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

Our top choices for Winter Garden 5-star hotels

Exterior

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
5.0 star property
Orlando
9.4 out of 10, Exceptional, (580 reviews)
"I loved everything it felt like Dubai like I was amazed please book now !!!"
United States
Winstina
The price is 7.425.348 ₫
9.832.461 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Outdoor pool, pool cabanas (surcharge), pool umbrellas

Conrad Orlando at Evermore

Conrad Orlando at Evermore
5.0 star property
Orlando
9.6 out of 10, Exceptional, (501 reviews)
"The hotel was very clean, the staff were friendly, and the location was extremely convenient to Disney Park which the hotel offers shuttle to and from."
United States
Diana
The price is 11.172.752 ₫
13.881.995 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Conrad Orlando at Evermore
3 outdoor pools, pool cabanas (surcharge), pool umbrellas

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, (926 reviews)
"Always amazing. The best place to stay at disney."
United States
Roxanne
The price is 24.809.085 ₫
29.534.493 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Property amenity

The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
5.0 star property
Orlando
9.4 out of 10, Exceptional, (1,000 reviews)
"Wonderful stay and an amazing staff. Would love to come back again."
United States
Brian
The price is 9.634.851 ₫
12.463.743 ₫ total
includes taxes & fees
31 Jul - 1 Aug
The Ritz-Carlton Orlando, Grande Lakes
Outdoor pool, open 9:00 AM to 6:00 PM, free pool cabanas, pool umbrellas

ette hotel

ette hotel
5.0 star property
Kissimmee
9.6 out of 10, Exceptional, (470 reviews)
"Great stay"
United States
Jason
The price is 6.615.756 ₫
7.508.882 ₫ total
includes taxes & fees
2 Aug - 3 Aug
ette hotel
Water park

Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,590 reviews)
"The property was clean and big. Had everything you would need."
United States
Bernissse
The price is 8.061.624 ₫
10.394.335 ₫ total
includes taxes & fees
4 Aug - 5 Aug
Reunion Resort & Golf Club
Water park

Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
5.0 star property
Kissimmee
8.4 out of 10, Very good, (1,003 reviews)
"This was a wonderful property! The hosts were incredibly friendly, welcoming, and helpful throughout our stay. My family truly enjoyed our time here and absolutely loved the property. We would definitely stay here again and highly recommend it to others."
United States
Makhia
The price is 5.323.725 ₫
17.381.306 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Encore Resort and Water Park at Reunion by Rentyl
3 outdoor pools

Disney's Beach Club Resort

Disney's Beach Club Resort
5.0 star property
Bay Lake
8.8 out of 10, Excellent, (714 reviews)
"The resort was clean and beautiful ... staff was friendly"
United States
Robert
The price is 12.106.545 ₫
13.619.864 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Disney's Beach Club Resort
Water park

Marvelous 4Bd with Pool at Storey Lake Resort 2601

Marvelous 4Bd with Pool at Storey Lake Resort 2601
5.0 star property
Kissimmee
10.0 out of 10, Exceptional, (6 reviews)
"Definitely booking again ❤️"
United States
Yolanda
Marvelous 4Bd with Pool at Storey Lake Resort 2601
3 outdoor pools

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
The price is 16.030.328 ₫
18.034.118 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Disney's Beach Club Villas
Water park

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
Townhome, 4 Bedrooms | In-room dining

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836
5.0 star property
Kissimmee
9.4 out of 10, Exceptional, (19 reviews)
"The place was amazing. I would definitely book again"
United States
Teddy
Gorgeous 4 Bedroom w/ Pool Close to Disney 4836
Water park

5 Bedroom at Storey Lake Orlando FL close to Disney 4851

5 Bedroom at Storey Lake Orlando FL close to Disney 4851
5.0 star property
Kissimmee
9.4 out of 10, Exceptional, (3 reviews)
"Pool heating cost additional. Property Lazy river and pool was heated in November, was awesome. great Spot for a vacation. Highly recomend."
United States
Nita
5 Bedroom at Storey Lake Orlando FL close to Disney 4851
Aerial view

Stunning 2 Bd Condo Close to Disney 304 3191

Stunning 2 Bd Condo Close to Disney 304 3191
5.0 star property
Kissimmee
5.0 out of 10, (6 reviews)
"Pools were filthy. The washer dryer combo did not work. Like a previous "
United States
Stephanie
Stunning 2 Bd Condo Close to Disney 304 3191
Aerial view

7 Bedroom Villa, Private Pool, Resort Amenities

7 Bedroom Villa, Private Pool, Resort Amenities
5.0 star property
Kissimmee
7.6 out of 10, Good, (20 reviews)
"Beautiful and the family loved it 😍! Close to Disney, excellent for large families"
Canada
LLoyd
7 Bedroom Villa, Private Pool, Resort Amenities
Water park

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

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
5.0 star property
Kissimmee
8.6 out of 10, Excellent, (4 reviews)
"Nice "
United States
Janismarie
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
2 outdoor pools, free pool cabanas, pool umbrellas

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
5.0 star property
Kissimmee
8.4 out of 10, Very good, (7 reviews)
"The accommodation not only has a good equipment and location, but is also absolutely top and highly recommended. I will be very happy to book here again."
Germany
Thomas
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
Indoor pool, outdoor pool, pool loungers, lifeguards on site

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

5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
5.0 star property
Kissimmee
10.0 out of 10, Exceptional, (4 reviews)
"Looks just like photos, very nice and spacious. I would book again."
United States
Kimesha
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
Interior

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
5.0 star property
Clermont
9.6 out of 10, Exceptional, (8 reviews)
"Wonderful stay!"
Canada
Angela
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
Outdoor pool

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
5.0 star property
Kissimmee
5.6 out of 10, (4 reviews)
"The coffee pot was broke, we emailed about it and received a new one within a a few hours. The listing says water park access but you don’t get water park access. The dryer was broken and unable to be fixed during our stay. The company is very attentive to needs. I brought up something’s in the house that probably need evaluated and they said things need to be addressed at the beginning on the stay. (Things like the fridge seal not being great, broken can opener, broken pool chairs ) make sure...
United States
Bronte
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
The price is 4.916.230 ₫ per night from 3 Aug to 4 Aug
4.916.230 ₫
5.530.890 ₫ total
3 Aug - 4 Aug
includes taxes & fees
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.
PoolSpaHot tubBreakfast includedWaterpark
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

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

10/10 Excellent
"Amazing hotel with excellent amenities close to all the theme parks."
Jacob 2-night trip
Posted 9 hours ago
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

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 4.998.386 ₫

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.