A two-story house with a balcony, surrounded by lush greenery and trees.

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Check availability on Winter Park 5 Star Hotels

Tonight
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for Winter Park 5-star hotels

A hotel with a swimming pool, lounge chairs, and palm trees.
A spacious hotel corridor with large windows, a blue carpet, and elegant chandeliers.
A grand lobby with a central clock, a chandelier, and a patterned floor.
A long dining table set with chairs, surrounded by hanging lights and greenery.

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

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
United States
Ray
$394 nightly
$443 total
Oct 4 - Oct 5
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.
A modern hotel entrance with a large wooden ceiling structure, glass doors, and a view of the outdoors.
A spacious lobby with a view of a body of water, large wooden columns, and a modern tiled floor.
A rooftop lounge with wicker furniture, round tables, and potted plants.

2. Conrad Orlando at Evermore

Conrad Orlando at Evermore
Orlando
United States
Marlon
$417 nightly
$469 total
Oct 11 - Oct 12
Total with taxes and fees
Conrad Orlando at Evermore
A pool with a waterfall, surrounded by tropical vegetation and a stone bridge.
A hotel with a central courtyard, a reflective pool, and a large building with a prominent entrance.
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.

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

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Golden Oak
United States
Patrick
$1,010 nightly
$1,136 total
Sep 30 - Oct 1
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 modern living room with a sofa set, coffee table, and decorative plants.
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
$554 nightly
$623 total
Oct 2 - Oct 3
Total with taxes and fees
The Ritz-Carlton Orlando, Grande Lakes
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A restaurant with round tables, wooden chairs, and large windows.
A hotel with a blue exterior, white railings, and a well-maintained garden with a central flower bed.
A waterfront hotel with multiple buildings, a large spherical structure in the background, and reflections on the water.

5. Disney's Beach Club Resort

Disney's Beach Club Resort
Bay Lake
United States
Carl
$713 nightly
$802 total
Sep 27 - Sep 28
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 kitchen with a central island, bar stools, stainless steel appliances, and pendant lighting.
A modern living room with a sofa, coffee table, and bar stools. There is a kitchen area with cabinets and appliances.

6. 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 resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A large, multi-story building with balconies and a waterfront view.
A row of white buildings with balconies, connected by a walkway with string lights and street lamps.
A restaurant with round tables, wooden chairs, and large windows.

7. Disney's Beach Club Villas

Disney's Beach Club Villas
Bay Lake
United States
Anonymous traveler
$713 nightly
$802 total
Sep 27 - Sep 28
Total with taxes and fees
Disney's Beach Club Villas
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 beach area with a hammock, palm trees, a chair, and a building with a white exterior.
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.

8. 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 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 bedroom with a bed, nightstands, a mirror, and a window with blinds.
A living room with a sectional sofa, a patterned armchair, a coffee table, and a TV.

9. 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 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.
A modern hotel room with a large bed, a nightstand with drawers, a wall-mounted painting, and a bathroom visible through an open door.

10. 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 wooden ship structure with ropes and a flag, surrounded by greenery and a clear sky.
A gym with various weightlifting equipment, including dumbbells and weight plates.
A spacious outdoor dining area with white chairs and tables, ceiling fans, and a bar area with a TV screen.

11. 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.
A modern living room with a white sectional sofa, a large abstract painting, and a view of a balcony with outdoor furniture.
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.

12. 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
A swimming pool with a glass enclosure, surrounded by a patio area with a view of a residential building.
A spacious living area with a sofa, armchairs, and a dining table. There is a kitchen in the background with white cabinets and a microwave.
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.

13. 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, a stainless steel refrigerator, a microwave, and a built-in oven.
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.

14. 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 modern living room with a grey sectional sofa, a glass coffee table, and a blue patterned rug.
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.

15. 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 modern indoor pool area with a dining setup and a view of the ocean.
A modern living room with a sectional sofa, a coffee table, and a TV on the wall.
A spacious kitchen with a large island, modern pendant lights, and a dining area with a long table and chairs.
A modern kitchen with a marble island, pendant lights, and a large window offering a view of palm trees.

