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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
The price is $478 per night from Dec 26 to Dec 27
$478
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
  • 1 hour drive from LEGOLAND® Florida
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 ...
ette hotel
Encore Resort at Reunion
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 at Reunion
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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 and Disney's ...
The Bear's Den Resort Orlando
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 Kissimmee. Enjoy free parking, private pools, and free water park access. Popular attractions ChampionsGate Golf ...
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
5 out of 5
  • 54 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 Disney's Animal Kingdom® ...
Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
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 Kissimmee. 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
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
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 Kissimmee. Enjoy free parking, private pools, and free water park access. Popular attractions ChampionsGate Golf ...
Gorgeous 5Bd Screened Pool at Champions Gate 1125
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 ChampionsGate Golf ...
Charming 3Bd Close to Disney @ Festival 1026
Gorgeous 3Bd Close to Disney @ Enclaves at Festival 1613
5 out of 5
  • 44 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 ChampionsGate Golf ...
Gorgeous 3Bd Close to Disney @ Enclaves at Festival 1613
7 Bedroom Villa, Private Pool, Resort Amenities
5 out of 5
  • 1 hour drive from LEGOLAND® Florida
Stay at this 5-star luxury villa in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Old Town and ESPN Wide World of Sports are ...
7 Bedroom Villa, Private Pool, Resort Amenities
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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 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 $446.

  • 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.