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

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 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 $184

CA $553 total

includes taxes & fees

Oct 5 - Oct 6

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

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

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

Kissimmee

Amanda D.

CA $192

CA $678 total

includes taxes & fees

Oct 5 - Oct 6

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

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 $203

CA $603 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 spacious living area with a sofa, coffee table, and TV, connected to a kitchen with wooden cabinets and a large window.

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

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 $214

CA $618 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 dining area with a wooden table, grey chairs, and a blue vase with green plants.

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

5. Jedi Training Camp Top Rated 5 Star Villa

Windsor Hills

Chad G.

CA $449

CA $997 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 large, modern building with a curved roof and multiple satellite dishes.

A modern bar area with a pool table, bar stools, and a counter.

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

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

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

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

7. Mills Cottage by the Little Lake

Lake Weldona

rick s.

CA $237

CA $536 total

includes taxes & fees

Oct 5 - Oct 6

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

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.

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.

8. Eastpark. Pet friendly! Lake Nona

East Park

Dania B.

CA $141

CA $402 total

includes taxes & fees

Oct 12 - Oct 13

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Top Kissimmee Hotel Reviews

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

8/10 Good

"The room is clean the air conditioner sound like it had problem. I do believe it needs to be check out to make sure that sound is more silent it was very noisey. But everything else was Excellent."

Seasons Florida Resort

10/10 Excellent

"Very convenient after hours check-in. Staff was amazing, everything was clean, including the outdoors and parking lot! Would definitely stay here again."

Ramada by Wyndham Kissimmee Gateway

8/10 Good

"Excellent location and room. Walking distance to Walmart and ample parking. Stayed in a standard king room where we could park our car infront of the room. Called for room service and room was cleaned when we arrived back from being out. About 10 mins to Disney property and 20 to universal. Comfortable bed, couch, desk, microwave and closet space with hangers in room. Ample storage space. Only issue with our room was we found a dead centipede on the floor prior to checking out. Front desk was very apologetic and approved a few upgrade for our next stay."

Gaylord Palms Resort & Convention Center

10/10 Excellent

"I really recommend it’s clean the staff is amazing we really enjoyed it s a family place that you really can enjoy with people you love ❤️"

Galleria Palms Hotel

10/10 Excellent

"Front desk service excellent"

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"Awesome！"

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"Excelente estadía limpia las instalaciones y el personal maravilloso; solo falta más personal en la recepción para que el chek in sea las rápido"

Vacation Village Orlando, Celebration

8/10 Good

"Siempre que viajo me quedo aquí súper tranquilo Serca de todo y lugares para comer me encanta las abitaciones nunca abia tenido problemas con los cuartos asepto está última ves que fui el baño tenía varios cabellos de dama y la tina de idro masaje también tuve que limpiar los y en la aria de la tina los interruptores botones 2 de ellos sucios pero es la primera ves que me pasa algo así todo lo demás super"

Delta Hotels by Marriott Orlando Celebration

8/10 Good

"Big property and pretty nice. We felt for the price it worked for us!"

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