Are there any 5-star vacation rentals in Winter Garden?

Our site doesn't have any 5-star vacation rentals in Winter Garden. However, you will still find a few top-rated properties where the only thing on your agenda will be to unpack and enjoy yourself. Discover what's available by checking out our vacation rentals in Winter Garden .

The Best 5 Star Hotels in Winter Garden, FL from $74

A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

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Our top choices for Winter Garden 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

$420 nightly

Nov 23 - Nov 24

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

Kelly

$433 nightly

Nov 29 - Nov 30

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

Benjamin

$1,315 nightly

Dec 11 - Dec 12

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

Jose

$690 nightly

Dec 9 - Dec 10

Total with taxes and fees

An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

7. Reunion Resort & Golf Club

Reunion

Karen G

$358 nightly

Nov 16 - Nov 17

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 17 - Nov 18

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

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

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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 Garden.

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

$215 nightly

$242 total

Nov 23 - Nov 24

Total with taxes and fees

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Pool Spa Hot tub Breakfast included Waterpark

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 Garden

Stroll the charming brick-lined streets of historic downtown where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

See all hotels in Winter Garden

A brick building with a clock tower and a sign that reads "Winter Garden."

Top Winter Garden Hotel Reviews

Find out more about Winter Garden

You enjoy the finer things in life, both at home and on vacation. Add an extra layer of enjoyment on your next trip to Winter Garden by treating yourself to the best of the best when it comes to accommodation. It's an ideal combination. There's no reason to delay a getaway to Winter Garden any longer. You'll join the multitudes of vacationers who have made Winter Garden so fashionable recently. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. You deserve the great vacation you're dreaming about. Reserve one of our 5-star hotels in Winter Garden and indulge in the finer things in life for a while.

5-Star Hotels in Winter Garden

Don't be afraid to be pampered during your trip. Spa treatments, delicious meals, and personalized service are all ready for you. You're sure to find exactly the accommodation you need. Additionally, the hotels in this area receive fantastic marks for customer satisfaction, so you know you'll be well cared for during your getaway. What kind of amenities will make your stay a wonderful one? A full-body massage to help your cares fall away? A concierge to help you make reservations at that outstanding restaurant? High thread-count sheets, piping hot coffees, and even spectacular views...these hotels are one-of-a-kind. Want to see for yourself? Then explore the 349 reviews various guests have left on Expedia and get to know these places.

You won't sleep and order room service the entire time, though. You're in luck. 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 Winter Garden are the perfect place to relax after a busy day.

Make Your Escape

The results are in, and Winter Garden 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. Expedia can help you land a great deal on accommodation. Your great getaway is just a mouse-click away. Choose one of Expedia's Winter Garden 5-star hotels today and soothe yourself in the lap of luxury tomorrow.

Frequently asked questions

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

How much you pay for a 5-star hotel in Winter Garden can vary according to what time of year you travel and how long you plan to stay, among other factors. Use our price per night filter and other search tools to score the best deal on a luxurious getaway.

Search for the lowest price per night from $74

What makes a hotel 5 stars in Winter Garden?

From high-end dining venues and all-day fitness centers to pools and deluxe bedding, the 5-star experience in Winter Garden is all about luxury and relaxation. But it calls for more than just upscale perks to get a 5-star rating. Accommodations also have to deliver exceptional services like in-room massages, dry cleaning and laundry and concierge services.

Are there any 5-star all-inclusive resorts in Winter Garden?

Find a luxury retreat that includes your room, meals, activities and entertainment in Winter Garden with our filters. Search for hotels rated 5 stars and click on the "All inclusive" filter. Make sure you check what's included in the purchase price. That way, you can take full advantage of the premium perks on offer from the moment you get there.

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Things to do in Winter Garden

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Check availability on Winter Garden 5 Star Hotels

Our top choices for Winter Garden 5-star hotels