Explore top 2026 5 Star Hotels in Winter Haven

Name: Gorgeous 5Bd Screened Pool at Champions Gate 1125
Rating: 9.4

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Top Winter Haven 5 Star hotels

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3001 Sherberth Rd Kissimmee FL

Fully refundableReserve now, pay when you stay

$415 nightly

$471 total

Dec 14 - Dec 15

Total with taxes and fees

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business ...

9.6/10 Exceptional! (373 reviews)

Great staff at every station/ area. Impecable rooms. The restaurant is an absolute must. Stayed three times and by far my favourite hotel on Florida. One of my top 5 across the globe. Special note to the staff at breakfast, as i am arriving to sit and my cold brew was brought without even asking. ...

Reviewed on Nov 26, 2025

Encore Resort and Water Park at Reunion by Rentyl

7635 Fairfax Dr Kissimmee FL

Fully refundableReserve now, pay when you stay

$629 nightly

$714 total

Dec 9 - Dec 10

Total with taxes and fees

This smoke-free resort features free water park access, a full-service spa, and 2 restaurants. There's fun for all ages with a free kid's club and a children's ...

8.2/10 Very Good! (1,000 reviews)

Clean house, any complaints of things that weren’t working correctly were addressed the same day and fixed the same day. Clean environment. Waterpark is super clean and nice. House was perfect for our family of 18.

Reviewed on Dec 2, 2025

Reunion Resort & Golf Club

7593 Gathering Drive Kissimmee FL

$354 nightly

$402 total

Dec 9 - Dec 10

Total with taxes and fees

This luxury aparthotel features a golf course, free water park access, and 7 restaurants. Bring the family and enjoy the lazy river, mini golf, and kid-friendly ...

8.6/10 Excellent! (1,435 reviews)

Family Friendly

Reviewed on Dec 3, 2025

The Bear's Den Resort Orlando

7880 Nicklaus Clubhouse Lane Kissimmee FL

This smoke-free vacation home features a golf course, free water park access, and a restaurant. Enjoy the outdoor pool and perks like free self parking and free ...

Great place , I recommend it to everyone.

Reviewed on Jan 8, 2025

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Cozy 3Bd Close to Disney @ Enclaves at Festival 808

808 Benoi Dr Davenport FL

Free water park access and an outdoor pool are featured at this luxury vacation home. There's fun for all ages with a lazy river and a children's pool, and families ...

6.6/10 (3 reviews)

Property was beautiful host was very attentive and answered all my questions and concerns area was safe and quiet the pool pass did not work was my only issue but everything else was top tier

Reviewed on Jul 30, 2025

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Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

8899 Cabot Cliffs Dr #101 Davenport FL

Free water park access and an outdoor pool are featured at this luxury apartment. Bring the family and enjoy the lazy river, children's pool, and waterslide. ...

8.6/10 Excellent! (8 reviews)

They kept in contact the whole time we stayed with them. They responded to any questions promptly.

Reviewed on Aug 2, 2025

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7 Bedroom Villa, Private Pool, Resort Amenities

112 Madiera Beach Boulevard Kissimmee FL

This villa features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. There's a poolside bar on site, and a terrace ...

9/10 Wonderful! (15 reviews)

The property was very minimally cleaned and there were bugs everywhere. The rental car shuttle was the last one to come to the airport, besides that, it was really visually appealing and there was plenty of stuff to do

Reviewed on Aug 13, 2025

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WonderFull 4Bd with Pool at Champions Gate 1174

1174 Kingsbarn St Davenport FL

Free water park access and an outdoor pool are featured at this luxury vacation home. There's fun for all ages with a lazy river and a children's pool, and families ...

9/10 Wonderful! (4 reviews)

Will be returning

This home was exactly as the pictures and more. It was beautiful and perfect size for my family. The pool was also perfect when we didn’t want to be in the crowds anymore at the resorts. Wonder vacation homes were amazing hosts and took great care of all of our questions

Reviewed on Apr 25, 2025

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Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

1536 Retreat Cir Clermont FL

Free water park access and an outdoor pool are featured at this luxury vacation home. Bring the family and enjoy the lazy river, children's pool, and waterslide. ...

9/10 Wonderful! (4 reviews)

went with grandkids they enjoyed the dipping pool and area was nice and quiet. The place was very clean.

Reviewed on Aug 13, 2025

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Gorgeous 5Bd Screened Pool at Champions Gate 1125

1125 Kingsbarn St Davenport FL

Free water park access and an outdoor pool are featured at this luxury vacation home. There's fun for all ages with a lazy river and a children's pool, and families ...

9.4/10 Exceptional! (3 reviews)

The house was exactly as the pictures posted. Very well maintained, cleaned, and well equipped with all essential equipment for cooking ext. My family and I loved it. It exceeded our expectations! We truly recommend this house, and will definitely rent this house again.

Reviewed on Aug 24, 2024

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Winter Haven Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Winter Haven to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Winter Haven 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Winter Haven before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.