Hotels with Pool & Resorts in Winter Garden from AU$185

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Best Winter Garden Hotels with Pool

Hilton Vacation Club Aqua Sol Orlando West
2 outdoor pools, pool umbrellas, pool loungers
Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
8.8 out of 10, Excellent, (3702)
"I loved everything about this property except for THE NOISE!!!!!! Omg, what were you guys doing!!!?? We couldn’t sleep past 7am because of the loud noises made by the workers repairing I don’t know what. Also, says that breakfast was included, but it’s actually an apple and a juice. "
The price is AU$192
includes taxes & fees
26 Nov - 27 Nov
Hilton Vacation Club Aqua Sol Orlando West
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
9.2 out of 10, Wonderful, (1854)
"Not much traffic to and from Disney Parks. Breakfast was great and staff was awesome!"
The price is AU$185
includes taxes & fees
2 Dec - 3 Dec
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
9.0 out of 10, Wonderful, (1334)
"I stay here every time I come to Disney. I am an annual pass holder and Florida resident. This hotel is extremely close to the parks. We have always had a wonderful experience at both hotels. "
The price is AU$185
includes taxes & fees
24 Nov - 25 Nov
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
The Grove Resort & Water Park Orlando
3 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas
The Grove Resort & Water Park Orlando
4.0 star property
8.2 out of 10, Very good, (6619)
"Apt are modern and spacious. The pool and slides are so nice and fun. "
The price is AU$296
includes taxes & fees
12 Dec - 13 Dec
The Grove Resort & Water Park Orlando
The Palisades Resort Orlando
Outdoor pool
The Palisades Resort Orlando
2.0 star property
7.6 out of 10, Good, (999)
"Check your notes I've called and I'm very upset thinking about taking legal action against you and them"
The Palisades Resort Orlando
Magical Palisades Resort Condo 2 Bedroom IPG Florida
Outdoor pool
Magical Palisades Resort Condo 2 Bedroom IPG Florida
3.5 star property
Magical Palisades Resort Condo 2 Bedroom IPG Florida
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.
Don't see what you're looking for?
See all available properties in Winter Garden
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 5 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: Features 3 outdoor swimming pools, a children’s pool and free water park access. Hilton Vacation Club Aqua Sol Orlando West: Offers 2 outdoor swimming pools, a children’s pool and free water park access. Aqua Sol, a Hilton Vacation Club: Features Smart televisions, a pool and air conditioning.
How many pool hotels will I find in Winter Garden?
Expedia has 5 hotels in Winter Garden for your poolside break.
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.