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Our top choices for Winter Garden 5-star hotels

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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, (510 reviews)
"We had a lovely stay, highly recommend this property. "
Canada
Diana
The price is 9.194.932 ₫
11.826.270 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Outdoor pool, pool cabanas (surcharge), pool umbrellas

Conrad Orlando at Evermore

Conrad Orlando at Evermore
5.0 star property
Orlando
9.6 out of 10, Exceptional, (447 reviews)
"Amazing stay!"
United States
Kristen
The price is 12.514.138 ₫
15.395.655 ₫ total
includes taxes & fees
2 Jun - 3 Jun
Conrad Orlando at Evermore
3 outdoor pools, pool 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, (904 reviews)
"Best hotel for Disney!!!! Delicious food and amazing property grounds!"
United States
Izabella
The price is 24.896.025 ₫
29.637.993 ₫ total
includes taxes & fees
14 Jun - 15 Jun
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
9.2 out of 10, Wonderful, (1,002 reviews)
"Amazing experience!! Definitely worth it"
United States
Glenda
The price is 13.409.605 ₫
16.716.034 ₫ total
includes taxes & fees
4 Jun - 5 Jun
The Ritz-Carlton Orlando, Grande Lakes
Outdoor pool, open 9:00 AM to 6:00 PM, free pool cabanas, pool umbrellas

ette hotel

ette hotel
5.0 star property
Kissimmee
9.6 out of 10, Exceptional, (446 reviews)
"Excelente"
United States
Daniel
The price is 8.621.401 ₫
9.785.290 ₫ total
includes taxes & fees
15 Jun - 16 Jun
ette hotel
Water park

Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
5.0 star property
Kissimmee
8.2 out of 10, Very good, (1,002 reviews)
"Great place to stay! We were so comfortable and private pool was amazing!"
United States
Martha Uribe
The price is 7.244.875 ₫
19.585.663 ₫ total
includes taxes & fees
18 May - 19 May
Encore Resort and Water Park at Reunion by Rentyl
Water park

Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,557 reviews)
"i would book again"
United States
Charmaine
Reunion Resort & Golf Club
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, (707 reviews)
"The resort was clean and beautiful ... staff was friendly"
United States
Robert
Disney's Beach Club Resort
Front of property

The Bear's Den Resort Orlando

The Bear's Den Resort Orlando
5.0 star property
Reunion
7.8 out of 10, Good, (24 reviews)
"Great place , I recommend it to everyone."
United States
Jacqueline
The Bear's Den Resort Orlando
Exclusive House | Children’s theme room

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
5.0 star property
Tuscan Hills
8.8 out of 10, Excellent, (8 reviews)
"The unique rooms were a hit with our children."
United States
Joseph
Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
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
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, (16 reviews)
"Clean, loved the pool"
United Kingdom
Stuart
Gorgeous 4 Bedroom w/ Pool Close to Disney 4836
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
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 traveller
Disney's Beach Club Villas
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, (20 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
Water park

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
5.0 star property
Davenport
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place so many things to do. Great place to stay for a large family especially with kids "
United States
Yesenia
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
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, (6 reviews)
"Parking was easy."
United States
Maria Belen
Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191
Water park

Gorgeous 5Bd Screened Pool at Champions Gate 1125

Gorgeous 5Bd Screened Pool at Champions Gate 1125
5.0 star property
Davenport
9.6 out of 10, Exceptional, (4 reviews)
"The house was exactly as the pictures posted. Very well maintained, cleaned, and well equipped with all essential equipment for cooking ext. My family and I loved it. It exceeded our expectations! We truly recommend this house, and will definitely rent this house again."
United States
Carmen
Gorgeous 5Bd Screened Pool at Champions Gate 1125
Front of property

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
5.0 star property
Davenport
8.6 out of 10, Excellent, (9 reviews)
"It was a very nice play with a lot to do. Everything was worth the money. Clean, friendly, and fun."
United States
Matthew Cyril
Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
Outdoor pool

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
5.0 star property
Kissimmee
5.6 out of 10, (4 reviews)
"The coffee pot was broke, we emailed about it and received a new one within a a few hours. The listing says water park access but you don’t get water park access. The dryer was broken and unable to be fixed during our stay. The company is very attentive to needs. I brought up something’s in the house that probably need evaluated and they said things need to be addressed at the beginning on the stay. (Things like the fridge seal not being great, broken can opener, broken pool chairs ) make sure...
United States
Bronte
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
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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 Garden.
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL
The price is 5.506.105 ₫ per night from 25 May to 26 May
5.506.105 ₫
6.194.500 ₫ total
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,154 reviews)
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Learn more about Winter Garden

Stroll the charming brick-lined streets of historic city centre where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

See all hotels in Winter Garden
ARM53A Historic Downtown Area and Clock of Winter Garden Florida

Top Winter Garden Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Garden?
The amount you pay for a 5-star hotel in Winter Garden depends on things such as when you want to go and the length of your holiday. An insider tip for scoring an awesome deal? Use our pricing filters to compare the available accommodation for your chosen dates.

  • Search for the lowest price per night from 3.856.053 ₫

What makes a hotel 5 stars in Winter Garden?
In Winter Garden, a hotel is required to offer a certain amount of top-notch amenities to earn 5 stars. These can include on-site gyms, gourmet restaurants, saunas and spas, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their exceptional service. You'll enjoy things like concierge services, nightly turn-down services and in-room massage. Some may also offer thoughtful touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Winter Garden?
Use Expedia's filter tool to find a luxury retreat in Winter Garden where most of what you need is included in the price. Next, narrow down your results for properties that have a rating of 5 stars and are deemed "All inclusive." The first thing on the to-do list at these stays? Relaxation and enjoyment.