A lakeside community with houses and boats.

Find 5 Star Hotels in Windermere, FL from $110

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Windermere 5 Star Hotels

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Windermere 5-star hotels

A hotel with a swimming pool, lounge chairs, and palm trees.
A bar area with multiple seating options, a marble countertop, and a decorative ceiling light.
A long dining table set with chairs, surrounded by hanging lights and greenery.
A grand lobby with a central clock, a chandelier, and a patterned floor.

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

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
United States
Ray
$461 nightly
$519 total
Oct 29 - Oct 30
Total with taxes and fees
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
A resort with multiple swimming pools, lounge areas, and a modern building with balconies.
An outdoor dining area with wicker furniture and hanging lights, overlooking a beach and hotel buildings.
A spacious lobby with a view of a body of water, large wooden columns, and a modern tiled floor.
A modern hotel entrance with a large wooden ceiling structure, glass doors, and a view of the outdoors.

2. Conrad Orlando at Evermore

Conrad Orlando at Evermore
Orlando
United States
Derick
$445 nightly
$500 total
Oct 8 - Oct 9
Total with taxes and fees
Conrad Orlando at Evermore
A pool with a waterfall, surrounded by tropical vegetation and a stone bridge.
A spacious lobby with a high ceiling, large windows, and a reflective floor.
A pathway lined with tall, vertically planted trees and well-maintained greenery, leading towards a building with classical architecture.
A hotel with a central courtyard, a reflective pool, and a large building with a prominent entrance.

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

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Golden Oak
United States
Caroline
$1,300 nightly
$1,463 total
Oct 6 - Oct 7
Total with taxes and fees
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
A water park with multiple slides and a pool area surrounded by palm trees and a golf course.
A courtyard with outdoor seating, palm trees, and a pool.
A spacious lobby with a high ceiling, large windows, and a variety of seating arrangements including sofas and armchairs.
A dining area with tables set for service, large arched windows, and wall-mounted lighting.

4. The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
Orlando
United States
Teresa
$479 nightly
$539 total
Oct 28 - Oct 29
Total with taxes and fees
The Ritz-Carlton Orlando, Grande Lakes
A pool area with lounge chairs and umbrellas, surrounded by tropical plants.
A person in a white bathrobe sitting at a breakfast table with plates of food, a teapot, and a cup.
A man in a white suit standing in a room with a marble countertop and a hanging black lamp.
A restaurant interior with wooden tables and chairs, a marble wall, and a seating area with a cushioned bench.

5. ette hotel Orlando

ette hotel Orlando
Kissimmee
United States
Manuel
$295 nightly
$335 total
Oct 6 - Oct 7
Total with taxes and fees
ette hotel Orlando
Water park
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with four bar stools.
A spacious lobby with a high ceiling, a unique wooden chandelier, a large arched glass door leading outside, and potted plants.
A large, two-story hotel with a prominent clock tower, a covered entrance, and a well-lit facade.

6. Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
Kissimmee
United States
Tara
$723 nightly
$820 total
Oct 10 - Oct 11
Total with taxes and fees
Encore Resort and Water Park at Reunion by Rentyl
An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.
A spacious lobby with a grand chandelier, a piano, and a reception desk.
A spacious lobby with a grand chandelier, a fountain, and a grand piano.
A patio area with wicker furniture, a fire pit, and palm trees.

7. Reunion Resort & Golf Club

Reunion Resort & Golf Club
Reunion
United States
RYAN
$371 nightly
$421 total
Oct 6 - Oct 7
Total with taxes and fees
Reunion Resort & Golf Club
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A spacious lobby with high ceilings, multiple chandeliers, and a polished wooden floor.
A restaurant with round tables, wooden chairs, and large windows.
A waterfront hotel with multiple buildings, a large spherical structure in the background, and reflections on the water.

8. Disney's Beach Club Resort

Disney's Beach Club Resort
Bay Lake
United States
Carl
$728 nightly
$819 total
Oct 6 - Oct 7
Total with taxes and fees
Disney's Beach Club Resort
A pool with inflatable rings, lounge chairs, and a wooden deck with stairs.
A modern kitchen with a central island, pendant lighting, and a dining area with a table and chairs.
A modern dining area with a white table set for four, light blue upholstered chairs, and decorative white feathers.
A modern kitchen with a central island, bar stools, stainless steel appliances, and pendant lighting.

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

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
Kissimmee
United States
Nydia
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
A swimming pool with lounge chairs, palm trees, and a golf course.
A residential area with multiple two-story houses, a well-maintained lawn, and a circular patio area with seating.
A golf course with a water slide, palm trees, and a clear sky.
A modern kitchen with a stainless steel refrigerator, a granite countertop, and a bar area with stools. There is a dining table set with plates and glasses, and a chandelier above.

10. 5 Bedroom at Storey Lake Orlando FL close to Disney 4851

5 Bedroom at Storey Lake Orlando FL close to Disney 4851
Kissimmee
United States
Nita
5 Bedroom at Storey Lake Orlando FL close to Disney 4851
A modern living room with a sofa, a TV mounted on the wall, and a balcony with glass doors.
A modern kitchen with a granite countertop, stainless steel appliances, and bar stools.
A covered outdoor area with a pool, two lounge chairs, and a view of trees.
A large rock with the words "HIDDEN FOREST" engraved on it, surrounded by colorful flowers.

