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Search Hotels with Swimming Pool in Winter Garden

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Check availability on Winter Garden Hotels with Swimming Pool

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
23 Oct - 25 Oct
Next weekend
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 lobby with a central seating area, wooden ceiling, and patterned carpet.
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
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.
₹7,181
₹8,079 total
includes taxes & fees
17 Nov - 18 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 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.

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.
₹9,198
₹10,348 total
includes taxes & fees
11 Nov - 12 Nov
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
Bar (on property)
A hotel room with a desk, chair, and bed.
A bar area with a long counter, multiple chairs, and a variety of bottles.

3. 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.
₹7,433
₹8,362 total
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 restaurant with outdoor seating, a fire feature, and a bar area.
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.

4. 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.
₹8,259
₹9,291 total
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.
An outdoor patio with round tables and chairs, a red umbrella, and a grill.
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

Home2 Suites By Hilton Winter Garden
Winter Garden
  • Sunny poolside retreats at the heart of Winter Garden offer a cool oasis after exploring.
₹11,619
₹13,071 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton 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 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.

6. 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.
₹16,992
₹24,349 total
includes taxes & fees
22 Oct - 23 Oct
The Grove Resort & Water Park Orlando
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 hotel room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.

7. 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.
₹8,952
₹12,741 total
includes taxes & fees
26 Oct - 27 Oct
Hilton Vacation Club Aqua Sol Orlando West
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.

8. Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
₹6,645
₹23,387 total
includes taxes & fees
3 Nov - 4 Nov
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 balcony with a view of a forest, a table with chairs, and a ceiling fan.
Room
A modern kitchen with white cabinets, a stainless steel refrigerator, and a green accent wall.

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

Modern 3BR Condo Near Disney- Pool and Hot Tub
Winter Garden
₹6,695
₹21,547 total
includes taxes & fees
3 Nov - 4 Nov
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.
Interior

10. Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
Winter Garden
₹6,835
₹23,601 total
includes taxes & fees
3 Nov - 4 Nov
Upstay Condo Near Disney w Pool & Sauna
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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 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.

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
₹7,181
₹8,079 total
includes taxes & fees
17 Nov - 18 Nov
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 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.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
₹9,263
₹10,421 total
includes taxes & fees
2 Nov - 3 Nov
Home2 Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
Bar (on property)
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
₹7,433
₹8,362 total
includes taxes & fees
26 Oct - 27 Oct
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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
₹9,198
₹10,348 total
includes taxes & fees
11 Nov - 12 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 fire feature, and a bar area.
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
₹8,259
₹9,291 total
includes taxes & fees
26 Oct - 27 Oct
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
An outdoor patio with round tables and chairs, a red umbrella, and a grill.
A swimming pool with lounge chairs and a view of a building in the background.
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.

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
₹11,619
₹13,071 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton Winter Garden
An outdoor patio with a barbecue grill, dining area, and umbrella.
A hotel entrance with a sign reading "HOMEWOOD SUITES by Hilton."
A gym with treadmills, stationary bikes, and free weights.
A hotel room with a large window, a bed, a bedside table with a lamp, and a wall-mounted air conditioner.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
₹12,139
₹13,656 total
includes taxes & fees
29 Oct - 30 Oct
Homewood Suites by Hilton Orlando at Flamingo Crossings
View all properties

Hotels with pools and hot tubs in Winter Garden

A pool area with lounge chairs, a fire pit, and palm trees.
Bar (on property)
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
₹7,433
₹8,362 total
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 restaurant with outdoor seating, a fire feature, and a bar area.
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
₹8,259
₹9,291 total
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 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.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
₹8,952
₹12,741 total
includes taxes & fees
26 Oct - 27 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
₹16,992
₹24,349 total
includes taxes & fees
22 Oct - 23 Oct
The Grove Resort & Water Park Orlando
Room
Room
A balcony with a view of a green landscape, a table with chairs, and a railing.
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
₹6,853
₹21,704 total
includes taxes & fees
2 Nov - 3 Nov
Upstay - Condo Near Disney w Pool Hot tub Sauna
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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 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.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
₹8,952
₹12,741 total
includes taxes & fees
26 Oct - 27 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
₹16,992
₹24,349 total
includes taxes & fees
22 Oct - 23 Oct
The Grove Resort & Water Park Orlando
Interior
Interior
Front of property
Interior

