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Hotels with Swimming Pools in Winter Garden

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Check availability on Winter Garden Hotels with Swimming Pools

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Winter Garden hotels with a pool

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 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.

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
  • Splash into endless fun with an outdoor pool and sunny loungers just steps from Disney magic.
S$109
includes taxes & fees
3 Nov - 4 Nov
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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 modern bathroom with a large mirror, two sinks, and a glass-enclosed shower area.
A large hotel with multiple floors, a central courtyard, and a reflective water feature.

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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
  • Sun-soaked pool sanctuary with poolside bar offers leisurely holiday escape in a serene setting.
S$128
includes taxes & fees
2 Nov - 3 Nov
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
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 hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.

3. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Splash into holiday mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
S$140
includes taxes & fees
27 Oct - 28 Oct
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.
A bar area with a long counter, multiple chairs, and a variety of bottles.

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
  • Heated outdoor pool paradise with hot tub sanctuary offers the perfect retreat after exploring nearby Disney theme parks.
S$113
includes taxes & fees
26 Oct - 27 Oct
SpringHill 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 hotel entrance with a sign reading "HOMEWOOD SUITES by Hilton."
A modern bathroom with a bathtub, shower, and a vanity with a mirror.
An outdoor patio with a barbecue grill, dining area, and umbrella.

5. Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Dive into poolside bliss with loungers and a thrilling waterslide at this spotless Orlando retreat.
S$164
includes taxes & fees
27 Oct - 28 Oct
Homewood Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
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.
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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
  • Dive into this heated outdoor oasis with poolside bar service, minutes from Disney parks and offering daily theme park shuttles.
S$125
includes taxes & fees
26 Oct - 27 Oct
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/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.
An outdoor patio with round tables and chairs, a red umbrella, and a grill.

7. Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
  • Sunny poolside retreats at the heart of Winter Garden offer a cool oasis after exploring.
S$176
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton Winter Garden
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 room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.
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
  • Splash into family fun with 2 outdoor pools and a free water park at this Disney-adjacent resort.
S$172
includes taxes & fees
29 Oct - 30 Oct
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 waterfront property with a dock, a gazebo, and a row of modern buildings in the background.
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
  • Splash into paradise at this resort with 6 outdoor pools, a lazy river, and a complimentary water park for endless aquatic fun.
S$356
includes taxes & fees
16 Nov - 17 Nov
The Grove Resort & Water Park Orlando
Interior
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.
A modern dining area with a glass table, white chairs, and decorative plates.
A bedroom with a bed, two bedside tables, a ceiling fan, and artwork on the walls.

10. Upstay: Modern Condo w Outdoor Pool - Near Disney!

Upstay: Modern Condo w Outdoor Pool - Near Disney!
Winter Garden
S$345
includes taxes & fees
29 Oct - 30 Oct
Upstay: Modern Condo w Outdoor Pool - Near Disney!
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Choose what matters most at hotels 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 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.

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
S$109
includes taxes & fees
3 Nov - 4 Nov
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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 covered outdoor seating area with tables and chairs, a ceiling fan, and a view of a pool and buildings in the background.
A hotel pool area with lounge chairs, a fire pit, and a large pool.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
S$128
includes taxes & fees
2 Nov - 3 Nov
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.
A bar area with a long counter, multiple chairs, and a variety of bottles.

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
S$113
includes taxes & fees
26 Oct - 27 Oct
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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 hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.
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
S$140
includes taxes & fees
27 Oct - 28 Oct
Home2 Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
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.
A lounge area with a fire feature, wicker furniture, and a bar in the background.

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
S$125
includes taxes & fees
26 Oct - 27 Oct
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
An outdoor patio with a barbecue grill, dining area, and umbrella.
A bar area with a stone wall, a flat-screen TV, and a beer tap.
Living area
A hotel entrance with a sign reading "HOMEWOOD SUITES by Hilton."

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
S$164
includes taxes & fees
27 Oct - 28 Oct
Homewood Suites by Hilton Orlando at Flamingo Crossings
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 swimming pool with lounge chairs and a view of a building in the background.

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
S$176
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton Winter Garden
View all properties

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.
A bar area with a long counter, multiple chairs, and a variety of bottles.

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
S$113
includes taxes & fees
26 Oct - 27 Oct
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
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.
A lounge area with a fire feature, wicker furniture, and a bar in the background.

