The Best Historic Hotels in Kissimmee, FL from AED 938 in 2026

Check availability on Kissimmee Historic Hotels

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Our top choices for Kissimmee historic hotels

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

Kissimmee

Sarah H.

AED 1,566 total

includes taxes & fees

9 Jun - 10 Jun

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

Royal Palm Bay

Angie S.

AED 938 total

includes taxes & fees

31 May - 1 Jun

Smart TV, video games, DVD player, foosball

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

kissimmee

Bryan H.

AED 1,618 total

includes taxes & fees

9 Jun - 10 Jun

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

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

Kissimmee

Stevon L.

AED 1,433 total

includes taxes & fees

1 Jun - 2 Jun

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

Kissimmee

Amanda D.

AED 1,892 total

includes taxes & fees

3 Jun - 4 Jun

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

Windsor Hills

Furkat R.

AED 2,296 total

includes taxes & fees

16 Jun - 17 Jun

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

Windsor Hills

Mattie B.

AED 2,203 total

includes taxes & fees

12 Jun - 13 Jun

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

Windsor Hills

Elias H.

AED 2,575 total

includes taxes & fees

28 Jun - 29 Jun

View all properties

Top Kissimmee Hotel Reviews

Galleria Palms Hotel

6/10 Okay

"I did not get clean room 1 day, not sure way, soap was not been replaced, had tomask for it, pool not available to use, air need mantainence, too loud, like something was broken"

Delta Hotels by Marriott Orlando Celebration

8/10 Good

"The check in staff and others were very friendly and helpful. Property is older but well maintained. It is large and sometimes a little confusing to find your way around. Would like to have had breakfast included but there is an area where you can purchase different items which saves money vs the restaurant which is nice and has a buffet but you can order omelets or waffles made in the kitchen to your specification. We would stay here again. It is convenient to Disney and other restaurants, venues, etc."

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent

"Booked the room with the mindset that our vacation wasn't going to be at wherever we stayed. The room was very nice and was exactly what we needed. The staff was very helpful and were great. Looking for a great place to sleep that's comfortable and quiet. Would highly recommend. Close to getting to Disney parks."

Vacation Village Orlando, Celebration

10/10 Excellent

"We booked this hotel for a long weekend for my son's soccer tournament. I briefly looked through the description and photos when I did my research. I was looking for location, a pool, and a room that accommodated 6 people. to my surprise, it was more than I could have expected. I honestly thought it was going to be too big rooms and the living areas. it was actually two suites. this meant more privacy for my teens and more space for my younger two. The pool was large and there was a kids pool and a hot tub as well. My kids enjoyed those very much. The rooms were spacious enough for our family of 6. The staff was professional and the staff always willing to help. Anyway, I recommend this hotel for large families the amenities it offers are very family friendly."

Westgate Vacation Villas Resort

6/10 Okay

"Other than Ernesto, this place was a complete disappointment. Ernesto was the only good thing about the entire resort he was incredibly kind and literally helped take us from the pool all the way to our room because it felt like we had to walk three miles just to get there. He actually cared about guests, unlike the rest of the experience. The bar that was supposedly open served the worst margarita I’ve ever had. It was overloaded with sugar, completely undrinkable, and the tequila tasted watered down just like most of the alcohol there $10-17 drinks deserve to taste better than that! The room looked nothing like the pictures we were shown when booking. Instead of a nice resort, it felt like a poorly remodeled Motel 6, it honestly felt like we were shoved into one of the worst rooms possible. The kitchen supplies were extremely limited, with barely any pots, pans, or basic necessities. On top of that, the bed was hard as a rock and unbelievably uncomfortable. I absolutely do not recommend staying here. Ernesto deserves better than this place because he was the only person who made the experience tolerable."

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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.

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Check availability on Kissimmee Historic Hotels

Our top choices for Kissimmee historic hotels

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

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