Explore top 2026 5 Star Hotels in Winter Haven

Name: Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
Rating: 8

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Top Winter Haven 5 Star hotels

ette hotel

3001 Sherberth Rd Kissimmee FL

Fully refundableReserve now, pay when you stay

$250 nightly

$284 total

Sep 8 - Sep 9

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 ...

Reunion Resort & Golf Club

7593 Gathering Drive Kissimmee FL

$305 nightly

$346 total

Sep 8 - Sep 9

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 ...

8.8/10 Excellent! (1,620 reviews)

"Room clean and property is very nice. Watch out for resort fees, the $40 per day was disclosed, but the other $20 resort access fee was not. When asked about thr fee the front desk stated that is a extra fee that you have to pay to stay on property. Clubhouse restaurant was amazing food but be aware ..."

Reviewed on Sep 7, 2026

Encore Resort and Water Park at Reunion by Rentyl

7635 Fairfax Dr Kissimmee FL

Fully refundableReserve now, pay when you stay

$690 nightly

$783 total

Sep 14 - Sep 15

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! (1,008 reviews)

"House water heater was broken"

Reviewed on Sep 7, 2026

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

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. ...

9.4/10 Exceptional! (9 reviews)

"The cleanliness of the room was not the best. We actually had to go out & buy a mop because the floors were flithy. Also, I did not appreciate the fact that we were responsible for washing the towels and sheets prior to check out ; among other “check out rules”. If these things weren’t done, then ..."

Reviewed on Jul 16, 2026

Get rates

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 ...

Get rates

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

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! (9 reviews)

"Everything as described… Loved it & would book again"

Reviewed on Jul 22, 2026

Get rates

Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub

273 Calabay Parc Blvd, Davenport, Fl Davenport FL

This vacation home features an outdoor pool and a hot tub. WiFi in public areas is free.

7.4/10 Good! (3 reviews)

"The fridge door was broke , tv was not working the whole time"

Reviewed on Aug 7, 2026

Get rates

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

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

Get rates

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

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 ...

Get rates

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

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 ...

8/10 Very Good! (10 reviews)

"The couch downstairs was very dirty. The drawers for the fridge were broken. The garbage can foot pedal was broken and cut my daughter’s foot. The barstools at the counter were very unsteady. Up stairs in the master bathroom there was black mold on the shower wall. The shower door frame rail was ..."

Reviewed on Aug 3, 2026

Get rates

Don't see what you're looking for?

See all available properties in Winter Haven

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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.

Recent Winter Haven hotel reviews by fellow wanderers

Best Western Plus Winter Haven Inn & Suites

5 out of 5

Posted less than an hour ago

Travelocity Verified Review

"We chose to stay here for a weekend at legoland! The room was extremely clean, the breakfast was great, the beds were comfy, and the drive to the park was less than 5minutes! Location matters and the savings of staying at this Best Western was WORTH WVERY PENNY! I truly hope this is a sign of Best Westerns making a comeback because this stay was 10/10 definitely recommend!"

A verified traveler stayed at Best Western Plus Winter Haven Inn & Suites