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

Vacation homes in Winter Garden

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November 2026

December 2026

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Vacation homes in Winter Garden

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

1. 6 Mi to Disney: Gem w/ Pool & Spa in Kissimmee

Calabria

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

2. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Kissimmee

$494 total

includes taxes & fees

Nov 11 - Nov 12

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

3. The Berkley, Orlando

Kissimmee

$163 total

includes taxes & fees

Dec 1 - Dec 2

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

4. Vacation Townhomes by IDILIQ at Encantada Resort

Kissimmee

$287 total

includes taxes & fees

Nov 11 - Nov 12

An indoor arcade with various gaming machines, including racing and shooting games.

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

Regal Palms

A swimming pool with lounge chairs and umbrellas, a covered seating area, and a building with a balcony in the background.

6. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Davenport

$132 total

includes taxes & fees

Nov 11 - Nov 12

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

7. Disney's Animal Kingdom Villas - Kidani Village

Bay Lake

$669 total

includes taxes & fees

Nov 30 - Dec 1

8. Bahama Bay Resort

Bahama Bay

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

9. Boulder Ridge Villas at Disney's Wilderness Lodge

Bay Lake

$705 total

includes taxes & fees

Nov 24 - Nov 25

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

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

Davenport

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

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

Kissimmee

$241 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Clermont

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

13. Davenport Vacation Homes by Shine FM

Tuscan Hills

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

14. Kissimmee Maingate Area Pool Homes by SVV

Kissimmee

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

15. Siena at Bella Collina

Montverde

$510 total

includes taxes & fees

Dec 8 - Dec 9

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

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

Bay Lake

$701 total

includes taxes & fees

Nov 23 - Nov 24

17. Clerbrook Golf & RV Resort - Caravan Park

Clermont

A house with a red roof, surrounded by trees and a lake.

18. Caribe Cove Resort

Kissimmee

A pool area with stone pillars, a clear blue pool, and a building with a yellow facade in the background.

19. 5 Mi to Walt Disney World! Gem w/ Resort Perks

Kissimmee

A resort with a large swimming pool, lounge chairs, and a view of a large body of water.

20. Bahama Bay 515 Rum run unit 515

Bahama Bay

$255 total

includes taxes & fees

Nov 11 - Nov 12

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Top neighborhoods in Winter Garden

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

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.

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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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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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 and The Wizarding World of Harry Potter™.