Explore top 2026 5 Star Hotels in Winter Haven

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Top Winter Haven 5 Star hotels

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ette hotel

5 out of 5
3001 Sherberth Rd Kissimmee FL
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $334 total per night from May 31 to Jun 1
$334 total
May 31 - Jun 1
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! (446 reviews)
Amazing stay from start to departure. Helpful courteous staff, great decor. Overall, a true 5+_star experience

Reviewed on May 5, 2026

Opens in a new windowette hotel
Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl

5 out of 5
7635 Fairfax Dr Kissimmee FL
Fully refundableReserve now, pay when you stay
$655 nightly
The price is $743 total per night from May 17 to May 18
$743 total
May 17 - May 18
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! (1,004 reviews)
Stayed with our family, the place was clean, staff were helpful. A couple of rules to keep in mind for checkout, but nothing out of the ordinary. The only thing they need to figure out is how to keep the pool at a decently cool temperature. Will definitely stay there again.

Reviewed on May 15, 2026

Opens in a new windowEncore Resort and Water Park at Reunion by Rentyl
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
7593 Gathering Drive Kissimmee FL
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 ...
8.8/10 Excellent! (1,560 reviews)
Very beautiful place! Hade a great stay with our family while visiting Disney!

Reviewed on May 16, 2026

Opens in a new windowReunion Resort & Golf Club
The Bear's Den Resort Orlando

The Bear's Den Resort Orlando

5 out of 5
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 ...
7.8/10 Good! (24 reviews)
Ivan at checkin was wonderful but the house had issues from the start. the entire pool deck wasn't cleaned, goggles floating in hot tub, crushed fruity pebbles, cigar and cigarettes butts on the ground and previous renters left heat on in spa/pool so pool was 103 degrees. Multiple calls to get resolution ...

Reviewed on Apr 21, 2026

Opens in a new windowThe Bear's Den Resort Orlando
Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

5 out of 5
313 Brunello Dr Davenport FL
An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. Traveling on business? Take advantage of the express check-out ...
8.8/10 Excellent! (8 reviews)
Great stay

Reviewed on Apr 24, 2026

Opens in a new windowMarvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

5 out of 5
1158 Kingsbarn St Davenport 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. ...
9.8/10 Exceptional! (7 reviews)
The condo was great. The pool heating was a bit warm for us but we are from the Northeast. Staff responded quickly to any concerns we had. Would suggest getting higher quality toilet paper. Check before getting coffee filters.

Reviewed on Apr 23, 2026

Opens in a new windowStunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
Gorgeous 5Bd Screened Pool at Champions Gate 1125

Gorgeous 5Bd Screened Pool at Champions Gate 1125

5 out of 5
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 ...
9.6/10 Exceptional! (4 reviews)
The resort community was very clean and felt very safe. The only con was that the home was advertised with amenities that you actually had to pay a significant amount to utilize, such as a crib, gas grill or heat for the hot tub!

Reviewed on May 8, 2026

Opens in a new windowGorgeous 5Bd Screened Pool at Champions Gate 1125
Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

5 out of 5
3814 Lana Ave 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 ...
8.6/10 Excellent! (9 reviews)
It was a very nice play with a lot to do. Everything was worth the money. Clean, friendly, and fun.

Reviewed on Mar 26, 2026

Opens in a new windowStunning 5Bd w/ Pool @ Windsor Island Resort 3814
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

5 out of 5
461 Lasso Drive Kissimmee FL
This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the children's pool and onsite laundry facilities. ...
5.6/10 (4 reviews)
Problemas con la ducha del baño, se dañó y quedó encendida con agua caliente saliendo no cerraba, tardaron 4 días en atender la situación. Los números de teléfono para llamar no funcionan, nadie los atiende, la asistencia al cliente vía Email, es decepcionante, Expedia me ayudo a contactarlos pero ...

Reviewed on Jul 22, 2025

Opens in a new windowWonderful 8Bd w/ Pool & GameRoom @ Encore 461
Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access

Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access

5 out of 5
8491 Oasis Key Cove Kissimmee FL
This villa's 2 outdoor pools and hot tub are among the featured amenities. Enjoy the sauna and perks like free self parking. A garden, a picnic area, and barbecue ...
8/10 Very Good! (4 reviews)
The rooms were a bit dusty and the bathrooms could be a bit cleaner

Reviewed on Feb 23, 2025

Opens in a new windowThemed 7 Bedroom Villa, 12 Min to Disney, Resort Access
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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.

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