Find Luxury Hotels in Winter Park, FL

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check availability on Winter Park Luxury Hotels

Next weekend
In two weeks

Compare Winter Park Luxury Hotels room rates, reviews, and availability. Most hotels are fully refundable.

The Alfond Inn

4.0 star property
9.4 out of 10, Exceptional, (1003)
"Excellent"
The price is AED 1,098
AED 1,318 total
includes taxes & fees
16 Feb - 17 Feb
The Alfond Inn

Park Plaza Hotel

3.0 star property
8.4 out of 10, Very Good, (918)
"Very cute, historic hotel "
The price is AED 652
AED 733 total
includes taxes & fees
16 Feb - 17 Feb
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.
Don't see what you're looking for?
See all available properties in Winter Park

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Winter Park?
Use Expedia and let us help you arrange a flight to Orlando Intl. Airport (MCO) airport or Orlando Sanford Intl. Airport (SFB) airport, and then select from different places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Winter Park offers. During your visit, you might want to enjoy the university which Winter Park is known for.
When can I expect good weather in Winter Park?
Planning for the weather is an important factor for making your trip to Winter Park a success, especially when you’re splurging. The hottest months are usually July and August with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Park are August, September, July, and June, with each month seeing an average of 7 inches of rainfall.
What's there to see and do in Winter Park?
When you’re in Winter Park, enjoy exploring the sights and attractions here including Morse Museum of American Art, Lake Virginia, and Winter Park Village. If you have some spare time during your trip, you might want to check out Albin Polasek Museum and Sculpture Gardens and Winter Park Country Club.
How can I get around Winter Park?
It’s easier to get around town comfortably when you know your options. If you want to venture outside of the area, hop on a train at Winter Park Station.