Find Hotels with a Pool in Winter Garden, FL

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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

2.5 star property
Bay Lake
9.4 out of 10, Exceptional, (4323)
"Really good place to stay "
United States
Lians
The price is ￥18,072
￥20,331 total
includes taxes & fees
Jan 4 - Jan 5, 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

3.0 star property
Bay Lake
9.2 out of 10, Wonderful, (5061)
"Great location nice breakfast and front desk people is amazing "
United States
Orlando
The price is ￥16,078
￥18,087 total
includes taxes & fees
Dec 16 - Dec 17
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, (2245)
"Great stay"
United States
Christopher
The price is ￥17,760
￥19,980 total
includes taxes & fees
Dec 21 - Dec 22
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Exterior
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, (4075)
"Room was clean, area quiet. "
United States
Sapphira
The price is ￥16,553
￥23,003 total
includes taxes & fees
Dec 17 - Dec 18
Hilton Vacation Club Aqua Sol Orlando West
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, (1638)
"Great room, easy check in and courteous staff. "
United States
Kevin
The price is ￥18,383
￥20,682 total
includes taxes & fees
Jan 4 - Jan 5, 2026
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/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

3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (2138)
"Our stay was great and location was convenient when looking for food!"
United States
Sofia Alexia
The price is ￥19,816
￥22,293 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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, (1972)
"Great stay"
United States
Windy Laine
The price is ￥22,278
￥25,064 total
includes taxes & fees
Dec 22 - Dec 23
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, (8792)
"It was a great place to stay."
United States
Katherine Mercedes Cruz
The price is ￥23,213
￥34,702 total
includes taxes & fees
Dec 11 - Dec 12
The Grove Resort & Water Park Orlando
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, (362)
"Friendly staff, clean rooms , and great breakfast "
United States
Julee
The price is ￥17,757
￥19,977 total
includes taxes & fees
Dec 18 - Dec 19
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

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 ￥16,825
￥37,330 total
includes taxes & fees
Dec 11 - Dec 12
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Beautiful resort"
Antonese 3-night trip
Posted 3 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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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 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.