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5 Star Hotels in Winter Haven

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Featured 5 Star Winter Haven Hotels

Reunion Resort & Golf Club
5 out of 5
  • 49 min drive from LEGOLAND® Florida
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
  • 1 hour drive from LEGOLAND® Florida
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
Encore Resort and Water Park At Reunion by Rentyl
5 out of 5
  • 52 min drive from LEGOLAND® Florida
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 and Water Park At Reunion by Rentyl
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Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
5 out of 5
  • 48 min drive from LEGOLAND® Florida
Stay at this 5-star luxury vacation home in Davenport. Enjoy free parking, private pools, and free water park access. Popular attractions Reunion Resort Golf ...
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
The Bear's Den Resort Orlando
5 out of 5
  • 50 min drive from LEGOLAND® Florida
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 Complex ...
The Bear's Den Resort Orlando
WonderFull 4Bd with Pool at Champions Gate 1174
5 out of 5
  • 48 min drive from LEGOLAND® Florida
Stay at this 5-star luxury vacation home in Davenport. Enjoy free parking, private pools, and free water park access. Popular attractions Reunion Resort Golf ...
WonderFull 4Bd with Pool at Champions Gate 1174
Charming 3Bd Close to Disney @ Festival 1026
5 out of 5
  • 43 min drive from LEGOLAND® Florida
Stay at this 5-star luxury vacation home in Davenport. Enjoy free parking, private pools, and free water park access. Popular attractions Reunion Resort Golf ...
Charming 3Bd Close to Disney @ Festival 1026
Gorgeous 5Bd Screened Pool at Champions Gate 1125
5 out of 5
  • 48 min drive from LEGOLAND® Florida
Stay at this 5-star luxury vacation home in Davenport. Enjoy free parking, private pools, and free water park access. Popular attractions Mystic Dunes Golf Club ...
Gorgeous 5Bd Screened Pool at Champions Gate 1125
Reunion Resort & Golf Club
5 out of 5
  • 49 min drive from LEGOLAND® Florida
Stay at this 5-star luxury aparthotel in Kissimmee. Enjoy free valet parking, 10 outdoor pools, and a full-service spa. Popular attractions ESPN Wide World of ...
Reunion Resort & Golf Club
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
5 out of 5
  • 1 hour drive from LEGOLAND® Florida
Stay at this 5-star luxury vacation home in Four Corners. Enjoy free parking, private pools, and free water park access. Popular attractions Disney's Animal ...
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
Family Friendly 2 Bd Close to Disney @ Champions Gate 8899
5 out of 5
  • 50 min drive from LEGOLAND® Florida
Stay at this 5-star luxury apartment in Davenport. Enjoy free parking, private pools, and free water park access. Popular attractions Disney's Animal Kingdom® ...
Family Friendly 2 Bd Close to Disney @ Champions Gate 8899
Gorgeous 4 Bedroom w/ Pool Close to Disney 920
5 out of 5
  • 1 hour drive from LEGOLAND® Florida
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 ...
Gorgeous 4 Bedroom w/ Pool Close to Disney 920
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5-Star Hotel in Winter Haven

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 Haven.

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 Haven for you. Sort by:

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

  • Amenities: Winter Haven 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 Haven—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 Haven your way.