Search for Cheap Deals on
5 Star Hotels in Winter Haven

Check Last Minute Winter Haven Hotel Deals

Tonight Nov 29 - Nov 30Next weekend Dec 5 - Dec 7

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


Featured 5 Star Winter Haven Hotels

ette hotel
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from LEGOLAND® Florida
Book a stay at this luxury hotel in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowette hotel
Encore Resort and Water Park at Reunion by Rentyl
5 out of 5
Fully refundableReserve now, pay when you stay
  • 52 min drive from LEGOLAND® Florida
Book a stay at this luxury resort in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. ...
Opens in a new windowEncore Resort and Water Park at Reunion by Rentyl
Reunion Resort & Golf Club
5 out of 5
  • 49 min drive from LEGOLAND® Florida
Book a stay at this luxury aparthotel in Kissimmee. Enjoy 11 outdoor pools, 7 restaurants, and a golf course. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowReunion Resort & Golf Club
Save an average of 15% on thousands of hotels when you're signed in
The Bear's Den Resort Orlando
5 out of 5
  • 50 min drive from LEGOLAND® Florida
Book a stay at this luxury vacation home in Kissimmee. Enjoy free WiFi, free parking, and a golf course. Popular attractions ESPN Wide World of Sports Complex ...
Opens in a new windowThe Bear's Den Resort Orlando
Cozy 3Bd Close to Disney @ Enclaves at Festival 808
5 out of 5
  • 45 min drive from LEGOLAND® Florida
Book a stay at this luxury vacation home in Four Corners. Enjoy free parking, private pools, and free water park access. Popular attractions Reunion Resort Golf ...
Opens in a new windowCozy 3Bd Close to Disney @ Enclaves at Festival 808
Family Friendly 2 Bd Close to Disney @ Champions Gate 8899
5 out of 5
  • 50 min drive from LEGOLAND® Florida
Book a stay at this luxury apartment in Four Corners. Enjoy free parking, private pools, and free water park access. Popular attractions Disney's Animal Kingdom® ...
Opens in a new windowFamily Friendly 2 Bd Close to Disney @ Champions Gate 8899
7 Bedroom Villa, Private Pool, Resort Amenities
5 out of 5
  • 1 hour drive from LEGOLAND® Florida
Book a stay at this luxury villa in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Old Town and ESPN Wide World of Sports Complex ...
Opens in a new window7 Bedroom Villa, Private Pool, Resort Amenities
WonderFull 4Bd with Pool at Champions Gate 1174
5 out of 5
  • 48 min drive from LEGOLAND® Florida
Book a stay at this luxury vacation home in Four Corners. Enjoy free parking, private pools, and free water park access. Popular attractions Reunion Resort Golf ...
Opens in a new windowWonderFull 4Bd with Pool at Champions Gate 1174
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
5 out of 5
  • 1 hour drive from LEGOLAND® Florida
Book a stay at this luxury vacation home in Four Corners. Enjoy free parking, private pools, and free water park access. Popular attractions Disney's Animal ...
Opens in a new windowMarvelous 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
Book a stay at this luxury vacation home in Four Corners. Enjoy free parking, private pools, and free water park access. Popular attractions Mystic Dunes Golf ...
Opens in a new windowGorgeous 5Bd Screened Pool at Champions Gate 1125
Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
5 out of 5
  • 54 min drive from LEGOLAND® Florida
Book a stay at this luxury vacation home in Four Corners. Enjoy free parking, private pools, and free water park access. Popular attractions Disney's Animal ...
Opens in a new windowStunning 5Bd w/ Pool @ Windsor Island Resort 3814
Gorgeous 4 Bedroom w/ Pool Close to Disney 920
5 out of 5
  • 1 hour drive from LEGOLAND® Florida
Book a stay at this luxury vacation home in Kissimmee. Enjoy free parking, private pools, and free water park access. Popular attractions Old Town and Disney ...
Opens in a new windowGorgeous 4 Bedroom w/ Pool Close to Disney 920
Don't see what you're looking for?
See all available properties in Winter Haven
View all properties
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 $380.

  • 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.