The Best Hotels with a Pool in Winter Garden, FL from ₩150,574 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.

ARM53A Historic Downtown Area and Clock of Winter Garden Florida

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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 3 - Jun 4

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 22 - Jun 23

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

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 11 - Jun 12

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

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.

₩370,732 total

includes taxes & fees

Jun 3 - Jun 4

Home2 Suites By Hilton Winter Garden

Winter Garden

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

₩221,775 total

includes taxes & fees

Jun 3 - Jun 4

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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 3 - Jun 4

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

₩166,587 total

includes taxes & fees

Jun 22 - Jun 23

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 11 - Jun 12

Home2 Suites By Hilton Winter Garden

Winter Garden

₩221,775 total

includes taxes & fees

Jun 3 - Jun 4

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

₩370,732 total

includes taxes & fees

Jun 3 - Jun 4

2 outdoor pools, pool umbrellas, sun loungers

Hilton Vacation Club Aqua Sol Orlando West

Winter Garden

₩212,582 total

includes taxes & fees

Jun 3 - Jun 4

View all properties

Top Winter Garden Hotel Reviews

B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

10/10 Excellent

"The best hotel I've been in Orlando, very clean, quiet and updated ,close to everything, I'll definitely stay there again."

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"We spent Memorial Day weekend at Westgate Lakes Resort & Spa and had an absolutely wonderful time! From the moment we arrived, the atmosphere was relaxing, welcoming, and family-friendly. The property is beautiful, clean, and well-maintained, with so many activities and amenities that there was never a dull moment. The staff was professional, friendly, and always willing to help with anything we needed. Our room was spacious, comfortable, and perfect for a weekend getaway. We especially enjoyed the pools, the peaceful scenery around the lakes, and the overall resort experience. It truly felt like a home away from home. Memorial Day weekend can be very busy, but the resort still managed to make everything enjoyable and organized. Whether you want to relax, spend time with family, or simply escape for a few days, this is definitely a great place to stay. Thank you to everyone at Westgate Lakes & Spa for making our weekend so memorable. We left feeling refreshed, happy, and already looking forward to coming back again!"

Universal's Cabana Bay Beach Resort

10/10 Excellent

"Todo super bueno lo mejor de todo el la entrada al parque de agua volcano queda dentro del hotel, las piscinas del hotel super buenas y en excelentes condiciones ,las habitaciones están en buen estado lo que recomendaría las luz del baño que las arreglen por lo menos en mi habitación 6646 , por lo general todo estuvo excelente. buen servicio y una excelente atención"

The Grove Resort & Water Park Orlando

8/10 Good

"The property was very good overall. It was a little out of the way, but worth it. The rooms were clean, the staff was great, the amenities were great overall and the space for my family was great as well. We spent a lot of time at the multiple pools, the adult ones were actually heated. The only shade I can throw just happens to be the same no matter where I go both professionally or personally, if an elevator is out, no matter how long my stay, it never gets fixed while I'm there! We stayed in the one tower where the elevator didn't work, and it was a pretty good haul every time trying to get to the car and the garage- slightly less than a haul when trying to get downstairs to do anything. I would have spent more money onsite if it was easier to get downstairs, we grabbed a few groceries for the room after the 2nd trip going the long way down the first day realizing we didn't want to have to do that for every meal and pool trip. The parking was a bit more than I expected at over $100 per vehicle for three days, we had 2. I would still recommend it to others as all the other things overshadowed the downsides."

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent

"It was in a safe area. Having three different pools were extremely helpful for me and my family. It was nice having 2 of pools open up earlier in morning before the water park pool opened up if you just wanted to swim. My 16 year old enjoyed having pool to himself in morning hours. Can see the changes Hilton has done to the hotel. Great improvements in facility."

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.

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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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Homewood Suites by Hilton Orlando at Flamingo Crossings

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

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

B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

Frequently asked questions

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