Hotels with Pool & Resorts in Winter Garden from AU$137

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (4,743 reviews)
  • cleanliness
    Splash into endless fun with an outdoor pool and sunny loungers just steps from Disney magic.
The price is AU$144
includes taxes & fees
20 May - 21 May
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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, (9,809 reviews)
  • cleanliness
    Splash into paradise at this resort with 6 outdoor pools, a lazy river, and a complimentary water park for endless aquatic fun.
The price is AU$332
includes taxes & fees
21 May - 22 May
The Grove Resort & Water Park Orlando
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, (1,716 reviews)
  • cleanliness
    Dive into this heated outdoor oasis with poolside bar service, minutes from Disney parks and offering daily theme park shuttles.
The price is AU$138
includes taxes & fees
31 May - 1 June
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
3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (2,046 reviews)
  • cleanliness
    Sun-soaked pool sanctuary with poolside bar offers leisurely holiday escape in a serene setting.
The price is AU$171
includes taxes & fees
8 June - 9 June
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
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, (2,229 reviews)
  • cleanliness
    Heated outdoor pool paradise with spa pool sanctuary offers the perfect retreat after exploring nearby Disney theme parks.
The price is AU$137
includes taxes & fees
17 May - 18 May
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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, (5,515 reviews)
  • cleanliness
    Splash into holiday mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
The price is AU$174
includes taxes & fees
9 June - 10 June
Home2 Suites by Hilton Orlando at Flamingo Crossings
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, (2,414 reviews)
  • cleanliness
    Dive into poolside bliss with loungers and a thrilling waterslide at this spotless Orlando retreat.
The price is AU$202
includes taxes & fees
21 May - 22 May
Homewood Suites by Hilton Orlando at Flamingo Crossings
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, (446 reviews)
  • cleanliness
    Sunny poolside retreats at the heart of Winter Garden offer a cool oasis after exploring.
The price is AU$202
includes taxes & fees
17 May - 18 May
Home2 Suites By Hilton Winter Garden
2 outdoor pools, pool umbrellas, pool loungers

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, (3,983 reviews)
  • cleanliness
    Splash into family fun with 2 outdoor pools and a free water park at this Disney-adjacent resort.
The price is AU$194
includes taxes & fees
18 May - 19 May
Hilton Vacation Club Aqua Sol Orlando West
Apartment

Upstay Condo w Pool Sauna Sleeps 8

Upstay Condo w Pool Sauna Sleeps 8
2.0 star property
Winter Garden
The price is AU$386
includes taxes & fees
11 May - 12 May
Upstay Condo w Pool Sauna Sleeps 8
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

Choose what matters most at hotels with a pool in Winter Garden

Breakfast included
Spa pool

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
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (4743)
The price is AU$144
includes taxes & fees
20 May - 21 May
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
View all properties

Hotels with pools and spa pools in Winter Garden

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, (9809)
The price is AU$332
includes taxes & fees
21 May - 22 May
The Grove Resort & Water Park Orlando
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

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

8/10 Good
"Stayed 4 nights, same breakfast every morning okay, "
William 4-night trip
Posted less than an hour ago
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

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 54 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, 1-minute walk from Flamingo Crossings Town Center. Offers buffet, an outdoor pool and complimentary wireless Internet access. Home2 Suites by Hilton Orlando at Flamingo Crossings: Hotel, 3-minute walk from Flamingo Crossings Town Center. Provides buffet, an outdoor pool and a 24-hour fitness centre. Homewood Suites by Hilton Orlando at Flamingo Crossings: Hotel, 1-minute walk from Flamingo Crossings Town Center. Features 2 bars, an outdoor pool and a snack bar/deli. Hilton Vacation Club Aqua Sol Orlando West: Hotel located near Flamingo Crossings Town Center. Offers 2 outdoor swimming pools, a children's pool and free water park access.
How many pool hotels will I find in Winter Garden?
Expedia's 54 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 Universal's Volcano Bay 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.