Find 5 Star Hotels in Windermere, FL

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check availability on Windermere 5 Star Hotels

Compare Windermere 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

5.0 star property
9.2 out of 10, Wonderful, (241)
"Bull & Bear was amazing!!! The hotel staff was 5 star!!"
The price is SAR 1,318
SAR 1,694 total
includes taxes & fees
9 May - 10 May
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Conrad Orlando

5.0 star property
9.4 out of 10, Exceptional, (192)
"My family and I have a blast at the Conrad. We love it there. God bless! "
The price is SAR 2,009
SAR 2,447 total
includes taxes & fees
30 Apr - 1 May
Conrad Orlando

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

5.0 star property
9.6 out of 10, Exceptional, (835)
"Great stay highly recommended "
The price is SAR 4,486
SAR 5,047 total
includes taxes & fees
27 Apr - 28 Apr
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1256)
"Quiet setting. Resort style. Staff friendliness. Cleanliness. "
The price is SAR 786
SAR 1,070 total
includes taxes & fees
28 Apr - 29 Apr
Reunion Resort & Golf Club

The Ritz-Carlton Orlando, Grande Lakes

5.0 star property
9.2 out of 10, Wonderful, (1001)
"TThis property surpasses the standards of a 5-star establishment. It is truly remarkable. The exceptional staff and accommodations make it a standout experience."
The price is SAR 2,098
SAR 2,593 total
includes taxes & fees
9 May - 10 May
The Ritz-Carlton Orlando, Grande Lakes

ette hotel

5.0 star property
9.8 out of 10, Exceptional, (285)
"Hi"
The price is SAR 1,351
SAR 1,534 total
includes taxes & fees
10 Apr - 11 Apr
ette hotel

Encore Resort and Water Park At Reunion by Rentyl

5.0 star property
8.4 out of 10, Very Good, (959)
"Beautiful property, convenient to parks, restaurants & amenities. Gorgeous homes in great shape & the water park is perfect for the family to relax. ❤️"
Encore Resort and Water Park At Reunion by Rentyl

Splendid 5Bd Close to Disney at Storey Lake 4251

5.0 star property
9.6 out of 10, Exceptional, (9)
" Very beautiful and clean property. "
Splendid 5Bd Close to Disney at Storey Lake 4251

Cozy 3Bd Close to Disney @ Enclaves at Festival 808

5.0 star property
6.0 out of 10, (1)
"The property itself was nice. Very big, comfortable, cute decor. However, there was an issue with the trash bins that were stored inside the garage (according to the instructions, the bins were to be stored inside/out of sight even though all the other houses had them outside near the garage). The trash containers were NASTY. They were full of maggots and with a fetid foul-smell that made it IMPOSSIBLE to be inside the garage and enjoy the games that were there. We were never able to use the...
Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Margarita Porch Paradise

5.0 star property
10.0 out of 10, Exceptional, (2)
"The house was beautiful and comfortable for our family, we would have stayed longer! The resort is fun, plenty of stores and good restaurants. We will definitely come back. "
Margarita Porch Paradise

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

5.0 star property
8.6 out of 10, Excellent, (4)
"Very nice facility"
Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

Amazing 4Bd Screened Pool Close to Disney 4572

5.0 star property
8.0 out of 10, Very Good, (1)
"It was a great location to go to Disney and other places. Some of the tv's did not work properly, had to change to English setting on main tv, no remote for the one bedroom upstairs, and the downstairs bedroom tv did nor work properly. Microwave light did not work. Had to connect the upstairs bathroom it was disconnected had to reconnect it. Not enough comfortable seating should have another small love seat in the living room. Overall it was a nice place."
Amazing 4Bd Screened Pool Close to Disney 4572

Gorgeous 5Bd Screened Pool at Champions Gate 1125

5.0 star property
9.4 out of 10, Exceptional, (3)
"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."
Gorgeous 5Bd Screened Pool at Champions Gate 1125

The Bear's Den Resort Orlando

5.0 star property
8.0 out of 10, Very Good, (22)
"Great place , I recommend it to everyone."
The Bear's Den Resort Orlando

Family Vacation Home, Water Park+Endless Amenities

5.0 star property
8.8 out of 10, Excellent, (17)
"Awesome staff, super helpful. And the resort was amazing"
Family Vacation Home, Water Park+Endless Amenities

7 Bedroom Villa, Private Pool, Resort Amenities

5.0 star property
9.0 out of 10, Wonderful, (11)
"The house was beautiful. Most of the upstairs televisions did not work but overall it was great would recommend it to friends and family "
7 Bedroom Villa, Private Pool, Resort Amenities

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (12)
"Very clean. Wondering why parental controls were on cable tv channels."
Reunion Resort & Golf Club

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

5.0 star property
10.0 out of 10, Exceptional, (1)
Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191

Charming 3Bd Close to Disney @ Festival 1026

5.0 star property
9.0 out of 10, Wonderful, (2)
"Nice location "
Charming 3Bd Close to Disney @ Festival 1026

Marvelous 4Bd with Pool at Storey Lake Resort 2601

5.0 star property
10.0 out of 10, Exceptional, (2)
Marvelous 4Bd with Pool at Storey Lake Resort 2601
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Windermere

Romantic Windermere awaits: its food, natural setting, beaches, and more!

Tibet Butler Preserve showing a garden and forests

Frequently asked questions

What are the best 5-star hotels in Windermere?
Offering premium amenities and services, Expedia travelers rate Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort as one of the leading 5-star hotels in Windermere. You’ll be in the lap of luxury from the moment you step foot into the lobby.
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 depending on when you want to travel and how long you plan to stay, among a number of factors. Take advantage of our price per night filter and other search tools to score the best rate on a luxurious stay.

  • Search for the lowest price per night

What makes a hotel 5 stars in Windermere?
Exemplary guest service is integral to every 5-star hotel in Windermere. From the minute you step through the door, staff cater to your every need, whether arranging valet parking or providing a nightly turn-down service. In addition, hotels have to offer upscale conveniences to be eligible for a 5-star rating. These can include luxury bathrobes, spas or saunas, pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Windermere?
Expedia’s filter tool is the best way to search for exactly what you want. Check the “All inclusive” and “5-star” boxes to see the most luxurious hotels in Windermere where your lodging, meals, entertainment and activities are included in the upfront price. At these escapes, your trip is pure relaxation and indulgence from the moment you check in.
What are the top 5-star spa hotels in Windermere?
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort combines plush accommodations with decadent well-being programs and experiences. Choose from a menu of massages, facials and more at this sought-after 5-star spa property in Windermere.
Does Windermere have any 5-star family resorts?
Delight the kids with a stay that combines fun and luxury at Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort. This 5-star property in Windermere features conveniences and services that cater to the needs of families, so that both adults and youngsters have a wonderful stay.
Are there any 5-star vacation rentals in Windermere?
There are no 5-star vacation rentals in Windermere on our site, but there are a few other top-rated properties worth looking into. Search through our vacation rentals in Windermere to discover the best place for your getaway.