Explore top 2026 5 Star Hotels in Lakeland - Winter Haven

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

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Top Lakeland - Winter Haven 5 Star hotels

Encore Resort and Water Park at Reunion by Rentyl

7635 Fairfax Dr Kissimmee FL

Fully refundableReserve now, pay when you stay

$606 nightly

$688 total

Mar 27 - Mar 28

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! (1,005 reviews)

The stay was amazing. The place was clean and kept accordingly. The only complaint was the shuttle return from the theme park took 2 hours to return(travel time). Otherwise we have no other complaints.

Reviewed on Mar 12, 2026

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 ...

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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 ...

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

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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. ...

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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. ...

9.8/10 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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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! (4 reviews)

Nice location

Reviewed on Aug 20, 2024

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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.

Lakeland - 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 Lakeland - 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. Lakeland - 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 Lakeland - 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.