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

Luxury Hotels & Resorts in Winter Garden from NZ$170

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Check availability on Winter Garden Luxury Hotels

Tonight
27 Sept - 28 Sept
Tomorrow
28 Sept - 29 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Winter Garden luxury hotels

A resort with a large pool, water slides, palm trees, and beach umbrellas.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.
A modern lobby with a reception desk, seating area, and a bar.

1. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
  • Lakeside luxury surrounds at this resort with 6 pools, a water park, and premium lake views.
NZ$435
includes taxes & fees
27 Oct - 28 Oct
The Grove Resort & Water Park Orlando
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A modern living room with a sofa, ottoman, and a TV on a stand.
A modern living room with a teal accent wall, a sofa, ottomans, a dining area with white chairs, and a balcony with a view.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.

2. Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
  • Upscale Disney-adjacent resort offers 2 pools, free water park access, and private balconies for families.
NZ$237
includes taxes & fees
1 Oct - 2 Oct
Hilton Vacation Club Aqua Sol Orlando West
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.
A modern living room with a sofa, armchairs, a coffee table, and a TV. There is a balcony with a view of trees and a railing.
A bedroom with a bed, a large window, a ceiling fan, and a bathroom with a bathtub and a framed picture on the wall.

3. Upstay Disney Area Condo w Pool Pet Friendly

Upstay Disney Area Condo w Pool Pet Friendly
Winter Garden
Upstay Disney Area Condo w Pool Pet Friendly
A modern living room with a sofa, coffee table, and a ceiling fan.
A kitchen with granite countertops, stainless steel appliances, and white cabinetry.
A bedroom with a bed, a dresser, a ceiling fan, and a TV on the wall.
A balcony with two black chairs and a table, a ceiling fan, and a view of greenery.

4. Upstay 3BR Condo w Pool & Patio Near Disney

Upstay 3BR Condo w Pool & Patio Near Disney
Winter Garden
NZ$479
includes taxes & fees
25 Oct - 26 Oct
Upstay 3BR Condo w Pool & Patio Near Disney
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.
A spacious living room with a sofa, a coffee table, and a TV. There is a balcony with a view of trees and buildings.

5. Spacious 3BR Family Getaway w Pool Near Disney

Spacious 3BR Family Getaway w Pool Near Disney
Winter Garden
NZ$439
includes taxes & fees
28 Sept - 29 Sept
Spacious 3BR Family Getaway w Pool Near Disney

6. Upstay Condo With Outdoor Pool & Sauna

Upstay Condo With Outdoor Pool & Sauna
Winter Garden
NZ$426
includes taxes & fees
26 Oct - 27 Oct
Upstay Condo With Outdoor Pool & Sauna
A spacious living room with a sofa, a coffee table, and a TV. There are large windows with curtains, a balcony, and a ceiling fan.
A modern kitchen with a central island, bar stools, and built-in appliances.
A modern living room with a grey sofa, a round coffee table, and a flat-screen TV mounted on the wall.

7. Condo w Pool, Games Room - Pet Friendly

Condo w Pool, Games Room - Pet Friendly
Winter Garden
NZ$419
includes taxes & fees
30 Sept - 1 Oct
Condo w Pool, Games Room - Pet Friendly
A bedroom with a bed, two bedside tables, a ceiling fan, and artwork on the walls.
A hotel with a sign reading 'PALISADES' surrounded by landscaped gardens and palm trees.
A bedroom with a patterned bedspread, a ceiling fan, a TV on the wall, and a view of a beach scene.
A gym with treadmills, a Cybex machine, and a weight bench.

8. Upstay: Modern Condo w Outdoor Pool - Near Disney!

Upstay: Modern Condo w Outdoor Pool - Near Disney!
Winter Garden
NZ$475
includes taxes & fees
14 Oct - 15 Oct
Upstay: Modern Condo w Outdoor Pool - Near Disney!
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.
A modern kitchen with white cabinets, a stainless steel oven, and a microwave.
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.

9. Family Fun Condo: Pool, Sauna Near Disney

Family Fun Condo: Pool, Sauna Near Disney
Winter Garden
NZ$473
includes taxes & fees
9 Oct - 10 Oct
Family Fun Condo: Pool, Sauna Near Disney
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.

10. Upstay Condo With Pool Near Disney & Pet Friendly

Upstay Condo With Pool Near Disney & Pet Friendly
Winter Garden
NZ$411
includes taxes & fees
28 Sept - 29 Sept
Upstay Condo With Pool Near Disney & Pet Friendly
View all properties

Top Winter Garden Hotel Reviews

Walt Disney World Dolphin

Walt Disney World Dolphin

8/10 Good
"First time staying here. The property is amazing. The staff is amazing and the amenities are amazing. The problem....is that no matter where you book your reservation whether it is directly with the hotel or through a secondary site like Hotels.com, The charges are not the actual charges. In my case, the taxes and resort fees total 41% of the room charge for both nights. So, when you budget for your stay, budget for 1.5x what they say that the room charge is plus parking. Also, the Dolphin is undergoing renovation (9/25-27/2026) and there is very limited parking. So, we either had to valet, $64.97/night or self park at the Swan and walk to the Dolphin, $42.60/night. Just beware of all of these extra charges when booking."
Charles 2-night trip
Posted less than an hour ago
Walt Disney World Dolphin
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

8/10 Good
"Ududue"
Rex 3-night trip
Posted 1 hour ago
Westgate Lakes Resort & Spa Universal Studios Area
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

8/10 Good
"They left food in the mini refrigerator"
Brianna 2-night trip
Posted 2 hours ago
Rosen Inn Lake Buena Vista
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Was one of the best places I have stayed in a long time great location to universal parks has free shuttle very convenient. Cute place great vibe loved everything about it would definitely stay again"
Desiree 2-night trip
Posted 2 hours ago
Universal's Cabana Bay Beach Resort
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Wonderful stress free mini trip. Customer service was excellent. I will absolutely stay again!"
marcella 1-night trip
Posted 2 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Loved the communication of when pools were opened or closed. If we needed anything there was a quick response. We loved this place so much we almost stayed another night. Just couldn't get someone to take our dogs for one more night."
Heather 6-night trip
Posted 3 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Winter Garden?
Expedia can help you get a flight to Orlando International Airport (MCO) airport or Kissimmee, FL (ISM-Kissimmee Gateway) airport, and then you can select from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay special. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Winter Garden offers. During your visit, you might want to enjoy the recreation choices and water parks which Winter Garden is known for.
When can I expect good weather in Winter Garden?
Planning for the weather is an important factor for making your trip to Winter Garden a success, especially when you're splurging. The hottest months are usually August and July, with an average temperature of 28°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Garden are August, July, September and June, with each month seeing an average of 217 mm of rainfall.
What's there to see and do in Winter Garden?
Enjoy all that Winter Garden has to offer when you visit Orange County National Golf Club, Lake Louisa State Park and Disney's Magnolia Golf Course. If you have a bit of extra time while you're in the area, you might want to check out Disney's Palm Golf Course and Flamingo Crossings Town Center.

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