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
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Winter Park 5-star hotels

A swimming pool with palm trees and umbrellas, surrounded by a building with a curved facade and multiple balconies.
A balcony with a table set for two, overlooking a golf course.
A modern bar area with a long counter, multiple seating options, and a television screen.
A modern living room with a Christmas tree, a sofa, a coffee table, and a large window with a view of a green landscape.

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

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
United States
John
£334
includes taxes & fees
12 Nov - 13 Nov
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
A resort with multiple swimming pools, lounge areas, and a modern building with balconies.
A rooftop lounge with wicker furniture, round tables, and potted plants.
A spacious lobby with a view of a body of water, large wooden columns, and a modern tiled floor.
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
YASIR
£508
includes taxes & fees
8 Nov - 9 Nov
Conrad Orlando at Evermore
A pool with a waterfall, surrounded by tropical vegetation and a stone bridge.
An indoor dining area with multiple tables and chairs, large windows, and a bar counter.
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
£1,249
includes taxes & fees
1 Nov - 2 Nov
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 dining area with tables set for service, large arched windows, and wall-mounted lighting.
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.

4. The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
Orlando
United States
Teresa
£468
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 spacious lobby with high ceilings, multiple chandeliers, and a polished wooden floor.
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
£606
includes taxes & fees
21 Oct - 22 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 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.

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 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 golf course with a water slide, palm trees, and a clear sky.

7. 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 living room with a sectional sofa, a patterned armchair, a coffee table, and a TV.
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.

8. 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 white cabinets, a black backsplash, and a dining area set with white plates, blue placemats, and clear wine glasses.
A modern kitchen with a central island, stainless steel appliances, and a dining area with bar stools.
A modern hotel room with a large bed, a nightstand with drawers, a wall-mounted painting, and a bathroom visible through an open door.

9. 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 modern living room with a grey sofa, glass coffee table, and a black and white rug.
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.

10. 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.
A modern living room with a white sectional sofa, a large abstract painting, and a view of a balcony with outdoor furniture.

11. 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 dining area with a wooden table, six chairs, a chandelier, and black and white patterned wallpaper.
A modern kitchen with white cabinets, a central island with wicker chairs, and pendant lighting.
A neatly made bed with a black and white color scheme, a metal headboard, and a bedside lamp.

12. 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 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.
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

13. 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 gym with various weightlifting equipment, including dumbbells and weight plates.
A wooden play structure with ropes and a slide, surrounded by palm trees and a clear sky.

14. 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 spacious kitchen with a large island, modern pendant lights, and a dining area with a long table and chairs.

15. 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 dining area with a wooden table, four grey chairs, and pendant lights.

16. 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 modern kitchen with granite countertops, a built-in island, and a dining area with a sofa and chairs.
A dining area with a table set for four, surrounded by chairs, and a sofa in the background.

17. 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 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.

18. Family Vacation Home, Water Park+Endless Amenities

Family Vacation Home, Water Park+Endless Amenities
Kissimmee
United States
Jasmine
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 modern kitchen with white cabinets, stainless steel appliances, a central island with stools, and pendant lighting.
A playground with wooden climbing structures and rope bridges.

19. 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
A modern dining area with a glass table, grey upholstered chairs, and yellow napkins.
A modern kitchen with a central island, a dining area with a glass table, and a living area with a sofa and TV.
A modern living room with two green velvet armchairs, a glass coffee table, a white sofa, and a large framed picture of a castle.
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

20. Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836
Kissimmee
United States
Teddy
Gorgeous 4 Bedroom w/ Pool Close to Disney 4836
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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

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£185
2 Nov - 3 Nov
includes taxes & fees
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Avanti International Resort

Avanti International Resort

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9 Nov - 10 Nov
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Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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includes taxes & fees
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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

Find out more about Winter Park

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Park?
You'll find many different pricing options for a 5-star hotel in Winter Park on Expedia. How much you'll pay will depend on when you want to travel, trip length and other factors. Compare all of the available accommodation for your chosen dates and make use of our pricing and other filters to lock in the perfect high-end stay.
  • Search for the lowest price per night from £79
What makes a hotel 5 stars in Winter Park?
Outstanding guest service characterises every 5-star hotel in Winter Park. From the minute you step through the door, staff cater to your every whim, whether answering room service calls 24/7 or providing in-room massages. In addition, hotels must feature upscale conveniences to meet the standard for a 5-star rating. These can include luxury toiletries, spa facilities, swimming pools, fine dining kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Winter Park?
Use Expedia's filters to find a luxury getaway in Winter Park where everything you need is included. From there, narrow your results for properties that have 5 stars and are described as "All inclusive." The most important thing on the to-do list at these stays? Pure enjoyment and indulgence.

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