Kissimmee Lakefront Park Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad

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Check availability on Winter Garden Hotels with a Pool

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, (4,947 reviews)
  • cleanliness
    Splash into endless fun with an outdoor pool and sunny loungers just steps from Disney magic.
The price is ￥16,239
￥18,268 total
includes taxes & fees
Jun 14 - Jun 15
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
9.2 out of 10, Wonderful, (5,641 reviews)
  • cleanliness
    Splash into vacation mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
The price is ￥15,666
￥17,624 total
includes taxes & fees
Jun 23 - Jun 24
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, (1,725 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 ￥15,734
￥17,701 total
includes taxes & fees
Jun 22 - Jun 23
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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, (2,211 reviews)
  • cleanliness
    Heated outdoor pool paradise with hot tub sanctuary offers the perfect retreat after exploring nearby Disney theme parks.
The price is ￥14,161
￥15,930 total
includes taxes & fees
Jun 22 - Jun 23
SpringHill 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, (465 reviews)
  • cleanliness
    Sunny poolside retreats at the heart of Winter Garden offer a cool oasis after exploring.
The price is ￥20,274
￥22,809 total
includes taxes & fees
Jul 2 - Jul 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, (2,494 reviews)
  • cleanliness
    Dive into poolside bliss with loungers and a thrilling waterslide at this spotless Orlando retreat.
The price is ￥19,054
￥21,435 total
includes taxes & fees
Jul 12 - Jul 13
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, (2,124 reviews)
  • cleanliness
    Sun-soaked pool sanctuary with poolside bar offers leisurely vacation escape in a serene setting.
The price is ￥19,105
￥21,494 total
includes taxes & fees
Jun 23 - Jun 24
Residence Inn by Marriott Orlando Flamingo Crossing/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, (10,180 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 ￥31,949
￥44,793 total
includes taxes & fees
Jun 14 - Jun 15
The Grove Resort & Water Park Orlando
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, (3,987 reviews)
  • cleanliness
    Splash into family fun with 2 outdoor pools and a free water park at this Disney-adjacent resort.
The price is ￥21,134
￥28,288 total
includes taxes & fees
Jul 7 - Jul 8
Hilton Vacation Club Aqua Sol Orlando West
House | 3 bedrooms, Internet

Upstay Condo w Pool Sauna Sleeps 8

Upstay Condo w Pool Sauna Sleeps 8
2.0 star property
Winter Garden
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.
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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, (4947)
The price is ￥16,239
￥18,268 total
includes taxes & fees
Jun 14 - Jun 15
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
View all properties

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, (1725)
The price is ￥15,734
￥17,701 total
includes taxes & fees
Jun 22 - Jun 23
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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
"Everything was great, we had a blast."
Brittney 3-night trip
Posted 2 hours 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 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 Island H2O Live!. 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 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.