5 Stars Hotels in Winter Garden, Florida from CA $142

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Winter Garden 5 Star Hotels

This weekend
Next weekend

Our top choices for Winter Garden 5-star hotels

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
5.0 star property
Orlando
9.2 out of 10, Wonderful, (501 reviews)
"We had a lovely stay, highly recommend this property. "
Canada
Diana
The price is CA $442
CA $574 total
includes taxes & fees
May 25 - May 26
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Conrad Orlando at Evermore

Conrad Orlando at Evermore
5.0 star property
Orlando
9.6 out of 10, Exceptional, (437 reviews)
"Amazing stay!"
United States
Kristen
The price is CA $817
CA $988 total
includes taxes & fees
May 10 - May 11
Conrad Orlando at Evermore

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
5.0 star property
Golden Oak
9.6 out of 10, Exceptional, (900 reviews)
"Best hotel for Disney!!!! Delicious food and amazing property grounds!"
United States
Izabella
The price is CA $1,374
CA $1,630 total
includes taxes & fees
May 26 - May 27
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
5.0 star property
Orlando
9.2 out of 10, Wonderful, (1,000 reviews)
"Amazing experience!! Definitely worth it"
United States
Glenda
The price is CA $812
CA $998 total
includes taxes & fees
May 17 - May 18
The Ritz-Carlton Orlando, Grande Lakes

ette hotel

ette hotel
5.0 star property
Kissimmee
9.6 out of 10, Exceptional, (441 reviews)
"Elegant and classy hotel. "
United States
SCOTT
The price is CA $398
CA $452 total
includes taxes & fees
May 10 - May 11
ette hotel

Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,538 reviews)
"Will stay here again in the future. "
United States
Keith
Reunion Resort & Golf Club

Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
5.0 star property
Kissimmee
8.2 out of 10, Very good, (1,004 reviews)
"Great place to stay! We were so comfortable and private pool was amazing!"
United States
Martha Uribe
The price is CA $301
CA $931 total
includes taxes & fees
May 3 - May 4
Encore Resort and Water Park at Reunion by Rentyl

Disney's Beach Club Resort

Disney's Beach Club Resort
5.0 star property
Bay Lake
8.8 out of 10, Excellent, (702 reviews)
"Clean, friendly staff, convenient, close to parks"
United States
Katie
Disney's Beach Club Resort

Disney's Beach Club Villas

Disney's Beach Club Villas
5.0 star property
Bay Lake
9.2 out of 10, Wonderful, (39 reviews)
"Clean and great location"
United States
Anonymous traveller
Disney's Beach Club Villas

Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653

Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
5.0 star property
Kissimmee
9.8 out of 10, Exceptional, (7 reviews)
"Overall wonderful home, great price, great property and amenities for families. Location is great near absolutely everything. "
United States
Lance
Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653

Splendid 5Bd Close to Disney at Storey Lake 4251

Splendid 5Bd Close to Disney at Storey Lake 4251
5.0 star property
Kissimmee
9.2 out of 10, Wonderful, (12 reviews)
"Everything that a big family needs for a vacation, plus a great location"
United States
omar
Splendid 5Bd Close to Disney at Storey Lake 4251

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

Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887
5.0 star property
Kissimmee
9.4 out of 10, Exceptional, (3 reviews)
"House was really good..but thermostat wasn't working at all..some part carpet was wet all time"
United States
Pareshkumar
Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887

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

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
5.0 star property
Tuscan Hills
8.8 out of 10, Excellent, (8 reviews)
"The unique rooms were a hit with our children."
United States
Joseph
Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

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

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
5.0 star property
Davenport
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place so many things to do. Great place to stay for a large family especially with kids "
United States
Yesenia
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191

Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191
5.0 star property
Kissimmee
8.8 out of 10, Excellent, (6 reviews)
"Parking was easy."
United States
Maria Belen
Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191

Gorgeous 2 Bedroom Apartment Close to Disney 305 3191

Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
5.0 star property
Kissimmee
9.2 out of 10, Wonderful, (7 reviews)
"Great location, beautiful spacious apartment, comfortable beds/space. It was well appointed with kitchen items, bathroom, and laundry. The apartment floors were a little dirty and there really needed to be a fan in the 2nd bedroom. It was pretty stuffy in there with the thermometer limited to 72 at night. The AC unit was a little loud but cooled well. Unfortunately, the pool was too packed to enjoy, and the gym that didn't open until 9am was also packed. The gym was well appointed, and there...
United States
Anonymous traveller
Gorgeous 2 Bedroom Apartment Close to Disney 305 3191

The Bear's Den Resort Orlando

The Bear's Den Resort Orlando
5.0 star property
Reunion
7.8 out of 10, Good, (24 reviews)
"Great place , I recommend it to everyone."
United States
Jacqueline
The Bear's Den Resort Orlando

Family Vacation Home, Water Park+Endless Amenities

Family Vacation Home, Water Park+Endless Amenities
5.0 star property
Kissimmee
7.6 out of 10, Good, (25 reviews)
"Falsely advertised. Waterpark was CLOSED and reopens in a month . The pictures of the condo did not reflect actual state. (broken handle on freezer door wall outlet cover that screwed in; blender doesn’t work,…) Also, floor was dirty.(white strip socks, turned black and bottom when walking around.) "
United States
Sara
Family Vacation Home, Water Park+Endless Amenities

2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms

2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms
5.0 star property
Kissimmee
8.2 out of 10, Very good, (20 reviews)
"Pool was great kids loved it. Came with blender and coffe maker. "
United States
casey paul
2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms

Charming 3Bd Close to Disney @ Festival 1026

Charming 3Bd Close to Disney @ Festival 1026
5.0 star property
Festival
8.4 out of 10, Very good, (5 reviews)
"Nice location "
United States
Jianzhuang
Charming 3Bd Close to Disney @ Festival 1026
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.
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 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.

ARM53A Historic Downtown Area and Clock of Winter Garden Florida

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 $142

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.

Explore a world of travel with Expedia