A two-story house with a balcony, surrounded by lush greenery and trees.

Find 5 Star Hotels in Winter Park, FL from SAR 414

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Park 5 Star Hotels

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for Winter Park 5-star hotels

Exterior

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
5.0 star property
Orlando
9.4 out of 10, Exceptional, (554 reviews)
"Great Hotel. Next to Disney Springs"
United States
Rafael
The price is SAR 1,348
SAR 1,728 total
includes taxes & fees
28 Jun - 29 Jun
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Outdoor pool, cabanas (surcharge), pool umbrellas

Conrad Orlando at Evermore

Conrad Orlando at Evermore
5.0 star property
Orlando
9.6 out of 10, Exceptional, (478 reviews)
"The hotel was very clean, the staff were friendly, and the location was extremely convenient to Disney Park which the hotel offers shuttle to and from."
United States
Diana
The price is SAR 1,908
SAR 2,334 total
includes taxes & fees
12 Jul - 13 Jul
Conrad Orlando at Evermore
3 outdoor pools, cabanas (surcharge), pool umbrellas

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
5.0 star property
Golden Oak
9.8 out of 10, Exceptional, (916 reviews)
"Very upscale"
United States
James
The price is SAR 3,492
SAR 4,161 total
includes taxes & fees
9 Jul - 10 Jul
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Property amenity

The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
5.0 star property
Orlando
9.4 out of 10, Exceptional, (1,002 reviews)
"Clean, helpful staff, great gift shops and food!"
United States
Telvia
The price is SAR 1,498
SAR 1,918 total
includes taxes & fees
11 Jul - 12 Jul
The Ritz-Carlton Orlando, Grande Lakes
3 outdoor pools

Disney's Beach Club Resort

Disney's Beach Club Resort
5.0 star property
Bay Lake
8.8 out of 10, Excellent, (711 reviews)
"The resort was clean and beautiful ... staff was friendly"
United States
Robert
Disney's Beach Club Resort
Water park

Marvelous 4Bd with Pool at Storey Lake Resort 2601

Marvelous 4Bd with Pool at Storey Lake Resort 2601
5.0 star property
Kissimmee
10.0 out of 10, Exceptional, (6 reviews)
"Definitely booking again ❤️"
United States
Yolanda
Marvelous 4Bd with Pool at Storey Lake Resort 2601
Water park

Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653

Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
5.0 star property
Kissimmee
9.6 out of 10, Exceptional, (9 reviews)
"Overall wonderful home, great price, great property and amenities for families. Location is great near absolutely everything. "
United States
Lance
Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
3 outdoor pools

Disney's Beach Club Villas

Disney's Beach Club Villas
5.0 star property
Bay Lake
9.2 out of 10, Wonderful, (39 reviews)
"Clean and great location"
United States
Anonymous traveler
Disney's Beach Club Villas
Water park

Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887

Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887
5.0 star property
Kissimmee
9.4 out of 10, Exceptional, (3 reviews)
"House was really good..but thermostat wasn't working at all..some part carpet was wet all time"
United States
Pareshkumar
Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887
Exterior

Gorgeous 2 Bedroom Apartment Close to Disney 305 3191

Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
5.0 star property
Kissimmee
9.4 out of 10, Exceptional, (9 reviews)
"Enjoyed the pools. The apartment included a washer and dryer. It was a calm, quiet community."
United States
Melissa
Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
Indoor pool, outdoor pool, sun loungers, lifeguards on site

5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759

5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
5.0 star property
Kissimmee
10.0 out of 10, Exceptional, (4 reviews)
"Looks just like photos, very nice and spacious. I would book again."
United States
Kimesha
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
Aerial view

Stunning 2 Bd Condo Close to Disney 304 3191

Stunning 2 Bd Condo Close to Disney 304 3191
5.0 star property
Kissimmee
5.0 out of 10, (6 reviews)
"Pools were filthy. The washer dryer combo did not work. Like a previous "
United States
Stephanie
Stunning 2 Bd Condo Close to Disney 304 3191
Outdoor pool

2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms

2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
5.0 star property
Kissimmee
8.2 out of 10, Very Good, (21 reviews)
"Pool was great kids loved it. Came with blender and coffe maker. "
United States
casey paul
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
2 outdoor pools, free cabanas, pool umbrellas

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
5.0 star property
Kissimmee
8.4 out of 10, Very Good, (7 reviews)
"The accommodation not only has a good equipment and location, but is also absolutely top and highly recommended. I will be very happy to book here again."
Germany
Thomas
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
Outdoor pool

Family Vacation Home, Water Park+Endless Amenities

Family Vacation Home, Water Park+Endless Amenities
5.0 star property
Kissimmee
7.6 out of 10, Good, (25 reviews)
"Rooms were clean but blankets had stains on them. Almost looked like dried blood or something dark of the nature. Shower was not clean, black mold was present in a couple spots, shower head did not appear to be clean either. Pool and slides and lazy river were nice. Parking was decent. Easy to locate. Easy to enter premises. Couches were small and uncomfortable. But we made the best of it. "
United States
LUIS
Family Vacation Home, Water Park+Endless Amenities
Resort view

Splendid 5Bd Close to Disney at Storey Lake 4251

Splendid 5Bd Close to Disney at Storey Lake 4251
5.0 star property
Kissimmee
9.2 out of 10, Wonderful, (12 reviews)
"Everything that a big family needs for a vacation, plus a great location"
United States
omar
Splendid 5Bd Close to Disney at Storey Lake 4251
Front of property - evening/night

5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney

5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
5.0 star property
Kissimmee
8.4 out of 10, Very Good, (8 reviews)
"My family and I truly enjoyed our stay. The team was friendly and communicated effectively the entire time. Will definitely stay again and recommend to others. "
United States
Ben-Jade
5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
Water park

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
5.0 star property
Kissimmee
8.8 out of 10, Excellent, (3 reviews)
"Nice "
United States
Janismarie
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
Water park

Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191

Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191
5.0 star property
Kissimmee
8.8 out of 10, Excellent, (8 reviews)
"Great stay!"
United States
Marlene
Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191
Water park

Stunning 4 Bd Close to Disney @ Storey Lake 2569

Stunning 4 Bd Close to Disney @ Storey Lake 2569
5.0 star property
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"The unit was clean and full accommodations. The overall resort is friendly and safe. Great parking close to parks and restaurants, grocery etc. "
United States
Claudine
Stunning 4 Bd Close to Disney @ Storey Lake 2569
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL
The price is SAR 635 per night from Jul 14 to Jul 15
SAR 635
SAR 714 total
14 Jul - 15 Jul
includes taxes & fees
9.2/10 Wonderful! (5,916 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.

Learn more about Winter Park

Stroll through the Morse Museum to see the world's largest collection of Tiffany glass, then boat through the Winter Park Chain of Lakes. Charming Park Avenue offers upscale shopping and outdoor cafés where you can people-watch before catching a sunset concert in Central Park.

See all hotels in Winter Park
A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.

Top Winter Park Hotel Reviews

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 SAR 414

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.

Explore a world of travel with Expedia