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5 Stars Hotels in Winter Garden, Florida from CA $204

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Check availability on Winter Garden 5 Star Hotels

Tonight
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Winter Garden 5-star hotels

A hotel with a swimming pool, lounge chairs, and palm trees.
A spacious hotel corridor with large windows, a blue carpet, and elegant chandeliers.
A long dining table set with chairs, surrounded by hanging lights and greenery.
A bar area with multiple seating options, a marble countertop, and a decorative ceiling light.

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

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
United States
Robbi
CA $411
CA $541 total
includes taxes & fees
Sep 27 - Sep 28
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
A resort with multiple swimming pools, lounge areas, and a modern building with balconies.
An outdoor dining area with wicker furniture and hanging lights, overlooking a beach and hotel buildings.
A rooftop lounge with wicker furniture, round tables, and potted plants.
A modern hotel entrance with a large wooden ceiling structure, glass doors, and a view of the outdoors.

2. Conrad Orlando at Evermore

Conrad Orlando at Evermore
Orlando
United States
Marlon
CA $555
CA $625 total
includes taxes & fees
Sep 30 - Oct 1
Conrad Orlando at Evermore
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 pathway lined with tall, vertically planted trees and well-maintained greenery, leading towards a building with classical architecture.
A spacious lobby with a high ceiling, large windows, and a reflective floor.

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

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Golden Oak
United States
Melissa
CA $1,304
CA $1,553 total
includes taxes & fees
Sep 20 - Sep 21
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
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 courtyard with outdoor seating, palm trees, and a pool.

4. The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
Orlando
United States
Teresa
CA $588
CA $747 total
includes taxes & fees
Oct 4 - Oct 5
The Ritz-Carlton Orlando, Grande Lakes
A pool area with lounge chairs and umbrellas, surrounded by tropical plants.
A man in a white suit standing in a room with a marble countertop and a hanging black lamp.
A person in a white bathrobe sitting at a breakfast table with plates of food, a teapot, and a cup.
A restaurant interior with wooden tables and chairs, a marble wall, and a seating area with a cushioned bench.

5. ette hotel Orlando

ette hotel Orlando
Kissimmee
United States
Lorie
CA $337
CA $382 total
includes taxes & fees
Sep 16 - Sep 17
ette hotel Orlando
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.

6. Reunion Resort & Golf Club

Reunion Resort & Golf Club
Reunion
United States
RYAN
CA $319
CA $428 total
includes taxes & fees
Sep 15 - Sep 16
Reunion Resort & Golf Club
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.
A large, multi-story hotel with a central entrance, multiple wings, and a clock tower.

7. Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
Kissimmee
United States
Tara
CA $387
CA $1,179 total
includes taxes & fees
Sep 15 - Sep 16
Encore Resort and Water Park at Reunion by Rentyl
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A hotel with a blue exterior, white railings, and a well-maintained garden with a central flower bed.
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
Disney's Beach Club Resort
A pool with inflatable rings, lounge chairs, and a wooden deck with stairs.
A modern living room with a sofa, coffee table, and bar stools. There is a kitchen area with cabinets and appliances.
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, pendant lighting, and a dining area with a table and chairs.

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

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
Kissimmee
United States
Janismarie
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A row of white buildings with balconies, connected by a walkway with string lights and street lamps.
A restaurant with round tables, wooden chairs, and large windows.
A large, multi-story building with balconies and a waterfront view.

10. Disney's Beach Club Villas

Disney's Beach Club Villas
Bay Lake
United States
Anonymous traveller
Disney's Beach Club Villas
A swimming pool with lounge chairs, palm trees, and a golf course.
A residential area with multiple two-story houses, a well-maintained lawn, and a circular patio area with seating.
A modern kitchen with a stainless steel refrigerator, a granite countertop, and a bar area with stools. There is a dining table set with plates and glasses, and a chandelier above.
A beach area with a hammock, palm trees, a chair, and a building with a white exterior.

11. 5 Bedroom at Storey Lake Orlando FL close to Disney 4851

5 Bedroom at Storey Lake Orlando FL close to Disney 4851
Kissimmee
United States
Nita
5 Bedroom at Storey Lake Orlando FL close to Disney 4851
A modern kitchen with a granite countertop, stainless steel appliances, and wooden cabinets. There are three bar stools and a hanging light fixture above the counter.
A dining area with a glass table and brown chairs, a blue vase, and a framed artwork on the wall.
A living room with a sectional sofa, a patterned armchair, a coffee table, and a TV.
A hallway with a glass-top console table, a white door at the end, and framed pictures on the walls.

