Find Historic Hotels in Winter Garden, FL

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Check availability on Winter Garden Historic Hotels

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Winter Garden Historic Hotels

Outdoor pool
The Oak View Place..

The Oak View Place..

Oakland
9.2 out of 10, Wonderful, (10)
"The VRBO looked brand new and I only knew it was not because of the reviews from previous years. The live oak trees on the property added to the beauty of the surroundings."
United States
Libba F.
The price is SAR 676
SAR 1,084 total
includes taxes & fees
7 Dec - 8 Dec
The Oak View Place..
Iron/ironing board, free WiFi, bed sheets
Home 1 Suites Extended Stay - Kissimmee

Home 1 Suites Extended Stay - Kissimmee

2.5 star property
Kissimmee
6.6 out of 10, (1001)
"Nice place to stay."
United States
Rosa
The price is SAR 235
SAR 267 total
includes taxes & fees
7 Dec - 8 Dec
Home 1 Suites Extended Stay - Kissimmee
Outdoor pool, pool umbrellas, sun loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

3.5 star property
International Drive District
7.4 out of 10, Good, (3853)
"Front desk was amazing!!! "
United States
Nicole
The price is SAR 234
SAR 339 total
includes taxes & fees
14 Dec - 15 Dec
Wyndham I-Drive Avanti Resort & Conference Center
Water park
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 star property
International Drive District
8.0 out of 10, Very Good, (3706)
"Great hotel "
United States
Eddie
The price is SAR 321
SAR 551 total
includes taxes & fees
4 Jan - 5 January 2026
CoCo Key Hotel and Water Resort 
Meeting facility
Hampton Inn & Suites Orlando Intl Dr N

Hampton Inn & Suites Orlando Intl Dr N

2.5 star property
International Drive District
9.2 out of 10, Wonderful, (1074)
"Second time staying at this hotel and loved it great hotel for family and close to the main attractions "
United States
Kadeisha
The price is SAR 335
SAR 377 total
includes taxes & fees
4 Jan - 5 January 2026
Hampton Inn & Suites Orlando Intl Dr N
Lobby
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

3.0 star property
International Drive District
8.8 out of 10, Excellent, (651)
"Hospitable staff and nice rooms."
United States
Iryna
The price is SAR 267
SAR 300 total
includes taxes & fees
14 Dec - 15 Dec
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool
The Citrus on the Lake

The Citrus on the Lake

3.0 star property
Tavares
8.2 out of 10, Very Good, (1007)
"Yes"
United States
John
The Citrus on the Lake
Exterior
Holiday Inn Express & Suites, International Drive by IHG

Holiday Inn Express & Suites, International Drive by IHG

3.5 star property
International Drive District
9.0 out of 10, Wonderful, (1829)
"Great for the price and location "
United Kingdom
Luke
The price is SAR 372
SAR 419 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites, International Drive by IHG
Front of property - evening/night
Rosen Inn International

Rosen Inn International

3.0 star property
International Drive District
8.4 out of 10, Very Good, (5905)
"Great Location "
United States
Diamond
The price is SAR 297
SAR 334 total
includes taxes & fees
8 Dec - 9 Dec
Rosen Inn International
Front of property
Historic Tremain Cottages

Historic Tremain Cottages

3.0 star property
Mount Dora
8.4 out of 10, Very Good, (32)
"Great location!"
United States
Lisa
Historic Tremain Cottages
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 Winter Garden Hotel Reviews

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

10/10 Excellent
"Great location! Accessibly to all of the parks, shopping, restaurants local culture. Highly recommended…we will be back soon!"
Rosalyn 5-night trip
Posted 1 day ago
Lake Buena Vista Resort Village & Spa

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Frequently asked questions

What should a history buff expect from a stay in Winter Garden?
The historical sites in Winter Garden are probably a big part of your travel plans. While you're here, you might want to visit the fun-filled theme parks and array of shops. And also relish a stop at the top-notch restaurants in this relaxing area.
How many historical hotels are there in Winter Garden?
In Winter Garden, there are 360 hotels and other lodging options bookable on Expedia but not many designated as historic hotels.
What are the most important historical places and other sights to visit in Winter Garden?
Landmarks like Central Florida Railroad Museum and Garden Theatre in Winter Garden might be worth a visit. Cultural venues include Winter Garden Art Association and Winter Garden Heritage Museum. In the area, you'll also find Universal Studios Florida and Universal Orlando Resort.
What is a historic hotel like in Winter Garden?
By choosing a historic hotel, you can enjoy a vacation in a place that has an officially recognized national historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be transformed into a historic hotel as long as it's of special interest. Traditional architecture and period features are typically found in the communal spaces and guestrooms of historic hotels in Winter Garden, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. but overall the terms are quite similar. The architecture and building of historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value and how it influenced the community.
Do historic hotels in Winter Garden have modern facilities?
Hotel interiors feature the modern conveniences and safety features you might expect, though efforts have been made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, free WiFi, and the amenities found in any hotel will also be available in a historic hotel. When you book a historic hotel in Winter Garden, don't worry that you'll be staying at a place that's uncomfortable for guests or simply rundown.