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5 Star Hotels in Winter Garden

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Tonight Feb 22 - Feb 23Next weekend Feb 28 - Mar 2

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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 $559 per night from Mar 14 to Mar 15
$559
includes taxes & fees
Mar 14 - Mar 15
Stay at this 5-star luxury resort 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
Conrad Orlando
5 out of 5
Fully refundableReserve now, pay when you stay
  • 16 min drive from Flamingo Crossings Town Center
The price is $573 per night from Feb 23 to Feb 24
$573
includes taxes & fees
Feb 23 - Feb 24
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
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
5 out of 5
Fully refundableReserve now, pay when you stay
  • 13 min drive from Flamingo Crossings Town Center
The price is $1,232 per night from Mar 2 to Mar 3
$1,232
includes taxes & fees
Mar 2 - Mar 3
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
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The Ritz-Carlton Orlando, Grande Lakes
5 out of 5
Fully refundableReserve now, pay when you stay
  • 31 min drive from Flamingo Crossings Town Center
The price is $871 per night from Feb 28 to Mar 1
$871
includes taxes & fees
Feb 28 - Mar 1
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
ette hotel
5 out of 5
Fully refundableReserve now, pay when you stay
  • 9 min drive from Flamingo Crossings Town Center
The price is $511 per night from Mar 8 to Mar 9
$511
includes taxes & fees
Mar 8 - Mar 9
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 ...
ette hotel
Reunion Resort & Golf Club
5 out of 5
  • 19 min drive from Flamingo Crossings Town Center
The price is $387 per night from Mar 2 to Mar 3
$387
includes taxes & fees
Mar 2 - Mar 3
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
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
Family Vacation Home, Water Park+Endless Amenities
5 out of 5
  • 23 min drive from Flamingo Crossings Town Center
Stay at this 5-star luxury villa in Kissimmee. Enjoy free WiFi, free parking, and free water park access. Popular attractions Disney Springs™ and ESPN Wide World ...
Family Vacation Home, Water Park+Endless Amenities
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
5 out of 5
  • 25 min drive from Flamingo Crossings Town Center
Stay at this 5-star luxury vacation home in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Disney Springs™ and ESPN Wide ...
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
Gorgeous 5Bd Screened Pool at Champions Gate 1125
5 out of 5
  • 18 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 Reunion Resort Golf ...
Gorgeous 5Bd Screened Pool at Champions Gate 1125
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
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
5 out of 5
  • 29 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 ...
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
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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 $387.

  • 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.