Hotels with a Pool in Winter Garden

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Tonight
Sep 9 - Sep 10
Tomorrow
Sep 10 - Sep 11
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Hotels with a Pool in Winter Garden

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 restaurant with a bar area, seating, and a view of greenery outside.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.

1. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Outdoor pool
  • Pool loungers
$90
$101 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
A bar area with a long counter, multiple chairs, and a variety of bottles.
A hotel room with a desk, chair, and bed.

2. 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
Sep 29 - Sep 30
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
A lobby with a central seating area, wooden ceiling, and patterned carpet.
A Marriott Fairfield hotel sign with a landscaped garden in front.
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

3. 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
$89
$100 total
includes taxes & fees
Sep 28 - Sep 29
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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 restaurant with outdoor seating, a fire feature, and a bar area.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

4. 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
$95
$107 total
includes taxes & fees
Oct 4 - Oct 5
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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 large hotel with multiple floors, a central courtyard, and a reflective water feature.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.

5. 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
$97
$109 total
includes taxes & fees
Sep 28 - Sep 29
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 modern hotel lobby with a central seating area, a kitchen in the background, and a television mounted on the wall.
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".

6. Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
  • Outdoor pool
$114
$128 total
includes taxes & fees
Sep 16 - Sep 17
Home2 Suites By Hilton Winter Garden
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
A large hotel with a central entrance, multiple floors, and a sign indicating 'Homewood Suites by Hilton.'
A modern kitchen with a large island, bar stools, pendant lighting, and a flat-screen TV.
A hotel room with a large window, a pool view, a chair, a table, a lamp, and a bed.

7. Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Outdoor pool
  • Pool loungers
$128
$144 total
includes taxes & fees
Sep 12 - Sep 13
Homewood Suites by Hilton Orlando at Flamingo Crossings
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A hotel with a blue roof, a reflection pool, and palm trees.
A hotel room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.
A modern living room with a sofa, ottoman, and a TV on a stand.

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
Sep 22 - Sep 23
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 resort with multiple swimming pools surrounded by lush greenery and a large hotel building.

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
$199
$279 total
includes taxes & fees
Sep 10 - Sep 11
The Grove Resort & Water Park Orlando
A pool area with lounge chairs and a small pool.
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 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.

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
Sep 10 - Sep 11
Upstay: Condo Near Disney w Pool, Sauna
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.
A living room with a sofa, ottoman, coffee table, and a TV.

11. 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
$75
$232 total
includes taxes & fees
Sep 10 - Sep 11
Upstay - Condo w Hot Tub and Pool - Near Disney
A pool area with lounge chairs and a small pool.
A modern kitchen with white cabinets, stainless steel appliances, and a view to a balcony with outdoor furniture.
A bedroom with a bed, nightstand, wall art, ceiling fan, and a mirror.
A multi-story building with a corner tower, surrounded by palm trees and greenery.

12. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
Winter Garden
  • Outdoor pool
$70
$246 total
includes taxes & fees
Sep 10 - Sep 11
Upstay Large Family Condo w Pool, Sauna
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

13. Upstay Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
Winter Garden
  • Free parking
  • Free WiFi
$67
$251 total
includes taxes & fees
Sep 10 - Sep 11
Upstay Tropical Style Family Condo w Pool
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

14. Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
  • Outdoor pool
$69
$245 total
includes taxes & fees
Sep 10 - Sep 11
Modern 3BR Resort Condo With Pool Near Disney
A balcony with a view of a green landscape, a table with chairs, and a railing.

15. 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
$75
$232 total
includes taxes & fees
Sep 10 - Sep 11
Upstay - Condo Near Disney w Pool Hot tub Sauna
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.

16. Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
Winter Garden
  • Outdoor pool
$69
$245 total
includes taxes & fees
Sep 10 - Sep 11
Upstay Condo Near Disney w Pool & Sauna
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.

17. 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
$88
$245 total
includes taxes & fees
Sep 30 - Oct 1
Modern 3BR Condo Near Disney- Pool and Hot Tub
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 multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.

