A two-story house with a balcony, surrounded by lush greenery and trees.

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Check availability on Winter Park Historic Hotels

This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Winter Park historic hotels

Exterior

1. Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (101 reviews)
"Very nice accommodations. Great stay!!"
United States
John G.
The price is AED 364
AED 1,043 total
includes taxes & fees
12 Aug - 13 Aug
Eastpark. Pet friendly! Lake Nona
Interior

2. Bella Breeze

Bella Breeze
Downtown Sanford
8.4 out of 10, Very Good, (6 reviews)
"Enjoyable stay. "
United States
Carolyn R.
The price is AED 312
AED 644 total
includes taxes & fees
12 Aug - 13 Aug
Bella Breeze
Exterior

3. Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!

Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Sanford
10.0 out of 10, Exceptional, (27 reviews)
"We absolutely loved this house! So cute and ample space. The outdoor space was so nice to grill and hangout!"
United States
Danielle C.
The price is AED 645
AED 1,626 total
includes taxes & fees
19 Aug - 20 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Outdoor pool, a heated pool

4. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
9.6 out of 10, Exceptional, (67 reviews)
"Great stay. "
United States
rick s.
The price is AED 719
AED 1,518 total
includes taxes & fees
10 Aug - 11 Aug
Mills Cottage by the Little Lake
Outdoor pool, a heated pool

5. Large, beautiful, very comfortable one bedroom on small lake

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
10.0 out of 10, Exceptional, (68 reviews)
"Love the location. "
United States
Jolyn W.
The price is AED 579
AED 1,161 total
includes taxes & fees
8 Aug - 9 Aug
Large, beautiful, very comfortable one bedroom on small lake
Exterior detail

6. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
9.8 out of 10, Exceptional, (61 reviews)
"Very convenient to downtown! The Host, Jerome was very accommodating! "
United States
Jason M.
The price is AED 845
AED 1,769 total
includes taxes & fees
17 Aug - 18 Aug
Lake House Pets allowed
Coffee/tea maker, fridge, microwave, oven

7. Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.

Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Paramore
9.2 out of 10, Wonderful, (18 reviews)
"Was a really nice stay we enjoyed ourselves and slept like a baby"
United States
Molly A.
The price is AED 793
AED 1,124 total
includes taxes & fees
10 Aug - 11 Aug
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Coffee/tea maker, fridge, microwave, oven

8. Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!

Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Orlando
9.8 out of 10, Exceptional, (273 reviews)
"Everything was great. This is the first place we will look for when we come back!"
United States
jeremy e.
The price is AED 724
AED 1,618 total
includes taxes & fees
19 Aug - 20 Aug
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Property grounds

9. Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning

Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
orlando
9.8 out of 10, Exceptional, (194 reviews)
"Great place, Irina was very accommodating. Couldn’t be happier with my stay!"
United States
Darby S.
The price is AED 584
AED 3,199 total
includes taxes & fees
3 Sep - 4 Sep
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
3 bedrooms, desk, iron/ironing board, WiFi (free)

10. Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8

Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
Orlando
10.0 out of 10, Exceptional, (175 reviews)
"This property was absolutely beautiful and the location was perfect. Our condo felt huge and open clean and welcoming The complex was a great too. We will definitely stay again when we visit again."
United States
Lindsay J.
The price is AED 584
AED 1,438 total
includes taxes & fees
11 Aug - 12 Aug
Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
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 Park Hotel Reviews

Caribe Royale Orlando

Caribe Royale Orlando

10/10 Excellent
"Very clean. We did have an issue with the shower head and there was miscommunication with the front desk and maintenance. Waited a very long time for someone to fix it and ended up changing rooms. Regardless of this issue, we love the property. It is our go to resort when staying in the area."
Elaine 4-night trip
Posted 3 hours ago
Caribe Royale Orlando

Frequently asked questions

What should a history enthusiast expect from a trip to Winter Park?
Significant historical sites in Winter Park are probably a big part of your travel plans. During your stay, you can visit the shops and restaurants.
How many historical hotels are there in Winter Park?
In Winter Park, there are 134 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the must-see historical places and other sights to visit in Winter Park?
Winter Park is notable for landmarks like Casa Feliz Historic Home Museum. Cultural venues include Albin Polasek Museum and Sculpture Gardens, Morse Museum of American Art, and Winter Park History Museum. Additionally, in the area you'll find Kia Center and Orlando International Premium Outlets.
What is a historic hotel like in Winter Park?
When you book a historic hotel, you'll stay in a place that has an officially recognized national 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 can be admired in the communal spaces and guestrooms of such hotels in Winter Park, 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, while "historic hotel" is a term often used in the U.S. though overall the terms are quite similar. The physical building and architecture of historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value as well as how it inspired the community.
Do historic hotels in Winter Park have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, while every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, free WiFi, and the popular amenities found in any hotel should be available at a historic hotel. When you book a historic hotel in Winter Park, don't worry that you'll find yourself staying at a place that is rundown or uncomfortable.