The Best Hotels with a Pool in Winter Garden, FL from ₩135,208 in 2026

Q: What are some accommodations with pools in Winter Garden?

The Grove Resort & Water Park Orlando : Resort located near Flamingo Crossings Town Center. Features 6 outdoor 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 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.

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Our top choices for Winter Garden hotels with a pool

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

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.

₩158,767 total

includes taxes & fees

Jun 2 - Jun 3

Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

Splash into vacation mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.

₩166,587 total

includes taxes & fees

Jun 9 - Jun 10

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.

₩167,303 total

includes taxes & fees

Jun 8 - Jun 9

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.

₩150,574 total

includes taxes & fees

Jun 8 - Jun 9

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

Sun-soaked pool sanctuary with poolside bar offers leisurely vacation escape in a serene setting.

₩187,790 total

includes taxes & fees

Jun 9 - Jun 10

Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

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.

₩208,582 total

includes taxes & fees

Jun 9 - Jun 10

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.

₩372,166 total

includes taxes & fees

May 31 - Jun 1

Home2 Suites By Hilton Winter Garden

Winter Garden

Sunny poolside retreats at the heart of Winter Garden offer a cool oasis after exploring.

₩222,582 total

includes taxes & fees

Jun 1 - Jun 2

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Choose what matters most at hotels with a pool in Winter Garden

Breakfast included

Hot tub

Hotels with pools and free breakfast in Winter Garden

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

Bay Lake

₩158,767 total

includes taxes & fees

Jun 2 - Jun 3

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

₩166,587 total

includes taxes & fees

Jun 9 - Jun 10

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

Bay Lake

₩167,303 total

includes taxes & fees

Jun 8 - Jun 9

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

Bay Lake

₩150,574 total

includes taxes & fees

Jun 8 - Jun 9

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

₩187,790 total

includes taxes & fees

Jun 9 - Jun 10

Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

₩208,582 total

includes taxes & fees

Jun 9 - Jun 10

Home2 Suites By Hilton Winter Garden

Winter Garden

₩222,582 total

includes taxes & fees

Jun 1 - Jun 2

View all properties

Hotels with pools and hot tubs in Winter Garden

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

Bay Lake

₩150,574 total

includes taxes & fees

Jun 8 - Jun 9

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

Bay Lake

₩167,303 total

includes taxes & fees

Jun 8 - Jun 9

The Grove Resort & Water Park Orlando

Winter Garden

₩372,166 total

includes taxes & fees

May 31 - Jun 1

2 outdoor pools, pool umbrellas, sun loungers

Hilton Vacation Club Aqua Sol Orlando West

Winter Garden

₩213,404 total

includes taxes & fees

Jun 1 - Jun 2

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Top Winter Garden Hotel Reviews

The Grove Resort & Water Park Orlando

2/10 Terrible

"The rooms were not well maintained. The sheets and towels were old and worn. On arrival and being checked in to our 1st room, the washer and dryer did not work. The fridge did not work. After calling about 3 times, we were then moved across the hall to another room. However, this room the dishwasher looked like it was coming out of the slot and there were hardly any pans to use to make breakfast. There was no kettle or hot water in the kitchen. We made do to avoid appearing to be a difficult customer NEVER TO RETURN AND MY FRIENDS WHO WERE PLANNING TO GO WILL NOT BE THERE EITHER….DO BETTER"

Holiday Inn Resort Orlando Suites - Waterpark by IHG

6/10 Okay

"I liked that everything was at hands reach such as food and etc. but the waterpark is really just slides in a pool in the center of the hotel, the waterpark was very crowded throughout the stay and the AC in room shut off in the middle of the night which have you waking up hot. Oh and the housekeeper bams on door very hard and if you don’t come when they knock they will open your door without you noticing. The stay came out as 5/10 for my family. I’m happy that we have annual passes to other theme parks around the area."

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"This is a great option for families or a longer stay. With a full kitchen, living room area and balcony there is plenty of space to make it feel like home. There is plenty to do on site, however keep in mind that it’s all at additional fees (mini golf, arcade, etc). The complex is huge, so much that they have a complementary shuttle to take you from one building or pool to the other, it looks and feels like a huge apartment complex rather than hotel. To that point, they do some sort of timeshare sales which they try to get you to sign up for when you check-in, but you certainly don’t have to. Overall, the apartment was clean and spacious. The water pressure was not great but really no other complaints. Would definitely recommend."

Vacation Village Orlando, Celebration

4/10 Poor

"Only stayed for one day and had to sleep in a hot box.. when we arrived the thermostat was set to heat so we gave it time to get cool while we got food just to come back and it’s still hot..just to find out AT CHECK OUT that “the circuit breaker” tripped and they gave no accommodation for it…was very unsatisfied."

Frequently asked questions

What's it like visiting Winter Garden?

If lounging by a pool is your idea of the perfect getaway, you might want to think about family-friendly Winter Garden, which has 54 places to stay with pools. During your trip, you can explore sights such as Universal Studios Florida and Universal Orlando Resort, and then relax and unwind poolside at one of the accommodations in Winter Garden that guests like for their pools.

What are some accommodations with pools in Winter Garden?

The Grove Resort & Water Park Orlando: Resort located near Flamingo Crossings Town Center. Features 6 outdoor 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 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 are there in Winter Garden?

Expedia's 54 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 like Universal Studios Florida, Universal Orlando Resort, and Universal's Volcano Bay while you're in the area. Make a point to visit attractions like Lake Butler 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 into account the local weather in Winter Garden can help you maximize your time at the pool during your trip. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Garden are August, July, September, and June, with each month seeing an average of 9 inches of rainfall.

Find Hotels with a Pool in Winter Garden, FL

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Check availability on Winter Garden Hotels with a Pool

Our top choices for Winter Garden hotels with a pool

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

Home2 Suites by Hilton Orlando at Flamingo Crossings

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

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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Homewood Suites by Hilton Orlando at Flamingo Crossings

The Grove Resort & Water Park Orlando

Home2 Suites By Hilton Winter Garden

Hilton Vacation Club Aqua Sol Orlando West

Choose what matters most at hotels with a pool in Winter Garden

Hotels with pools and free breakfast in Winter Garden

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

Hotels with pools and hot tubs in Winter Garden

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

Top Winter Garden Hotel Reviews

The Grove Resort & Water Park Orlando

Frequently asked questions

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