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Top Winter Park 5 Star Hotels

Waldorf Astoria Orlando
2 outdoor pools, cabanas (surcharge), pool umbrellas
Waldorf Astoria Orlando
5.0 star property
9.0 out of 10, Wonderful, (18)
"Check in was smooth, our room was fantastic! Our evening at Bull & Bear was exceptional. We thoroughly enjoyed our stay! "
The price is CA $438
CA $570 total
includes taxes & fees
Jun 23 - Jun 24
Waldorf Astoria Orlando
Conrad Orlando
Outdoor pool, cabanas (surcharge), pool umbrellas
Conrad Orlando
5.0 star property
9.8 out of 10, Exceptional, (34)
"Beautiful property. "
The price is CA $542
CA $686 total
includes taxes & fees
Jun 19 - Jun 20
Conrad Orlando
The Ritz-Carlton Orlando, Grande Lakes
Property amenity
The Ritz-Carlton Orlando, Grande Lakes
5.0 star property
9.2 out of 10, Wonderful, (1000)
"Ester was an excellent host. "
The price is CA $545
CA $685 total
includes taxes & fees
Jun 15 - Jun 16
The Ritz-Carlton Orlando, Grande Lakes
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Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
3 outdoor pools, cabanas (surcharge), pool umbrellas
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
5.0 star property
9.6 out of 10, Exceptional, (782)
"We stayed at the four seasons for our family getaway and we dont know where to start from phenomenal resort. The staff were amazing service was above and beyond. Restaurants amazing and great food! Very family friendly and a very safe resort. We would definitely recommend."
The price is CA $1,372
CA $1,543 total
includes taxes & fees
Jun 23 - Jun 24
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Splendid 5Bd Close to Disney at Storey Lake 4251
Water park
Splendid 5Bd Close to Disney at Storey Lake 4251
5.0 star property
9.4 out of 10, Exceptional, (3)
"Excellent property . Really clean and lots of space. Really close to Disney and plenty of restaurants a short drive away. My only complaint is the communication for check in. I got message and phone call 30 mins before check in saying if I don't fill out check in form my booking would be cancelled. This really wasn't ideal as I was driving. After I did it I received so many text and emails to help with my stay. I was getting them from several different numbers. Then 3 hrs after checking out. 4...
Splendid 5Bd Close to Disney at Storey Lake 4251
Waterpark Near Disney - Luxury Townhome
Water park
Waterpark Near Disney - Luxury Townhome
5.0 star property
8.2 out of 10, Very good, (12)
"All the pool amenities and activities were great. The resort staff was great and stuck to the rules. I would say they could lighten up on the required tubes in the river and no jumping in the big pool. Place is for families and my kids got disappointed when they were asked to not jump in the pool at all, not even just a cannon ball. Im 41 and was told i needed a tube in the 3' lazy river. I was just walking around the river with my little kids"
Waterpark Near Disney - Luxury Townhome
Apartamento en Orlando Fl.
Living area
Apartamento en Orlando Fl.
5.0 star property
2.0 out of 10, (1)
The price is CA $769
CA $866 total
includes taxes & fees
Jun 5 - Jun 6
Apartamento en Orlando Fl.
Luxury 8Bd with Pool @ Sonoma Resort 2639
Outdoor pool, sun loungers, lifeguards on site
Luxury 8Bd with Pool @ Sonoma Resort 2639
5.0 star property
2.0 out of 10, (1)
"The property had 8 bedrooms, only 2 were king size. All the beds are so low to the ground. The refrigerator was broken. The coffee table was broken. They charge a massive deposit. Then they send you an email after check out that they deducted money from your deposit and say that you have things damaged. I called the first day to tell them the defects and no one response. I wonder never recommend this place. "
Luxury 8Bd with Pool @ Sonoma Resort 2639
The Ritz-Carlton Residences Orlando, Grande Lakes
Bathroom
The Ritz-Carlton Residences Orlando, Grande Lakes
5.0 star property
The Ritz-Carlton Residences Orlando, Grande Lakes
4 Bedroom Townhouse, Resort, 15 Mins to Disney, Themed Rooms perfect for Kids
Luxury Villa, 4 Bedrooms, Pool Access | Courtyard view
4 Bedroom Townhouse, Resort, 15 Mins to Disney, Themed Rooms perfect for Kids
5.0 star property
6.0 out of 10, (4)
"One of the toilets was broken, a fan was broken and we weren’t left with anything to maintain the cleanliness of the home while we were there for two weeks. The location was great and it was a perfect size home for my family. "
4 Bedroom Townhouse, Resort, 15 Mins to Disney, Themed Rooms perfect for Kids
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
Outdoor pool
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
5.0 star property
6.2 out of 10, (7)
"Overall OK but property in need of some upgrading. Needed to use kitchen pots as BBQ was a long way away and they were not clean."
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
Storey Lake Resort 5br Cozy Home 2609
Outdoor pool
Storey Lake Resort 5br Cozy Home 2609
5.0 star property
8.0 out of 10, Very good, (1)
"Construcción "
Storey Lake Resort 5br Cozy Home 2609
5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
Full-size fridge, microwave, oven, stovetop
5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
5.0 star property
5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
Storey Lake Resort 8br Cozy Home With Theater 2703
Outdoor pool
Storey Lake Resort 8br Cozy Home With Theater 2703
5.0 star property
6.0 out of 10, (1)
Storey Lake Resort 8br Cozy Home With Theater 2703
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
Indoor pool, outdoor pool, sun loungers, lifeguards on site
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
5.0 star property
10.0 out of 10, Exceptional, (1)
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
Family Friendly 5 Bedrooms Home Close to Disney 4849
Interior
Family Friendly 5 Bedrooms Home Close to Disney 4849
5.0 star property
Family Friendly 5 Bedrooms Home Close to Disney 4849
Deluxe 3 Bedroom Apartment Vista Cay Resort 404
Townhome, 3 Bedrooms | Balcony
Deluxe 3 Bedroom Apartment Vista Cay Resort 404
5.0 star property
2.0 out of 10, (1)
"They just cancelled my trip without any notifications. When i spoke to the seller, it looks like they want you to book directly on their portal. Hotels.com should remove such postings"
Deluxe 3 Bedroom Apartment Vista Cay Resort 404
Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
Aerial view
Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
5.0 star property
8.0 out of 10, Very good, (1)
"Es war dunkel bei der Ankunft und wir konnten die Nummern an den Gebäuden in der riesigen Anlage nicht erkennen. Der Herr an der Torschranke hat es zweimal falsch erklärt. "
Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
Storey Lake Lakeview Villa 2967
Outdoor pool
Storey Lake Lakeview Villa 2967
5.0 star property
Storey Lake Lakeview Villa 2967
Storey Lake Fantastic Star Wars Villa With Lakeview 2913
Outdoor pool
Storey Lake Fantastic Star Wars Villa With Lakeview 2913
5.0 star property
Storey Lake Fantastic Star Wars Villa With Lakeview 2913

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winter Park.
DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive, Orlando, FL
Get rates
7/10 Good! (8,796 reviews)
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Five Star Hotels in Winter Park

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Winter Park so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Winter Park and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Winter Park

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Winter Park

The results are in, and Winter Park 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Winter Park! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winter Park today and settle down in the lap of luxury tomorrow.