18. Condo With Sauna, Games, Poolnear Disney

Condo With Sauna, Games, Poolnear Disney
Winter Garden
  • Outdoor pool
$84
$262 total
includes taxes & fees
Sep 14 - Sep 15
Condo With Sauna, Games, Poolnear Disney
A bunk bed with a nightstand and a lamp, a polka dot wall, and a carpeted floor.
A modern kitchen with white cabinets, stainless steel appliances, a microwave, a stove, and a dishwasher.
A multi-story building with a modern architectural design, surrounded by lush greenery and palm trees.

19. Upstay Large Family Condo w Pool Sauna

Upstay Large Family Condo w Pool Sauna
Winter Garden
  • Free parking
  • Free WiFi
$73
$258 total
includes taxes & fees
Sep 10 - Sep 11
Upstay Large Family Condo w Pool Sauna
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.

20. Upstay Condo With Pool Near Disney & Pet Friendly

Upstay Condo With Pool Near Disney & Pet Friendly
Winter Garden
  • Outdoor pool
Upstay Condo With Pool Near Disney & Pet Friendly
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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

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 restaurant with a bar area, seating, and a view of greenery outside.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
$90
$101 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites by Hilton Orlando at Flamingo Crossings
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
A Marriott Fairfield hotel sign with a landscaped garden in front.
A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
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
$89
$100 total
includes taxes & fees
Sep 28 - Sep 29
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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 restaurant with outdoor seating, a fire feature, and a bar area.
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
$95
$107 total
includes taxes & fees
Oct 4 - Oct 5
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
A large hotel with a central entrance, multiple floors, and a sign indicating 'Homewood Suites by Hilton.'
A modern kitchen with a large island, bar stools, pendant lighting, and a flat-screen TV.
A hotel room with a large window, a pool view, a chair, a table, a lamp, and a bed.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
$128
$144 total
includes taxes & fees
Sep 12 - Sep 13
Homewood Suites by Hilton Orlando at Flamingo Crossings
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 pool area with lounge chairs, a fire pit, and a large pool.
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
$97
$109 total
includes taxes & fees
Sep 28 - Sep 29
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A bar area with a long counter, multiple chairs, and a variety of bottles.
A hotel room with a desk, chair, and bed.

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
Sep 29 - Sep 30
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
An outdoor patio with round tables and chairs, a red umbrella, and a grill.
A modern hotel lobby with a central seating area, a kitchen in the background, and a television mounted on the wall.
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".

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
$114
$128 total
includes taxes & fees
Sep 16 - Sep 17
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 lounge area with a fire feature, wicker furniture, and a bar in the background.
A restaurant with outdoor seating, a fire feature, and a bar area.
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
$95
$107 total
includes taxes & fees
Oct 4 - Oct 5
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A bar area with a long counter, multiple chairs, and a variety of bottles.
A hotel room with a desk, chair, and bed.

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
Sep 29 - Sep 30
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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 resort with multiple swimming pools surrounded by lush greenery and a large hotel building.

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
$199
$279 total
includes taxes & fees
Sep 10 - Sep 11
The Grove Resort & Water Park Orlando
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 hotel room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.
A modern living room with a sofa, ottoman, and a TV on a stand.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
$94
$134 total
includes taxes & fees
Sep 22 - Sep 23
Hilton Vacation Club Aqua Sol Orlando West
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 balcony with a view of a natural landscape, a table, and two chairs.

Upstay Large Family Condo w Pool Sauna

Upstay Large Family Condo w Pool Sauna
Winter Garden
$73
$258 total
includes taxes & fees
Sep 10 - Sep 11
Upstay Large Family Condo w Pool Sauna
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 grey sofa, a coffee table, and a large plant. There is a balcony with outdoor furniture and a TV mounted on the wall.
A modern living room with a grey sofa, a coffee table, and a TV mounted on the wall.

Upstay - Modern Family Apartment w Pool Hot Tub

Upstay - Modern Family Apartment w Pool Hot Tub
Winter Garden
Upstay - Modern Family Apartment w Pool Hot Tub
A modern living room with a TV, seating area, kitchen, and a ceiling fan.
A balcony with a view of a green landscape, a table with chairs, and a railing.

Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna
Winter Garden
$75
$232 total
includes taxes & fees
Sep 10 - Sep 11
Upstay - Condo Near Disney w Pool Hot tub Sauna
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.

Modern 3BR Condo Near Disney- Pool and Hot Tub

Modern 3BR Condo Near Disney- Pool and Hot Tub
Winter Garden
$88
$245 total
includes taxes & fees
Sep 30 - Oct 1
Modern 3BR Condo Near Disney- Pool and Hot Tub
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
$67
$251 total
includes taxes & fees
Sep 10 - Sep 11
Upstay Tropical Style Family Condo w Pool
A balcony with a view of palm trees and a clear sky.
A modern living room with a sofa, green chairs, a coffee table, and a kitchen in the background.
An aerial view of a resort with a large central pool, multiple lounge areas, and surrounding greenery.

Upstay - Condo w Hot Tub and Pool - Near Disney

Upstay - Condo w Hot Tub and Pool - Near Disney
Winter Garden
$75
$232 total
includes taxes & fees
Sep 10 - Sep 11
Upstay - Condo w Hot Tub and Pool - Near Disney
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4-star hotels with pools in Winter Garden

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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
$199
$279 total
includes taxes & fees
Sep 10 - Sep 11
The Grove Resort & Water Park Orlando
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 hotel room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.
A modern living room with a sofa, ottoman, and a TV on a stand.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
$94
$134 total
includes taxes & fees
Sep 22 - Sep 23
Hilton Vacation Club Aqua Sol Orlando West
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 Family-friendly Condo w Pool Near Disney

Upstay Family-friendly Condo w Pool Near Disney
Winter Garden
$81
$259 total
includes taxes & fees
Sep 10 - Sep 11
Upstay Family-friendly Condo w Pool Near Disney
A bathroom with two sinks, a large mirror, and a vanity with a light fixture.
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.

Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
$69
$245 total
includes taxes & fees
Sep 10 - Sep 11
Upstay: Condo Near Disney w Pool, Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
$69
$245 total
includes taxes & fees
Sep 10 - Sep 11
Modern 3BR Resort Condo With Pool Near Disney
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.

Upstay: 3BR Family Condo w Pool & Sauna

Upstay: 3BR Family Condo w Pool & Sauna
Winter Garden
$81
$259 total
includes taxes & fees
Sep 13 - Sep 14
Upstay: 3BR Family Condo w Pool & Sauna
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.

Spacious 3BR Family Getaway w Pool Near Disney

Spacious 3BR Family Getaway w Pool Near Disney
Winter Garden
$115
$297 total
includes taxes & fees
Sep 11 - Sep 12
Spacious 3BR Family Getaway w Pool Near Disney
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.

Upstay 3BR Condo w Pool & Patio Near Disney

Upstay 3BR Condo w Pool & Patio Near Disney
Winter Garden
$72
$249 total
includes taxes & fees
Sep 13 - Sep 14
Upstay 3BR Condo w Pool & Patio Near Disney
A modern kitchen with a granite countertop, a built-in dishwasher, and a large window.

Upstay - Pet-friendly Suite w Pool, Sauna

Upstay - Pet-friendly Suite w Pool, Sauna
Winter Garden
$93
$250 total
includes taxes & fees
Sep 16 - Sep 17
Upstay - Pet-friendly Suite w Pool, Sauna
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.
A bathroom with a bathtub, a circular wall decoration, and a ceiling fan.

Upstay: Condo w Pool, Sauna for 6 Guests

Upstay: Condo w Pool, Sauna for 6 Guests
Winter Garden
$81
$236 total
includes taxes & fees
Sep 10 - Sep 11
Upstay: Condo w Pool, Sauna for 6 Guests
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 street lined with large trees and historic brick buildings, including a 'Local' sign.
Photo by Shannon Maya
A tree-lined sidewalk with parked cars and a clear sky.
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, 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 other activities you might want to enjoy such as 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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Resurrection Catholic Church

8.4/10 (309 reviews)
Resurrection Catholic Church is 1.2 mi (1.9 km) from central Winter Garden, why not stop by during your stay.
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