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Top Winter Haven 5 Star hotels

ette hotel

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 10 to May 11
$334 total
May 10 - May 11
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! (440 reviews)
Good

Reviewed on Apr 22, 2026

Opens in a new windowette hotel
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! (1,536 reviews)
Nice property!!

Reviewed on Apr 20, 2026

Opens in a new windowReunion Resort & Golf Club
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
$600 nightly
The price is $681 total per night from Apr 26 to Apr 27
$681 total
Apr 26 - Apr 27
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! (1,002 reviews)
Great place to stay! We were so comfortable and private pool was amazing!

Reviewed on Apr 23, 2026

Opens in a new windowEncore Resort and Water Park at Reunion by Rentyl
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 ...
8.6/10 Excellent! (7 reviews)
The house was clean that was about it. I was asked by the host to take the garbage from the last persons out, pretty sure thats why theres a cleaning fee. The kids games rooms dont actually come with games every thingnis extra. Communication with persons at the property were terrible and unprofessional. ...

Reviewed on Mar 13, 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
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
Charming 3Bd Close to Disney @ Festival 1026

Charming 3Bd Close to Disney @ Festival 1026

5 out of 5
1026 Plantation Ln 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 ...
Opens in a new windowCharming 3Bd Close to Disney @ Festival 1026
Amazing 4Bd Screened Pool Close to Disney 4572

Amazing 4Bd Screened Pool Close to Disney 4572

5 out of 5
4572 Baleno Ln Kissimmee 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 ...
8.4/10 Very Good! (6 reviews)
Great for our family, close to activities, parks, attractiins

Reviewed on Jan 11, 2026

Opens in a new windowAmazing 4Bd Screened Pool Close to Disney 4572
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 ...
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
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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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