Hotels with a Pool in Winter Garden

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Oct 17 - Oct 18
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Oct 18 - Oct 19
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Oct 23 - Oct 25
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Oct 30 - Nov 1

Hotels with a Pool in Winter Garden

A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
A Marriott Fairfield hotel sign with a landscaped garden in front.
A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

1. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
$76
$85 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.
A restaurant with a bar area, seating, and a view of greenery outside.

2. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Outdoor pool
  • Pool loungers
$98
$110 total
includes taxes & fees
Oct 26 - Oct 27
Home2 Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
A restaurant with outdoor seating, a bar, and a fire feature.
A hotel room with a desk, chair, and bed.
Bar (on property)

3. SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Hot tub
$87
$98 total
includes taxes & fees
Oct 26 - Oct 27
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A hotel pool area with lounge chairs, a fire pit, and a large pool.
A large hotel with multiple floors, a central courtyard, and a reflective water feature.
A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.

4. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
$86
$97 total
includes taxes & fees
Nov 3 - Nov 4
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A swimming pool with lounge chairs and a view of a building in the background.
A hotel room with a kitchenette, a sofa, a desk, and a dining area.
A hotel entrance with a sign reading "HOME 2 SUITES BY HILTON".
A modern hotel lobby with a central seating area, a kitchen in the background, and a television mounted on the wall.

5. Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
  • Outdoor pool
$122
$138 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites By Hilton Winter Garden
A pool area with lounge chairs, a fire pit, and palm trees.
A lounge area with a fire feature, wicker furniture, and a bar in the background.
A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

6. TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Hot tub
$87
$98 total
includes taxes & fees
Oct 26 - Oct 27
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a slide and a small waterfall feature, surrounded by lounge chairs and umbrellas.
A bar area with a stone wall, a flat-screen TV, and a beer tap.
An outdoor patio with a barbecue grill, dining area, and umbrella.
A hotel entrance with a sign reading "HOMEWOOD SUITES by Hilton."

7. Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Outdoor pool
  • Pool loungers
$114
$128 total
includes taxes & fees
Oct 26 - Oct 27
Homewood Suites by Hilton Orlando at Flamingo Crossings
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 hotel with a blue roof, a reflection pool, and palm trees.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.

8. Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
  • 2 outdoor pools
  • Poolside bar
  • Pool loungers
  • Hot tub
$94
$134 total
includes taxes & fees
Oct 29 - Oct 30
Hilton Vacation Club Aqua Sol Orlando West
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 modern lobby with a reception desk, seating area, and a bar.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.

9. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
  • 6 outdoor pools
  • 3 poolside bars
  • Pool loungers
  • 2 hot tubs
$179
$257 total
includes taxes & fees
Nov 9 - Nov 10
The Grove Resort & Water Park Orlando
A pool area with lounge chairs and a small pool.
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
Interior
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.

10. Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
  • Outdoor pool
$69
$245 total
includes taxes & fees
Oct 18 - Oct 19
Upstay: Condo Near Disney w Pool, Sauna
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
Room
Room
Room

11. Upstay Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
Winter Garden
  • Free parking
  • Free WiFi
$69
$254 total
includes taxes & fees
Oct 18 - Oct 19
Upstay Tropical Style Family Condo w Pool
Interior
Interior
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.
Interior

12. Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
Winter Garden
  • Outdoor pool
$70
$246 total
includes taxes & fees
Oct 20 - Oct 21
Upstay Condo Near Disney w Pool & Sauna
Room
Room
Room
A balcony with a view of a green landscape, a table with chairs, and a railing.

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

Upstay - Condo Near Disney w Pool Hot tub Sauna
Winter Garden
  • Pet friendly
  • Free parking
  • Free WiFi
$80
$236 total
includes taxes & fees
Oct 18 - Oct 19
Upstay - Condo Near Disney w Pool Hot tub Sauna
Interior
Interior
Interior
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.

14. Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
  • Outdoor pool
$79
$257 total
includes taxes & fees
Nov 4 - Nov 5
Modern 3BR Resort Condo With Pool Near Disney
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.
Room

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

Modern 3BR Condo Near Disney- Pool and Hot Tub
Winter Garden
  • Pet friendly
  • Free parking
  • Free WiFi
  • Gym
$80
$236 total
includes taxes & fees
Oct 18 - Oct 19
Modern 3BR Condo Near Disney- Pool and Hot Tub
Interior
Interior
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.

16. Upstay Family-friendly Condo w Pool Near Disney

Upstay Family-friendly Condo w Pool Near Disney
Winter Garden
  • Outdoor pool
$75
$252 total
includes taxes & fees
Oct 21 - Oct 22
Upstay Family-friendly Condo w Pool Near Disney
An aerial view of a resort with a large central pool, multiple lounge areas, and surrounding greenery.
Room
Room
A balcony with a view of palm trees and a clear sky.

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

Upstay - Condo w Hot Tub and Pool - Near Disney
Winter Garden
  • Pet friendly
  • Free parking
  • Free WiFi
$125
$282 total
includes taxes & fees
Nov 11 - Nov 12
Upstay - Condo w Hot Tub and Pool - Near Disney
Interior
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
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 bedroom with a large bed, a bathroom with a bathtub, and a balcony with a view.