16. The Ritz-Carlton Residences Orlando, Grande Lakes

The Ritz-Carlton Residences Orlando, Grande Lakes
Orlando
The Ritz-Carlton Residences Orlando, Grande Lakes
A resort with multiple swimming pools, sun loungers, and palm trees.
A modern dining area with a wooden table, four grey chairs, and pendant lights.
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.

17. Marvelous 4Bd with Pool at Storey Lake Resort 2601

Marvelous 4Bd with Pool at Storey Lake Resort 2601
Kissimmee
United States
Yolanda
Marvelous 4Bd with Pool at Storey Lake Resort 2601
A row of modern two-story houses with attached garages, well-maintained lawns, and a street lamp.
A kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and a built-in oven. There are three white bar stools and a small island with a yellow vase.
A dining area with a table set for four, surrounded by chairs, and a sofa in the background.
A modern kitchen with granite countertops, a built-in island, and a dining area with a sofa and chairs.

18. 5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney

5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
Kissimmee
United States
Ben-Jade
5126 Compass Bay Resort Orlando 4Bedrooms Close to Disney
A pool area with lounge chairs, umbrellas, and a water slide structure.
A covered outdoor seating area with lounge chairs and a table, surrounded by palm trees and a fountain.
A bedroom with a bed, nightstands, a ceiling fan, and a window with curtains.
A modern kitchen with white cabinets, granite countertops, and teal bar stools.

19. Family Vacation Home, Water Park+Endless Amenities

Family Vacation Home, Water Park+Endless Amenities
Kissimmee
United States
LUIS
Family Vacation Home, Water Park+Endless Amenities
A swimming pool area with multiple water features and lounge chairs.
A spacious outdoor patio with a bar area, seating arrangements, and ceiling fans.
A playground with wooden climbing structures and rope bridges.
A modern living room with a grey sectional sofa, a round coffee table, and a staircase leading to the upper floor.

20. Splendid 5Bd Close to Disney at Storey Lake 4251

Splendid 5Bd Close to Disney at Storey Lake 4251
Kissimmee
United States
omar
Splendid 5Bd Close to Disney at Storey Lake 4251
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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 Winter Park.
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL
$219 nightly
$246 total
Oct 5 - Oct 6
Total with taxes and fees
Hyatt Regency Orlando International Airport
Avanti International Resort

Avanti International Resort

8738 International Dr Orlando FL
$90 nightly
$102 total
Sep 28 - Sep 29
Total with taxes and fees
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 18 - Oct 19
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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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 Winter Park

Stroll through the Morse Museum to see the world's largest collection of Tiffany glass, then boat through the Winter Park Chain of Lakes. Charming Park Avenue offers upscale shopping and outdoor cafés where you can people-watch before catching a sunset concert in Central Park.

See all hotels in Winter Park
A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.

Top Winter Park Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Park?
How much you pay for a 5-star hotel in Winter Park depends on things like when you want to go and the length of your escape. Our top tip for bagging an awesome deal? Use our pricing filters to compare the available options for your chosen dates.
  • Search for the lowest price per night from $102
What makes a hotel 5 stars in Winter Park?
From gourmet dining venues and 24/7 fitness centers to swimming pools and dreamy bedding, the 5-star experience in Winter Park is all about luxury and comfort. But it requires more than just top-notch conveniences to earn a 5-star rating. Stays must also offer extraordinary guest-centric services like beauty treatments, on-site laundry and dry cleaning and 24/7 room service.
Are there any 5-star all-inclusive resorts in Winter Park?
Use Expedia's filter tool to find an upmarket retreat in Winter Park where everything you need is included in the price. From there, refine your results for resorts that have a rating of 5 stars and are categorized as "All inclusive." The main thing on the schedule at these stays? Relaxation and enjoyment.

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