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
S$125
includes taxes & fees
26 Oct - 27 Oct
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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 room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
S$172
includes taxes & fees
29 Oct - 30 Oct
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 waterfront property with a dock, a gazebo, and a row of modern buildings in the background.
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
S$356
includes taxes & fees
16 Nov - 17 Nov
The Grove Resort & Water Park Orlando
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
S$289
includes taxes & fees
2 Nov - 3 Nov
Modern 3BR Condo Near Disney- Pool and Hot Tub
View all properties

4-star hotels with pools in Winter Garden

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 room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
S$172
includes taxes & fees
29 Oct - 30 Oct
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 waterfront property with a dock, a gazebo, and a row of modern buildings in the background.
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
S$356
includes taxes & fees
16 Nov - 17 Nov
The Grove Resort & Water Park Orlando
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 leather sofas, a central coffee table, and large windows offering a view of greenery outside.
Front of property
Interior
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
S$324
includes taxes & fees
4 Nov - 5 Nov
Modern 3BR Resort Condo With Pool Near Disney
Interior
Interior
Interior
A spacious living room with a sofa, a coffee table, and a TV. There is a balcony with a view of trees and buildings.

Spacious 3BR Family Getaway w Pool Near Disney

Spacious 3BR Family Getaway w Pool Near Disney
Winter Garden
Spacious 3BR Family Getaway w Pool Near Disney
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 modern living room with a sofa, coffee table, and a dining area with chairs and a table.
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
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.
Interior

Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
S$314
includes taxes & fees
19 Oct - 20 Oct
Upstay: Condo Near Disney 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 modern kitchen with a dishwasher, a dining area with a table and chairs, and a view of the outside.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A spacious living area with a sofa, coffee table, and a view of the kitchen.

Upstay Disney Pet Friendly Condo w Pool Spa Games

Upstay Disney Pet Friendly Condo w Pool Spa Games
Winter Garden
S$288
includes taxes & fees
29 Oct - 30 Oct
Upstay Disney Pet Friendly Condo w Pool Spa Games
A hotel room with a large bed, two bedside tables, a painting, and a view of the outdoors through a sliding glass door.
Interior
A bunk bed with a colorful mural of sea creatures on the wall behind it.
A modern living room with a grey sofa, a coffee table, and two armchairs. There is a kitchen area with white cabinets and a bar stool.

Upstay - Large Condo Near Disney w Pool and Gym

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
S$306
includes taxes & fees
20 Oct - 21 Oct
Upstay - Large Condo Near Disney w Pool and Gym
Interior
A bedroom with a large bed, a bathroom with a bathtub, and a balcony with a view.
A balcony with a view of a construction site, a table with a vase of flowers, and two chairs.
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

Bright Family Escape With Game Room and Sauna

Bright Family Escape With Game Room and Sauna
Winter Garden
Bright Family Escape With Game Room and Sauna
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 Winter Garden Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Love the place. Great amenities and love the water park."
Saed 3-night trip
Posted 3 hours ago
The Grove Resort & Water Park Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"great place to stay!"
Julie 8-night trip
Posted 4 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"We love everything about this resort. Very convenient to all universal attractions. Great pools and we love the lazy river and pool bars. Bar in lobby is nice too. Rooms are very clean and staff is extremely friendly. Baylinder Diner is very convenient and food is good and not overpriced. The only thing I can say that needs to be improved from this trip is the lighting wasn’t working on some of the walkways and the keycard locks were not working on some of the pool gates."
Anna Marie 5-night trip
Posted 5 hours ago
Universal's Cabana Bay Beach Resort

Frequently asked questions

What's it like visiting Winter Garden?
If lounging by a pool is your idea of the perfect getaway, you may want to consider family-friendly Winter Garden, which has 53 places to stay with pools. During your trip, you can explore sights such as Universal Studios Florida and Universal Orlando Resort, and then unwind poolside at one of the accommodation options in Winter Garden that guests like for their pools.
What are some accommodation options with pools in Winter Garden?
The Grove Resort & Water Park Orlando: Resort located near Flamingo Crossings Town Center. Features 6 outdoor swimming pools, a children's pool and free water park access. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center: Hotel, 1-minute walk from Flamingo Crossings Town Center. Offers buffet, an outdoor pool and complimentary wireless Internet access. Hilton Vacation Club Aqua Sol Orlando West: Hotel located near Flamingo Crossings Town Center. Provides 2 outdoor swimming pools, a children's pool and free water park access. TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance: Hotel, 4-minute walk from Flamingo Crossings Town Center. Features a snack bar/deli, a pool and buffet.
How many pool hotels will I find in Winter Garden?
Expedia's 53 hotels in Winter Garden give you a great choice for your poolside getaway.
What is there to see and do in Winter Garden?
Explore places such as Universal Studios Florida, Universal Orlando Resort and Magic Kingdom® Park while you're in the area. Make a point to visit attractions such as Lake Louisa State Park and Surfari Water Park. Winter Garden appeals to visitors with its array of dining options, fun-filled attractions and major shopping area.
When is the best time to book a hotel with a pool in Winter Garden?
Taking the local weather in Winter Garden into account can help you maximise your time at the pool during your trip. The hottest months are usually August and July, with an average temperature of 28°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Garden are August, July, September and June, with each month seeing an average of 217 mm of rainfall.

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