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
$315 nightly
The price is $358 total per night from Apr 7 to Apr 8
$358 total
Apr 7 - Apr 8
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! (415 reviews)
Elegant and classy hotel.

Reviewed on Mar 8, 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! (1,484 reviews)
We booked a three bedroom villa for myself and three of my adult children for 8 nights. I have stayed at Reunion 3 times in the past with the last time being 2016. The initial villa assigned to us was very "tired". The arm chair in the living room had a broken leg and was not usable. The dining chair ...

Reviewed on Mar 8, 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
$550 nightly
The price is $624 total per night from Mar 10 to Mar 11
$624 total
Mar 10 - Mar 11
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 ...
8.4/10 Very Good! (1,012 reviews)
Waterpark is an excellent added feature we used daily! Breakfast is just eggs and sausage with a tray of pastries and white bread (one toaster for the entire resort). This part was the only significant disappointment with young kids. When booking this resort we didn’t find it clear EAST VS WEST on ...

Reviewed on Mar 6, 2026

Opens in a new windowEncore Resort and Water Park at Reunion by Rentyl
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
Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Cozy 3Bd Close to Disney @ Enclaves at Festival 808

5 out of 5
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 ...
6.8/10 (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

Opens in a new windowCozy 3Bd Close to Disney @ Enclaves at Festival 808
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 ...
8.6/10 Excellent! (4 reviews)
Nice location

Reviewed on Aug 20, 2024

Opens in a new windowCharming 3Bd Close to Disney @ Festival 1026
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 ...
Opens in a new windowThe Bear's Den Resort Orlando
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
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! (8 reviews)
Clean home. Pool and deck were great. Resort area was fun, clean and easy to use.

Reviewed on Dec 15, 2025

Opens in a new windowStunning 5Bd w/ Pool @ Windsor Island Resort 3814
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 ...
9.4/10 Exceptional! (6 reviews)
Pool was nice house was nice & neighborhood nice & quiet. The only complaint is the couch. I sat on it & fell into a hole, the couch needs to be replaced. Decorated themed rooms very cool.

Reviewed on Nov 12, 2025

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