A wooden pier extending over calm water, reflecting a sunset sky.

Vacation homes in Winter Garden

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Vacation homes in Winter Garden

A swimming pool with a bridge, surrounded by palm trees and rocks.

A spa area with a hot tub, tiled walls, and a window providing natural light.

A bedroom with a wooden bed, a ceiling fan, a red upholstered chair, and a wooden wardrobe.

A hallway with a brick wall, a wooden handrail, and a series of framed pictures.

1. Fully Themed Harry Potter Getaway Close Disney 3 Bedroom Townhouse

Regal Palms

$215

$420 total

includes taxes & fees

Sep 17 - Sep 18

An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

A water park with multiple slides and a swimming pool surrounded by lounge areas and umbrellas.

A spacious dining area with hexagonal ceiling and large windows offering views of the city.

A spacious lobby with high ceilings, exposed beams, and a tropical theme featuring palm trees and hanging lights.

2. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Kissimmee

$204

$500 total

includes taxes & fees

Sep 17 - Sep 18

A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

A resort with a large pool, outdoor seating, and a covered area.

A spacious lobby with a curved staircase, a reception desk, and a large mirror.

A spacious lobby with a high ceiling, chandeliers, and a view of the outdoors.

3. The Berkley, Orlando

Kissimmee

$119

$145 total

includes taxes & fees

Sep 30 - Oct 1

A rustic outdoor seating area with wooden chairs and a fire pit, surrounded by a wooden fence and palm trees.

A spacious lobby with high ceilings, ornate wooden railings, and multiple seating areas.

A spacious lobby with high ceilings, wooden beams, and a large window offering a view of the sky. Furnishings include wicker chairs and tables, and the area is well-lit with hanging lamps.

A hotel with a covered entrance, palm trees, and a well-lit driveway.

4. Disney's Animal Kingdom Villas - Kidani Village

Bay Lake

$448

$504 total

includes taxes & fees

Sep 30 - Oct 1

A spacious lobby with modern furniture, large windows, and a high ceiling.

A modern living room with a grey sofa, a wooden coffee table, and a cityscape painting on the wall.

A spacious living room with a staircase, white walls, and large windows.

An aerial view of a pool area with checkered flooring, lounge chairs, and umbrellas.

5. Encantada Resort Vacation Townhomes by IDILIQ

Kissimmee

$102

$313 total

includes taxes & fees

Sep 17 - Sep 18

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

A modern bedroom with a large bed, a wooden headboard, and a built-in bench with a plant.

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

A modern kitchen with a central island, white cabinetry, and a built-in dishwasher. There is a staircase leading to an upper level, and a seating area with a sofa and chairs.

6. Luxury 5BR Home w/ Private Pool Near Disney

Davenport

A golf course with a large rock formation, palm trees, and a well-maintained green.

A building with a sign reading "Registration & Activities" and a number "100" on the facade.

A balcony with two chairs, a view of a parking lot, and a building with multiple balconies and palm trees.

A swimming pool with a lifeguard tower, lounge chairs, and a covered area with a clock.

7. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Davenport

$107

$141 total

includes taxes & fees

Sep 18 - Sep 19

A wooden hot tub surrounded by a wooden deck, large windows, and a stone wall.

A spacious lobby with a high wooden ceiling, a central chandelier, and a stone fireplace.

A resort with a large pool surrounded by rock formations and multiple-story buildings with balconies.

A spacious lobby with high wooden ceilings, large chandeliers, and a central seating area.

8. Boulder Ridge Villas at Disney's Wilderness Lodge

Bay Lake

$902

$1,015 total

includes taxes & fees

Sep 30 - Oct 1

A residential area with multiple houses, a swimming pool, and a lake in the background.

A spacious lobby with a central water feature, seating areas, and a view of the outside.

A balcony with wicker chairs, a glass table, and a view of trees and a pathway.

9. Bahama Bay Resort

Bahama Bay

$191

$458 total

includes taxes & fees

Sep 20 - Sep 21

A modern kitchen with a dining area, featuring a large island, grey and beige furniture, and a TV mounted on the wall.

A multi-story residential building with a central courtyard featuring a swimming pool, surrounded by palm trees and a well-maintained lawn.

A dining area with a round table set for four, chairs, and a ceiling fan.

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with grey upholstered chairs and a round table set for four.

10. Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Kissimmee

$94

$241 total

includes taxes & fees

Sep 21 - Sep 22

A residential house with a garage, a driveway, and a well-maintained lawn.

A backyard pool with a hot tub and a covered seating area.

A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled floor.

A living room with two dark brown sofas, a glass coffee table, a TV on a wooden stand, a ceiling fan, and a potted plant.

