Kissimmee Hotel Guide - Historic Hotels in Kissimmee, Orlando

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Our top choices for Kissimmee historic hotels

Reception
Home 1 Suites Extended Stay - Kissimmee

Home 1 Suites Extended Stay - Kissimmee

Home 1 Suites Extended Stay - Kissimmee
2.5 star property
Kissimmee
6.6 out of 10, (1002)
"Nice place to stay."
United States
Rosa
Home 1 Suites Extended Stay - Kissimmee
Pool
2BR/2BA Getaway – 7 Miles from Orlando Parks

2BR/2BA Getaway – 7 Miles from Orlando Parks

2BR/2BA Getaway – 7 Miles from Orlando Parks
Kissimmee
10.0 out of 10, Exceptional, (1)
"We had a wonderful time at this condo. Very clean a bit outdated with a few things that could improve but the overall experience at this condo was very good. It is a lot bigger then seen in photos both bedrooms are fairly big and nice big walk in closet in both rooms and two full bathrooms and. Laundry in suite was an excellent addition and convenient will definitely returning in the future ! "
Canada
Jessica R.
The price is €193
includes taxes & fees
13 Jan - 14 Jan 2026
2BR/2BA Getaway – 7 Miles from Orlando Parks
Smart TV, video games, DVD player, table football
*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works

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

*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works
kissimmee
9.4 out of 10, Exceptional, (77)
"The house was absolutely great and perfect for our family. Its located close to Disney. We have finally found our Disney vacation spot!"
United States
Terrianne T.
The price is €380
includes taxes & fees
17 Dec - 18 Dec
*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works
4 bedrooms, memory-foam beds, desk, iron/ironing board
ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!

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

ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
Kissimmee
9.6 out of 10, Exceptional, (112)
"The location can’t be beat and the condo was great. The owner was extremely helpful and attentive. Highly recommend! "
United States
Leila P.
The price is €355
includes taxes & fees
17 Dec - 18 Dec
ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
Smart TV, DVD player, table football, books
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

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

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Kissimmee
9.6 out of 10, Exceptional, (135)
"The pool was great for the whole family, and everything worked and matched the listing "
United States
Robert S.
The price is €380
includes taxes & fees
17 Dec - 18 Dec
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
A heated pool
🌴 Relax & Recharge Near Disney – Top-Floor 3BR Condo at Windsor Palms 🌴

🌴 Relax & Recharge Near Disney – Top-Floor 3BR Condo at Windsor Palms 🌴

🌴 Relax & Recharge Near Disney – Top-Floor 3BR Condo at Windsor Palms 🌴
Kissimmee
9.8 out of 10, Exceptional, (19)
"I really enjoyed the Disney theme at the place"
United States
Anonymous traveller
The price is €285
includes taxes & fees
25 Dec - 26 Dec
🌴 Relax & Recharge Near Disney – Top-Floor 3BR Condo at Windsor Palms 🌴
Sports court
7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!

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

7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!
Kissimmee
9.2 out of 10, Wonderful, (59)
"Plenty of living space, a lovely pool/hot tub, and fantastic game room with pool table, foosball and pac man. The management were responsive to our needs and the clubhouse offered another pool and other amenities. The kids enjoyed basketball, golf and a tennis court. This was our second year in this house. I highly recommend it."
United States
John W.
The price is €504
includes taxes & fees
17 Dec - 18 Dec
7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!
Exterior
7613 Villa -8BD Private Pool/Spa-Game- near Disney

7613 Villa -8BD Private Pool/Spa-Game- near Disney

7613 Villa -8BD Private Pool/Spa-Game- near Disney
Kissimmee
8.0 out of 10, Very good, (14)
"The property was great overall. The carpets are dirty but overall it was a great place. We really had fun."
United States
Larynthia W.
The price is €763
includes taxes & fees
17 Dec - 18 Dec
7613 Villa -8BD Private Pool/Spa-Game- near Disney
A heated pool
7541 Huge 8BD Home - POOL&Spa - Game/Movie room

7541 Huge 8BD Home - POOL&Spa - Game/Movie room

7541 Huge 8BD Home - POOL&Spa - Game/Movie room
Kissimmee
8.8 out of 10, Excellent, (20)
"Good location, pet friendly, large space for big family. only issue pool lights wasn't working during stay"
United States
cassandra d.
The price is €830
includes taxes & fees
11 Jan - 12 Jan 2026
7541 Huge 8BD Home - POOL&Spa - Game/Movie room
Outdoor pool, a heated pool
Luxury 6BR, Theater, Game Rooms, Pool–Min to Disney/Universal Epic Universe!

Luxury 6BR, Theater, Game Rooms, Pool–Min to Disney/Universal Epic Universe!

Luxury 6BR, Theater, Game Rooms, Pool–Min to Disney/Universal Epic Universe!
Reunion
9.2 out of 10, Wonderful, (77)
"Beautiful house, 5 stars on the entire stay!"
United States
Elmer G.
The price is €643
includes taxes & fees
19 Dec - 20 Dec
Luxury 6BR, Theater, Game Rooms, Pool–Min to Disney/Universal Epic Universe!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Kissimmee Hotel Reviews

Seasons Florida Resort

Seasons Florida Resort

10/10 Excellent
"Clean, had fridge & microwave, comfy"
Melissa F 1-night trip
Posted 1 day ago
Seasons Florida Resort

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Frequently asked questions

What should I expect on my historical trip to Kissimmee?
A trip to the historical sites in Kissimmee is probably first on your sightseeing list. Be sure to check out the fun-filled theme parks and lively festivals while you're here. You can also take time at the major shopping area in this family-friendly area.
What's the best accommodation in Kissimmee to be near 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 centre and private pools. A couple of other options to soak up the local history include AMAZING 2 BEDROOM AT WESTGATE TOWN CENTER & SPA RESORT NEAR DISNEY and GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY.
How many historical hotels are located in Kissimmee?
In Kissimmee, you'll find 27826 hotels and other accommodation options bookable on Expedia, including 22 historic hotels or hotels close to historic sites.
What are the most important 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 Epcot®.
What is a historic hotel like in Kissimmee?
Guests who choose a historic hotel can stay in a place that has an officially recognised historic designation. A castle, a palace or even a pub or an old police station can be identified as a historic hotel as long as it's a place of special interest. Traditional architecture and period features are often preserved in the communal spaces and guestrooms of such hotels in Kissimmee, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. overall though the terms are similar. The architecture and building of a historic hotel is generally the most significant aspect. For a heritage hotel, often it's the cultural value along with how it shaped the community.
Do historic hotels in Kissimmee have modern facilities?
Hotels include modern conveniences and safety features you've come to expect, though efforts have been made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities and the popular amenities found in a hotel will be available in a historic hotel. Rest assured that when you select a historic hotel in Kissimmee, you won't find a place that's uncomfortable for guests or simply rundown.