18. Near Disney - Family Condo w Pool, Games, and More

Near Disney - Family Condo w Pool, Games, and More
Winter Garden
  • Outdoor pool
$69
$245 total
includes taxes & fees
Oct 19 - Oct 20
Near Disney - Family Condo w Pool, Games, and More
A rectangular swimming pool with a brick deck, surrounded by tall trees and lounge chairs.
A modern kitchen with stainless steel appliances, white cabinetry, and a view to a balcony with outdoor furniture.
A bathroom with a white sink, a mirror, and a shower area.
A bedroom with a bed, nightstand, wall art, ceiling fan, and a mirror.

19. Upstay Large Family Condo w Pool Sauna

Upstay Large Family Condo w Pool Sauna
Winter Garden
  • Free parking
  • Free WiFi
$66
$250 total
includes taxes & fees
Oct 18 - Oct 19
Upstay Large Family Condo w Pool Sauna
Interior
A balcony with a view of a green landscape and distant buildings.
A spacious living room with a large TV, comfortable seating, and a balcony with a view.
A bedroom with a bed, a large window, a ceiling fan, and a bathroom with a bathtub and a framed picture on the wall.

20. Upstay: Condo Near Disney w Games, Pool

Upstay: Condo Near Disney w Games, Pool
Winter Garden
  • Outdoor pool
$69
$245 total
includes taxes & fees
Oct 18 - Oct 19
Upstay: Condo Near Disney w Games, Pool
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Discover your perfect hotel with a pool in Winter Garden

Breakfast included
Hot tub
4 stars
Water park
5 stars

Hotels with pools and free breakfast in Winter Garden

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.
A lobby with a central seating area, wooden ceiling, and patterned carpet.

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Bay Lake
$76
$85 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.
A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.
A restaurant with a bar area, seating, and a view of greenery outside.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
$98
$110 total
includes taxes & fees
Oct 26 - Oct 27
Home2 Suites by Hilton Orlando at Flamingo Crossings
A large hotel with multiple floors, a central courtyard, and a reflective water feature.
A hotel pool area with lounge chairs, a fire pit, and a large pool.
A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
$86
$97 total
includes taxes & fees
Nov 3 - Nov 4
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A restaurant with outdoor seating, a bar, and a fire feature.
A hotel room with a desk, chair, and bed.
Bar (on property)

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
$87
$98 total
includes taxes & fees
Oct 26 - Oct 27
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A lounge area with a fire feature, wicker furniture, and a bar in the background.
A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
$87
$98 total
includes taxes & fees
Oct 26 - Oct 27
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
An outdoor patio with a barbecue grill, dining area, and umbrella.
A hotel room with two beds, a desk with a lamp, a TV, and a door leading to another room.
A hotel entrance with a sign reading "HOMEWOOD SUITES by Hilton."
A bar area with a stone wall, a flat-screen TV, and a beer tap.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
$114
$128 total
includes taxes & fees
Oct 26 - Oct 27
Homewood Suites by Hilton Orlando at Flamingo Crossings
An outdoor patio with round tables and chairs, a red umbrella, and a grill.
A hotel room with a kitchenette, a sofa, a desk, and a dining area.
A hotel entrance with a sign reading "HOME 2 SUITES BY HILTON".
A modern hotel lobby with a central seating area, a kitchen in the background, and a television mounted on the wall.

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
$122
$138 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites By Hilton Winter Garden
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Hotels with pools and hot tubs in Winter Garden

A pool area with lounge chairs, a fire pit, and palm trees.
A restaurant with outdoor seating, a bar, and a fire feature.
A hotel room with a desk, chair, and bed.
Bar (on property)

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
$87
$98 total
includes taxes & fees
Oct 26 - Oct 27
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A lounge area with a fire feature, wicker furniture, and a bar in the background.
A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
$87
$98 total
includes taxes & fees
Oct 26 - Oct 27
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A miniature golf course with a sign indicating hole 5 and a par 3.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.
A hotel room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
$94
$134 total
includes taxes & fees
Oct 29 - Oct 30
Hilton Vacation Club Aqua Sol Orlando West
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 modern lobby with a reception desk, seating area, and a bar.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
$179
$257 total
includes taxes & fees
Nov 9 - Nov 10
The Grove Resort & Water Park Orlando
Room
Room
An aerial view of a resort with a large central pool, multiple lounge areas, and surrounding greenery.
A balcony with a view of palm trees and a clear sky.

Upstay - Condo w Hot Tub and Pool - Near Disney

Upstay - Condo w Hot Tub and Pool - Near Disney
Winter Garden
$125
$282 total
includes taxes & fees
Nov 11 - Nov 12
Upstay - Condo w Hot Tub and Pool - Near Disney
Room
Room
Room
A covered balcony with wicker chairs, a ceiling fan, and a view of trees.

