Find Luxury Hotels in Winter Park, FL

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Check availability on Winter Park Luxury Hotels

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Winter Park luxury hotels

Exterior
The Alfond Inn

The Alfond Inn

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1000)
"Beautiful, classy hotel w/o breaking the bank. Pretty grounds and conveniently located."
United States
Craig
The Alfond Inn
Free daily buffet breakfast
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1409)
"Good location, good breakfast "
United States
Andrea
The price is ₩170,132
₩191,398 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hyatt House Orlando International Drive
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4374)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is ₩171,604
₩193,054 total
includes taxes & fees
Jan 23 - Jan 24, 2026
Rosen Shingle Creek
2 outdoor pools
Disney's Contemporary Resort

Disney's Contemporary Resort

Disney's Contemporary Resort
4.5 star property
Bay Lake
8.4 out of 10, Very Good, (1001)
"Room smelled badly & I was charged for valet parking even though I had a disability placard & it was supposed to be complimentary. "
United States
Sarah
Disney's Contemporary Resort
4 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)
Marriott's Grande Vista

Marriott's Grande Vista

Marriott's Grande Vista
4.0 star property
Orlando
9.0 out of 10, Wonderful, (3744)
"We enjoyed the property, amenities, cafe and our room was comfortable, clean and quiet. "
Canada
Maria
The price is ₩170,418
₩191,720 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Marriott's Grande Vista
Property grounds
DoubleTree by Hilton Hotel Orlando East - UCF Area

DoubleTree by Hilton Hotel Orlando East - UCF Area

DoubleTree by Hilton Hotel Orlando East - UCF Area
4.0 star property
Orlando
8.6 out of 10, Excellent, (1001)
"Great staff, nice room. "
United States
Jerod
The price is ₩152,284
₩171,319 total
includes taxes & fees
Jan 11 - Jan 12, 2026
DoubleTree by Hilton Hotel Orlando East - UCF Area
Exterior
Universal's Helios Grand Hotel, a Loews Hotel

Universal's Helios Grand Hotel, a Loews Hotel

Universal's Helios Grand Hotel, a Loews Hotel
4.0 star property
Orlando
9.8 out of 10, Exceptional, (98)
"Great service beautiful property, spectacular view from the room."
United States
Yakquelina
The price is ₩606,184
₩681,957 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Universal's Helios Grand Hotel, a Loews Hotel
Outdoor pool, cabanas (surcharge), pool umbrellas
Hyatt Regency Orlando

Hyatt Regency Orlando

Hyatt Regency Orlando
4.5 star property
International Drive District
9.2 out of 10, Wonderful, (1916)
"Great stay, cleanliness, staff"
United States
wathik
The price is ₩191,935
₩295,289 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hyatt Regency Orlando
Terrace/patio
The Point by Edge

The Point by Edge

The Point by Edge
4.0 star property
Florida Center
8.4 out of 10, Very Good, (834)
"Awesome and clean place to stay for the holidays"
United States
Moses
The price is ₩82,350
₩110,335 total
includes taxes & fees
Jan 15 - Jan 16, 2026
The Point by Edge
Exterior
Holiday Inn Express & Suites Sanford- Lake Mary by IHG

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

Holiday Inn Express & Suites Sanford- Lake Mary by IHG
4.0 star property
Sanford
9.4 out of 10, Exceptional, (1032)
"It was an enjoyable stay "
United States
mike
The price is ₩152,601
₩175,952 total
includes taxes & fees
Jan 29 - Jan 30, 2026
Holiday Inn Express & Suites Sanford- Lake Mary by IHG
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Yes overall excellent experience"
Racquel 5-night trip
Posted 11 hours ago
Rosen Inn at Pointe Orlando

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Winter Park?
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 luxury hotel with 2 outdoor pools and spa services, and it's a popular choice for Expedia travelers looking for an elegant place to 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 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 Casa Feliz Historic Home Museum, Winter Park Village, and Morse Museum of American Art. If you have some spare time during your trip, you might want to check out Kraft Azalea Gardens and Lake Virginia.
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.