Are there any 5-star vacation rentals in Winter Haven?

There are no 5-star vacation rentals in Winter Haven on our site, but there are a few other highly rated options worth checking out. Scan through our vacation rentals in Winter Haven to discover the perfect place for your stay.

The Best 5 Star Hotels in Winter Haven, FL from $132

A castle entrance with flags and banners, including a LEGO Kingdoms banner.

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Our top choices for Winter Haven 5-star hotels

A pool area with lounge chairs and umbrellas, surrounded by tropical plants.

1. ette hotel Orlando

Kissimmee

Manuel

$327 nightly

Oct 28 - Oct 29

Total with taxes and fees

A rectangular swimming pool with lounge chairs and palm trees.

2. Encore Resort and Water Park at Reunion by Rentyl

Kissimmee

paula

$726 nightly

Oct 30 - Oct 31

Total with taxes and fees

A pool area with a waterfall, palm trees, and a rocky backdrop.

3. Reunion Resort & Golf Club

Reunion

Karen G

$371 nightly

Oct 28 - Oct 29

Total with taxes and fees

A modern living room with a sofa, a TV mounted on the wall, and a balcony with glass doors.

4. Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Clermont

Angela

A bedroom with a brick wall, a large bed with red bedding, two bedside lamps, a nightstand, a potted plant, and a red door.

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

Tuscan Hills

Tiffany

An aerial view of a resort with a central swimming pool, surrounded by lounge chairs and palm trees, with a body of water and buildings in the background.

6. Amazing 4Bd Screened Pool Close to Disney 4572

Bellavida

Charlene

A rectangular swimming pool with a tiled edge, surrounded by a brick patio. There are lounge chairs and a small table near the pool.

7. Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

Kissimmee

Denise

A resort with multiple swimming pools, palm trees, and lounge areas.

8. Gorgeous 5Bd Screened Pool at Champions Gate 1125

Davenport

Carmen

A pool area with a building featuring a red-tiled roof, columns, and outdoor seating.

9. Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access

Kissimmee

Tameko

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table set for four.

10. Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Festival

Brittany

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

Davenport

Emmanuel

A modern kitchen with a stainless steel refrigerator, a built-in oven, a coffee maker, and a toaster.

12. Jasmine 4 Bedrooms

Seasons

Jose Antonio

A swimming pool with a glass enclosure, a hot tub, and a covered seating area.

13. 7 Bedroom Villa, Private Pool, Resort Amenities

Kissimmee

LLoyd

A resort with a large swimming pool, palm trees, and a boat-shaped water feature.

14. Charming 3Bd Close to Disney @ Festival 1026

Festival

Jianzhuang

A large pool area with multiple swimming lanes, surrounded by palm trees and lounge chairs.

15. Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

Davenport

Rudi

16. Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

Davenport

Donald Lester

A spacious lobby with a grand chandelier, a fountain, and a grand piano.

17. Reunion Resort & Golf Club

Reunion

Anonymous traveler

18. WonderFull 4Bd with Pool at Champions Gate 1174

Davenport

Anonymous traveler

19. The Bear's Den Resort Orlando

Reunion

Lauren

A resort with a large central pool, palm trees, and a slide.

20. Anchor Cove Villa

Solterra Resort

"Everything was literally perfect. Just as the pictures advertised. Our kids lost it when they walked in and explored the house and found the themed rooms, the theater and the pool. Pool was amazing! We opted for heat which made the stay even better having a hot tub. White rose was very responsive to our needs and had quick response time. The resort amenities were clean, the staff was friends and helped us find parking when the pool lot was full. Lazy river was a blast for the kids. Plenty of...

Jessica

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winter Haven.

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

$196 nightly

$220 total

Oct 30 - Oct 31

Total with taxes and fees

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Pool Spa Hot tub Breakfast included Waterpark

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.

Learn more about Winter Haven

Glide through LEGOLAND's colorful rides before cooling off at their water park on hot Florida afternoons. Chain of Lakes offers peaceful kayaking spots where you can paddle between waterways and spot wildlife at your own pace.

See all hotels in Winter Haven

A LEGO-themed welcome sign with 'LEGO FLORIDA' and 'WELCOME' in large letters, surrounded by greenery.

Top Winter Haven Hotel Reviews

Find out more about Winter Haven

Why not ask for the best during your trip to Winter Haven? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Winter Haven so popular in the last year. There's no reason to delay a getaway to Winter Haven any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Book one of Expedia's luxurious 5-star hotels in Winter Haven and get ready to be pampered like never before. Don't wait any longer!

5-Star Hotels in Winter Haven

A stay in one of these hotels is bound to be special. Highly-rated eateries, concierges, and pillow-fluffing are all at the ready. You're sure to find exactly the accommodation you need. You'll also enjoy a high standard of care and meticulous guest relations, so get ready to kick back and indulge. How do you want to relax? A full-body massage to help your cares fall away? A concierge to help you pick out your next adventure? Beautiful furniture, delectable chocolate desserts, and even a hot tub in the bathroom...these hotels will astonish you. Want to see for yourself? Explore our listings and pick the perfect accommodation for your needs.

Can't wait to get outside? You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Winter Haven are the perfect place to rest up after a busy day.

Your Getaway Starts Today

The results are in, and Winter Haven 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Don't put off your dream vacation any longer -- Expedia can help you land a great deal on accommodation. Choose one of our Winter Haven 5-star hotels today and settle down in complete comfort when you're ready.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Haven?

How much you pay for a 5-star hotel in Winter Haven depends on factors such as when you plan to go and the length of your stay. Our top tip for scoring the best deal? Use our pricing filters to check out the available hotels for your preferred dates.

Search for the lowest price per night from $132

What makes a hotel 5 stars in Winter Haven?

Flawless guest service is at the heart of every 5-star hotel in Winter Haven. From the minute you arrive, staff attend to your every whim, whether recommending activities and tours or providing a nightly turn-down service. Plus, hotels have to feature superior amenities to be eligible for a 5-star rating. These can include luxury bathrooms, a wellness center, pools, gastronomic kitchens and knowledgeable concierge.

Are there any 5-star all-inclusive resorts in Winter Haven?

Our filter tool is the easiest way to search for exactly what you want. Select "5-star" and "All inclusive" to show the finest properties in Winter Haven where your room, meals, activities and entertainment are included in the upfront price. At these getaways, your vacation is pure indulgence from the moment you enter the lobby.

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