5 Stars Hotels in Winter Park, Orlando from CA $135

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Check availability on Winter Park 5 Star Hotels

Tonight
Mar 4 - Mar 5
Tomorrow
Mar 5 - Mar 6
This weekend
Mar 6 - Mar 8
Next weekend
Mar 13 - Mar 15

Our top choices for Winter Park 5-star hotels

View from room

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
5.0 star property
Orlando
9.2 out of 10, Wonderful, (473 reviews)
"Loved our stay here, it was quiet, clean and great dining options, would come back again!"
Canada
Robert
The price is CA $538
CA $682 total
includes taxes & fees
Mar 30 - Mar 31
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, (391 reviews)
"The property is beautiful and staff was exceptional "
United States
John
The price is CA $650
CA $799 total
includes taxes & fees
Mar 18 - Mar 19
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
9.6 out of 10, Exceptional, (886 reviews)
"Great Hotel "
United States
Huan
The price is CA $1,846
CA $2,162 total
includes taxes & fees
Mar 5 - Mar 6
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, (1,001 reviews)
"Great service, clean rooms, large property with many amenities . Fabulous food at highball & harvest. "
United States
SAUL
The price is CA $1,161
CA $1,391 total
includes taxes & fees
Mar 26 - Mar 27
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, (701 reviews)
"Very nice place to stay in Disney World resort place for vacation which has shuttle buses for every where and walking distance to EPCOT. Wonderful experience there!"
United States
Yong Hoon
Disney's Beach Club Resort
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
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
9.8 out of 10, Exceptional, (6 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
Exclusive House

Family Friendly Four Bedroom w GameRoom @Disney 5145

Family Friendly Four Bedroom w GameRoom @Disney 5145
5.0 star property
Kissimmee
8.0 out of 10, Very good, (8 reviews)
"The property was beautiful and suited my family’s needs perfectly. We traveled with 6 people and had more than enough space and room for us all!! The host was more than accommodating when our travel plans were affected by flight changes due to weather. We did Disney and Universal and both were very easily accessible from here. We would recommend this place 100 percent and will definitely stay here again. "
United States
Kathleen
Family Friendly Four Bedroom w GameRoom @Disney 5145
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
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
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
10.0 out of 10, Exceptional, (4 reviews)
"It was a clean and nice "
United States
Danielle
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
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

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
Water park

Gorgeous 4Bd with Pool @ Storey Lake Resort 4475

Gorgeous 4Bd with Pool @ Storey Lake Resort 4475
5.0 star property
Kissimmee
7.6 out of 10, Good, (5 reviews)
"First off the house was not clean. It was only clean where a vacuum can fit. Behind all toilets was dirty, every shower had hair from previous guests. We have a three year old so we were in a rush to leave to get on our cruise and left behind our iPad. We wrote and apparently a cleaner took over two days to get to the house to only come back and say there was no iPad. Security didn’t even ask for ID. The back gate is open to let anyone just enter. Would never stay here again. Didn’t feel clean...
Canada
Shawnte
Gorgeous 4Bd with Pool @ Storey Lake Resort 4475
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
6.6 out of 10, (4 reviews)
"The Place Awesome it was a family trip we had great time my 2 kids love the Pool, the Lazy river. they love the hold place. places are not far from Condo. Great communication they always was checking if we needed anything it was great. Thank You "
United States
Gema
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
8.0 out of 10, Very good, (18 reviews)
"Great stay"
United States
Tedra
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
Exterior

Gorgeous 2 Bedroom Apartment Close to Disney 305 3191

Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
5.0 star property
Kissimmee
9.2 out of 10, Wonderful, (7 reviews)
"Great location, beautiful spacious apartment, comfortable beds/space. It was well appointed with kitchen items, bathroom, and laundry. The apartment floors were a little dirty and there really needed to be a fan in the 2nd bedroom. It was pretty stuffy in there with the thermometer limited to 72 at night. The AC unit was a little loud but cooled well. Unfortunately, the pool was too packed to enjoy, and the gym that didn't open until 9am was also packed. The gym was well appointed, and there...
United States
Anonymous traveller
Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
Townhome, 4 Bedrooms | In-room dining

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836
5.0 star property
Kissimmee
9.2 out of 10, Wonderful, (15 reviews)
"Clean, loved the pool"
United Kingdom
Stuart
Gorgeous 4 Bedroom w/ Pool Close to Disney 4836
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, (3 reviews)
Marvelous 4Bd with Pool at Storey Lake Resort 2601
3 outdoor pools, free cabanas, pool umbrellas

Stunning 4Bd With Pool At Storey Lake Resort 4821

Stunning 4Bd With Pool At Storey Lake Resort 4821
5.0 star property
Kissimmee
7.4 out of 10, Good, (3 reviews)
"They ripp you off with the cleaning and ma"
United States
Ernest
Stunning 4Bd With Pool At Storey Lake Resort 4821
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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 CA $179 per night from Mar 26 to Mar 27
CA $179
CA $202 total
Mar 26 - Mar 27
includes taxes & fees
9.2/10 Wonderful! (4,759 reviews)
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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
Kraft Azalea Gardens showing a fountain, a park and a pond

Top Winter Park Hotel Reviews

Find out more about Winter Park

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.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Park?
There are various pricing options for 5-star hotels in Winter Park on Expedia. How much you'll pay will depend on when you plan to travel, length of your trip and other factors. Compare available properties for your chosen dates and make use of our pricing and other filters to land the ideal high-end stay.

  • Search for the lowest price per night from CA $135

What makes a hotel 5 stars in Winter Park?
From high-end restaurants and 24-hour fitness centres to swimming pools and premium bedding, the 5-star experience in Winter Park is all about comfort and indulgence. But it calls for more than just top-notch conveniences to receive a 5-star rating. Stays must also deliver exceptional guest services like massage treatments, laundry and dry cleaning and 24-hour room service.
Are there any 5-star all-inclusive resorts in Winter Park?
Find a luxurious escape that includes your lodging, meals, drinks and entertainment in Winter Park with Expedia's filter tool. Search for resorts with a 5-star rating and select the "All inclusive" filter. Make sure you check what's included in the price. That way, you're ready to take advantage of the many perks on offer as soon as you arrive.

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