A lakeside community with houses and boats.

Find 5 Star Hotels in Windermere, FL from ￥11,338

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Check availability on Windermere 5 Star Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Windermere 5-star hotels

A hotel with a swimming pool, lounge chairs, and palm trees.

1. 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, (678 reviews)
"Very nice hotel in every way."
United States
John
The price is ￥54,747
￥70,458 total
includes taxes & fees
Nov 22 - Nov 23
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
A resort with multiple swimming pools, lounge areas, and a modern building with balconies.

2. Conrad Orlando at Evermore

Conrad Orlando at Evermore
5.0 star property
Orlando
9.6 out of 10, Exceptional, (611 reviews)
"Wonderful stay, everything was as advertised!"
United States
YASIR
The price is ￥76,251
￥94,650 total
includes taxes & fees
Nov 19 - Nov 20
Conrad Orlando at Evermore
A water park with multiple slides and a pool area surrounded by palm trees and a golf course.

3. The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
5.0 star property
Orlando
9.2 out of 10, Wonderful, (1,009 reviews)
"Great hotel!"
United States
Teresa
The price is ￥75,551
￥94,750 total
includes taxes & fees
Nov 29 - Nov 30
The Ritz-Carlton Orlando, Grande Lakes
A pool with a waterfall, surrounded by tropical vegetation and a stone bridge.

4. 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, (972 reviews)
"One of the best hotels I have ever stayed in. Absolutely superb."
United States
Caroline
The price is ￥221,512
￥259,842 total
includes taxes & fees
Nov 22 - Nov 23
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
A pool area with lounge chairs and umbrellas, surrounded by tropical plants.

5. ette hotel Orlando

ette hotel Orlando
5.0 star property
Kissimmee
9.6 out of 10, Exceptional, (515 reviews)
"Great Services. Great hotel. Great atmosphere!"
United States
Wigberto
The price is ￥51,240
￥58,158 total
includes taxes & fees
Nov 1 - Nov 2
ette hotel Orlando
Water park

6. 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, (1,001 reviews)
"Loved the bedrooms with their own separate bathrooms. Water park was enjoyed by all!!"
United States
paula
The price is ￥45,437
￥135,734 total
includes taxes & fees
Oct 31 - Nov 1
Encore Resort and Water Park at Reunion by Rentyl
An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

7. Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,633 reviews)
"Huge property - not a golfer but still enjoyed the stay"
United States
Karen G
The price is ￥39,214
￥51,981 total
includes taxes & fees
Nov 30 - Dec 1
Reunion Resort & Golf Club
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.

8. Disney's Beach Club Resort

Disney's Beach Club Resort
5.0 star property
Bay Lake
8.8 out of 10, Excellent, (720 reviews)
"The best"
United States
Carl
The price is ￥114,776
￥129,123 total
includes taxes & fees
Nov 1 - Nov 2
Disney's Beach Club Resort
A pool with inflatable rings, lounge chairs, and a wooden deck with stairs.

9. 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
8.8 out of 10, Excellent, (5 reviews)
"Awesome pools. Family friendly."
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.

10. 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, (10 reviews)
"Wonderful stay!"
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.

11. 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
9.0 out of 10, Wonderful, (10 reviews)
"Great stay"
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.

12. 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
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.

13. Amazing 4Bd Screened Pool Close to Disney 4572

Amazing 4Bd Screened Pool Close to Disney 4572
5.0 star property
Bellavida
8.0 out of 10, Very good, (7 reviews)
" Great for our family, close to activities, parks, attractiins"
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.

14. 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
A row of modern two-story houses with attached garages, well-maintained lawns, and a street lamp.

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

5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
5.0 star property
Kissimmee
8.0 out of 10, Very good, (10 reviews)
"My family and I truly enjoyed our stay. The team was friendly and communicated effectively the entire time. Will definitely stay again and recommend to others. "
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.

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
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
An aerial view of a resort with a large water park, multiple swimming pools, and a variety of recreational facilities.

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
5.0 star property
Kissimmee
8.4 out of 10, Very good, (11 reviews)
"Very roomy, clean and equipped apartment, worth for the money paid."
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.

18. Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
5.0 star property
Kissimmee
6.4 out of 10, (5 reviews)
"The communication was exceptional, before, during and after the stay. Friendly. Everything was like in the pictures. You got everything you need to make your stay as comfortable as your own home."
United States
Denise
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
An aerial view of a resort with a large swimming pool, palm trees, and a water slide.

19. 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
8.6 out of 10, Excellent, (8 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
A resort with multiple swimming pools, palm trees, and lounge areas.

20. Gorgeous 5Bd Screened Pool at Champions Gate 1125

Gorgeous 5Bd Screened Pool at Champions Gate 1125
5.0 star property
Davenport
9.6 out of 10, Exceptional, (8 reviews)
"The house was exactly as the pictures posted. Very well maintained, cleaned, and well equipped with all essential equipment for cooking ext. My family and I loved it. It exceeded our expectations! We truly recommend this house, and will definitely rent this house again."
United States
Carmen
Gorgeous 5Bd Screened Pool at Champions Gate 1125
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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 Windermere.
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL
The price is ￥34,528 per night from Nov 2 to Nov 3
￥34,528
￥38,845 total
Nov 2 - Nov 3
includes taxes & fees
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Learn more about Windermere

Nestled among pristine lakes, this charming town offers a peaceful escape with upscale golf courses and country clubs. Nature lovers can explore the Tibet-Butler Preserve's trails, while four-legged friends enjoy romping at Buena Vista Place Dog Park.

See all hotels in Windermere
A lakeside community with houses and boats.

Top Windermere Hotel Reviews

Frequently asked questions

What are the best 5-star hotels in Windermere?
If you're seeking a 5-star experience, Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort offers one of the best of them according to Expedia traveler reviews. Stay at this Windermere getaway and get ready for first-rate service, well-appointed guest rooms and top-of-the-line amenities.
How much does it cost to stay in a 5-star hotel in Windermere?
How much you pay for a 5-star hotel in Windermere can vary based on what time of year you travel and how long you plan to be away, among several factors. Take advantage of our price per night filter and other search tools to find the best deal on a luxurious getaway.

  • Search for the lowest price per night from ￥11,338

What makes a hotel 5 stars in Windermere?
From gourmet dining venues and 24-hour fitness centers to pools and luxury bedding, the 5-star experience in Windermere is all about comfort and luxury. But it takes more than just upscale amenities to earn a 5-star rating. Hotels must also deliver remarkable guest services like beauty treatments, on-site dry cleaning and laundry and a nightly turn-down service.

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