Kissimmee Lakefront Park Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad

5 Star Hotels in Winter Garden, Florida

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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, (533 reviews)
"This hotel offers an exceptional experience!"
United States
Radmila
The price is €357
includes taxes & fees
24 Jun - 25 Jun
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, (461 reviews)
"The view when you walk into the lobby is just breath taking!"
United States
Kelly Denise
The price is €507
includes taxes & fees
24 Jun - 25 Jun
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, (910 reviews)
"Best place"
United States
Waell
The price is €961
includes taxes & fees
2 Jul - 3 Jul
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, (1,003 reviews)
"Clean, helpful staff, great gift shops and food!"
United States
Telvia
The price is €466
includes taxes & fees
25 Jun - 26 Jun
The Ritz-Carlton Orlando, Grande Lakes

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, (1,002 reviews)
"Our stay was perfect for my family and I. Location was convenient to stores, food, and of course Disney. This is our 2nd time staying here we will definitely be back for a 3rd visit."
United States
Ebony
The price is €625
includes taxes & fees
11 Jun - 12 Jun
Encore Resort and Water Park at Reunion by Rentyl

ette hotel

ette hotel
5.0 star property
Kissimmee
9.6 out of 10, Exceptional, (457 reviews)
"Everything was excellent spent 2 nights and lived it."
United States
Xavier
The price is €264
includes taxes & fees
1 Jul - 2 Jul
ette hotel

Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,567 reviews)
"Great resort for families very clear and friendly "
Canada
Cory
Reunion Resort & Golf Club

Disney's Beach Club Resort

Disney's Beach Club Resort
5.0 star property
Bay Lake
8.8 out of 10, Excellent, (709 reviews)
"The resort was clean and beautiful ... staff was friendly"
United States
Robert
Disney's Beach Club Resort

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, (8 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

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, (5 reviews)
"Definitely booking again ❤️"
United States
Yolanda
Marvelous 4Bd with Pool at Storey Lake Resort 2601

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)
"Great stay"
United States
Tiffany
Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

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, (7 reviews)
"Wonderful stay!"
Canada
Angela
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

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

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

Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Cozy 3Bd Close to Disney @ Enclaves at Festival 808
5.0 star property
Festival
8.0 out of 10, Very good, (5 reviews)
"This home was excellent and easy to find. this location felt very safe, and when I entered, I was impressed- Wow, such a beautiful and comfortable home. The house rules were clear, and everything was organized. A few lights were not working, but it was not a big issue. i especially loved the pool and the gym. I really enjoyed them during our stay. We had a great, relaxing week and were not bothered by anything. the only small issue was 8-ball pool table, which has some broken parts, we...
United States
Alexandra
Cozy 3Bd Close to Disney @ Enclaves at Festival 808

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

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

Gorgeous 2 Bedroom Apartment Close to Disney 305 3191

Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
5.0 star property
Kissimmee
9.4 out of 10, Exceptional, (8 reviews)
"Enjoyed the pools. The apartment included a washer and dryer. It was a calm, quiet community."
United States
Melissa
Gorgeous 2 Bedroom Apartment Close to Disney 305 3191

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
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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.

ARM53A Historic Downtown Area and Clock of Winter Garden Florida

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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 depends on things such as when you plan to travel and the length of your break. A top tip for scoring an awesome deal? Use our pricing filters to check out the available options for your selected dates.

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What makes a hotel 5 stars in Winter Garden?
In Winter Garden, a hotel must offer a certain level of high-end conveniences to be rated 5 stars. These can include saunas and spas, on-site gyms, gourmet restaurants, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their extraordinary service. You'll enjoy things like nightly turn-down services, in-room massages and concierge services. Some may even offer special touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Winter Garden?
Find a luxury getaway that includes your room, meals, drinks and entertainment in Winter Garden with the help of our filter tool. Search for resorts with a 5-star rating and select the "All inclusive" filter. Double-check what's included in the price. This way, you can take full advantage of the premium perks on offer from the moment you step into the lobby.