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

2 Star Hotels in Winter Garden

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2 Star Hotels in Winter Garden

A covered balcony with wicker chairs, a ceiling fan, and a view of trees.

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

1. Upstay Tropical Style Family Condo w Pool

Winter Garden

$67

$251 total

includes taxes & fees

Sep 24 - Sep 25

A modern living room with a sofa, green chairs, a coffee table, and a kitchen in the background.

A balcony with a view of palm trees and a clear sky.

2. Upstay - Condo w Hot Tub and Pool - Near Disney

Winter Garden

$86

$242 total

includes taxes & fees

Sep 29 - Sep 30

A balcony with a view of a green landscape, a table with chairs, and a railing.

3. Upstay - Condo Near Disney w Pool Hot tub Sauna

Winter Garden

$77

$234 total

includes taxes & fees

Oct 20 - Oct 21

An aerial view of a resort with a large, irregularly shaped pool surrounded by lounge chairs and umbrellas, set against a backdrop of palm trees and a multi-story building.

A gym with exercise equipment, large windows, and a view of greenery.

A balcony with a view of a forest, a table with chairs, and a ceiling fan.

4. Modern 3BR Condo Near Disney- Pool and Hot Tub

Winter Garden

$77

$234 total

includes taxes & fees

Sep 30 - Oct 1

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 view of a swimming pool surrounded by palm trees and lounge chairs, with a clear blue sky above.

A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.

A spacious lobby with a large sofa, a coffee table, and a TV mounted on the wall.

5. Upstay Modern 2BR Condo Near Disney

Winter Garden

$81

$244 total

includes taxes & fees

Sep 28 - Sep 29

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.

6. Upstay - Condo Near Disney w Pool-spa-sauna-games

Winter Garden

$76

$238 total

includes taxes & fees

Sep 29 - Sep 30

A spacious living room with a grey sofa, a coffee table, and a large plant. There is a balcony with outdoor furniture and a TV mounted on the wall.

A dining area with a round table set for four, surrounded by wicker chairs.

A modern living room with a grey sofa, a coffee table, and a TV mounted on the wall.

7. Upstay - Modern Family Apartment w Pool Hot Tub

Winter Garden

$86

$242 total

includes taxes & fees

Sep 30 - Oct 1

8. Upstay Stylish 3BR Condo w Patio Near Disney

Winter Garden

$78

$264 total

includes taxes & fees

Oct 12 - Oct 13

A bunk bed with a nightstand and a lamp, a polka dot wall, and a carpeted floor.

A hotel with a sign reading 'PALISTADES' surrounded by landscaped gardens and palm trees.

A modern living room with a sofa, coffee table, and decorative wall art.

A balcony with a view of a natural landscape, a table, and two chairs.

9. Upstay Large Family Condo w Pool Sauna

Winter Garden

$67

$251 total

includes taxes & fees

Oct 20 - Oct 21

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

A modern living room with a sofa, two small tables, a ceiling fan, a TV, and a balcony with outdoor furniture.

10. Upstay 3BR Condo w Pool Patio Near Disney

Winter Garden

$120

$311 total

includes taxes & fees

Oct 3 - Oct 4

A spacious living area with a large sofa, a coffee table, and a TV mounted on the wall. There are large windows offering a view of the outdoors.

11. Upstay Condo w Pool Sauna Sleeps 8

Winter Garden

$78

$264 total

includes taxes & fees

Sep 27 - Sep 28

A breakfast area with a counter, coffee machines, and a chalkboard menu.

A reception desk with a "Welcome to the Sun Shine State" sign, a "Hilton" sign, and a "Fats" sign.

A snack and beverage kiosk with a variety of snacks and drinks, including a 'Fuel Up' and 'Snacks to Go' section, and a 'Chill Out' cooler.

A Hampton Inn hotel with a modern design, featuring a prominent entrance with a blue canopy and a large sign.

