes taxes & fees
24 Feb - 25 Feb
Luxury 6BR, Theater, Game Rooms, Pool–Min to Disney/Universal Epic Universe!
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)
"Everything was excellent! A wonderful family trip !"
United States
Dawn M.
Magical Adv 5 Star Villa Movie Room Arcade Pool and More
1 bedroom, iron/ironing board, free WiFi, bed sheets

Vacation Retreat in the Heart of Orlando – Close to Theme Parks

Vacation Retreat in the Heart of Orlando – Close to Theme Parks
International Drive District
The price is £167
includes taxes & fees
2 Mar - 3 Mar
Vacation Retreat in the Heart of Orlando – Close to Theme Parks
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, (54 reviews)
"Great place to stay and explore other no-theme park areas of Orlando. "
United States
Karla
The price is £269
includes taxes & fees
23 Feb - 24 Feb
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.
View all properties

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.
Book now

Top Kissimmee Hotel Reviews

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent
"Yes. All of that."
Shakir 1-night trip
Posted 22 hours ago
Ramada by Wyndham Kissimmee Gateway

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 renowned opera 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 private pools. 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 27690 hotels and other accommodation options bookable on Expedia, including 19 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 Epcot®.
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