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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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
Bay Lake
9.4 out of 10, Exceptional, (4349)
"Really good place to stay "
United States
Lians
The price is 3.051.612 ₫
3.433.063 ₫ total
includes taxes & fees
4 Jan - 5 Jan 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, pool 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, (5081)
"Great location nice breakfast and front desk people is amazing "
United States
Orlando
The price is 2.714.882 ₫
3.054.242 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2247)
"Great stay"
United States
Christopher
The price is 2.893.770 ₫
3.255.491 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
2 outdoor pools, pool umbrellas, pool loungers
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, (4074)
"Room was clean, area quiet. "
United States
Sapphira
The price is 2.795.650 ₫
3.885.493 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (1647)
"best place "
United States
Pedro
The price is 2.788.542 ₫
3.137.110 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (1978)
"Great location, good, staff, and rooms "
Canada
Jobin
The price is 3.761.901 ₫
4.232.138 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
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

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 3.346.250 ₫
3.764.531 ₫ total
includes taxes & fees
5 Jan - 6 Jan 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 3.656.673 ₫
5.563.930 ₫ total
includes taxes & fees
18 Dec - 19 Dec
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 3.237.165 ₫
3.641.810 ₫ total
includes taxes & fees
22 Dec - 23 Dec
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 2.841.156 ₫
6.303.814 ₫ total
includes taxes & fees
17 Dec - 18 Dec
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.
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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
2.5 star property
Bay Lake
9.4 out of 10, Exceptional, (4349)
The price is 3.051.612 ₫
3.433.063 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
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

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, (2247)
The price is 2.893.770 ₫
3.255.491 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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Top Winter Garden Hotel Reviews

Explore a world of travel with Expedia

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 23 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.
How many pool hotels will I find 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 such as Universal Studios Florida, Universal Orlando Resort and Magic Kingdom® Park 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.