4 Star Hotels in Winter Garden

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4 Star Hotels in Winter Garden

A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.

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 modern living room with a sofa, ottoman, and a TV on a stand.

A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.

1. Hilton Vacation Club Aqua Sol Orlando West

Winter Garden

$94

$134 total

includes taxes & fees

Oct 1 - Oct 2

A resort with a large pool, water slides, palm trees, and beach umbrellas.

A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.

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.

2. The Grove Resort & Water Park Orlando

Winter Garden

$170

$246 total

includes taxes & fees

Oct 27 - Oct 28

A bathroom with two sinks, a large mirror, and a vanity with a light fixture.

A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

3. Upstay: Condo Near Disney w Pool, Sauna

Winter Garden

$69

$245 total

includes taxes & fees

Sep 27 - Sep 28

A spacious living room with a sofa, a coffee table, and a TV. There is a balcony with a view of trees and buildings.

A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.

4. Spacious 3BR Family Getaway w Pool Near Disney

Winter Garden

$72

$249 total

includes taxes & fees

Sep 27 - Sep 28

A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.

5. Modern 3BR Resort Condo With Pool Near Disney

Winter Garden

$69

$245 total

includes taxes & fees

Sep 28 - Sep 29

A modern living room with a sofa, coffee table, and a ceiling fan.

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.

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

Winter Garden

$103

$284 total

includes taxes & fees

Oct 3 - Oct 4

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.

An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

A modern kitchen with a dishwasher, a dining area with a table and chairs, and a view of the outside.

7. Upstay Disney Pet Friendly Condo w Pool Spa Games

Winter Garden

$72

$226 total

includes taxes & fees

Sep 30 - Oct 1

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 hallway with a round mirror, a console table, and a tiled floor.

A modern kitchen with a central island, bar stools, and built-in appliances.

8. Condo w Pool, Games Room - Pet Friendly

Winter Garden

$86

$242 total

includes taxes & fees

Sep 29 - Sep 30

9. Upstay: Resort Style Condo w Pool, Sauna

Winter Garden

$69

$223 total

includes taxes & fees

Sep 27 - Sep 28

10. Upstay Condo With Pool Near Disney & Pet Friendly

Winter Garden

$81

$236 total

includes taxes & fees

Sep 28 - Sep 29

11. Upstay: Stylish 3BR Condo w Pationear Disney

Winter Garden

$64

$240 total

includes taxes & fees

Oct 4 - Oct 5

A bedroom with a large bed, a bathroom with a bathtub, and a balcony with a view.

12. Bright Family Escape With Game Room and Sauna

Winter Garden

$79

$234 total

includes taxes & fees

Oct 1 - Oct 2

A dining area with a table, chairs, and two wall-mounted mirrors.

A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

13. Family Fun Condo: Pool, Sauna Near Disney

Winter Garden

$81

$236 total

includes taxes & fees

Sep 30 - Oct 1

A bedroom with a bed, a large window, a ceiling fan, and a bathroom with a bathtub and a framed picture on the wall.

A poolside area with lounge chairs and a pool.

A modern dining area with a glass table, white chairs, and decorative plates.

14. Upstay - LRG Condo w Outdoor Pool, Sauna

Winter Garden

$69

$245 total

includes taxes & fees

Sep 27 - Sep 28

15. Upstay Condo With Outdoor Pool & Sauna

Winter Garden

$74

$228 total

includes taxes & fees

Sep 27 - Sep 28

16. Upstay Pet-friendly Condo Near Disney w Balcony

Winter Garden

$77

$254 total

includes taxes & fees

Sep 28 - Sep 29

17. Upstay Pet Friendly Condo 6 Minutes From Disney

Winter Garden

$86

$242 total

includes taxes & fees

Sep 29 - Sep 30

A modern kitchen with a granite countertop, a built-in dishwasher, and a large window.

18. Upstay - Pet-friendly Suite w Pool, Sauna

Winter Garden

$92

$249 total

includes taxes & fees

Oct 20 - Oct 21

A hotel room with a large bed, two bedside tables, a painting, and a view of the outdoors through a sliding glass door.

A bunk bed with a colorful mural of sea creatures on the wall behind it.

A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop. There are two bar stools under the counter.

19. Upstay - Large Condo Near Disney w Pool and Gym

Winter Garden

$69

$245 total

includes taxes & fees

Sep 27 - Sep 28

A spacious living room with a large window, a ceiling fan, and a flat-screen TV mounted on the wall.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave. There are two black bar stools in front of the counter.

A modern living room with a kitchen in the background, a dining area, and a large TV mounted on the wall.

20. Modern Escape With Private Patio, Spa Tub & Pool

Winter Garden

$77

$232 total

includes taxes & fees

Sep 30 - Oct 1

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Top neighborhoods in Winter Garden

A tree-lined sidewalk with parked cars and a clear sky.

A street lined with large trees and historic brick buildings, including a 'Local' sign.

A bakery interior with a display case, shelves with jars, and a counter with a menu board.

A café with a variety of food items and beverages on display, including boxes of snacks and bottles of wine.

A bar with a polished floor, metal chairs, and a brick wall with a TV.

