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
28 Sep - 29 Sep
Tomorrow
29 Sep - 30 Sep
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Winter Park 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 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.

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

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
United States
Ray
SAR 1,292
SAR 1,665 total
includes taxes & fees
4 Oct - 5 Oct
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
A resort with multiple swimming pools, lounge areas, and a modern building with balconies.
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.
An outdoor dining area with wicker furniture and hanging lights, overlooking a beach and hotel buildings.

2. Conrad Orlando at Evermore

Conrad Orlando at Evermore
Orlando
United States
Marlon
SAR 1,451
SAR 1,820 total
includes taxes & fees
11 Oct - 12 Oct
Conrad Orlando at Evermore
A pool with a waterfall, surrounded by tropical vegetation and a stone bridge.
A pathway lined with tall, vertically planted trees and well-maintained greenery, leading towards a building with classical architecture.
An indoor dining area with multiple tables and chairs, large windows, and a bar counter.
A spacious lobby with a high ceiling, large windows, and a reflective floor.

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

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Golden Oak
United States
Patrick
SAR 3,586
SAR 4,266 total
includes taxes & fees
30 Sep - 1 Oct
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 modern living room with a sofa set, coffee table, and decorative plants.
A spacious lobby with a high ceiling, large windows, and a variety of seating arrangements including sofas and armchairs.
A courtyard with outdoor seating, palm trees, and a pool.

4. The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
Orlando
United States
Teresa
SAR 1,592
SAR 2,023 total
includes taxes & fees
28 Oct - 29 Oct
The Ritz-Carlton Orlando, Grande Lakes
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
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.
A restaurant with round tables, wooden chairs, and large windows.

5. Disney's Beach Club Resort

Disney's Beach Club Resort
Bay Lake
United States
Carl
SAR 2,733
SAR 3,075 total
includes taxes & fees
12 Oct - 13 Oct
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, bar stools, stainless steel appliances, and pendant lighting.
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, pendant lighting, and a dining area with a table and chairs.

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 restaurant with round tables, wooden chairs, and large windows.
A row of white buildings with balconies, connected by a walkway with string lights and street lamps.
A spacious lobby with a central round rug, multiple doors, and potted plants.

7. Disney's Beach Club Villas

Disney's Beach Club Villas
Bay Lake
United States
Anonymous traveler
Disney's Beach Club Villas
A swimming pool with lounge chairs, palm trees, and a golf course.
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.
A beach area with a hammock, palm trees, a chair, and a building with a white exterior.

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 hallway with a glass-top console table, a white door at the end, and framed pictures on the walls.
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.

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 hotel room with a large bed, a nightstand with drawers, a wall-mounted painting, and a bathroom visible through an open door.
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 living room with a beige sectional sofa, a white coffee table, and a flat-screen TV mounted on the wall.

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 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.
A wooden ship structure with ropes and a flag, surrounded by greenery and a clear sky.

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 kitchen with white cabinets, a microwave, and a coffee station with white cups and orange flowers.
A wooden play structure with ropes and a slide, surrounded by palm trees and a clear sky.
An aerial view of a resort with a large central pool, multiple smaller pools, and a covered pavilion.

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 modern kitchen with white cabinets, a central island with wicker chairs, and pendant lighting.
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 dining area with a wooden table, six chairs, a chandelier, and black and white patterned wallpaper.

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 dining area with a table and chairs, and a living room with a sofa and a coffee table.
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, stainless steel appliances, and a central island with bar stools.

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 wooden play structure with ropes and a slide, surrounded by palm trees and a clear sky.

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 two-story house with a brick driveway, white exterior, and multiple chimneys.
A modern living room with a sectional sofa, a coffee table, and a TV on the wall.
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 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.
A modern living room with a sofa, coffee table, and a view of the outdoors through large windows.

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 modern kitchen with dark cabinets, a central island with bar stools, and a microwave above the island.
A modern kitchen with granite countertops, a built-in island, and a dining area with a sofa and chairs.
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.

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 modern kitchen with white cabinets, granite countertops, and teal bar stools.
A bedroom with a bed, nightstands, a ceiling fan, and a window with curtains.
A modern kitchen with white cabinetry, a built-in microwave, an oven, and a dishwasher.

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 modern living room with a grey sectional sofa, a round coffee table, and a staircase leading to the upper floor.
A spacious outdoor patio with a bar area, seating arrangements, and ceiling fans.
A playground with wooden climbing structures and rope bridges.

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
SAR 864
SAR 971 total
26 Oct - 27 Oct
includes taxes & fees
Hyatt Regency Orlando International Airport
Avanti International Resort

Avanti International Resort

8738 International Dr Orlando FL
SAR 267
SAR 377 total
29 Sep - 30 Sep
includes taxes & 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
SAR 514
SAR 578 total
18 Oct - 19 Oct
includes taxes & 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 SAR 377
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.