Search Hotels with Swimming Pool in Winter Garden

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Check availability on Winter Garden Hotels with Swimming Pool

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Winter Garden Hotels with Swimming 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

2.5 star property
Bay Lake
9.4 out of 10, Exceptional, (4310)
"Really good place to stay "
United States
Lians
The price is ₹10,439
₹11,744 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

3.0 star property
Bay Lake
9.2 out of 10, Wonderful, (5056)
"Great location nice breakfast and front desk people is amazing "
United States
Orlando
The price is ₹9,287
₹10,448 total
includes taxes & fees
14 Dec - 15 Dec
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, (2249)
"Great stay"
United States
Christopher
The price is ₹10,259
₹11,542 total
includes taxes & fees
11 Dec - 12 Dec
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, (4070)
"Really nice place friendly staff. "
United States
Keith
The price is ₹9,562
₹13,288 total
includes taxes & fees
17 Dec - 18 Dec
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, (1643)
"Amazing! Will come back soon!"
United States
DeAndre
The price is ₹10,619
₹11,947 total
includes taxes & fees
4 Jan - 5 Jan 2026
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/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

3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (2130)
"Our stay was great and location was convenient when looking for food!"
United States
Sofia Alexia
The price is ₹11,447
₹12,878 total
includes taxes & fees
15 Dec - 16 Dec
Homewood Suites by Hilton Orlando at Flamingo Crossings
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

3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (1969)
"Great stay"
United States
Windy Laine
The price is ₹12,869
₹14,478 total
includes taxes & fees
21 Dec - 22 Dec
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, (8782)
"Everything about it was excellent The staff , the rooms , the resort , very convenient location .We were very very pleased with everything very beautiful area "
United States
Ruben
The price is ₹13,409
₹20,046 total
includes taxes & fees
9 Dec - 10 Dec
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, (361)
"Room was clean and beds very comfortable"
United States
Arne
The price is ₹10,257
₹11,540 total
includes taxes & fees
18 Dec - 19 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

3.5 star property
Winter Garden
10.0 out of 10, Exceptional, (1)
"Room was very clean apartment has everything that you need all necessary things for stay like cops plates utensils host was very nice. Communication with him was very easy. Everything was ready when we arrive. We didn’t have to wait for anything. Highly recommended."
Canada
Ramiz
The price is ₹8,099
₹19,742 total
includes taxes & fees
9 Dec - 10 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.
View all properties

Top Winter Garden Hotel Reviews

Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"Our room was fantastic, everyone we encountered was very helpful and courteous. The housekeeping staff was also amazing!"
Kelly 6-night trip
Posted 23 hours ago
Walt Disney World Dolphin

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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 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.
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 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 swimming 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.
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 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 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.