Find 5 Star Hotels in Winter Park, FL from $76

Most hotels are fully refundable. Because flexibility matters.

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Search over 2.9 million properties and 550 airlines worldwide.

Compare Winter Park 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

2 outdoor pools, cabanas (surcharge), pool umbrellas
Waldorf Astoria Orlando
5.0 star property
9.2 out of 10, Wonderful, (17)
"Check in was smooth, our room was fantastic! Our evening at Bull & Bear was exceptional. We thoroughly enjoyed our stay! "
The price is $335
$433 total
includes taxes & fees
Jun 6 - Jun 7
Waldorf Astoria Orlando
Outdoor pool, cabanas (surcharge), pool umbrellas
Conrad Orlando
5.0 star property
9.6 out of 10, Exceptional, (29)
"It’s gorgeous and the level of hospitality exceeds expectations. "
The price is $397
$503 total
includes taxes & fees
Jun 9 - Jun 10
Conrad Orlando
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 $399
$502 total
includes taxes & fees
Jun 6 - Jun 7
The Ritz-Carlton Orlando, Grande Lakes
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 $1,130
$1,271 total
includes taxes & fees
May 28 - May 29
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
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
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
Living area
Apartamento en Orlando Fl.
5.0 star property
2.0 out of 10, (1)
The price is $596
$671 total
includes taxes & fees
May 24 - May 25
Apartamento en Orlando Fl.
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
Bathroom
The Ritz-Carlton Residences Orlando, Grande Lakes
5.0 star property
The Ritz-Carlton Residences Orlando, Grande Lakes
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
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
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
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
Apartment, 2 Bedrooms | Private kitchen | Full-size fridge, microwave, oven, stovetop
2 Bd Sleeps 8 Apartment Close to Disney 103 4751
5.0 star property
10.0 out of 10, Exceptional, (1)
"Great two bedroom apartment near Disney. We stayed for four nights, and it was very clean and comfortable. A little light on things like soap, shampoo, etc., but we had our own. Would stay there again."
2 Bd Sleeps 8 Apartment Close to Disney 103 4751
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
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
Interior
Family Friendly 5 Bedrooms Home Close to Disney 4849
5.0 star property
Family Friendly 5 Bedrooms Home Close to Disney 4849
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
Aerial view
Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
5.0 star property
Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
Interior
Storey Lake Lakeview Villa 2967
5.0 star property
Storey Lake Lakeview Villa 2967

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
The price is $76 per night from May 28 to May 29
$76
$113 total
includes taxes & fees
May 28 - May 29
7/10 Good! (9,003 reviews)
Still don't see what you're looking for?
See all properties in Winter Park.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

There's nothing wrong with enjoying the finer things in life. Add an extra layer of luxury on your next trip to Winter Park by treating yourself to the best of the best when it comes to accommodation. It's an ideal pairing. There's no reason to delay a getaway to Winter Park any longer. You'll join the multitudes of vacationers who have made Winter Park so fashionable in the last few seasons. Additionally, the hotels in this area receive outstanding marks for guest services, so you know you'll be well cared for during your getaway. What are you waiting for? Our 5-star hotels in Winter Park are the perfect places to relax in during your next chunk of time off.

5-Star Hotels in Winter Park

Don't be afraid to live the high life while you're on vacation, along with the best conditions. Spa treatments, delicious meals, and personalized service are all waiting for you. You're sure to find exactly the accommodation you need. We should also mention, the hotels in this area receive noteworthy marks for customer satisfaction, so you know you'll be well cared for during your getaway. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that filet mignon in the wee hours of the morning? A reflexology treatment that will leave you feeling refreshed and alive? Butler services? Whatever it is your heart desires, you're bound to find it here. Want to see for yourself? Plenty of visitors recommend this location.

But you aren't going to spend your entire vacation in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Winter Park are waiting for you to relax after an exciting day.

Make Your Escape

The results are in, and Winter Park 5-star hotels are the place to be when you book your next vacation. Additionally, these accommodations are highly rated -- 90% of visitors recommended 5-star hotels in Winter Park! Expedia can help you land a great deal on accommodation. It's time to plan your next great escape. Opt for one of our Winter Park 5-star hotels today and relax in total tranquility tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Park?
How much you pay for a 5-star hotel in Winter Park depends on things like when you want to go and the length of your escape. Our top tip for bagging an awesome deal? Use our pricing filters to compare the available options for your chosen dates.

  • Search for the lowest price per night from $76

What makes a hotel 5 stars in Winter Park?
From gourmet dining venues and 24/7 fitness centers to swimming pools and dreamy bedding, the 5-star experience in Winter Park is all about luxury and comfort. But it requires more than just top-notch conveniences to earn a 5-star rating. Stays must also offer extraordinary guest-centric services like beauty treatments, on-site laundry and dry cleaning and 24/7 room service.
Are there any 5-star all-inclusive resorts in Winter Park?
Use Expedia’s filter tool to find an upmarket retreat in Winter Park where everything you need is included in the price. From there, refine your results for resorts that have a rating of 5 stars and are categorized as “All inclusive.” The main thing on the schedule at these stays? Relaxation and enjoyment.
Are there any 5-star vacation rentals in Winter Park?
Our site doesn’t offer any 5-star vacation rentals in Winter Park. However, you will still find some top-rated retreats where the only thing on your agenda will be to relax and enjoy yourself. See what’s available by searching through our vacation rentals in Winter Park.