A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

Compare and book 5 Star hotels in Winter Garden, Florida

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Garden 5 Star Hotels

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Winter Garden 5-star hotels

A swimming pool with palm trees and umbrellas, surrounded by a building with a curved facade and multiple balconies.
A balcony with a table set for two, overlooking a golf course.
A spacious corridor with large windows, a polished floor, and a grand chandelier.
A modern living room with a Christmas tree, a sofa, a coffee table, and a large window with a view of a green landscape.

1. Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
United States
John
₹29,617
₹38,660 total
includes taxes & fees
22 Nov - 23 Nov
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
A resort with multiple swimming pools, lounge areas, and a modern building with balconies.
A rooftop lounge with wicker furniture, round tables, and potted plants.
An outdoor dining area with wicker furniture and hanging lights, overlooking a beach and hotel buildings.
A spacious lobby with a view of a body of water, large wooden columns, and a modern tiled floor.

2. Conrad Orlando at Evermore

Conrad Orlando at Evermore
Orlando
United States
YASIR
₹45,863
₹56,337 total
includes taxes & fees
18 Nov - 19 Nov
Conrad Orlando at Evermore
A water park with multiple slides and a pool area surrounded by palm trees and a golf course.
A modern living room with a sofa set, coffee table, and decorative plants.
A spacious lobby with a high ceiling, large windows, and a variety of seating arrangements including sofas and armchairs.
A dining area with tables set for service, large arched windows, and wall-mounted lighting.

3. The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
Orlando
United States
Teresa
₹47,376
₹59,174 total
includes taxes & fees
28 Oct - 29 Oct
The Ritz-Carlton Orlando, Grande Lakes
A pool with a waterfall, surrounded by tropical vegetation and a stone bridge.
A hotel with a central courtyard, a reflective pool, and a large building with a prominent entrance.
A spacious lobby with a high ceiling, large windows, and a reflective floor.
An indoor dining area with multiple tables and chairs, large windows, and a bar counter.

4. Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Golden Oak
United States
Caroline
₹133,231
₹156,285 total
includes taxes & fees
1 Nov - 2 Nov
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
A pool area with lounge chairs and umbrellas, surrounded by tropical plants.
A woman sitting on a white sofa reading a magazine in a modern room with a mannequin in the background.
A restaurant interior with wooden tables and chairs, a marble wall, and a seating area with a cushioned bench.
A man in a white suit standing in a room with a marble countertop and a hanging black lamp.

5. ette hotel Orlando

ette hotel Orlando
Kissimmee
United States
Manuel
₹33,663
₹38,208 total
includes taxes & fees
1 Nov - 2 Nov
ette hotel Orlando
Water park
A spacious lobby with a central reception desk, a staircase, and a view of the outside.
A spacious lobby with a high ceiling, a unique wooden chandelier, a large arched glass door leading outside, and potted plants.
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with four bar stools.

6. Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
Kissimmee
United States
paula
₹26,457
₹80,614 total
includes taxes & fees
26 Oct - 27 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 patio area with wicker furniture, a fire pit, and palm trees.
A spacious lobby with a grand chandelier, a fountain, and a grand piano.

7. Reunion Resort & Golf Club

Reunion Resort & Golf Club
Reunion
United States
Karen G
₹28,078
₹36,363 total
includes taxes & fees
25 Oct - 26 Oct
Reunion Resort & Golf Club
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A restaurant with round tables, wooden chairs, and large windows.
A waterfront hotel with multiple buildings, a large spherical structure in the background, and reflections on the water.
A spacious lobby with high ceilings, multiple chandeliers, and a polished wooden floor.

8. Disney's Beach Club Resort

Disney's Beach Club Resort
Bay Lake
United States
Carl
₹69,118
₹77,758 total
includes taxes & fees
3 Nov - 4 Nov
Disney's Beach Club Resort
A pool with inflatable rings, lounge chairs, and a wooden deck with stairs.
A modern kitchen with a central island, pendant lighting, and a dining area with a table and chairs.
A modern dining area with a white table set for four, light blue upholstered chairs, and decorative white feathers.
A modern kitchen with a central island, bar stools, stainless steel appliances, and pendant lighting.

9. Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
Kissimmee
United States
Nydia
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
A modern living room with a sofa, a TV mounted on the wall, and a balcony with glass doors.
A large rock with the words "HIDDEN FOREST" engraved on it, surrounded by colorful flowers.
A covered outdoor area with a pool, two lounge chairs, and a view of trees.
A modern kitchen with a granite countertop, stainless steel appliances, and bar stools.

10. 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
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 dining area with a round wooden table, six chairs, and a chandelier.
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.

11. 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 swimming pool, water slides, and a mini-golf area.
A modern kitchen with white cabinets, a black backsplash, and a dining area set with white plates, blue placemats, and clear wine glasses.
A modern kitchen with a central island, stainless steel appliances, and a dining area with bar stools.
A modern living room with a beige sectional sofa, a white coffee table, and a flat-screen TV mounted on the wall.

12. Stunning 2 Bd Condo Close to Disney 304 3191

Stunning 2 Bd Condo Close to Disney 304 3191
Kissimmee
United States
Stephanie
Stunning 2 Bd Condo Close to Disney 304 3191
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 covered patio area with a round table and four cushioned chairs, large arched windows, and a ceiling fan.
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.