Upstay: Stylish 3BR Condo w Pationear Disney

Upstay: Stylish 3BR Condo w Pationear Disney
Winter Garden
₹5,801
₹22,438 total
includes taxes & fees
25 Oct - 26 Oct
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.
Interior
Front of property
Interior

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
₹6,944
₹23,724 total
includes taxes & fees
3 Nov - 4 Nov
Modern 3BR Resort Condo With Pool Near Disney
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.
Interior

Upstay: 3BR Family Condo w Pool & Sauna

Upstay: 3BR Family Condo w Pool & Sauna
Winter Garden
Upstay: 3BR Family Condo 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 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
₹6,645
₹23,387 total
includes taxes & fees
3 Nov - 4 Nov
Upstay: Condo Near Disney 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 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 and Sauna Near Disney

Family Fun Condo Pool and Sauna Near Disney
Winter Garden
₹8,093
₹22,881 total
includes taxes & fees
26 Oct - 27 Oct
Family Fun Condo Pool and Sauna Near Disney
A modern kitchen with a stainless steel refrigerator, microwave, oven, and dishwasher.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.
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.

Upstay: Resort Style Condo w Pool, Sauna

Upstay: Resort Style Condo w Pool, Sauna
Winter Garden
₹7,612
₹22,340 total
includes taxes & fees
25 Oct - 26 Oct
Upstay: Resort Style Condo w Pool, Sauna
Interior
Interior
Interior
Interior

Upstay Condo With Outdoor Pool & Sauna

Upstay Condo With Outdoor Pool & Sauna
Winter Garden
₹7,012
₹21,665 total
includes taxes & fees
2 Nov - 3 Nov
Upstay Condo With Outdoor Pool & Sauna
Interior
A spacious living room with a large sliding glass door leading to a balcony, a ceiling fan, a flat-screen TV, and a minimalist furniture arrangement.
A modern living room with a sofa, coffee table, and a dining area with a TV.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

Pet-friendly Resort Getaway With Patio and Pool

Pet-friendly Resort Getaway With Patio and Pool
Winter Garden
₹6,484
₹21,071 total
includes taxes & fees
3 Nov - 4 Nov
Pet-friendly Resort Getaway With Patio and Pool
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

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"I was greeted professionally at the hotel. My room had a wet carpet from cleaning, so I called the front desk and they moved me right away and gave me free breakfast for my whole stay as an apology, which was fantastic; the restaurant staff were so kind and the food was great. The place was really clean and nice. I’d definitely recommend it to others."
Mauricio 2-night trip
Posted less than an hour ago
Rosen Inn Lake Buena Vista
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Loved everything about the property. Fantastic is all I can say"
Christopher 5-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Our favorite off property hotel! Free breakfast( Mickey waffles are delish), KickBack snack buffet and 3 complimentary drinks are a wonderful,inviting perk as well.The rooms are always clean and comfortable,and the shuttle service is always on time!."
Dustin 3-night trip
Posted 1 hour ago
Drury Plaza Hotel Orlando - Disney Springs Area
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Great spot near the heart of Universal"
Bryan 6-night trip
Posted 1 hour ago
Universal's Cabana Bay Beach Resort
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"One of the best resorts me and my family been to."
Elene 2-night trip
Posted 2 hours ago
The Grove Resort & Water Park Orlando
Marriott's Grande Vista

Marriott's Grande Vista

8/10 Good
"Emplacement"
Daniel 2-night trip
Posted 4 hours ago
Marriott's Grande Vista
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Second time staying at this property. Amazing staff. Super clean. Room was perfect. Great place to stay off property for the parks. So close to both Disney and universal."
Brianna 6-night trip
Posted 6 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"It was great, convenient, every airport should have a hotel like the Hyatt in them!"
Jessica 1-night trip
Posted 7 hours ago
Hyatt Regency Orlando International Airport
Walt Disney World Dolphin

Walt Disney World Dolphin

8/10 Good
"Despite its elegant decor and a high end attention to detail, this resort feels comfortably familiar and cozy. I have stayed here many times and the Dolphin Hotel has never disappointed me."
maria 2-night trip
Posted 8 hours ago
Walt Disney World Dolphin

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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