Upstay Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
Winter Garden
$69
$254 total
includes taxes & fees
Oct 18 - Oct 19
Upstay Tropical Style Family Condo w Pool
Room
A balcony with a view of a green landscape, a table with chairs, and a railing.
Room
A modern living room with a TV, seating area, kitchen, and a ceiling fan.

Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna
Winter Garden
$80
$236 total
includes taxes & fees
Oct 18 - Oct 19
Upstay - Condo Near Disney w Pool Hot tub Sauna
Room
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.
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.

Modern 3BR Condo Near Disney- Pool and Hot Tub

Modern 3BR Condo Near Disney- Pool and Hot Tub
Winter Garden
$80
$236 total
includes taxes & fees
Oct 18 - Oct 19
Modern 3BR Condo Near Disney- Pool and Hot Tub
Room
Room
Room
Room

Upstay Stylish 3BR Condo w Patio Near Disney

Upstay Stylish 3BR Condo w Patio Near Disney
Winter Garden
Upstay Stylish 3BR Condo w Patio Near Disney
A laundry area with a washing machine, dryer, and a wall-mounted decorative piece.
A modern kitchen with stainless steel appliances, white cabinetry, and a view to a balcony with outdoor furniture.
A hotel room with a bed, two bedside tables, a nightstand, a balcony with a view, and two wall-mounted mirrors.
A bedroom with a bed, nightstand, wall art, ceiling fan, and a mirror.

Upstay Large Family Condo w Pool Sauna

Upstay Large Family Condo w Pool Sauna
Winter Garden
$66
$250 total
includes taxes & fees
Oct 18 - Oct 19
Upstay Large Family Condo w Pool Sauna
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4-star hotels with pools in Winter Garden

A miniature golf course with a sign indicating hole 5 and a par 3.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.
A hotel room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
$94
$134 total
includes taxes & fees
Oct 29 - Oct 30
Hilton Vacation Club Aqua Sol Orlando West
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 modern lobby with a reception desk, seating area, and a bar.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
$179
$257 total
includes taxes & fees
Nov 9 - Nov 10
The Grove Resort & Water Park Orlando
Interior
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 spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A bathroom with two sinks, a large mirror, and a vanity with a light fixture.

Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
$69
$245 total
includes taxes & fees
Oct 18 - Oct 19
Upstay: Condo Near Disney w Pool, Sauna
Interior
Interior
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.

Upstay - 3BR Condo w Pool and Sauna

Upstay - 3BR Condo w Pool and Sauna
Winter Garden
Upstay - 3BR Condo w Pool and Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
Interior
Front of property
Interior

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
$79
$257 total
includes taxes & fees
Nov 4 - Nov 5
Modern 3BR Resort Condo With Pool Near Disney
A modern kitchen with a granite countertop, a built-in dishwasher, and a large window.
Interior
Interior
Interior

Upstay - Pet-friendly Suite w Pool, Sauna

Upstay - Pet-friendly Suite w Pool, Sauna
Winter Garden
$77
$232 total
includes taxes & fees
Oct 21 - Oct 22
Upstay - Pet-friendly Suite w Pool, Sauna
Interior
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 dining area with a table, chairs, and two wall-mounted mirrors.
A modern kitchen with white cabinets, a stainless steel oven, and a microwave.

Family Fun Condo: Pool, Sauna Near Disney

Family Fun Condo: Pool, Sauna Near Disney
Winter Garden
Family Fun Condo: Pool, Sauna Near Disney
Interior
Interior
Interior
Interior

Upstay: Stylish 3BR Condo w Pationear Disney

Upstay: Stylish 3BR Condo w Pationear Disney
Winter Garden
Upstay: Stylish 3BR Condo w Pationear 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 bathroom with a bathtub, a circular wall decoration, and a ceiling fan.
Interior
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.

Upstay: Condo w Pool, Sauna for 6 Guests

Upstay: Condo w Pool, Sauna for 6 Guests
Winter Garden
$81
$236 total
includes taxes & fees
Oct 18 - Oct 19
Upstay: Condo w Pool, Sauna for 6 Guests
A bedroom with a bed, two bedside tables, a ceiling fan, and artwork on the walls.
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.
A rectangular swimming pool with a brick deck, surrounded by tall trees and lounge chairs.

Upstay: Modern Condo w Outdoor Pool - Near Disney!

Upstay: Modern Condo w Outdoor Pool - Near Disney!
Winter Garden
$69
$245 total
includes taxes & fees
Oct 18 - Oct 19
Upstay: Modern Condo w Outdoor Pool - Near Disney!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.
Photo by Shannon Maya
A bakery interior with a display case, shelves with jars, and a counter with a menu board.
Photo by JoyFilledWander
A café with a variety of food items and beverages on display, including boxes of snacks and bottles of wine.
Photo by JoyFilledWander
A bar with a polished floor, metal chairs, and a brick wall with a TV.
Photo by Nancy

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.

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.

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.

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.
Photo by Gregg Yutko

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.

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

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.

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, Grand Cypress 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 Lake Golf 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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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 Winter Garden Heritage Museum, West Orange Trail, and AdventHealth Winter Garden.
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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 Lake Golf are also nearby.
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