13. 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 swimming pool with a glass enclosure, surrounded by a patio area with a view of a residential building.
A dining area with a wooden table, six chairs, a chandelier, and black and white patterned wallpaper.
A spacious living area with a sofa, armchairs, and a dining table. There is a kitchen in the background with white cabinets and a microwave.
A modern kitchen with white cabinets, a central island with wicker chairs, and pendant lighting.

14. 5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759

5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
Kissimmee
United States
Kimesha
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
A row of modern two-story houses with attached garages, well-maintained lawns, and a street lamp.
A modern kitchen with granite countertops, a built-in island, and a dining area with a sofa and chairs.
A kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and a built-in oven. There are three white bar stools and a small island with a yellow vase.
A dining area with a table set for four, surrounded by chairs, and a sofa in the background.

15. 5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney

5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
Kissimmee
United States
Ben-Jade
5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.
An outdoor dining area with white tables and chairs, ceiling fans, and a bar area with a TV screen.
A wooden play structure with ropes and a slide, surrounded by greenery and palm trees.
A modern kitchen with a central island, a dining area with a long table and chairs, and a living area with a sofa and a coffee table.

16. Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887

Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887
Kissimmee
United States
Pareshkumar
Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887
An aerial view of a resort with a large water park, multiple swimming pools, and a variety of recreational facilities.
A modern living room with a grey sofa, a purple armchair, and a large window with a view of greenery.
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a built-in oven.

17. Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort

Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort
Kissimmee
United States
Prasad
Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort
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 spacious dining area with a long table, multiple chairs, and a large mirror on the wall.

18. 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
An aerial view of a resort with a large swimming pool, palm trees, and a water slide.
An aerial view of a resort with a large central pool, multiple smaller pools, and a covered pavilion.
A wooden play structure with ropes and a slide, surrounded by palm trees and a clear sky.
A modern kitchen with white cabinets, a microwave, and a coffee station with white cups and orange flowers.

19. Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
Kissimmee
Germany
Thomas
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
A resort with multiple swimming pools, palm trees, and lounge areas.
A modern building with a central courtyard, arched walkways, and a symmetrical design.
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.

20. 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
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winter Garden.
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL
₹20,792
₹23,391 total
2 Nov - 3 Nov
includes taxes & fees
Hyatt Regency Orlando International Airport
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL
₹8,786
₹9,884 total
16 Nov - 17 Nov
includes taxes & fees
8.6/10 Excellent! (7,128 reviews)
DoubleTree by Hilton at the Entrance to Universal Orlando
DoubleTree by Hilton Orlando Theme Park Resort

DoubleTree by Hilton Orlando Theme Park Resort

10100 International Drive Orlando FL
₹6,061
₹9,486 total
22 Nov - 23 Nov
includes taxes & fees
7.6/10 Good! (6,506 reviews)
DoubleTree by Hilton Orlando Theme Park Resort
Still don't see what you're looking for?
See all properties in Winter Garden.
You can also use these popular filters to refine your search.
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 Garden

Stroll the charming brick-lined streets of historic city centre where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

See all hotels in Winter Garden
A brick building with a clock tower and a sign that reads "Winter Garden."

Top Winter Garden Hotel Reviews

Find out more about Winter Garden

Stay in Luxury: 5 Star Hotels in Winter Garden

There's nothing wrong with enjoying the finer things in life. Indulge your every desire on your upcoming leisure time. Treat yourself with a stay in a 5-star hotel during your Winter Garden trip. You'll join the multitudes of holidaymakers who have made Winter Garden so fashionable recently. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Winter Garden and indulge in the finer things in life for a while.

5-Star Hotels in Winter Garden

You'll have a wonderful time at one of these 5-star hotels. Exceptional customer care, luxurious bedding, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A body scrub that will leave you feeling refreshed and alive? Butler services? Whatever it is your heart desires, you're bound to find it here. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs. 

But you aren't going to spend your entire holiday in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Winter Garden are waiting for you to relax after an exciting day.

Make Your Escape

The results are in, and Winter Garden 5-star hotels are the place to be when you book your next holiday. If you've been dreaming about a holiday set here, then go ahead and book it. It's time to plan your next great escape -- this is a great time to find 5-star hotel deals in Winter Garden! Choose one of our Winter Garden 5-star hotels today and soothe yourself in luxe surroundings at your convenience.

Expedia India is rated 4 stars by Feefo based on 1038 reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Garden?
The amount you pay for a 5-star hotel in Winter Garden depends on things such as when you want to go and the length of your holiday. An insider tip for scoring an awesome deal? Use our pricing filters to compare the available accommodation for your chosen dates.
  • Search for the lowest price per night from ₹9,486
What makes a hotel 5 stars in Winter Garden?
In Winter Garden, a hotel is required to offer a certain amount of top-notch amenities to earn 5 stars. These can include on-site gyms, gourmet restaurants, saunas and spas, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their exceptional service. You'll enjoy things like concierge services, nightly turn-down services and in-room massage. Some may also offer thoughtful touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Winter Garden?
Use Expedia's filter tool to find a luxury retreat in Winter Garden where most of what you need is included in the price. Next, narrow down your results for properties that have a rating of 5 stars and are deemed "All inclusive." The first thing on the to-do list at these stays? Relaxation and enjoyment.

Explore a world of travel with Expedia