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Our top choices for Winter Garden hotels with a pool

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, (4,697 reviews)
  • cleanliness
    Splash into endless fun with an outdoor pool and sunny loungers just steps from Disney magic.
The price is Rp1.738.311
Rp1.955.601 total
includes taxes & fees
17 May - 18 May
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.2 out of 10, Wonderful, (5,475 reviews)
  • cleanliness
    Splash into holiday mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
The price is Rp1.961.710
Rp2.206.924 total
includes taxes & fees
21 May - 22 May
Home2 Suites by Hilton Orlando at Flamingo Crossings

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, (1,710 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 Rp1.962.054
Rp2.207.310 total
includes taxes & fees
14 May - 15 May
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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, (9,694 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 Rp2.839.815
Rp4.143.548 total
includes taxes & fees
14 May - 15 May
The Grove Resort & Water Park Orlando

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, (2,225 reviews)
  • cleanliness
    Heated outdoor pool paradise with hot tub sanctuary offers the perfect retreat after exploring nearby Disney theme parks.
The price is Rp1.641.929
Rp1.847.170 total
includes taxes & fees
17 May - 18 May
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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, (2,036 reviews)
  • cleanliness
    Sun-soaked pool sanctuary with poolside bar offers leisurely holiday escape in a serene setting.
The price is Rp2.030.898
Rp2.284.759 total
includes taxes & fees
21 May - 22 May
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

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, (2,382 reviews)
  • cleanliness
    Dive into poolside bliss with loungers and a thrilling waterslide at this spotless Orlando retreat.
The price is Rp2.596.796
Rp2.921.396 total
includes taxes & fees
17 May - 18 May
Homewood Suites by Hilton Orlando at Flamingo Crossings

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, (3,988 reviews)
  • cleanliness
    Splash into family fun with 2 outdoor pools and a free water park at this Disney-adjacent resort.
The price is Rp1.721.100
Rp2.420.383 total
includes taxes & fees
5 May - 6 May
Hilton Vacation Club Aqua Sol Orlando West

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
3.0 star property
Winter Garden
9.4 out of 10, Exceptional, (440 reviews)
  • cleanliness
    Sunny poolside retreats at the heart of Winter Garden offer a cool oasis after exploring.
The price is Rp2.243.970
Rp2.524.466 total
includes taxes & fees
24 May - 25 May
Home2 Suites By Hilton Winter Garden

Upstay Condo w Pool Sauna Sleeps 8

Upstay Condo w Pool Sauna Sleeps 8
2.0 star property
Winter Garden
The price is Rp1.588.437
Rp4.819.403 total
includes taxes & fees
29 Apr - 30 Apr
Upstay Condo w Pool Sauna Sleeps 8
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.

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

Hotels with pools and free breakfast in Winter Garden

Hotels with pools and hot tubs in Winter Garden

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.

Top Winter Garden Hotel Reviews

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 50 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 50 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 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 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.