Find 5 Star Hotels in Winter Garden, FL from $111

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Find properties with these dates

Tonight
May 13 - May 14
Tomorrow
May 14 - May 15
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

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

Property grounds
Endless Summer at Margaritaville
5.0 star property
10.0 out of 10, Exceptional, (5)
" Beautiful property lots of room perfect for our needs! "
Endless Summer at Margaritaville
Outdoor pool
House of Fun at Windsor Westside
5.0 star property
10.0 out of 10, Exceptional, (1)
"Very Nice. Great communication."
House of Fun at Windsor Westside
Exterior
Chasing Adventures
5.0 star property
10.0 out of 10, Exceptional, (1)
"Very clean and roomy. Great location to Disney and lots of restaurants and stores. "
Chasing Adventures
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Property grounds
Up to Scale at Margaritaville
5.0 star property
10.0 out of 10, Exceptional, (1)
"Otima experiência. Localização excelente. Facil acesso aos parques da Disney. Proxima a supermercados, restaurantes, e lojas. A casa é muito congortavel e o Check in e check out muito faceis de realizar. Retornaremos com certeza."
Up to Scale at Margaritaville
Outdoor pool
The Good Life at Legacy Park
5.0 star property
10.0 out of 10, Exceptional, (1)
"The host were quick to respond and friendly. The house is beautiful and clean. I felt like we were at a five star hotel. Our girls loved it so much they rathered stay at the house instead of going to explore Florida. We will definitely book this place again!"
The Good Life at Legacy Park
Interior
Magical Memories Villa
5.0 star property
10.0 out of 10, Exceptional, (1)
Magical Memories Villa
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
Exterior
Santa Cruz Retreat
5.0 star property
10.0 out of 10, Exceptional, (1)
"Quiets, clean, nice backyard! "
Santa Cruz Retreat
Outdoor pool, cabanas (surcharge), pool umbrellas
Conrad Orlando
5.0 star property
9.6 out of 10, Exceptional, (26)
"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
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, (781)
"Amaizing costumer service!"
The price is $1,125
$1,266 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
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
May 31 - Jun 1
The Ritz-Carlton Orlando, Grande Lakes
2 outdoor pools, cabanas (surcharge), pool umbrellas
Waldorf Astoria Orlando
5.0 star property
9.0 out of 10, Wonderful, (15)
"Awesome "
The price is $335
$433 total
includes taxes & fees
Jun 6 - Jun 7
Waldorf Astoria Orlando
Exterior
Family Vacation Home, Water Park, Endless Resort Amenities
5.0 star property
9.0 out of 10, Wonderful, (24)
"My entire family enjoyed our stay. The unit was spacious, comfortable, clean, and well equipped. The resort amenities kept the kids busy. The resort staff and security were friendly and helpful."
Family Vacation Home, Water Park, Endless Resort Amenities
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1118)
"Great hotel "
Reunion Resort & Golf Club
8 Bedroom Home Elite Near Water Park, Private Pool | Living room | Flat-screen TV
Encore Resort at Reunion
5.0 star property
8.4 out of 10, Very Good, (719)
"the waterpark and that I was able to fit my family in it."
Encore Resort at Reunion
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
Luxury Villa, Multiple Bedrooms, Private Pool | Courtyard view
7 Bedroom Villa, Private Pool, Resort Amenities
5.0 star property
8.0 out of 10, Very Good, (3)
"Everything was nice "
7 Bedroom Villa, Private Pool, Resort Amenities
Outdoor pool
House of Dreams at Windsor Westside
5.0 star property
8.0 out of 10, Very Good, (1)
"We travelled with 2 other couples making the total 6 adults. The property was very nice with lots of room to accommodate all 6 of us quite nicely. We all had our private bathroom which worked great. The pool right off the living room was a treat alter had to pay extra for the heat and believe me we needed it if you wanted to get in it in the evening, which we did. The kitchen was lovely and spacious with a large island and all the convenience we needed. There was multiple tv’s throughout the...
House of Dreams at Windsor Westside
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

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 $199 per night from May 29 to May 30
$199
$224 total
includes taxes & fees
May 29 - May 30
9.4/10 Exceptional! (4,803 reviews)
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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.

You enjoy the finer things in life, both at home and on vacation. Add an extra layer of enjoyment on your next trip to Winter Garden by treating yourself to the best of the best when it comes to accommodation. It's an ideal combination. There's no reason to delay a getaway to Winter Garden any longer. You'll join the multitudes of vacationers who have made Winter Garden so fashionable recently. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. You deserve the great vacation you're dreaming about. Reserve one of our 5-star hotels in Winter Garden and indulge in the finer things in life for a while.

5-Star Hotels in Winter Garden

Don't be afraid to be pampered during your trip. Spa treatments, delicious meals, and personalized service are all ready for you. You're sure to find exactly the accommodation you need. Additionally, the hotels in this area receive fantastic 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? A full-body massage to help your cares fall away? A concierge to help you make reservations at that outstanding restaurant? High thread-count sheets, piping hot coffees, and even spectacular views...these hotels are one-of-a-kind. Want to see for yourself? Then explore the 349 reviews various guests have left on Expedia and get to know these places.

You won't sleep and order room service the entire time, though. 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 Garden are the perfect place to relax after a busy day.

Make Your Escape

The results are in, and Winter Garden 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. Expedia can help you land a great deal on accommodation. Your great getaway is just a mouse-click away. Choose one of Expedia's Winter Garden 5-star hotels today and soothe yourself in the lap of luxury tomorrow.

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 can vary according to what time of year you travel and how long you plan to stay, among other factors. Use our price per night filter and other search tools to score the best deal on a luxurious getaway.

  • Search for the lowest price per night from $111

What makes a hotel 5 stars in Winter Garden?
From high-end dining venues and all-day fitness centers to pools and deluxe bedding, the 5-star experience in Winter Garden is all about luxury and relaxation. But it calls for more than just upscale perks to get a 5-star rating. Accommodations also have to deliver exceptional services like in-room massages, dry cleaning and laundry and concierge services.
Are there any 5-star all-inclusive resorts in Winter Garden?
Find a luxury retreat that includes your room, meals, activities and entertainment in Winter Garden with our filters. Search for hotels rated 5 stars and click on the “All inclusive” filter. Make sure you check what’s included in the purchase price. That way, you can take full advantage of the premium perks on offer from the moment you get there.
Are there any 5-star vacation rentals in Winter Garden?
Our site doesn’t have any 5-star vacation rentals in Winter Garden. However, you will still find a few top-rated properties where the only thing on your agenda will be to unpack and enjoy yourself. Discover what’s available by checking out our vacation rentals in Winter Garden.