Explore top 2025 5 Star Hotels in Winter Haven

Name: Charming 3Bd Close to Disney @ Festival 1026
Rating: 8.6

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Top Winter Haven 5 Star hotels

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3001 Sherberth Rd, Kissimmee, FL

Fully refundableReserve now, pay when you stay

$306 nightly

$347 total

Oct 25 - Oct 26

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! (347 reviews)

Very good

Reviewed on Oct 11, 2025

Reunion Resort & Golf Club

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 ...

8.6/10 Excellent! (1,417 reviews)

Clean room, everything that was needed was in the room. I highly recommend this resort.

Reviewed on Oct 13, 2025

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Encore Resort and Water Park at Reunion by Rentyl

7635 Fairfax Dr, Kissimmee, FL

Fully refundableReserve now, pay when you stay

$629 nightly

$714 total

Oct 24 - Oct 25

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! (1,000 reviews)

Good

Reviewed on Oct 20, 2025

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. ...

9.6/10 Exceptional! (6 reviews)

Very nice place so many things to do. Great place to stay for a large family especially with kids

Reviewed on Oct 15, 2025

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Amazing 4Bd Screened Pool Close to Disney 4572

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 ...

9.6/10 Exceptional! (4 reviews)

The dryer didnt work and No Highchair , also never received my tickets to Water park with Lazy pool ticket. Other than that My Family enjoyed Everything. Pool is a Plus

Reviewed on May 28, 2025

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Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

8899 Cabot Cliffs Dr #101, Davenport, FL

Free water park access and an outdoor pool are featured at this luxury apartment. Bring the family and enjoy the lazy river, children's pool, and waterslide. ...

8.6/10 Excellent! (8 reviews)

They kept in contact the whole time we stayed with them. They responded to any questions promptly.

Reviewed on Aug 2, 2025

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Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

1536 Retreat Cir, Clermont, 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. ...

9/10 Wonderful! (4 reviews)

went with grandkids they enjoyed the dipping pool and area was nice and quiet. The place was very clean.

Reviewed on Aug 13, 2025

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The Bear's Den Resort Orlando

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 ...

Great place , I recommend it to everyone.

Reviewed on Jan 8, 2025

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7 Bedroom Villa, Private Pool, Resort Amenities

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 ...

9/10 Wonderful! (15 reviews)

The property was very minimally cleaned and there were bugs everywhere. The rental car shuttle was the last one to come to the airport, besides that, it was really visually appealing and there was plenty of stuff to do

Reviewed on Aug 13, 2025

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Charming 3Bd Close to Disney @ Festival 1026

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! (3 reviews)

Nice location

Reviewed on Aug 20, 2024

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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.

Recent Winter Haven hotel reviews by fellow wanderers

Comfort Inn & Suites Kissimmee by the Parks

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"I was very pleased with my stay at this hotel. "

A verified traveler from Miami stayed at Comfort Inn & Suites Kissimmee by the Parks

Kompose Boutique Resort at Theme Parks

5 out of 5

Posted 3 days ago

Travelocity Verified Review

"Overall our one night stay was amazing. It was in a good location close to the parks and also around food areas. The room was clean and spacious and very modern. The staff was friendly and helpful during the stay. The breakfast was really good for a hotel buffet. Food was fresh with options and tasted good! My only issue which was very minimal was th check in process took a long time. It was late when we got there and only 2 people working the desk so they were trying their best and still friendly even when other guest kept interrupting them. The next morning for breakfast, we didn’t get our tickets at check in that we paid for so we had to go back and get them so make sure you get the tickets in case your room isn’t on the list. Overall experience was good with the small hiccups. I would definitely return to this hotel and can’t wait to see when the rest is finished! "

A verified traveler stayed at Kompose Boutique Resort at Theme Parks

Holiday Inn Club Vacations at Orange Lake Resort by IHG

5 out of 5

Posted 4 days ago

Travelocity Verified Review

"The staff was very nice, lazy river area was very large, the rooms are to update and were very clean. The only issue I had was the photos online, did not represent the room I actually had. For example there was no jacuzzi tub in the two room villa, even tho there was photos of it and listed as it did. There is ton of restaurants within 5 mins of the hotel and aleast to the Orlando Outlets it’s about 35ish mins with traffic. "

A verified traveler stayed at Holiday Inn Club Vacations at Orange Lake Resort by IHG