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.

The Best 5 Star Hotels in Windermere, FL from SAR 446

A hidden gem among all the typical Disney schmultz, this nature preserve is a perfect, peaceful getaway. There are several miles of trail, some are closed because of flood conditions, and a couple sections of boardwalk planks. There is a great variety of terrain from sawgrass marshes to pine flatwoods, bay swamp and oak hammock. The Fallen Log Crossing and Osprey Overlook trails are the must see parts of the preserve. You might luck out and see an osprey or eagle, or even a gopher tortoise. It's just a magical slice of heaven here in Central Florida that makes you forget you are just a few miles from the craziness of Disney and Universal. #LocalSecrets #KidsFun #NatureWalk

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Our top choices for Windermere 5-star hotels

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Orlando

Robert

SAR 2,359 total

includes taxes & fees

22 Feb - 23 Feb

Outdoor pool, cabanas (surcharge), pool umbrellas

Conrad Orlando at Evermore

Orlando

John

SAR 2,086 total

includes taxes & fees

12 Feb - 13 Feb

3 outdoor pools, cabanas (surcharge), pool umbrellas

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Golden Oak

Huan

SAR 5,484 total

includes taxes & fees

1 Feb - 2 Feb

The Ritz-Carlton Orlando, Grande Lakes

Orlando

SAUL

SAR 3,096 total

includes taxes & fees

27 Feb - 28 Feb

Outdoor pool, open 9:00 AM to 6:00 PM, free cabanas, pool umbrellas

ette hotel

Kissimmee

Steve

SAR 1,560 total

includes taxes & fees

9 Feb - 10 Feb

Encore Resort and Water Park at Reunion by Rentyl

Kissimmee

Ruth

SAR 2,677 total

includes taxes & fees

6 Feb - 7 Feb

Reunion Resort & Golf Club

Reunion

Jessica

Disney's Beach Club Resort

Bay Lake

Yong Hoon

Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort

Kissimmee

Prasad

The Bear's Den Resort Orlando

Reunion

Jacqueline

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

Kissimmee

"This place was great. We stayed here for 6 nights in Jan 2026. Family of 4. We were able to check in a couple hours early - thank you Wonder Vacations team. The place is spacious and airy and was prepared very well for our arrival: everything was clean and tidy. It is newly renovated condo with updated bathrooms and modern furniture. We appreciated the "starter kit" with a paper towel, garbage bags, laundry and dishwasher pods. We enjoyed the heated pool with slides and lazy river which are a...

Anastasia

Exclusive House | 4 bedrooms, in-room safe, individually decorated, individually furnished

Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Festival

Brittany

Stunning 2 Bd Condo Close to Disney 304 3191

Kissimmee

Gema

2 outdoor pools, free cabanas, pool umbrellas

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131

Kissimmee

Danielle

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

Kissimmee

Stuart

Gorgeous 4Bd with Pool @ Storey Lake Resort 4475

Kissimmee

"First off the house was not clean. It was only clean where a vacuum can fit. Behind all toilets was dirty, every shower had hair from previous guests. We have a three year old so we were in a rush to leave to get on our cruise and left behind our iPad. We wrote and apparently a cleaner took over two days to get to the house to only come back and say there was no iPad. Security didn’t even ask for ID. The back gate is open to let anyone just enter. Would never stay here again. Didn’t feel clean...

Shawnte

Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

Davenport

Jose A

7 Bedroom Villa, Private Pool, Resort Amenities

Kissimmee

Abraham

Splendid 5Bd Close to Disney at Storey Lake 4251

Kissimmee

omar

Marvelous 4Bd with Pool at Storey Lake Resort 2601

Kissimmee

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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.

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

SAR 397

SAR 446 total

25 Feb - 26 Feb

includes taxes & fees

8.4/10 Very Good! (6,960 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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 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.

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Aerial Overlooking Lakeside Homes in Central Florida

Top Windermere Hotel Reviews

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 from SAR 446

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.

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Our top choices for Windermere 5-star hotels