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

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
Clermont
Canada
Angela
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
A modern kitchen with a granite countertop, stainless steel appliances, and wooden cabinets. There are three bar stools and a hanging light fixture above the counter.
A dining area with a glass table and brown chairs, a blue vase, and a framed artwork on the wall.
A living room with a sectional sofa, a patterned armchair, a coffee table, and a TV.
A bedroom with a bed, nightstands, a mirror, and a window with blinds.

12. Family Friendly 5 Bedrooms Home Close to Disney 4849

Family Friendly 5 Bedrooms Home Close to Disney 4849
Kissimmee
United States
Raquel
Family Friendly 5 Bedrooms Home Close to Disney 4849
An aerial view of a resort with a large swimming pool, water slides, and a mini-golf area.
A modern living room with a beige sectional sofa, a white coffee table, and a flat-screen TV mounted on the wall.
A modern kitchen with a central island, stainless steel appliances, and a dining area with bar stools.
A modern kitchen with white cabinets, a black backsplash, and a dining area set with white plates, blue placemats, and clear wine glasses.

13. Stunning 2 Bd Condo Close to Disney 304 3191

Stunning 2 Bd Condo Close to Disney 304 3191
Kissimmee
United States
Stephanie
Stunning 2 Bd Condo Close to Disney 304 3191
A resort with multiple swimming pools, sun loungers, and palm trees.
A spacious outdoor dining area with white chairs and tables, ceiling fans, and a bar area with a TV screen.
A gym with various weightlifting equipment, including dumbbells and weight plates.
A wooden ship structure with ropes and a flag, surrounded by greenery and a clear sky.

14. Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653

Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
Kissimmee
United States
Lance
Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
An aerial view of a resort with a large swimming pool, palm trees, and a water slide.
An aerial view of a resort with a large central pool, multiple smaller pools, and a covered pavilion.
A wooden play structure with ropes and a slide, surrounded by palm trees and a clear sky.
A modern kitchen with white cabinets, a microwave, and a coffee station with white cups and orange flowers.

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

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
Kissimmee
Germany
Thomas
Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131
An aerial view of a courtyard with a tennis court, surrounded by trees and a building with a tiled roof.
A hotel room with a wooden console table, a round mirror, a globe, and a small plant.
Restaurant
Water park

16. Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
Davenport
United States
Emmanuel
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
A swimming pool with a glass enclosure, surrounded by a patio area with a view of a residential building.
A dining area with a wooden table, six chairs, a chandelier, and black and white patterned wallpaper.
A neatly made bed with a black and white color scheme, a metal headboard, and a bedside lamp.
A modern kitchen with white cabinets, a central island with wicker chairs, and pendant lighting.

17. 5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759

5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
Kissimmee
United States
Kimesha
5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759
An aerial view of a resort with a large water park, multiple swimming pools, and a variety of recreational facilities.
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.
A modern living room with a grey sofa, a purple armchair, and a large window with a view of greenery.
A modern kitchen with white cabinets, a dining area with a table and chairs, and a living room with a sofa and a coffee table.

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

Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort
Kissimmee
United States
Prasad
Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort
An aerial view of a resort with multiple swimming pools, sun loungers, and palm trees.
A spacious outdoor dining area with multiple tables and chairs, ceiling fans, and a bar area with stools.
A gym with various weightlifting equipment, including dumbbells and weight plates.
A modern living room with a grey sectional sofa, a glass coffee table, and a blue patterned rug.

19. Stunning 4 Bd Close to Disney @ Storey Lake 2569

Stunning 4 Bd Close to Disney @ Storey Lake 2569
Kissimmee
United States
Claudine
Stunning 4 Bd Close to Disney @ Storey Lake 2569
A rectangular swimming pool with a tiled edge, surrounded by a brick patio. There are lounge chairs and a small table near the pool.
A spacious dining area with a long table, multiple chairs, and a large mirror on the wall.
A two-story house with a brick driveway and a stone facade.
A modern kitchen with dark wood cabinets, stainless steel appliances, and a large island with bar stools.

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

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
Kissimmee
United States
Bronte
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
Save an average of 15% on thousands of hotels when you're signed in

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
$220 nightly
$248 total
Nov 2 - Nov 3
Total with taxes and fees
9.4/10 Exceptional! (4,499 reviews)
Hyatt Regency Orlando International Airport
Avanti International Resort

Avanti International Resort

8738 International Dr Orlando FL
$98 nightly
$110 total
Oct 21 - Oct 22
Total with taxes and fees
8/10 Very Good! (4,602 reviews)
Avanti International Resort
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL
$137 nightly
$154 total
Oct 27 - Oct 28
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Still don't see what you're looking for?
See all properties in Windermere.
You can also use these popular filters to refine your search.
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.

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

Top Windermere Hotel Reviews

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 $110
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.

Explore a world of travel with Expedia