Hotels with a Pool in Winter Garden

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Hotels with a Pool in Winter Garden

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 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

Bay Lake

Outdoor pool
Poolside bar
Pool loungers

$76

$85 total

includes taxes & fees

Oct 27 - Oct 28

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.

A modern bathroom with a large mirror, two sinks, and a glass-enclosed shower area.

A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.

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

Bay Lake

Outdoor pool
Poolside bar
Pool loungers

$82

$93 total

includes taxes & fees

Oct 28 - Oct 29

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.

3. 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

A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.

A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.

A restaurant with a bar area, seating, and a view of greenery outside.

An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

4. Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

Outdoor pool
Pool loungers

$98

$110 total

includes taxes & fees

Oct 20 - Oct 21

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 entrance with a sign reading "HOME 2 SUITES BY HILTON".

A hotel room with a kitchenette, a sofa, a desk, and a dining area.

5. Home2 Suites By Hilton Winter Garden

Winter Garden

Outdoor pool

$122

$138 total

includes taxes & fees

Oct 18 - Oct 19

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.

A lounge area with a fire feature, wicker furniture, and a bar in the background.

6. 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

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 hotel room with a large window, a pool view, a chair, a table, a lamp, and a bed.

An outdoor patio with a barbecue grill, dining area, and umbrella.

7. Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

Outdoor pool
Pool loungers

$114

$128 total

includes taxes & fees

Oct 26 - Oct 27

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

Winter Garden

2 outdoor pools
Poolside bar
Pool loungers
Hot tub

$94

$134 total

includes taxes & fees

Oct 19 - Oct 20

A resort with a large pool, water slides, palm trees, and beach umbrellas.

A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.

A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.

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

9. The Grove Resort & Water Park Orlando

Winter Garden

6 outdoor pools
3 poolside bars
Pool loungers
2 hot tubs

$170

$246 total

includes taxes & fees

Nov 9 - Nov 10

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.

A bathroom with two sinks, a large mirror, and a vanity with a light fixture.

10. Upstay: Condo Near Disney w Pool, Sauna

Winter Garden

Outdoor pool

$69

$245 total

includes taxes & fees

Oct 12 - Oct 13

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

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

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

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

Winter Garden

Pet friendly
Free parking
Free WiFi

$106

$263 total

includes taxes & fees

Oct 12 - Oct 13

A swimming pool with a brick deck, surrounded by tall trees and lounge chairs.

A bedroom with a bed, nightstand, wall art, ceiling fan, and a mirror.

A hotel with a sign labeled 'PALISADES,' surrounded by lush greenery and palm trees.

A vending machine with snacks and drinks, two wooden chairs, and a mirror on the wall.

12. Upstay Large Family Condo w Pool, Sauna

Winter Garden

Outdoor pool

$74

$251 total

includes taxes & fees

Oct 14 - Oct 15

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 laundry area with a washing machine, dryer, and a wall-mounted decorative piece.

13. Upstay Large Family Condo w Pool Sauna

Winter Garden

Free parking
Free WiFi

$86

$273 total

includes taxes & fees

Oct 14 - Oct 15

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

Winter Garden

Outdoor pool

$78

$255 total

includes taxes & fees

Nov 2 - Nov 3

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

Winter Garden

Pet friendly
Free parking
Free WiFi

$88

$245 total

includes taxes & fees

Oct 12 - Oct 13

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

Winter Garden

Outdoor pool

$81

$259 total

includes taxes & fees

Nov 2 - Nov 3

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 modern kitchen with white cabinets, a stainless steel refrigerator, and a green accent wall.

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

Winter Garden

Pet friendly
Free parking
Free WiFi
Gym

$85

$242 total

includes taxes & fees

Nov 2 - Nov 3

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

Winter Garden

Outdoor pool

$71

$248 total

includes taxes & fees

Oct 12 - Oct 13

19. Upstay Stylish 3BR Condo w Patio Near Disney

Winter Garden

Free parking
Free WiFi

$86

$273 total

includes taxes & fees

Oct 15 - Oct 16

A dining area with a table set for four, a sofa in the background, and a kitchen area with a dishwasher.

A spacious living room with a large TV, comfortable seating, and a balcony with a view.

A balcony with a view of a green landscape and distant buildings.

20. Upstay: Condo Near Disney w Games, Pool

Winter Garden

Outdoor pool

$71

$248 total

includes taxes & fees

Nov 3 - Nov 4

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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 Marriott Fairfield hotel sign with a landscaped garden in front.

