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Find Historic Hotels in Kissimmee, FL from $39

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Top Kissimmee Historic Hotels

Barefoot N Resort by Diamond Resorts
3 out of 5
2754 Florida Plaza Blvd, Kissimmee, FL
Free CancellationReserve now, pay when you stay
The price is $59 per night from Jan 24 to Jan 25
4.5/5Wonderful! (983 reviews)

"Very clean quiet resort. Staff was oblivious to the fact that we were waiting to leave, they had a car blocking the parking lot while they were conversing."…"

Reviewed on Jan 10, 2021

Barefoot N Resort by Diamond Resorts
Comfort Suites Maingate East
3 out of 5
2775 Florida Plaza Blvd, Kissimmee, FL
Free CancellationReserve now, pay when you stay
The price is $99 per night from Jan 24 to Jan 25
4.5/5Wonderful! (1,661 reviews)

"Very nice property! Beautiful pool and hot tub! Housekeeping didn’t clean our room at all we kept asking but nothing at all!"…"

Reviewed on Jan 11, 2021

Comfort Suites Maingate East
Barefoot Suites
3 out of 5
2750 Florida Plaza Blvd, Kissimmee, FL
The price is $79 per night from Jan 24 to Jan 25
4.5/5Wonderful! (1,076 reviews)

"Very nice place. A little old, but well maintained. Age mostly seen by wine stains on carpet, small tv, older refrigerator, but clean and bright and nice."…"

Reviewed on Dec 17, 2020

Barefoot Suites
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Staybridge Suites Orlando Royale Parc Suites
3 out of 5
5876 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Free Cancellation
The price is $85 per night from Jan 24 to Jan 25
4/5Very Good! (1,929 reviews)

"Clean and good location walk away from old town and spacious for big family"…"

Reviewed on Jan 4, 2021

Staybridge Suites Orlando Royale Parc Suites
Celebration Suites
3 out of 5
5820 W Irlo Bronson Memorial Hwy, Kissimmee, FL
The price is $80 per night from Jan 24 to Jan 25
3.7/5Good! (4,327 reviews)

"Excellent service, cleaning and very close of all."…"

Reviewed on Jan 19, 2021

Celebration Suites
Holiday Inn Orlando SW - Celebration Area
3 out of 5
5711 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Free Cancellation
The price is $70 per night from Jan 25 to Jan 26
3.6/5Good! (993 reviews)

"very nice and clean please, Very good location, great please"…"

Reviewed on Jan 4, 2021

Holiday Inn Orlando SW - Celebration Area
Super 8 by Wyndham Kissimmee/Maingate/Orlando Area
2 out of 5
5875 W Irlo Bronson Hwy, Kissimmee, FL
Free CancellationReserve now, pay when you stay
The price is $50 per night from Jan 22 to Jan 23
3.6/5Good! (995 reviews)
Second time was a charm

"This was my second time staying at this Hotel. It is a great location close to outlets, the flea market and the food truck family spot and Fun Spot Theme park. Most restaurants are also in walking distance. I would definitely recommend this hotel."…"

Reviewed on Sep 8, 2020

Super 8 by Wyndham Kissimmee/Maingate/Orlando Area
Days Inn by Wyndham Kissimmee West
2.5 out of 5
4125 W Vine St, Kissimmee, FL
Free Cancellation
The price is $52 per night from Feb 21 to Feb 22
3.2/5 (997 reviews)

"We were looking for a reasonable, clean room in the Kissimmee area. Our room was nice, the bed was very comfortable. It's great for no frills lodging."…"

Reviewed on Feb 9, 2020

Days Inn by Wyndham Kissimmee West
Seralago Hotel & Suites Main Gate East
3 out of 5
5678 West Irlo Bronson Memorial Hwy, Kissimmee, FL
Free CancellationReserve now, pay when you stay
The price is $39 per night from Jan 24 to Jan 25
3.1/5 (3,791 reviews)

"Good family friendly hotel. Worth the money. Good amenities"…"

Reviewed on Jan 5, 2021

Seralago Hotel & Suites Main Gate East
Resort at Heritage Park
2 out of 5
2050 E Irlo Bronson Hwy, Kissimmee, FL
Get Rates
2.7/5 (269 reviews)

"This was dirty and scary. People were working on their car in the parking lot, trash looked like it hadn't been collected in a month, it was overflowing all over the parking lot. People were hanging over the balcony, it looked like an hourly rental hotel. Wi fi does not work there, keys didnt work ..."…"

Reviewed on Oct 24, 2016

Resort at Heritage Park
Roomba Inn & Suites at Old Town
3 out of 5
5840 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Get Rates
2.2/5 (1,000 reviews)
I think we did drugs.

"The resort fee is bull spit. My reservation was for a non smoking room. The moment we walked in, we might as well have slept in the mouths of one of the Olsen twins. Nothing but the stench of cigarette smell to punch you in the face. When I asked front desk for a new room, I was told there was nothing ..."…"

Reviewed on Jun 24, 2018

Roomba Inn & Suites at Old Town
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About Kissimmee Historic Hotels

Visiting new cities can be more than just highlighting a place on the map, it can also be about taking in the history and culture of an area. One of the best ways to get a feel for the culture of a region is to learn about its past. Exploring the region's museums or landmarks is a fine beginning, but staying in a Kissimmee historic hotel can carry you back to another time period. Get ready to pack your luggage (you won't need a time machine) as your Kissimmee famous hotel awaits.

Old-World Charm, New World Amenities

A visit to one of these Kissimmee historic accommodations can transport you to a historic period as soon as you step into the lobby. From unique architecture to some of the oldest hotels in Kissimmee infused with a rich past, these surroundings will make you instantly get the sense like you are a time traveler, not a tourist. Thankfully, you won't have to live totally in the past. While these hotels are historic, they have many modern comforts to help you relax during your getaway. You'll notice rooms outfitted with a comfortable bed and just about anything else you'll need for a marvelous getaway.

Once you have explored the hotel property, you can continue to take in this culturally-rich area by checking out the museums and prominent landmarks. Of course, all this time traveling can stimulate your appetite. Make sure to ask your hotel's front desk staff to point you to where some of the area's favorite areas to enjoy a cold one or breakfast in Kissimmee are. Read Expedia's 18021 guest reviews for recommendations from like-minded travelers to help make your Kissimmee visit great.

Reserve Your Kissimmee Historic Hotel Today!

If you want to get the most from your Kissimmee visit, a stay in a vintage hotel will elevate your time spent in this historic region. Having 32190 of these one-of-a-kind lodgings to decide from. Rates on these Kissimmee historic hotels range from $39 to . You're bound to discover one that ideal for your stay. However, like the past civilizations, these rates won't last forever. Reserve soon to get a place in one of these unique properties.

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 renowned opera 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, Celebration Suites is a top 3-star aparthotel for history buffs booking on Expedia, and it features 3 outdoor pools and 2 restaurants. A couple of other options near historic sites include Seralago Hotel & Suites Main Gate East and Barefoot N Resort by Diamond Resorts.
How many historical hotels will I find in Kissimmee?
In Kissimmee, there are 32865 hotel accommodations bookable on Expedia, including 179 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 Old Town, Kissimmee Lakefront Park, and Silver Spurs Arena. Other popular sights include Osceola Heritage Park and Give Kids the World Village.
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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