Find 5 Star Hotels in Winter Garden, FL from ￥15,598

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Check availability on Winter Garden 5 Star Hotels

Tonight
Dec 5 - Dec 6
Tomorrow
Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

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

Exterior
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

5.0 star property
Orlando
9.2 out of 10, Wonderful, (413)
"Excellent dining and stay"
Canada
RAJ
The price is ￥50,739
￥65,805 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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, (335)
"Place was freaking amazing!"
United States
Shaun
The price is ￥72,391
￥89,197 total
includes taxes & fees
Dec 14 - Dec 15
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, (878)
"Fantastic hotel, lovely front desk and housekeeping staff. "
United States
Tanis
The price is ￥184,605
￥216,408 total
includes taxes & fees
Dec 15 - Dec 16
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
View from property
The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes

5.0 star property
Orlando
9.2 out of 10, Wonderful, (1000)
"Great service, clean rooms, large property with many amenities . Fabulous food at highball & harvest. "
United States
SAUL
The price is ￥99,128
￥121,118 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Ritz-Carlton Orlando, Grande Lakes
Outdoor pool, open 9:00 AM to 6:00 PM, free cabanas, pool umbrellas
ette hotel

ette hotel

5.0 star property
Kissimmee
9.8 out of 10, Exceptional, (373)
"If you're looking to stay at hotel with all the top amenities, great staff and amazing restaurant at a very nice price...this is the spot! Location is a bit busy but all is made up quality inside the hotel. "
United States
michael
The price is ￥57,941
￥65,762 total
includes taxes & fees
Dec 14 - Dec 15
ette hotel
Outdoor pool, a heated pool, cabanas (surcharge), pool umbrellas
Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl

5.0 star property
Kissimmee
8.4 out of 10, Very Good, (1000)
"House was super clean! Staff were amazing and location was perfect!"
United States
Donovan
The price is ￥38,627
￥110,749 total
includes taxes & fees
Dec 7 - Dec 8
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, (1435)
"Family Friendly"
United States
Janaya
The price is ￥36,487
￥48,765 total
includes taxes & fees
Dec 9 - Dec 10
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, (696)
"Location location location!! Best pool!!"
United States
Seung Hoon
Disney's Beach Club Resort
Aerial view
Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort

Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort

5.0 star property
Kissimmee
8.4 out of 10, Very Good, (10)
"The complex was nice and very nice clean rooms, the water park was nice and huge. Definitely would visit again "
United States
Vernon
Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort
Front of property
The Bear's Den Resort Orlando

The Bear's Den Resort Orlando

5.0 star property
Reunion
8.0 out of 10, Very Good, (22)
"Great place , I recommend it to everyone."
United States
Jacqueline
The Bear's Den Resort Orlando
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
10.0 out of 10, Exceptional, (3)
"Fabulous apartment, great equipment as excellent location! We stayed for 11 nights in October visiting Disney 10 days and Kennedy Space Centre for a days. Parking was easy and there is a decent gym and nice water park on site. Flawless communiction throughout our stay. Would definately stay again!"
United Kingdom
Dean
Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191
Exclusive House | 4 bedrooms, in-room safe, individually decorated, individually furnished
Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Cozy 3Bd Close to Disney @ Enclaves at Festival 808

5.0 star property
Festival
6.8 out of 10, (3)
"Property was beautiful host was very attentive and answered all my questions and concerns area was safe and quiet the pool pass did not work was my only issue but everything else was top tier "
United States
Brittany
Cozy 3Bd Close to Disney @ Enclaves at Festival 808
Exterior
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)
"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
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)
"It was a clean and nice "
United States
Danielle
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
Townhome, 4 Bedrooms | Private pool
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, (13)
"Super clean and confortable. "
United States
Heralda
Gorgeous 4 Bedroom w/ Pool Close to Disney 4836
Water park
Gorgeous 4Bd with Pool @ Storey Lake Resort 4475

Gorgeous 4Bd with Pool @ Storey Lake Resort 4475

5.0 star property
Kissimmee
9.0 out of 10, Wonderful, (4)
Gorgeous 4Bd with Pool @ Storey Lake Resort 4475
Water park
Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

5.0 star property
Davenport
8.6 out of 10, Excellent, (8)
"They kept in contact the whole time we stayed with them. They responded to any questions promptly."
United States
Tiffany
Family Friendly 2 Bd Close to Disney @ Champions Gate 8899
Luxury Villa, Multiple Bedrooms, Private Pool | Courtyard view
7 Bedroom Villa, Private Pool, Resort Amenities

7 Bedroom Villa, Private Pool, Resort Amenities

5.0 star property
Kissimmee
9.0 out of 10, Wonderful, (15)
"Beautiful and the family loved it 😍! Close to Disney, excellent for large families"
Canada
LLoyd
7 Bedroom Villa, Private Pool, Resort Amenities
Water park
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)
"Home was great super clean and very cozy and comfortable. "
United States
Ubeiman
Splendid 5Bd Close to Disney at Storey Lake 4251
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, (2)
Marvelous 4Bd with Pool at Storey Lake Resort 2601
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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.
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL
The price is ￥13,866 per night from Dec 15 to Dec 16
￥13,866
￥15,598 total
Dec 15 - Dec 16
includes taxes & fees
8.4/10 Very Good! (6,934 reviews)
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Learn more about Winter Garden

Stroll the charming brick-lined streets of historic downtown 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?
How much you pay for a 5-star hotel in Winter Garden depends on things such as when you plan to travel and the length of your break. A top tip for scoring an awesome deal? Use our pricing filters to check out the available options for your selected dates.

  • Search for the lowest price per night from ￥15,598

What makes a hotel 5 stars in Winter Garden?
In Winter Garden, a hotel must offer a certain level of high-end conveniences to be rated 5 stars. These can include saunas and spas, on-site gyms, gourmet restaurants, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their extraordinary service. You'll enjoy things like nightly turn-down services, in-room massages and concierge services. Some may even offer special touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Winter Garden?
Find a luxury getaway that includes your room, meals, drinks and entertainment in Winter Garden with the help of our filter tool. Search for resorts with a 5-star rating and select the "All inclusive" filter. Double-check what's included in the price. This way, you can take full advantage of the premium perks on offer from the moment you step into the lobby.

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