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Find Hotels with a Pool in Winter Garden, FL

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Check availability on Winter Garden Hotels with a Pool

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (5,284 reviews)
  • cleanliness
    Splash into endless fun with an outdoor pool and sunny loungers just steps from Disney magic.
The price is ￥14,065
￥15,824 total
includes taxes & fees
Aug 9 - Aug 10
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (5,844 reviews)
  • cleanliness
    Splash into vacation mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
The price is ￥15,987
￥17,985 total
includes taxes & fees
Aug 9 - Aug 10
Home2 Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, a heated pool

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2,241 reviews)
  • cleanliness
    Heated outdoor pool paradise with hot tub sanctuary offers the perfect retreat after exploring nearby Disney theme parks.
The price is ￥15,334
￥17,251 total
includes taxes & fees
Jul 30 - Jul 31
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (1,793 reviews)
  • cleanliness
    Dive into this heated outdoor oasis with poolside bar service, minutes from Disney parks and offering daily theme park shuttles.
The price is ￥15,178
￥17,075 total
includes taxes & fees
Aug 9 - Aug 10
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
3.0 star property
Winter Garden
9.4 out of 10, Exceptional, (484 reviews)
  • cleanliness
    Sunny poolside retreats at the heart of Winter Garden offer a cool oasis after exploring.
The price is ￥19,345
￥21,764 total
includes taxes & fees
Aug 2 - Aug 3
Home2 Suites By Hilton Winter Garden
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (2,621 reviews)
  • cleanliness
    Dive into poolside bliss with loungers and a thrilling waterslide at this spotless Orlando retreat.
The price is ￥17,330
￥19,497 total
includes taxes & fees
Aug 9 - Aug 10
Homewood Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (2,191 reviews)
  • cleanliness
    Sun-soaked pool sanctuary with poolside bar offers leisurely vacation escape in a serene setting.
The price is ￥16,572
￥18,644 total
includes taxes & fees
Aug 2 - Aug 3
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Property amenity

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Holiday Inn Express & Suites Clermont Se West Orlando by IHG
2.5 star property
Clermont
8.4 out of 10, Very Good, (1,498 reviews)
  • cleanliness
    Splash into family fun with 5 outdoor pools and a water park at this amenity-rich hotel with poolside dining.
The price is ￥12,079
￥13,409 total
includes taxes & fees
Aug 23 - Aug 24
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
2 outdoor pools, pool umbrellas, sun loungers

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
Winter Garden
8.8 out of 10, Excellent, (3,973 reviews)
  • cleanliness
    Splash into family fun with 2 outdoor pools and a free water park at this Disney-adjacent resort.
The price is ￥16,793
￥23,501 total
includes taxes & fees
Aug 9 - Aug 10
Hilton Vacation Club Aqua Sol Orlando West
Royal Room, 2 Queen Beds, Pool View | Pool | Outdoor pool, a heated pool, open 9 AM to 9:00 PM, free cabanas

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,191 reviews)
  • cleanliness
    Splash into family fun at this sun-drenched resort where poolside luxury meets kid-friendly adventure.
The price is ￥6,824
￥13,322 total
includes taxes & fees
Aug 2 - Aug 3
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
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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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

Free daily buffet breakfast
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (5284)
The price is ￥14,065
￥15,824 total
includes taxes & fees
Aug 9 - Aug 10
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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Hotels with pools and hot tubs in Winter Garden

Outdoor pool, a heated pool
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (1793)
The price is ￥15,178
￥17,075 total
includes taxes & fees
Aug 9 - Aug 10
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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4-star hotels with pools in Winter Garden

6 outdoor pools, a heated pool, cabanas (surcharge), pool umbrellas
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
Winter Garden
8.0 out of 10, Very Good, (10561)
The price is ￥29,306
￥42,000 total
includes taxes & fees
Aug 25 - Aug 26
The Grove Resort & Water Park Orlando
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Loved your place. Super cute in its theming. Lazy river and slide were a plus. Bonus pools were open till 12 some nights!!!"
Joshua 1-night trip
Posted less than an hour 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 might want to think about family-friendly Winter Garden, which has 56 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 56 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 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 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.