Find Hotels with a Pool in Winter Garden, FL

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Check availability on Winter Garden Hotels with a Pool

Tonight
Dec 20 - Dec 21
Tomorrow
Dec 21 - Dec 22
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
Bay Lake
9.4 out of 10, Exceptional, (4360)
"Great trip great place to stay"
United States
Tammy
The price is ￥18,050
￥20,306 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.2 out of 10, Wonderful, (5094)
"Great location nice breakfast and front desk people is amazing "
United States
Orlando
The price is ￥16,459
￥18,517 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Home2 Suites by Hilton Orlando at Flamingo Crossings
Exterior
Hilton Vacation Club Aqua Sol Orlando West

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, (4072)
"Clean hotel, very spacious and the staff was very friendly even in a very late check in "
United States
Ana
The price is ￥16,533
￥22,976 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Hilton Vacation Club Aqua Sol Orlando West
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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2244)
"Great stay"
United States
Christopher
The price is ￥17,738
￥19,955 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (1648)
"best place "
United States
Pedro
The price is ￥17,738
￥19,956 total
includes taxes & fees
Dec 22 - Dec 23
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (1975)
"Great location, good, staff, and rooms "
Canada
Jobin
The price is ￥21,029
￥23,657 total
includes taxes & fees
Dec 23 - Dec 24
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
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

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (2147)
"Great room and stay!"
United States
christopher michael
The price is ￥20,567
￥23,138 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Homewood Suites by Hilton Orlando at Flamingo Crossings
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, (8797)
"It was a great place to stay."
United States
Katherine Mercedes Cruz
The price is ￥21,628
￥32,909 total
includes taxes & fees
Dec 21 - Dec 22
The Grove Resort & Water Park Orlando
Outdoor pool
Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
3.0 star property
Winter Garden
9.4 out of 10, Exceptional, (364)
"Friendly staff, clean rooms , and great breakfast "
United States
Julee
The price is ￥20,771
￥23,367 total
includes taxes & fees
Dec 22 - Dec 23
Home2 Suites By Hilton Winter Garden
Outdoor pool
Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
3.5 star property
Winter Garden
10.0 out of 10, Exceptional, (2)
"Beautiful apartment, clean, quiet, and beautiful location. Host was very helpful. I would recommend this beautiful apartment for anyone wanting a home away from home."
United States
Kowanda
The price is ￥21,006
￥42,011 total
includes taxes & fees
Dec 21 - Dec 22
Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Great hotel great food"
Malika 3-night trip
Posted 1 day ago
DoubleTree by Hilton at the Entrance to Universal 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 23 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 steps 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, 1-minute walk from Flamingo Crossings Town Center. Features a snack bar/deli, a pool, and buffet. Orange Lake Holiday Inn Resort 2 Bedroom Villa In Beautiful Orlando/Kissimmee: Resort located near Walt Disney World® Resort. Offers complimentary wireless internet access, a pool, and kitchens.
How many pool hotels are there in Winter Garden?
Expedia's 23 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 Magic Kingdom® Park 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.