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Check availability on Winter Garden Hotels with Pool

Our top choices for Winter Garden hotels with a pool

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, pool 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, (5,177 reviews)
  • cleanliness
    Splash into endless fun with an outdoor pool and sunny loungers just steps from Disney magic.
The price is ฿3,085
฿3,470 total
includes taxes & fees
28 Jul - 29 Jul
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3 bedrooms, Internet

Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna
2.0 star property
Winter Garden
The price is ฿3,751
฿8,960 total
includes taxes & fees
4 Aug - 5 Aug
Upstay - Condo Near Disney w Pool Hot tub Sauna
Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, pool 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, (5,765 reviews)
  • cleanliness
    Splash into holiday mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
The price is ฿3,249
฿3,655 total
includes taxes & fees
22 Jul - 23 Jul
Home2 Suites by Hilton Orlando at Flamingo Crossings
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, (1,786 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 ฿2,896
฿3,259 total
includes taxes & fees
3 Aug - 4 Aug
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, (479 reviews)
  • cleanliness
    Sunny poolside retreats at the heart of Winter Garden offer a cool oasis after exploring.
The price is ฿3,660
฿4,117 total
includes taxes & fees
26 Jul - 27 Jul
Home2 Suites By Hilton Winter Garden
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, (2,236 reviews)
  • cleanliness
    Heated outdoor pool paradise with hot tub sanctuary offers the perfect retreat after exploring nearby Disney theme parks.
The price is ฿2,936
฿3,303 total
includes taxes & fees
3 Aug - 4 Aug
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Aerial view

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, (10,411 reviews)
  • cleanliness
    Splash into paradise at this resort with 6 outdoor pools, a lazy river, and a complimentary water park for endless aquatic fun.
The price is ฿6,126
฿8,727 total
includes taxes & fees
9 Aug - 10 Aug
The Grove Resort & Water Park Orlando
Outdoor pool, open 9:00 AM to 10:00 PM, pool 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, (2,572 reviews)
  • cleanliness
    Dive into poolside bliss with loungers and a thrilling waterslide at this spotless Orlando retreat.
The price is ฿3,522
฿3,962 total
includes taxes & fees
9 Aug - 10 Aug
Homewood Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, pool 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, (2,170 reviews)
  • cleanliness
    Sun-soaked pool sanctuary with poolside bar offers leisurely holiday escape in a serene setting.
The price is ฿3,962
฿4,457 total
includes taxes & fees
15 Jul - 16 Jul
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
2 outdoor pools, pool umbrellas, pool 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, (3,968 reviews)
  • cleanliness
    Splash into family fun with 2 outdoor pools and a free water park at this Disney-adjacent resort.
The price is ฿3,329
฿4,682 total
includes taxes & fees
22 Jul - 23 Jul
Hilton Vacation Club Aqua Sol Orlando West
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, (5177)
The price is ฿3,085
฿3,470 total
includes taxes & fees
28 Jul - 29 Jul
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

3 bedrooms, Internet
Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna
2.0 star property
Winter Garden
The price is ฿3,751
฿8,960 total
includes taxes & fees
4 Aug - 5 Aug
Upstay - Condo Near Disney w Pool Hot tub Sauna
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4-star hotels with pools in Winter Garden

Aerial view
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, (10411)
The price is ฿6,126
฿8,727 total
includes taxes & fees
9 Aug - 10 Aug
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.
View all properties

Top Winter Garden Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"still clean and easy to communicate with staff!"
Sean 4-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

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 56 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. TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance: Hotel, 4-minute walk from Flamingo Crossings Town Center. Provides a snack bar/deli, a pool and buffet. Hilton Vacation Club Aqua Sol Orlando West: Hotel located near Flamingo Crossings Town Center. Features 2 outdoor swimming pools, a children's pool and free water park access.
How many pool hotels will I find 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 such as Universal Studios Florida, Universal Orlando Resort and Universal's Volcano Bay 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.