12. Hampton Inn By Hilton Ocoee Orlando

Ocoee

$92

$103 total

includes taxes & fees

Oct 11 - Oct 12

A hotel room with a large bed, a bathroom with a bathtub, and a mirror reflecting the room.

A sign for Lakeridge Winery surrounded by tall trees and a clear blue sky.

A pool area with a diving board, lounge chairs, and an umbrella.

A hotel workspace with two monitors, a printer, and two office chairs.

13. Holiday Inn Express Clermont by IHG

Clermont

$97

$108 total

includes taxes & fees

Sep 27 - Sep 28

A hotel lobby with a reception desk, seating area, and a large mirror.

A swimming pool with a brick border, surrounded by white chairs and a fence.

A reception desk with a 'Welcome to Orlando' sign, framed pictures, and a lamp.

A Hampton Inn Suites building with a clear entrance, a sign indicating clearance, and a modern architectural design.

14. Hampton Inn & Suites Orlando-John Young Pkwy/S. Park

Orlando

$84

$94 total

includes taxes & fees

Sep 27 - Sep 28

A Hampton Inn hotel with a modern design, featuring a clear entrance, a flag, and a well-lit exterior.

A hotel reception desk with a 'Welcome to the Sun Shine State' sign, a reception area, and a bookshelf with various items.

A modern hotel lobby with a long communal table, blue and red seating, and a patterned carpet.

A hotel room with a large bed, a desk, a chair, a window with blinds, a wall-mounted TV, and a painting.

15. Hampton Inn Kissimmee North

Kissimmee

$106

$120 total

includes taxes & fees

Sep 29 - Sep 30

A room with a mural of Orlando, a wooden stool, a chair, and a tiled floor.

A room with a ping pong table, a mirror, a yellow chair, and a vase.

A brightly colored hallway with a large clock, a dining area with a yellow chair, and a kitchen visible through an open door.

A spacious living room with a green sofa, a brown leather chair, and a large mirror.

16. Banana Leaf Villa

Orlovista

$64

$83 total

includes taxes & fees

Sep 28 - Sep 29

A modern interior with a seating area, a kitchen, and a large TV on the wall.

A modern hotel with a two-story structure, a covered entrance, and a parking area.

A modern kitchen with a built-in stove, sink, and dark cabinetry.

A hotel room with two beds, a desk, a chair, and a window with curtains.

17. Suburban Studios Orlando - Ocoee/Winter Garden

Ocoee

$89

$100 total

includes taxes & fees

Oct 14 - Oct 15

A modern office space with a large TV, comfortable seating, and a view of the outdoors.

A hotel room with a bed, a desk with a chair, a TV, and a wardrobe with shelves.

A clean, modern food court with a variety of beverage options and a coffee machine.

A spacious cafeteria with multiple tables and chairs, a buffet counter with food items, and a large window providing natural light.

18. Baymont by Wyndham Orlando North Millenia

Orlando

$51

$65 total

includes taxes & fees

Oct 20 - Oct 21

A hotel room with two beds, a desk, and a TV.

A Days Inn by Wyndham with a large sign, a parking lot, and a building with multiple floors and balconies.

A swimming pool with a sun terrace, a Days Inn sign, and a building with yellow and blue accents.

A compact kitchen with a blue wall, a microwave, a coffee machine, and a toaster. There are wooden tables and chairs.

19. Days Inn by Wyndham Apopka/Orlando

Apopka

$68

$77 total

includes taxes & fees

Sep 26 - Sep 27

A spacious room with wooden flooring, large windows, and a green carpet. There are two orange rocking chairs and a round table.

A reception desk with a modern design, featuring a wooden finish and a green carpet.

A modern kitchen area with wooden cabinets, a countertop with appliances, and a view of greenery outside.

A hotel room with a bed, a chair, a desk, and a lamp.

20. Spark by Hilton Orlando near Universal

Florida Center

$80

$90 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 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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