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

A bedroom with a large bed, two bedside tables with lamps, a ceiling light, and a view through a sliding door to the outside.

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

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

Kissimmee

Jacklyn

CA $181

CA $547 total

includes taxes & fees

Oct 26 - Oct 27

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

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

2. 7BR Private Pool/Hot Tub, Games Room, Disney & ESPN Sports

Kissimmee

Amanda D.

CA $222

CA $710 total

includes taxes & fees

Oct 22 - Oct 23

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

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

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

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

3. #2780 Priv Spa Pool 2 Masters Disney Universal.

Kissimmee

corinne n.

CA $248

CA $601 total

includes taxes & fees

Nov 16 - Nov 17

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

A residential house with a garage, a well-maintained lawn, and a palm tree.

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

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

Kissimmee

bryan s.

CA $190

CA $585 total

includes taxes & fees

Oct 22 - Oct 23

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

A residential house with a well-maintained lawn, a palm tree, and a garage.

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.

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

kissimmee

Amanda S.

CA $190

CA $585 total

includes taxes & fees

Nov 19 - Nov 20

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

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

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

A patio with a brick floor, a wooden table and chairs, a glass greenhouse, and bamboo plants.

6. Mills Cottage by the Little Lake

Lake Weldona

rick s.

CA $200

CA $486 total

includes taxes & fees

Oct 27 - Oct 28

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

A dining area with a wooden table and chairs, a chandelier, and a large tapestry on the wall.

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.

7. Eastpark. Pet friendly! Lake Nona

East Park

Dania B.

CA $176

CA $446 total

includes taxes & fees

Nov 1 - Nov 2

A patio with a table and stools overlooking a body of water with boats and an American flag.

A compact kitchen with white cabinets, a microwave, an oven, and a sink.

A boat docked at a marina with a building in the background.

A park with a green bench, palm trees, and a playground with colorful equipment.

8. Private home and entrance, stocked kitchen, fenced yard, Pets, boats ok,Parking

St. Cloud

Scott D.

CA $204

CA $486 total

includes taxes & fees

Oct 22 - Oct 23

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Top Kissimmee Hotel Reviews

Legacy Vacation Resorts - Kissimmee/Orlando

10/10 Excellent

"La habitación está muy buena pero no hay servicio de limpieza. Más iluminación y no hay asiento"

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"The property is beautiful."

Embassy Suites by Hilton Orlando Lake Buena Vista South

8/10 Good

"Overall, I had very good experience. Most front desk staff were very helpful, except for one. I wish they would not disconnect our wifi from 8am when we paid to leave until 11 am. Complementary breakfast is very good."

Ramada by Wyndham Kissimmee Gateway

8/10 Good

"Foi uma boa hospedagem. Precisam melhorar na limpeza."

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent

"Todo muy limpio muy buen servicio"

Gaylord Palms Resort & Convention Center

8/10 Good

"The room was not cleaned"

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. 7BR Private Pool/Hot Tub, Games Room, Disney & ESPN Sports

3. #2780 Priv Spa Pool 2 Masters Disney Universal.

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