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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
$220 nightly
The price is $249 total per night from Jul 20 to Jul 21
$249 total
Jul 20 - Jul 21
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! (461 reviews)
"Very poor facility."

Reviewed on Jun 24, 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
$601 nightly
The price is $682 total per night from Jul 13 to Jul 14
$682 total
Jul 13 - Jul 14
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! (1,000 reviews)
"We went to the waterpark two times during our stay. Both days it closed after being there for maybe 30 minutes. They said due to lightening 5 miles away. The two times we called the front desk for something, the reason we called wasn't addressed in a timely manner. We called to get gas delivered ..."

Reviewed on Jun 29, 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! (1,576 reviews)
"The property was in need of repair and cleaning. It isn't located near the parks, as advertised. It was okay though."

Reviewed on Jun 28, 2026

Opens in a new windowReunion Resort & Golf Club
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
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
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 ...
8.4/10 Very Good! (6 reviews)
"La ubicación La facilidad de entrada Y el precio Lo recomiendo"

Reviewed on Jun 14, 2026

Opens in a new windowCozy 3Bd Close to Disney @ Enclaves at Festival 808
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

5 out of 5
1536 Retreat Cir Clermont FL
An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. Families will appreciate the children's pool and barbecue grills. ...
9.6/10 Exceptional! (8 reviews)
"House was clean, comfortable, and safe! My only issue is the king size bed is super thin and hard and I couldn’t sleep well but overall I absolutely enjoyed my stay!"

Reviewed on Jun 17, 2026

Opens in a new windowMarvelous 3Bd w/ Pool Near Disney at Serenity 1536
7 Bedroom Villa, Private Pool, Resort Amenities

7 Bedroom Villa, Private Pool, Resort Amenities

5 out of 5
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 ...
7.6/10 Good! (20 reviews)
"We were very disappointed with this property. I asked to get hot tub and pool heated and i was willing to pay the $40 fee. I received no response from Expedia or the property manager until 2nd last day. I was trying everyday a few times a day. I finally got a response that the hot tub and pool heater ..."

Reviewed on Apr 9, 2026

Opens in a new window7 Bedroom Villa, Private Pool, Resort Amenities
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! (8 reviews)
"House was super clean, felt like I was home…"

Reviewed on May 29, 2026

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