12. Family Friendly 5 Bedrooms Home Close to Disney 4849

Family Friendly 5 Bedrooms Home Close to Disney 4849
Kissimmee
United States
Raquel
Family Friendly 5 Bedrooms Home Close to Disney 4849
An aerial view of a resort with a large swimming pool, water slides, and a mini-golf area.
A modern living room with a beige sectional sofa, a white coffee table, and a flat-screen TV mounted on the wall.
A modern hotel room with a large bed, a nightstand with drawers, a wall-mounted painting, and a bathroom visible through an open door.
A modern kitchen with white cabinets, a black backsplash, and a dining area set with white plates, blue placemats, and clear wine glasses.

13. 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
A resort with multiple swimming pools, sun loungers, and palm trees.
A spacious outdoor dining area with white chairs and tables, ceiling fans, and a bar area with a TV screen.
A modern living room with a grey sofa, glass coffee table, and a black and white rug.
A wooden ship structure with ropes and a flag, surrounded by greenery and a clear sky.

14. Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653

Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
Kissimmee
United States
Lance
Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
An aerial view of a resort with a large swimming pool, palm trees, and a water slide.
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.
An aerial view of a resort with a large central pool, multiple smaller pools, and a covered pavilion.

15. 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 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.

16. 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 covered outdoor dining area with white tables and chairs, a central bar, and ceiling fans.
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 modern living room with a dining area, featuring a large table, chairs, a sofa, and a TV.

17. 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 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 covered outdoor area with a pool, two lounge chairs, and a view of trees.
A large rock with the words "HIDDEN FOREST" engraved on it, surrounded by colorful flowers.

18. 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 swimming pool with a glass enclosure, a patio with wicker furniture, and a door leading to a covered area.
A living room with a beige sectional sofa, a white coffee table, and a bookshelf. There is a window with blue curtains, a ceiling fan, and a clock on the wall.
A single-story house with a beige exterior, a white garage door, and a front entrance with a blue door.
A bedroom with a wooden bed, two bedside tables, a ceiling fan, and artwork on the wall.

19. Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub

Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub
Davenport
United States
Valerie
Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub
A resort with multiple swimming pools, sun loungers, and palm trees.
A gym with various weightlifting equipment, including dumbbells and weight plates.
A wooden ship structure with ropes and a flag, surrounded by greenery and a clear sky.
A modern dining area with a dark wooden table set for six, surrounded by grey upholstered chairs. A kitchen with white cabinets and stainless steel appliances is visible in the background.

20. Gorgeous 4Bd with Pool @ Storey Lake Resort 4475

Gorgeous 4Bd with Pool @ Storey Lake Resort 4475
Kissimmee
Canada
Shawnte
Gorgeous 4Bd with Pool @ Storey Lake Resort 4475
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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 Garden.
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL
CA $304
CA $342 total
Sep 20 - Sep 21
includes taxes & fees
Hyatt Regency Orlando International Airport
Walt Disney World Dolphin

Walt Disney World Dolphin

1500 Epcot Resort Blvd Lake Buena Vista FL
CA $289
CA $403 total
Oct 15 - Oct 16
includes taxes & fees
Walt Disney World Dolphin
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL
CA $182
CA $204 total
Sep 21 - Sep 22
includes taxes & fees
9.2/10 Wonderful! (6,741 reviews)
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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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.

Learn more about Winter Garden

Stroll the charming brick-lined streets of historic downtown 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

Five Star Hotels in Winter Garden

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Winter Garden so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Winter Garden and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Winter Garden

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Winter Garden

The results are in, and Winter Garden 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Winter Garden! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winter Garden today and settle down in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Garden?
How much you pay for a 5-star hotel in Winter Garden can vary based on what time of year you travel and how long you plan to be away, among a number of factors. Use our price per night filter and other search tools to score the best rate on a plush stay.
  • Search for the lowest price per night from CA $204
What makes a hotel 5 stars in Winter Garden?
In Winter Garden, a hotel is required to offer a specific level of high-end amenities to be designated 5 stars. These can include gourmet restaurants, saunas and spas, on-site gyms, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-centric standard of service. You'll enjoy things like concierge services, in-room massages and nightly turn-down services. Some may even offer thoughtful touches like a welcome gift.
Are there any 5-star all-inclusive resorts in Winter Garden?
Find a luxurious escape that includes your room, meals, activities and entertainment in Winter Garden with our handy filters. Search for properties rated 5 stars and click on the "All inclusive" filter. Be sure to check what's included in the price. That way, you can take full advantage of all the perks on offer as soon as you arrive.

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