Hotels in Winter Park

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Check prices for these dates

Tonight
Dec 23 - Dec 24
Tomorrow
Dec 24 - Dec 25
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Where to stay in Winter Park?

Front of property
Park Plaza Hotel
Park Plaza Hotel
3.0 star property
8.6 out of 10, Excellent, (1000)
  • cleanliness
    Walk to the train with ease from this boutique hotel in charming Winter Park.
The price is $157
$177 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Park Plaza Hotel
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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When is the best time to visit Winter Park?

Our prices for hotels in Winter Park are cheapest in August
Price trends for hotels in Winter Park
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Winter Park
December
High crowds
High 23°C / low 14°C. Sunny most days.
View properties in December
23°
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December, High crowds, average high temperature 23 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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21°
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January, Low crowds, average high temperature 21 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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23°
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February, Low crowds, average high temperature 23 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
25°
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March, Moderate crowds, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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28°
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April, Low crowds, average high temperature 28 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
30°
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May, High crowds, average high temperature 30 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
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31°
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June, High crowds, average high temperature 31 degrees Celsius, average low temperature 24 degrees Celsius. Sunny most days.
24°
32°
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July, Low crowds, average high temperature 32 degrees Celsius, average low temperature 25 degrees Celsius. Sunny most days.
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32°
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August, Moderate crowds, average high temperature 32 degrees Celsius, average low temperature 25 degrees Celsius. Partly sunny.
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31°
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September, Moderate crowds, average high temperature 31 degrees Celsius, average low temperature 24 degrees Celsius. Sunny most days.
24°
28°
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October, High crowds, average high temperature 28 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
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24°
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November, Moderate crowds, average high temperature 24 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
Monthly weather averages (˚C)

Top neighborhoods in Winter Park

Winter Park Historical Museum which includes signage

Hannibal Square

The Hannibal Square neighborhood has lots to see including Hannibal Square Heritage Center and Winter Park History Museum.

Morse Museum of American Art showing a church or cathedral, interior views and heritage elements

Park Avenue District

The Park Avenue District neighborhood offers attractions such as Morse Museum of American Art and Cahall Sandspur Field.

Top landmarks in Winter Park

Great place to grab something to eat or drink while visiting Full Sail University. Try the Mount St Helen's Zingers!
Photo by Jay Mullenix
Open Photo by Jay Mullenix

Full Sail University

3.9/5 (39 reviews)
If you'd like to get a taste of Winter Park student life, check out Full Sail University, located 2.2 mi (3.6 km) from central Winter Park.
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This historic old Florida estate was moved from its original location to this current site adjacent to the Winter Park Country Club. #CasaFeliz
Photo by Matt Merkel
Open Photo by Matt Merkel

Casa Feliz Historic Home Museum

4.6/5 (5 reviews)
If museums are on your list of things to see in Winter Park, then you might want to head to Casa Feliz Historic Home Museum. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you want to see more of the museums in Winter Park, you can easily walk to Morse Museum of American Art or Winter Park History Museum.
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Learn more about Winter Park

Escape the theme park frenzy on Park Avenue's brick-paved elegance, where upscale boutiques and outdoor cafes create a sophisticated small-town atmosphere. The Morse Museum houses an unrivaled collection of Tiffany glass that sparkles like frozen sunlight. Paddle a swan boat across Lake Osceola for postcard-worthy photos, or explore the hidden beauty of Kraft Azalea Gardens. Rollins College campus offers Spanish Mediterranean architecture worth admiring before browsing the Albin Polasek Museum's sculpture gardens. Winter Park Village provides shopping without the mall madness, while Casa Feliz Historic Home Museum reveals the city's wealthy winter resident past. Visit during a festival when the already-charming streets transform into celebration central.

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Kraft Azalea Gardens showing a fountain, a park and a pond

Check out reviews of Winter Park hotels guests love

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Yes and yes, would definitely recommend."
Omar Antonio Rivera 6-night trip
Posted 17 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Frequently asked questions

What hotels do travelers like in Winter Park?
Hilton Garden Inn Winter Park, The Alfond Inn and SpringHill Suites by Marriott Winter Park are all properties that our guests really like.
Can I book a refundable hotel in Winter Park?
If you're looking for the flexibility to change your plans to Winter Park, most hotels offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Winter Park if I want a vacation home instead of a traditional hotel?
If you want a good alternative to a hotel, browse our selection of 34 vacation homes. In addition, you can choose from 8 apartments.
What will the weather in Winter Park be like during my vacation?
July and August are typically the warmest months in Winter Park when the average temp is 82°F. January and February are the coldest months when the average temperature is 64°F. August and September are the months with the most rain.
Why should I book my Winter Park hotel through Hotels.com?
There are lots of reasons to book your Winter Park trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.