Book the Best HISTORIC Hotels in Kissimmee in 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

A bedroom with a large bed, two bedside tables, a chandelier, and a view of the outdoors.

A modern kitchen with white cabinets, stainless steel appliances, a large island with a sink, and a view of the outdoors through a large window.

A hallway with a large 'HOME' sign on the wall.

A modern living room with a sectional sofa, a glass coffee table, and a kitchen area with a bar.

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

Kissimmee

Scott F.

CA $183

CA $550 total

includes taxes & fees

Oct 12 - Oct 13

An aerial view of a resort with a basketball court, swimming pool, and palm trees.

A two-story house with a garage, a front porch, and a well-maintained lawn with palm trees.

A modern kitchen with a central island, a dining area with a glass table, and a living area with a red sofa.

A residential area with a stone wall labeled "Temra Verde" and a pathway leading to a house with a red-tiled roof.

2. Disney 7 BDRM, Private Pool/HotTub, Games Room, Clean, Fab!

Kissimmee

Amanda D.

CA $302

CA $817 total

includes taxes & fees

Oct 25 - Oct 26

A spacious living room with a large flat-screen TV, a glass coffee table, and a comfortable sofa. A kitchen with modern appliances is visible in the background.

A dining area with a table set for four, a bench, and a chandelier.

A spacious living room with a large TV, a sofa, and a glass coffee table.

A covered pool area with a hot tub, lounge chairs, and a view of the surrounding landscape.

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

Kissimmee

bryan s.

CA $192

CA $588 total

includes taxes & fees

Oct 11 - Oct 12

A spacious living area with a large flat-screen TV, a sofa, and a wooden coffee table.

A covered swimming pool area with a ceiling structure, a patio with chairs, and a view of neighboring buildings.

A spacious living area with a sofa, coffee table, and TV, connected to a kitchen with wooden cabinets and a large window.

A single-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

kissimmee

Amanda S.

CA $192

CA $588 total

includes taxes & fees

Oct 19 - Oct 20

A resort with a large swimming pool, palm trees, and a building with multiple balconies.

A modern kitchen with wooden cabinets, stainless steel appliances, and a granite countertop.

A hallway with a staircase, a chandelier, and a door with a mirror.

A dining area with a wooden table, grey chairs, and a blue vase with green plants.

5. Jedi Training Camp Top Rated 5 Star Villa

Windsor Hills

Chad G.

CA $483

CA $1,026 total

includes taxes & fees

Oct 12 - Oct 13

A resort pool area with a large pool, lounge chairs, and a building with a red roof.

A modern lobby with a fireplace, two sofas, and a small table.

A poolside dining area with tables and chairs, overlooking a swimming pool and palm trees.

A large, modern building with a curved roof and multiple satellite dishes.

6. #2780 Priv Spa Pool 2 Masters Disney Universal.

Kissimmee

corinne n.

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

A stone staircase leading to a pond surrounded by lush greenery and stone railings.

A small, rustic building with a metal roof and a red door, surrounded by lush greenery and a pond.

A rustic bar with wooden shelves stocked with bottles, a coffee machine, and bar stools.

7. Mills Cottage by the Little Lake

Lake Weldona

rick s.

CA $278

CA $588 total

includes taxes & fees

Oct 12 - Oct 13

A residential area with houses, a lake, and a fountain.

A fenced outdoor area with a palm tree, a sign, and a body of water.

A dining area with a round table, wooden chairs, a chandelier, and a window with curtains.

A living room with a brown leather sofa, patterned armchair, and a coffee table. There's a chandelier, a desk with a computer, and a TV.

8. Eastpark. Pet friendly! Lake Nona

East Park

Dania B.

CA $141

CA $404 total

includes taxes & fees

Oct 12 - Oct 13

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Top Kissimmee Hotel Reviews

Embassy Suites by Hilton Orlando Lake Buena Vista South

10/10 Excellent

"My mom, aunt and I stayed there and got adjoining rooms. The rooms were large, comfortable and clean and the beds were great. The large sofa in the living room was also nice as was the oversized fridge. A favorite of ours was the happy hour each night (free sangria or margaritas with snacks) and the made to order omelets for breakfast (all included). The location was also excellent- minutes to great restaurants, the parks, grocery and stores. We were not there for entertainment but due to the proximity of the hotel, we went to Old Town one night (7 mins drive) and enjoyed the year round haunted house, shops, fresh pina coladas. This Embassy Suites would also be a great affordable place to stay for families going to Disney who want to conserve their cash for the parks. You cannot go wrong with this hotel. Staff were at the ready with any need. Two quick notes: while the decor was a little outdated, it is very well maintained and we did have to request housekeeping after two days but they came immediately and did a great job."

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"I had a great stay and I truly enjoyed it."

Legacy Vacation Resorts - Kissimmee/Orlando

10/10 Excellent

"Excellent place to stay"

Quality Inn & Suites By the Parks

8/10 Good

"Muy buena. Alguito que mejorar en los baños como cocina de baño, el lavamos. De lo demás todo bien."

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"The space was excellent. Excellent value for what I paid for my family to stay in a two bedroom villa. I love the size of the entire property and especially loved how peaceful environment and the privacy that our villa provided. River Island was awesome, my entire family loved every bit of it. For a three night getaway I didn’t get to do all that this property has to offer, but I was perfectly fine with what we did enjoy doing. I must say, however, that being a first time renter at this property, I foolishly agreed to their “tour of the property“ that they offer you. After you complete the tour you would receive a $200 gift card to use on the property. I knew that this was an old school timeshare proposition, but they swore that they wouldn’t give you the hard sell at the end of the tour, and I foolishly believed it. Needless to say that what was supposed to be a 90 minute tour turned into 2 1/2 hours of wasted time and they just wouldn’t take no for an answer at least for a good 20 or 30 minutes or so. Then finally they gave in and I got myself the gift card. Now, if it wasn’t that, it was a rainy day to begin with, I perhaps would’ve been more upset at the experience. But since we were basically going to be rained in for most of that day, I just rolled with it as best as I could. Otherwise, I absolutely loved my time there, and I would absolutely look into renting there again in the future. I’ll just make sure to avoid their “tour of the property“… Never again."

Galleria Palms Hotel

10/10 Excellent

"."

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent

"It was great for our stay, they kept our room nice and clean! Having the Dunkin at the hotel was convenient since we didn’t opt in for breakfast. The shuttle service reservation to the Disney Parks was a huge plus."

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 lively festivals 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 27974 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 ESPN Wide World of Sports Complex.

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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Room 1

Change your mind

Treat yourself

Be picky

Check availability on Kissimmee Historic Hotels

Our top choices for Kissimmee historic hotels

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

2. Disney 7 BDRM, Private Pool/HotTub, Games Room, Clean, Fab!

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

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

5. Jedi Training Camp Top Rated 5 Star Villa