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

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Check availability on Winter Haven 5 Star Hotels

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Oct 18 - Oct 19
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Oct 23 - Oct 25
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Oct 30 - Nov 1

Our top choices for Winter Haven 5-star hotels

A pool area with lounge chairs and umbrellas, surrounded by tropical plants.
A person in a white bathrobe sitting at a breakfast table with plates of food, a teapot, and a cup.
A man in a white suit standing in a room with a marble countertop and a hanging black lamp.
A woman sitting on a white sofa reading a magazine in a modern room with a mannequin in the background.

1. ette hotel Orlando

ette hotel Orlando
Kissimmee
United States
Manuel
$295 nightly
$335 total
Oct 20 - Oct 21
Total with taxes and fees
ette hotel Orlando
Water park
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with four bar stools.
A large, two-story hotel with a prominent clock tower, a covered entrance, and a well-lit facade.
A spacious lobby with a high ceiling, a unique wooden chandelier, a large arched glass door leading outside, and potted plants.

2. Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
Kissimmee
United States
Kelly
$718 nightly
$815 total
Oct 21 - Oct 22
Total with taxes and fees
Encore Resort and Water Park at Reunion by Rentyl
An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.
A spacious lobby with a grand chandelier, a piano, and a reception desk.
A patio area with wicker furniture, a fire pit, and palm trees.
A spacious lobby with a grand chandelier, a fountain, and a grand piano.

3. Reunion Resort & Golf Club

Reunion Resort & Golf Club
Reunion
United States
Karen G
$312 nightly
$354 total
Nov 18 - Nov 19
Total with taxes and fees
Reunion Resort & Golf Club
A modern living room with a sofa, a TV mounted on the wall, and a balcony with glass doors.
A modern kitchen with a granite countertop, stainless steel appliances, and bar stools.
A modern living room with a glass coffee table, a black sofa, and a dining area with a TV displaying a castle.
A covered outdoor area with a pool, two lounge chairs, and a view of trees.

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

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
Clermont
Canada
Angela
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
Water park
A covered outdoor dining area with multiple tables and chairs, a kitchen counter, and a ceiling fan.
A hotel room with a wooden console table, a round mirror, a globe, and a small plant.
A modern kitchen with a central island, bar stools, and a dining area with a sofa and chairs.

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

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
Davenport
United States
Emmanuel
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
A rectangular swimming pool with a tiled edge, surrounded by a brick patio. There are lounge chairs and a small table near the pool.
A living room with a sofa, coffee table, TV, and decorative items.
A spacious dining area with a long table, multiple chairs, and a large mirror on the wall.
A two-story house with a brick driveway and a stone facade.

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

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
Kissimmee
United States
Bronte
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
A modern open-plan living area with a kitchen, grey leather sofas, a glass coffee table, and a ceiling fan.
A bedroom with a bunk bed, a desk, a window with curtains, and a staircase.
A poolside area with a covered seating area, lounge chairs, and a bar.
A modern kitchen with grey cabinets, stainless steel appliances, a central island, and a dining area with wooden chairs.

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

Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access
Kissimmee
United States
Tameko
Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access
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.
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.
A modern living room with a sofa, armchair, coffee table, and a small side table.
A spacious dining area with multiple wooden tables and chairs, ceiling fans, and recessed lighting.

8. Amazing 4Bd Screened Pool Close to Disney 4572

Amazing 4Bd Screened Pool Close to Disney 4572
Bellavida
United States
Charlene
Amazing 4Bd Screened Pool Close to Disney 4572
A pirate-themed water play area with a ship structure, slides, and a crocodile float.
A gym with treadmills, ellipticals, and a stationary bike.
A modern kitchen with white cabinets, stainless steel appliances, a central island with bar stools, and pendant lighting.
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table set for four.

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

Cozy 3Bd Close to Disney @ Enclaves at Festival 808
Festival
United States
Brittany
Cozy 3Bd Close to Disney @ Enclaves at Festival 808
A resort with a large swimming pool, palm trees, and a boat-shaped water feature.
A water play area with a pirate ship, palm trees, and outdoor seating.
A neatly made bed with a wooden tray, white bedding, and a wall-mounted floral artwork.
A wooden boat with a yellow and black striped flag, a green sign, and a yellow and black striped flag on a dock.

10. Charming 3Bd Close to Disney @ Festival 1026

Charming 3Bd Close to Disney @ Festival 1026
Festival
United States
Jianzhuang
Charming 3Bd Close to Disney @ Festival 1026
A resort with a large central pool, palm trees, and a slide.
A spacious hotel lobby with a bar area, seating arrangements, and a modern ceiling design.
A modern kitchen with dark cabinetry, stainless steel appliances, and a central island with a fruit bowl.
A residential house with a two-story design, a brick driveway, and a well-maintained garden with palm trees.

