TOP Historic Hotels in Kissimmee, FL for 2026

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

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Our top choices for Kissimmee historic hotels

Coffee/tea maker, fridge, microwave, oven

3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Royal Palm Bay

kathy m.

£192

includes taxes & fees

18 Aug - 19 Aug

4 bedrooms, memory-foam beds, desk, iron/ironing board

Smart TV, DVD player, books, video library

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

Kissimmee

Stanford S.

£275

includes taxes & fees

15 Sept - 16 Sept

3. 4Bed Private Pool 10 Guests Champions gate - 8981

Davenport

Janelle K.

£351

includes taxes & fees

16 Sept - 17 Sept

Smart TV, DVD player, table football, books

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

Kissimmee

Annette D.

£303

includes taxes & fees

31 Aug - 1 Sept

5. Luxury 5 Beds Villa with Private Pool - Carefully Sanitized - 8843 GC

Kissimmee

Megan F.

£377

includes taxes & fees

7 Sept - 8 Sept

6. 7 BDRM, Private Pool/HotTub, Heat Included, Games

Kissimmee

Michele P.

£350

includes taxes & fees

23 Aug - 24 Aug

Smart TV, video games, DVD player, table football

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

kissimmee

Amanda S.

£309

includes taxes & fees

31 Aug - 1 Sept

8. 6BR Luxury Home: Private Pool - Sleeps 16 - Champions Gate - 8908

Davenport

Torsha G.

£459

includes taxes & fees

7 Sept - 8 Sept

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Top Kissimmee Hotel Reviews

Seasons Florida Resort

8/10 Good

"The motel seemed deserted when I arrived as only 3 cars were present with only about 15 cars there in morning so lots of parking and fenced for security. The office check in and out area lighted and opens at 8 AM. The pool was clean and microwave and refrigerator in rooms worked fine. The rooms were clean and beds good. Extremely good location close to lots of retail, easy to get to and great value for the money. Employees were nice and helpful. There was a resturant with entertainment on premises and it was very busy."

Vacation Village Orlando, Celebration

10/10 Excellent

"l loved everything about this resort, the rooms were amazing. The price was great, and the amenities were awesome!"

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"We had an absolutely wonderful stay at this Florida villa! The property was beautiful, exceptionally clean, and very well maintained. Everything was thoughtfully provided, and the amenities made our stay comfortable, relaxing, and enjoyable. The rooms were spotless, spacious, and incredibly comfortable, making it easy to feel right at home. The entire property was clean and welcoming, and we truly appreciated the attention to detail. Great for families with kids. Lazy river was great, pool open until 11pm was a perk! Close to shopping, grocery and H2O Water park. The amenities were fantastic and gave us everything we needed to enjoy our time in Florida. After a busy day out, it was so nice to come back to such a comfortable and peaceful place. We would definitely recommend this villa to anyone looking for a clean, comfortable, and well-equipped place to stay in Florida. We loved our experience and would happily stay here again!"

Galleria Palms Hotel

10/10 Excellent

"Loved the cookies when we checked in late at night. The kids even went down to ask for one more before bed."

Gaylord Palms Resort & Convention Center

10/10 Excellent

"Todo muy limpio y muy buena atención"

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 lively festivals 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 Two-Bedroom Villa at WESTGATE VACATION VILLAS Resort just One Mile from DISNEY.

How many historical hotels are located in Kissimmee?

In Kissimmee, you'll find 27313 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 ESPN Wide World of Sports Complex.

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.

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Room 1

Change your mind

Treat yourself

Be picky

Check availability on Kissimmee Historic Hotels

Our top choices for Kissimmee historic hotels

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

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

3. 4Bed Private Pool 10 Guests Champions gate - 8981

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

5. Luxury 5 Beds Villa with Private Pool - Carefully Sanitized - 8843 GC

6. 7 BDRM, Private Pool/HotTub, Heat Included, Games

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

8. 6BR Luxury Home: Private Pool - Sleeps 16 - Champions Gate - 8908

9. Magical Adv 5 Star Villa Movie Room Arcade Pool and More

10. Mills Cottage by the Little Lake