Find luxury hotels in Winter Park, FL

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Top Luxury Hotels in Winter Park

The Alfond Inn
4 out of 5
300 East New England Avenue, Winter Park, FL, 32789
The price is $228 per night from Dec 20 to Dec 21
per night
Dec 20 - Dec 21
The Alfond Inn is a Winter Park luxury 4-star boutique property where you can treat yourself to pillowtop beds, late night room service, and more. The outdoor pool, poolside bar, and restaurant are just some of the popular amenities at this deluxe hotel.
4.7/5 Exceptional! (999 reviews)
"Wonderful place and great location."

Reviewed on Dec 1, 2022

The Alfond Inn
Park Plaza Hotel
3 out of 5
307 South Park Avenue , Winter Park, FL, 32789
The price is $209 per night from Dec 11 to Dec 12
per night
Dec 11 - Dec 12
Choose luxury at Park Plaza Hotel, where you can enjoy amenities like Champagne service, premium mattresses, and more. Notable amenities include a restaurant, a bar, and a terrace.
4.2/5 Excellent! (665 reviews)
"I haven’t been to the Plaza in twenty years, and I was excited to see that it had not changed. It’s classic style and friendly atmosphere are the things that impressed me back then and now! Carry on the tradition"

Reviewed on Nov 1, 2022

Park Plaza Hotel
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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.

Popular luxurious hotels

Most upscale stays in Winter Park in 2023

Winter Park Luxury Hotels information


Luxury Hotels in Winter Park


Highest price $228
Cheapest price $209
Number of guest reviews 1664
Total number of hotels in Winter Park 12454


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.

What's the best high-end hotel 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 travelers looking for a pampering 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 temp of 83°F, while the coldest months are January and December with an average of 63°F. The rainiest months in Winter Park are June, August, July, and September, 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 Casa Feliz Historic Home Museum, Winter Park Village, and Lee Road Shopping Center. 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.

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