The Best 5 Star Hotels in Windermere, FL from $391

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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

Orlando

John

$398 nightly

Nov 22 - Nov 23

Total with taxes and fees

A resort with multiple swimming pools, lounge areas, and a modern building with balconies.

2. Conrad Orlando at Evermore

Orlando

YASIR

$528 nightly

Nov 20 - Nov 21

Total with taxes and fees

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

Orlando

Teresa

$534 nightly

Nov 25 - Nov 26

Total with taxes and fees

A pool with a waterfall, surrounded by tropical vegetation and a stone bridge.

4. Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Golden Oak

Caroline

$1,405 nightly

Dec 4 - Dec 5

Total with taxes and fees

A pool area with lounge chairs and umbrellas, surrounded by tropical plants.

5. ette hotel Orlando

Kissimmee

Wigberto

$345 nightly

Nov 22 - Nov 23

Total with taxes and fees

6. Encore Resort and Water Park at Reunion by Rentyl

Kissimmee

paula

$795 nightly

Dec 4 - Dec 5

Total with taxes and fees

7. Reunion Resort & Golf Club

Reunion

Karen G

$371 nightly

Nov 8 - Nov 9

Total with taxes and fees

A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.

8. Disney's Beach Club Resort

Bay Lake

Carl

$728 nightly

Nov 15 - Nov 16

Total with taxes and fees

A pool with inflatable rings, lounge chairs, and a wooden deck with stairs.

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

Kissimmee

Nydia

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

Clermont

Angela

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

Tuscan Hills

Tiffany

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

Kissimmee

Stephanie

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

Bellavida

Charlene

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

Kissimmee

Kimesha

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

Kissimmee

Ben-Jade

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

Kissimmee

Pareshkumar

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

Kissimmee

Prasad

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

Kissimmee

Denise

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

Kissimmee

Thomas

A resort with multiple swimming pools, palm trees, and lounge areas.

20. Gorgeous 5Bd Screened Pool at Champions Gate 1125

Davenport

Carmen

Top Windermere Hotel Reviews

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Golden Oak

10/10 Excellent

Alex

Conrad Orlando at Evermore

Orlando

10/10 Excellent

Jiefeng

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Orlando

10/10 Excellent

samuel

Disney's Beach Club Resort

Bay Lake

10/10 Excellent

My wife and I have been to Disney World more times than we can count, with kids and without kids. We've stayed at many of the Disney resorts but this was our first stay at the Beach Club and in the Boardwalk area. We don't intend to stay anywhere else from now on. In my opinion this is the best location in the park, you're walking distance to Epcot, and I mean walking distance, from the Beach Club it's at most five minutes, from the Yacht Club add 2-3 minutes and maybe another ten from the...

K

ette hotel Orlando

Kissimmee

10/10 Excellent

I absolutely loved this place! It is so clean, charming, & beautifully decorated. The set-up and design of the rooms was so thought out and not a single detail was missed. The room had amazing linens, high-end bathrobes, toiletries and slippers. I was offered turn down service with fresh water every night and my room was always nice and clean when I returned at the end of the day. I love that's it's family owned - the owners did such a great job at making me feel at home. The restaurant has...

Michelle

Encore Resort and Water Park at Reunion by Rentyl

Kissimmee

10/10 Excellent

Kelsey

Find out more about Windermere

Why not demand the best during your holiday to Windermere? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Windermere so popular in the last year. There's no reason to delay a getaway to Windermere any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Windermere are the perfect places to relax in during your next getaway. What are you waiting for?

Get a Great Deal on 5-Star Hotels in Windermere

You'll have a fantastic time at one of these 5-star hotels. Spa treatments, delicious meals, and one-on-one attention are all waiting for you. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready to kick back and indulge. What kind of amenities will make your stay a wonderful one? A concierge to help you make reservations at that outstanding restaurant? A rejuvenating facial treatment to help your cares fall away? Plush carpeting, lip-smacking main courses, and even space for your family pet in some cases...these hotels have it all.

Can't wait to get outside? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Windermere are waiting for you to relax after a busy day. Ready to learn more? Plenty of visitors recommend this location.

Your Getaway Starts Today

The results are in, and Windermere 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. Your great getaway is just a mouse-click away -- Expedia can help you land a great deal on accommodation. Pick out one of the 5-star hotels in Windermere today and relax in luxe surroundings tomorrow.

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 $391

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.

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Find 5 Star Hotels in Windermere, FL from $391

Upfront pricing

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windermere 5-star hotels

1. Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

2. Conrad Orlando at Evermore

3. The Ritz-Carlton Orlando, Grande Lakes

4. Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

5. ette hotel Orlando

6. Encore Resort and Water Park at Reunion by Rentyl

7. Reunion Resort & Golf Club

8. Disney's Beach Club Resort

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

10. Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

11. Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

12. Stunning 2 Bd Condo Close to Disney 304 3191

13. Amazing 4Bd Screened Pool Close to Disney 4572

14. 5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759

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

16. Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887

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

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

19. Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131

20. Gorgeous 5Bd Screened Pool at Champions Gate 1125

Top Windermere Hotel Reviews

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

10/10 Excellent

Find out more about Windermere

Get a Great Deal on 5-Star Hotels in Windermere

Your Getaway Starts Today

Frequently Asked Questions

What are the best 5-star hotels in Windermere?

How much does it cost to stay in a 5-star hotel in Windermere?

What makes a hotel 5 stars in Windermere?

Are there any 5-star all-inclusive resorts in Windermere?

What are the top 5-star spa hotels in Windermere?

Does Windermere have any 5-star family resorts?

Are there any 5-star vacation rentals in Windermere?

Explore a world of travel with Expedia