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

Winter Haven 5 Stars Hotels

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Check availability on Winter Haven 5 Star Hotels

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 woman sitting on a white sofa reading a magazine in a modern room with a mannequin in the background.
A man in a white suit standing in a room with a marble countertop and a hanging black lamp.

1. ette hotel Orlando

ette hotel Orlando
Kissimmee
United States
Manuel
HK$2,088
HK$2,370 total
includes taxes & fees
3 Oct - 4 Oct
ette hotel Orlando
Water park
A spacious lobby with a high ceiling, a unique wooden chandelier, a large arched glass door leading outside, and potted plants.
A spacious lobby with a central reception desk, a staircase, and a view of the outside.
A large, two-story hotel with a prominent clock tower, a covered entrance, and a well-lit facade.

2. Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
Kissimmee
United States
Tara
HK$2,188
HK$6,668 total
includes taxes & fees
1 Oct - 2 Oct
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 multi-story hotel with a central courtyard, a bell tower, and a covered entrance.
A spacious lobby with a grand chandelier, a fountain, and a grand piano.
A spacious lobby with a grand chandelier, a piano, and a reception desk.

3. Reunion Resort & Golf Club

Reunion Resort & Golf Club
Reunion
United States
RYAN
HK$1,807
HK$2,422 total
includes taxes & fees
30 Sept - 1 Oct
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 living room with a glass coffee table, a black sofa, and a dining area with a TV displaying a castle.
A large rock with the words "HIDDEN FOREST" engraved on it, surrounded by colorful flowers.
A modern kitchen with a granite countertop, stainless steel appliances, and bar stools.

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 modern kitchen with a central island, bar stools, and a dining area with a sofa and chairs.
A hotel room with a wooden console table, a round mirror, a globe, and a small plant.
A covered outdoor dining area with multiple tables and chairs, a kitchen counter, and a ceiling fan.

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 resort with multiple swimming pools, palm trees, and lounge areas.
A spacious living room with a high ceiling, a dining area with a modern table and chairs, and a large flat-screen TV mounted on the wall.
A covered outdoor dining area with white tables and chairs, a central bar, and ceiling fans.
A modern living room with a dining area, featuring a large table, chairs, a sofa, and a TV.

6. Gorgeous 5Bd Screened Pool at Champions Gate 1125

Gorgeous 5Bd Screened Pool at Champions Gate 1125
Davenport
United States
Carmen
Gorgeous 5Bd Screened Pool at Champions Gate 1125
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 modern kitchen with dark wood cabinets, stainless steel appliances, and a large island with bar stools.
A living room with a sofa, coffee table, TV, and decorative items.
A two-story house with a brick driveway and a stone facade.

7. 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 dining room with a dark wooden table, six upholstered chairs, and a chandelier.
A modern kitchen with grey cabinets, stainless steel appliances, a central island, and a dining area with wooden chairs.

8. 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 spacious dining area with multiple wooden tables and chairs, ceiling fans, and recessed lighting.
A covered patio area with a round table and four cushioned chairs, large arched windows, and a ceiling fan.

9. 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, and a dining area with a wooden table set for four.
A modern kitchen with white cabinets, stainless steel appliances, a central island with bar stools, and pendant lighting.

10. 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 wooden boat with a yellow and black striped flag, a green sign, and a yellow and black striped flag on a dock.
A spacious restaurant with high ceilings, wooden tables and chairs, a bar area, and a large window providing natural light.
A water play area with a pirate ship, palm trees, and outdoor seating.

11. 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.

12. Anchor Cove Villa

Anchor Cove Villa
Solterra Resort
United States
Jessica
Anchor Cove Villa
A resort with multiple swimming pools, palm trees, and lounge areas.
A modern living room with a sofa, a coffee table, and a potted plant.
A modern living room with a sofa, a coffee table, and a plant.
A golf course with bunkers, a pond, and residential buildings in the background.

13. 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 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 residential area with houses, a swimming pool, and a small lake.
A modern living room with a ceiling fan, a flat-screen TV, and a kitchen area in the background.

14. 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 dining room with a central table, six chairs, and a chandelier.
A modern kitchen with white cabinetry, stainless steel appliances, and a dining area with a round table and chairs.
An aerial view of a resort with a central swimming pool, a covered area with seating, and a water slide.

15. 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 clear blue pool with a waterfall feature surrounded by lush greenery and palm trees.
A spacious lobby with a grand chandelier, a fountain, and a grand piano.
An outdoor seating area with wicker furniture, a fire feature, and palm trees.
A multi-story hotel with a central entrance, surrounded by palm trees and a well-maintained lawn.

16. Reunion Resort & Golf Club

Reunion Resort & Golf Club
Reunion
United States
Anonymous traveller
HK$1,916
HK$2,564 total
includes taxes & fees
5 Oct - 6 Oct
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.
Tuscan Hills sign with a landscaped entrance featuring palm trees and a hedge.
An indoor swimming pool with a glass ceiling, surrounded by greenery and a clear view of palm trees.
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.

17. 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 cabinetry, stainless steel appliances, and a central island.
Mini-golf
A beachside area with sun loungers, umbrellas, and a hammock.

18. 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
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.

19. 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
Outdoor pool
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar-style seating.
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.

20. WonderFull 4Bd with Pool at Champions Gate 1174

WonderFull 4Bd with Pool at Champions Gate 1174
Davenport
United States
Anonymous traveller
WonderFull 4Bd with Pool at Champions Gate 1174
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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
HK$1,334
HK$1,933 total
28 Oct - 29 Oct
includes taxes & fees
8/10 Very good! (10,927 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
HK$678
HK$1,036 total
7 Oct - 8 Oct
includes taxes & fees
9/10 Wonderful! (4,815 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
HK$754
HK$1,245 total
30 Sept - 1 Oct
includes taxes & fees
8.8/10 Excellent! (3,370 reviews)
Holiday Inn Club Vacations at Orange Lake Resort by IHG
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Learn more about Winter Haven

Glide through LEGOLAND's colourful 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 castle entrance with flags and banners, including a LEGO Kingdoms banner.

Top Winter Haven Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Haven?
There are a range of pricing options for 5-star hotels in Winter Haven on Expedia. How much you'll pay will depend on when you travel, length of your trip and other factors. Compare all of the available accommodation for your preferred dates and use our pricing and other filters to score the perfect high-end stay.
  • Search for the lowest price per night from HK$1,036
What makes a hotel 5 stars in Winter Haven?
From gourmet dining venues and all-day fitness centers to pools and the finest bedding, the 5-star experience in Winter Haven is all about indulgence and comfort. But it takes more than just top-notch conveniences to earn a 5-star rating. Stays must also offer outstanding guest-focused services like in-room massage treatments, laundry and dry cleaning and concierge services.
Are there any 5-star all-inclusive resorts in Winter Haven?
Our convenient filters are the quickest way to search for exactly what you're looking for. Check the "All inclusive" and "5-star" boxes to show the finest properties in Winter Haven where your meals, accommodation, entertainment and activities are included in the price. At these getaways, your trip is pure extravagance from the moment you enter the lobby.

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