Downtown Winter Garden

Plant Street bursts with small-town charm in Downtown Winter Garden. The restored 1935 Garden Theatre anchors the brick-lined pedestrian zone where locals and visitors stroll past historic storefronts. Hop on the West Orange Trail for a scenic bike ride or browse the weekly farmers market for fresh Florida citrus and artisanal goods. Farm-to-table restaurants with outdoor seating line the main drag, while boutique bed & breakfasts offer cozy accommodations in restored buildings. The pedestrian-friendly layout means you can park once and explore everything on foot, from antique shops to the Central Florida Railroad Museum.

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A city skyline at dusk with illuminated buildings reflecting on a calm body of water.

Horizon West

Winter Garden's Horizon West neighborhood has a host of places to visit such as Walt Disney World® Resort and Orange County National Golf Club.

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A sunset over a body of water with silhouetted land in the distance and tall grasses in the foreground.

Vista del Lago

Vista del Lago is a peaceful retreat just minutes from Orlando's major attractions. Vacation homes with private pools and resort amenities offer the perfect landing spot after action-packed theme park days. Disney's Animal Kingdom and Magic Kingdom are just a short drive away, while community pools provide refreshing breaks between adventures. Dining options require a quick drive to nearby Championsgate or Disney Springs, where choices range from casual to upscale. Most travelers appreciate having rental cars to navigate between the quiet neighborhood and Orlando's entertainment districts. Many vacation rentals feature full kitchens and game rooms, creating the ideal home base for family theme park trips.

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A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.

A calm lake with lily pads and reeds in the foreground, surrounded by trees and a cloudy sky.

Oakland

Oakland's historic charm lives on through preserved Victorian homes and oak-canopied streets. Wander downtown to discover the 1889 Healthy House Museum and local artisan shops. The 128-acre Oakland Nature Preserve invites you to explore cypress wetlands and spot some of the 200+ bird species that call Lake Apopka home. Southern comfort food dominates the dining scene with most spots closing early. The area is best explored by car, though downtown remains pleasantly walkable. Cozy bed and breakfasts in historic homes offer an intimate alternative to Orlando's bustling tourist accommodations just 15 minutes away.

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Killarney

Killarney offers a peaceful retreat from Orlando's tourist bustle while keeping adventure within reach. The Oakland Nature Preserve invites you to explore scenic trails while the nearby West Orange Trail is perfect for morning bike rides. Lake Apopka provides a serene backdrop for fishing or simply watching the sunset paint the Florida sky. When you're ready for more action, Winter Garden's charming downtown is just minutes away. Accommodation options include budget-friendly extended-stay hotels and vacation homes with pools and kitchenettes. A car is essential for getting around, though rideshare services are readily available. The quiet suburban streets make evening strolls pleasant after busy days exploring nearby attractions.

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Top landmarks in Winter Garden

Flamingo Crossings Town Center

8.6/10 (131 reviews)

If you want to give your credit card some exercise, head out to Flamingo Crossings Town Center in Bay Lake.

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Disney's Palm Golf Course

8.4/10 (457 reviews)

You might want to practice your swing at Disney's Palm Golf Course, a golf course located 11.2 mi (18.1 km) from central Winter Garden. If Disney's Palm Golf Course doesn't quite scratch your golfing itch, Orange County National Golf Club, and Grand Cypress Golf Club are also nearby.

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Orange County National Golf Club

8.4/10 (647 reviews)

You might want to play some rounds at Orange County National Golf Club, located 8.9 mi (14.4 km) from central Winter Garden. If Orange County National Golf Club doesn't quite scratch your golfing itch, Disney's Palm Golf Course, and Disney's Magnolia Golf Course are also nearby.

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Disney's Magnolia Golf Course

8.4/10 (552 reviews)

You might want to play some rounds at Disney's Magnolia Golf Course, located 11.1 mi (17.9 km) from central Winter Garden. If Disney's Magnolia Golf Course doesn't quite scratch your golfing itch, Disney's Palm Golf Course, and Orange County National Golf Club are also nearby.

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Surfari Water Park

9.0/10 (2,086 reviews)

If thrills are what you're after, head to Surfari Water Park, located 2.3 mi (3.8 km) from central Four Corners. If you have fun at Surfari Water Park, you'll love Disney's Animal Kingdom® Theme Park and Island H2O Live!, both located nearby.

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West Orange Trail

8.4/10 (337 reviews)

Downtown Winter Garden is home to West Orange Trail, so why not stop by during your stay in Winter Garden. Winter Garden has lots of other activities such as Camping World Stadium and Kia Center.

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Disney's Oak Trail Golf Course

8.4/10 (377 reviews)

You might want to play some rounds at Disney's Oak Trail Golf Course, located 11.2 mi (18 km) from central Winter Garden. If Disney's Oak Trail Golf Course doesn't quite scratch your golfing itch, Disney's Palm Golf Course, and Orange County National Golf Club are also nearby.

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Garden Theatre

8.4/10 (219 reviews)

If you want to see a show while you're in town, try and grab some tickets at Garden Theatre in Downtown Winter Garden. If you want to experience more of the culture Winter Garden has to offer, head to West Orange Trail, AdventHealth Winter Garden, and Orlando Health - Health Central Hospital.

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