Find Hotels with a Pool in Winter Garden, FL

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Check availability on Winter Garden Hotels with a Pool

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top 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, (4310)
"Really good place to stay "
United States
Lians
The price is SAR 435
SAR 490 total
includes taxes & fees
4 Jan - 5 January 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, (5056)
"Great location nice breakfast and front desk people is amazing "
United States
Orlando
The price is SAR 387
SAR 436 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 SAR 428
SAR 481 total
includes taxes & fees
10 Dec - 11 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 SAR 399
SAR 554 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 SAR 443
SAR 498 total
includes taxes & fees
4 Jan - 5 January 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, (2129)
"Our stay was great and location was convenient when looking for food!"
United States
Sofia Alexia
The price is SAR 459
SAR 517 total
includes taxes & fees
21 Dec - 22 Dec
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, (1969)
"Great stay"
United States
Windy Laine
The price is SAR 537
SAR 604 total
includes taxes & fees
17 Dec - 18 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, (8779)
"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 SAR 559
SAR 836 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 SAR 428
SAR 481 total
includes taxes & fees
17 Dec - 18 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 SAR 372
SAR 861 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.
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Top Winter Garden Hotel Reviews

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Very clean . Nice staff "
Jevaughn 3-night trip
Posted 10 hours ago
Hilton Vacation Club Aqua Sol Orlando West

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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.