Luxury Hotels & Resorts in Winter Park from AU$307

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Best Winter Park Luxury Hotels

The Alfond Inn

4.0 star property
9.4 out of 10, Exceptional, (1003)
"They had a heated pool & beautiful spa with a separate pool for the spa. "
The price is AU$465
includes taxes & fees
1 Dec - 2 Dec
The Alfond Inn

Park Plaza Hotel

3.0 star property
8.4 out of 10, Very good, (879)
"We love the history of the place and the setting along Park Avenue in Winter Park. The hotel is definitely dated without all the modern conveniences, but frankly that's what we liked because we wanted to see and appreciate the historical nature of this hotel."
The price is AU$307
includes taxes & fees
15 Dec - 16 Dec
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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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 International Airport (MCO) airport or Orlando, FL (SFB-Orlando Sanford Intl.) 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.
What's the best high-end place to stay in Winter Park?
The Alfond Inn is a 4-star hotel with valet parking and a terrace, and it’s a popular choice for Expedia travellers looking for a pampered stay.
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 temperature of 28°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Park are August, September, July and June, with each month seeing an average of 185 mm 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 Casa Feliz Historic Home Museum, Winter Park Village and Albin Polasek Museum and Sculpture Gardens. If you have some spare time during your trip, you might want to check out Winter Park Country Club and Morse Museum of American Art.
How can I get around Winter Park?
It’s easier to get around town comfortably when you know your options. To see more of the larger area, hop aboard a train at Winter Park Station.