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

Bay Lake

$76

$85 total

includes taxes & fees

Oct 27 - Oct 28

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

A covered outdoor seating area with tables and chairs, a ceiling fan, and a view of a pool and buildings in the background.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

$82

$93 total

includes taxes & fees

Oct 28 - Oct 29

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

Bay Lake

$87

$98 total

includes taxes & fees

Oct 26 - Oct 27

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

$98

$110 total

includes taxes & fees

Oct 20 - Oct 21

An outdoor patio with round tables and chairs, a red umbrella, and a grill.

Home2 Suites By Hilton Winter Garden

Winter Garden

$122

$138 total

includes taxes & fees

Oct 18 - Oct 19

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

Bay Lake

$87

$98 total

includes taxes & fees

Oct 26 - Oct 27

Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

$114

$128 total

includes taxes & fees

Oct 26 - Oct 27

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Hotels with pools and hot tubs in Winter Garden

SpringHill 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

Bay Lake

$87

$98 total

includes taxes & fees

Oct 26 - Oct 27

A modern living room with a teal accent wall, a sofa, ottomans, a dining area with white chairs, and a balcony with a view.

Hilton Vacation Club Aqua Sol Orlando West

Winter Garden

$94

$134 total

includes taxes & fees

Oct 19 - Oct 20

The Grove Resort & Water Park Orlando

Winter Garden

$170

$246 total

includes taxes & fees

Nov 9 - Nov 10

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

Upstay - Condo w Hot Tub and Pool - Near Disney

Winter Garden

$106

$263 total

includes taxes & fees

Oct 12 - Oct 13

A hotel room with a bed, two bedside tables, a nightstand, a balcony with a view, and two wall-mounted mirrors.

Upstay Large Family Condo w Pool Sauna

Winter Garden

$86

$273 total

includes taxes & fees

Oct 14 - Oct 15

A modern living room with a TV, seating area, kitchen, and a ceiling fan.

Upstay - Condo Near Disney w Pool Hot tub Sauna

Winter Garden

$88

$245 total

includes taxes & fees

Oct 12 - Oct 13

Modern 3BR Condo Near Disney- Pool and Hot Tub

Winter Garden

$85

$242 total

includes taxes & fees

Nov 2 - Nov 3

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

Upstay Tropical Style Family Condo w Pool

Winter Garden

$74

$259 total

includes taxes & fees

Oct 12 - Oct 13

Upstay Stylish 3BR Condo w Patio Near Disney

Winter Garden

$86

$273 total

includes taxes & fees

Oct 15 - Oct 16

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4-star hotels with pools in Winter Garden

Hilton Vacation Club Aqua Sol Orlando West

Winter Garden

$94

$134 total

includes taxes & fees

Oct 19 - Oct 20

The Grove Resort & Water Park Orlando

Winter Garden

$170

$246 total

includes taxes & fees

Nov 9 - Nov 10

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

Winter Garden

$69

$245 total

includes taxes & fees

Oct 12 - Oct 13

Modern 3BR Resort Condo With Pool Near Disney

Winter Garden

$78

$255 total

includes taxes & fees

Nov 2 - Nov 3

Upstay: 3BR Family Condo w Pool & Sauna

Winter Garden

$72

$249 total

includes taxes & fees

Oct 13 - Oct 14

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

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

Family Fun Condo: Pool, Sauna Near Disney

Winter Garden

$115

$275 total

includes taxes & fees

Oct 16 - Oct 17

A modern kitchen with a granite countertop, a built-in dishwasher, and a large window.

Upstay - Pet-friendly Suite w Pool, Sauna

Winter Garden

$81

$236 total

includes taxes & fees

Nov 4 - Nov 5

A bedroom with a bed, two bedside tables, a ceiling fan, and artwork on the walls.

A gym with treadmills, a Cybex machine, and a weight bench.

A bedroom with a patterned bedspread, a ceiling fan, a TV on the wall, and a view of a beach scene.

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

Upstay: Modern Condo w Outdoor Pool - Near Disney!

Winter Garden

$72

$249 total

includes taxes & fees

Oct 18 - Oct 19

A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave. There are two black bar stools in front of the counter.

A modern living room with a kitchen in the background, a dining area, and a large TV mounted on the wall.

Modern Escape With Private Patio, Spa Tub & Pool

Winter Garden

$121

$281 total

includes taxes & fees

Oct 22 - Oct 23

A view from a balcony overlooking a swimming pool with lounge chairs and palm trees.

An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

Spacious Resort Suite With Private Patio & Sauna

Winter Garden

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.

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, 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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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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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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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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