11. Davenport Vacation Homes by Shine FM

Tuscan Hills

A pool area with large rocks and a wooden building in the background.

A modern living room with a sofa, armchairs, and a coffee table. There is a kitchen area with a microwave and stove. The room has wooden beams on the ceiling and a large window.

A row of wooden cabins with large windows, surrounded by tall trees and a body of water.

A spacious living area with a stone fireplace, large windows overlooking a forested lake, and a dining area with a wooden table and chairs.

12. Copper Creek Villas & Cabins at Disney's Wilderness Lodge

Bay Lake

$430

$483 total

includes taxes & fees

Sep 29 - Sep 30

A multi-story hotel with a central courtyard, featuring a mix of stone and stucco exteriors, balconies, and a well-maintained garden with palm trees and red flowers.

An outdoor patio with tables and chairs, wooden beams, and hanging lanterns.

A golf course with bunkers, a clubhouse, and a large estate with multiple buildings.

A modern kitchen with a large island, stainless steel appliances, and a view of the outdoors.

13. Siena at Bella Collina

Montverde

$506

$562 total

includes taxes & fees

Sep 21 - Sep 22

A two-story house with a garage, a driveway, and a well-maintained lawn.

A covered outdoor swimming pool with a hot tub, surrounded by a metal fence and brick flooring.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

A dining area with a glass-top table, wicker chairs, and a chandelier.

14. 6 Mi to Disney: Gem w/ Pool & Spa in Kissimmee

Calabria

An outdoor swimming pool with a covered patio area, a brick pathway, and a view of the surrounding landscape.

A single-story house with a garage, a small porch, and a tree in the front yard.

A kitchen with wooden cabinets, a white refrigerator, a microwave, an oven, and a dishwasher.

A spacious dining area with a long wooden table set for four, flanked by wooden chairs. A chandelier hangs above the table, and a ceiling fan is visible in the background.

15. Kissimmee Maingate Area Pool Homes by SVV

Kissimmee

16. Vista Grande - Resort&spa - 15 Min to Disney!

Bahama Bay

A modern dining area with a glass table, chairs, and a ceiling light.

A modern kitchen with dark cabinets, a central island with bar stools, and pendant lighting.

A modern kitchen with granite countertops, stainless steel appliances, and a central island.

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

17. Ultimate Getaway - Your Best Vacation Home

Clermont

A street view of West Lake Village Resort with a clear road, palm trees, and a signboard.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and an oven.

A living room with a flat-screen TV displaying 'Mandalorian', a dark wooden coffee table with a tray and a bowl of snacks, a dark entertainment unit, and a beige wall.

A residential complex with multiple two-story houses, a central swimming pool, and a parking area.

18. Moana's Hut Miles From World's Best Theme Parks!

Kissimmee

A modern living room with a sofa, a TV mounted on the wall, and a balcony with glass doors.

A large rock with the words "HIDDEN FOREST" engraved on it, surrounded by colorful flowers.

A modern living room with a glass coffee table, a black sofa, and a dining area with a TV displaying a castle.

A covered outdoor area with a pool, two lounge chairs, and a view of trees.

19. Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Clermont

A modern kitchen with white cabinetry, granite countertops, a built-in dishwasher, and a large window overlooking a patio area.

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

A glass-enclosed patio with a pool, outdoor seating, and a view of the neighborhood.

A bedroom with a bed, a desk, a chair, a ceiling fan, and artwork on the walls.

20. Davenport Home w/ Pool & Game Room: Near Disney!

Esprit

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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 Orange Lake Golf 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, Resurrection Catholic Church, and AdventHealth Winter Garden.

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Learn more about Winter Garden

Brick-lined Plant Street forms the heart of this upscale Orlando suburb, where historic buildings house artisanal shops and farm-to-table restaurants. The West Orange Trail cuts through downtown, offering miles of paved path for cyclists and joggers seeking respite from theme park crowds. Catch a performance at the restored Garden Theatre, a 1935 gem that anchors the thriving arts scene. Families enjoy Surfari Water Park while history buffs explore the Railroad Museum. Plant Street Market buzzes with local vendors selling craft beer to handmade soaps. Lake Butler provides a peaceful escape for paddleboarders, while nearby Lake Louisa State Park offers hiking through pristine Florida wilderness. Golf enthusiasts find paradise at Orange County National's courses.

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

About the destination

Winter Garden is a family-friendly place known for its theme park and waterparks. Simply book an excursion to enjoy your stay a little more. Plan a fun excursion to Orange County National Golf Club and Disney's Magnolia Golf Course while here. Popular sights in the surrounding area include Universal Studios Florida.