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5 Star Hotels in Winter Garden

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Featured 5 Star Winter Garden Hotels

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
5 out of 5
Fully refundableReserve now, pay when you stay
  • 15 min drive from Flamingo Crossings Town Center
The price is $460 per night from Jan 5 to Jan 6
$460
includes taxes & fees
Jan 5 - Jan 6, 2025
Stay at this 5-star luxury hotel in Orlando. Enjoy 2 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff in our reviews. ...
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
5 out of 5
  • 13 min drive from Flamingo Crossings Town Center
The price is $1,119 per night from Dec 19 to Dec 20
$1,119
includes taxes & fees
Dec 19 - Dec 20
Stay at this 5-star luxury resort in Lake Buena Vista. Enjoy 3 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff in our ...
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Conrad Orlando
5 out of 5
Fully refundableReserve now, pay when you stay
  • 16 min drive from Flamingo Crossings Town Center
The price is $520 per night from Jan 6 to Jan 7
$520
includes taxes & fees
Jan 6 - Jan 7, 2025
Stay at this 5-star luxury hotel in Orlando. Enjoy a full-service spa, 5 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. ...
Conrad Orlando
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The Ritz-Carlton Orlando, Grande Lakes
5 out of 5
  • 31 min drive from Flamingo Crossings Town Center
The price is $779 per night from Jan 8 to Jan 9
$779
includes taxes & fees
Jan 8 - Jan 9, 2025
Stay at this 5-star luxury hotel in Orlando. Enjoy a full-service spa, 7 restaurants, and a golf course. Our guests praise the helpful staff and the property ...
The Ritz-Carlton Orlando, Grande Lakes
Reunion Resort & Golf Club
5 out of 5
  • 19 min drive from Flamingo Crossings Town Center
The price is $444 per night from Dec 26 to Dec 27
$444
includes taxes & fees
Dec 26 - Dec 27
Stay at this 5-star luxury aparthotel in Kissimmee. Enjoy 11 outdoor pools, 7 restaurants, and a golf course. Our guests praise the helpful staff in our reviews. ...
Reunion Resort & Golf Club
ette hotel
5 out of 5
Fully refundableReserve now, pay when you stay
  • 9 min drive from Flamingo Crossings Town Center
The price is $446 per night from Jan 17 to Jan 18
$446
includes taxes & fees
Jan 17 - Jan 18, 2025
Stay at this 5-star luxury hotel in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
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Encore Resort at Reunion
5 out of 5
  • 16 min drive from Flamingo Crossings Town Center
Stay at this 5-star luxury resort in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Encore Resort at Reunion
The Bear's Den Resort Orlando
5 out of 5
  • 17 min drive from Flamingo Crossings Town Center
Stay at this 5-star luxury vacation home in Kissimmee. Enjoy free WiFi, free parking, and a golf course. Popular attractions ESPN Wide World of Sports and Disney's ...
The Bear's Den Resort Orlando
Family Friendly Four Bedroom w GameRoom @Disney 5145
5 out of 5
  • 22 min drive from Flamingo Crossings Town Center
Stay at this 5-star luxury vacation home in Kissimmee. Enjoy free parking, private pools, and free water park access. Popular attractions Old Town and Disney ...
Family Friendly Four Bedroom w GameRoom @Disney 5145
Splendid 5Bd Close to Disney at Storey Lake 4251
5 out of 5
  • 28 min drive from Flamingo Crossings Town Center
Stay at this 5-star luxury vacation home in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Old Town and Disney Springs™ are ...
Splendid 5Bd Close to Disney at Storey Lake 4251
Free Resort Access 4 Bedroom Near Disney with Themed Rooms
5 out of 5
  • 27 min drive from Flamingo Crossings Town Center
Stay at this 5-star luxury villa in Kissimmee. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Old Town and Disney Springs™ are located ...
Free Resort Access 4 Bedroom Near Disney with Themed Rooms
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
5 out of 5
  • 25 min drive from Flamingo Crossings Town Center
Stay at this 5-star luxury villa in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Old Town and Disney Springs™ are located ...
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
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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.

5-Star Hotel in Winter Garden

It’s time. No more meh motels and so-so stays. This vacation it’s all about living it up, and that starts with a great hotel. You want first-class service and award-winning restaurants. Well, let us introduce you to a 5-star hotel in Winter Garden.

So nice you’ll blink twice

What makes a hotel worthy of supreme star-age? For starters, the service has to be top-notch and personalized. These hotels often have 24-hour room service, a welcome gift upon your arrival, and help you with your bags—even if you travel light.

Are they nicer? Heck yeah, they are! Most 5-star hotels have jaw-dropping aesthetics that give an authentic feel of class. And we’re not talking about that faux-gold soap dish your Aunt Tilda puts out for the guests—it’s the real deal.

Stars in your eyes

Are 5-stars hotels worth it? If you like the finer things in life, then yes, they sure are. But we also know you’re the type that likes to get your caviar on a fish stick budget. We’re right there with you, and that is why we make it easy to find the best 5-star hotel in Winter Garden for you. Sort by:

  • Price: Want to live large, but keep that budget balanced? We got you. We have 5-star hotels starting at $444.

  • Amenities: Winter Garden skyline view? Maybe a heated indoor pool? Looking for a Michelin-star restaurant? Search for the hotels that have the amenities you desire.

  • Hotwire Hot Rate: We’ll tell you the name of the hotel after you book, and you might just save a ton.

When you’re looking for the top 5-star hotels in Winter Garden—but don’t want to pay top dollar—let us help you out. You can get that posh palace of your dreams, and have money left to take on Winter Garden your way.