11. Anchor Cove Villa

Anchor Cove Villa
Solterra Resort
United States
Jessica
Anchor Cove Villa
A modern kitchen with a stainless steel refrigerator, a built-in oven, a coffee maker, and a toaster.
A swimming pool with a glass enclosure, lounge chairs, and a patio area.
A modern dining area with a round table, six chairs, and a blue accent wall.
A residential area with houses, a swimming pool, and a small lake.

12. Jasmine 4 Bedrooms

Jasmine 4 Bedrooms
Seasons
United States
Jose Antonio
Jasmine 4 Bedrooms
A resort with a central swimming pool, multiple tennis courts, and a variety of outdoor seating areas.
A modern kitchen with white cabinetry, stainless steel appliances, and a dining area with a round table and chairs.
A dining room with a central table, six chairs, and a chandelier.
An aerial view of a resort with a central swimming pool, a covered area with seating, and a water slide.

13. 7 Bedroom Villa, Private Pool, Resort Amenities

7 Bedroom Villa, Private Pool, Resort Amenities
Kissimmee
Canada
LLoyd
7 Bedroom Villa, Private Pool, Resort Amenities
A resort with multiple swimming pools, palm trees, and lounge areas.
A hotel with a central courtyard, palm trees, a swimming pool, and a fountain.
A modern living room with a sofa, a coffee table, and a potted plant.
A golf course with bunkers, a pond, and residential buildings in the background.

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

Family Friendly 2 Bd Close to Disney @ Champions Gate 8899
Davenport
United States
Donald Lester
Family Friendly 2 Bd Close to Disney @ Champions Gate 8899
A clear blue pool with a waterfall feature surrounded by lush greenery and palm trees.
A multi-story hotel with a central entrance, surrounded by palm trees and a well-maintained lawn.
A grand lobby with a grand piano, a chandelier, and a large arched doorway labeled "101".
An outdoor seating area with wicker furniture, a fire feature, and palm trees.

15. Reunion Resort & Golf Club

Reunion Resort & Golf Club
Reunion
United States
Anonymous traveler
Reunion Resort & Golf Club
A bedroom with a brick wall, a large bed with red bedding, two bedside lamps, a nightstand, a potted plant, and a red door.
A living room with a brown leather sofa, a wooden coffee table, and a TV on a stand. There is a sliding glass door leading to a pool area.
Tuscan Hills sign with a landscaped entrance featuring palm trees and a hedge.
A dining area with a round wooden table, six chairs, and a chandelier.

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

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
Tuscan Hills
United States
Tiffany
Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
An aerial view of a resort with a large central pool, multiple water slides, and sun loungers.
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.
Mini-golf

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

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
Davenport
Canada
Rudi
Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
Outdoor pool
Restaurant
A covered outdoor dining area with multiple tables and chairs, a kitchen counter, and a ceiling fan.
A modern living room with a grey sofa, a wooden coffee table, and a kitchen area with white cabinets and a black trash bin.

18. WonderFull 4Bd with Pool at Champions Gate 1174

WonderFull 4Bd with Pool at Champions Gate 1174
Davenport
United States
Anonymous traveler
WonderFull 4Bd with Pool at Champions Gate 1174
A modern two-story house with a garage, a balcony, and a well-maintained garden.
A modern kitchen with grey cabinets, stainless steel appliances, and a central island with bar stools.
A modern outdoor pool area with lounge chairs, a pergola, and a view of palm trees against a sunset sky.
A modern living room with a sectional sofa, a coffee table, and a dining area with chairs.

19. The Bear's Den Resort Orlando

The Bear's Den Resort Orlando
Reunion
United States
Lauren
The Bear's Den Resort Orlando
An aerial view of a resort with multiple swimming pools surrounded by palm trees and resort buildings.
A modern kitchen with a central island, bar stools, pendant lighting, and a dining area with a high chair.
A modern living room with a black leather sofa, a round coffee table, and a chandelier.
A modern dining area with a long table set for four, a chandelier, and a view of the kitchen and living area in the background.

20. Luxury 5Bd Close To Disney With Pool At Windsor Cay 1285

Luxury 5Bd Close To Disney With Pool At Windsor Cay 1285
Clermont
United Kingdom
Kyle
Luxury 5Bd Close To Disney With Pool At Windsor Cay 1285
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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

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL
$244 nightly
$274 total
Nov 18 - Nov 19
Total with taxes and fees
8/10 Very Good! (10,924 reviews)
The Grove Resort & Water Park Orlando
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL
$116 nightly
$132 total
Oct 25 - Oct 26
Total with taxes and fees
9/10 Wonderful! (4,821 reviews)
Hilton Vacation Club Mystic Dunes Orlando
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL
$153 nightly
$172 total
Oct 26 - Oct 27
Total with taxes and fees
Holiday Inn Club Vacations at Orange Lake Resort by IHG
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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.
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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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