A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

Find Hotels with a Pool in Winter Garden, FL

  • 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 a Pool

Tonight
Aug 10 - Aug 11
Tomorrow
Aug 11 - Aug 12
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

Our top choices for Winter Garden hotels with a pool

Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers
Bar (on property)
Exterior
42-inch flat-screen TV with satellite channels, TV

1. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Splash into vacation mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
NT$2,672
NT$3,006 total
includes taxes & fees
Aug 24 - Aug 25
Home2 Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Lobby
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Exterior

2. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Bay Lake
  • Splash into endless fun with an outdoor pool and sunny loungers just steps from Disney magic.
NT$2,389
NT$2,687 total
includes taxes & fees
Aug 27 - Aug 28
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
2 bars/lounges
BBQ/picnic area
49-inch LED TV with cable channels, TV, Netflix

3. Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Dive into poolside bliss with loungers and a thrilling waterslide at this spotless Orlando retreat.
NT$3,408
NT$3,834 total
includes taxes & fees
Aug 23 - Aug 24
Homewood Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, a heated pool
Bar (on property)
Bar (on property)
Bar (on property)

4. SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
  • Heated outdoor pool paradise with hot tub sanctuary offers the perfect retreat after exploring nearby Disney theme parks.
NT$2,529
NT$2,846 total
includes taxes & fees
Aug 27 - Aug 28
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Exterior
Shower, free toiletries, hair dryer, towels
Lobby

5. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
  • Sun-soaked pool sanctuary with poolside bar offers leisurely vacation escape in a serene setting.
NT$2,554
NT$2,873 total
includes taxes & fees
Sep 8 - Sep 9
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Outdoor pool, a heated pool
Premium bedding, desk, laptop workspace, soundproofing
Premium bedding, desk, laptop workspace, soundproofing
Bar (on property)

6. TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
  • Dive into this heated outdoor oasis with poolside bar service, minutes from Disney parks and offering daily theme park shuttles.
NT$2,985
NT$3,358 total
includes taxes & fees
Sep 1 - Sep 2
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool
Exterior
Suite, 1 Bedroom | In-room safe, desk, laptop workspace, blackout drapes
Exterior

7. Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
  • Sunny poolside retreats at the heart of Winter Garden offer a cool oasis after exploring.
NT$3,417
NT$3,844 total
includes taxes & fees
Aug 22 - Aug 23
Home2 Suites By Hilton Winter Garden
Waterslide
Lake
Lobby
Aerial view

8. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
  • Splash into paradise at this resort with 6 outdoor pools, a lazy river, and a complimentary water park for endless aquatic fun.
NT$5,445
NT$7,902 total
includes taxes & fees
Aug 25 - Aug 26
The Grove Resort & Water Park Orlando
2 outdoor pools, cabanas (surcharge), pool umbrellas
Flat-screen TV, DVD player
Lobby
Exterior

9. Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
  • Splash into family fun with 2 outdoor pools and a free water park at this Disney-adjacent resort.
NT$3,302
NT$4,622 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Vacation Club Aqua Sol Orlando West
House | 3 bedrooms, high-speed internet
House | 3 bedrooms, high-speed internet
House | 3 bedrooms, high-speed internet
House | 3 bedrooms, high-speed internet

10. Upstay Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
Winter Garden
NT$2,537
NT$8,540 total
includes taxes & fees
Aug 17 - Aug 18
Upstay Tropical Style Family Condo w Pool
View all properties

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

Breakfast included
Hot tub
4 stars
Water park
5 stars

Hotels with pools and free breakfast in Winter Garden

Free daily buffet breakfast
Exterior
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
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
Bay Lake
NT$2,389
NT$2,687 total
includes taxes & fees
Aug 27 - Aug 28
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Exterior
Bar (on property)
Exterior
42-inch flat-screen TV with satellite channels, TV

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
NT$2,672
NT$3,006 total
includes taxes & fees
Aug 24 - Aug 25
Home2 Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, a heated pool
Bar (on property)
Bar (on property)
Bar (on property)

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
NT$2,529
NT$2,846 total
includes taxes & fees
Aug 27 - Aug 28
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Exterior
Exterior
Suite, 1 Bedroom | In-room safe, desk, laptop workspace, blackout drapes
Outdoor pool

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
NT$3,417
NT$3,844 total
includes taxes & fees
Aug 22 - Aug 23
Home2 Suites By Hilton Winter Garden
Outdoor pool, a heated pool
Premium bedding, desk, laptop workspace, soundproofing
Premium bedding, desk, laptop workspace, soundproofing
Bar (on property)

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
NT$2,985
NT$3,358 total
includes taxes & fees
Sep 1 - Sep 2
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Exterior
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Gazebo
Lobby

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
NT$2,554
NT$2,873 total
includes taxes & fees
Sep 8 - Sep 9
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
2 bars/lounges
BBQ/picnic area
49-inch LED TV with cable channels, TV, Netflix

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
NT$3,408
NT$3,834 total
includes taxes & fees
Aug 23 - Aug 24
Homewood Suites by Hilton Orlando at Flamingo Crossings
View all properties

Hotels with pools and hot tubs in Winter Garden

Outdoor pool, a heated pool
Premium bedding, desk, laptop workspace, soundproofing
Premium bedding, desk, laptop workspace, soundproofing
Bar (on property)

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
NT$2,985
NT$3,358 total
includes taxes & fees
Sep 1 - Sep 2
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool
Bar (on property)
Bar (on property)
Bar (on property)

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
NT$2,529
NT$2,846 total
includes taxes & fees
Aug 27 - Aug 28
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Waterslide
Lake
Lobby
Aerial view

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
NT$5,445
NT$7,902 total
includes taxes & fees
Aug 25 - Aug 26
The Grove Resort & Water Park Orlando
2 outdoor pools, cabanas (surcharge), pool umbrellas
Flat-screen TV, DVD player
Lobby
Flat-screen TV, DVD player

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
NT$3,302
NT$4,622 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Vacation Club Aqua Sol Orlando West
House | 3 bedrooms, high-speed internet
House | 3 bedrooms, high-speed internet
House | 3 bedrooms, high-speed internet
House | 3 bedrooms, high-speed internet

Upstay Large Family Condo w Pool Sauna

Upstay Large Family Condo w Pool Sauna
Winter Garden
NT$2,530
NT$8,517 total
includes taxes & fees
Sep 8 - Sep 9
Upstay Large Family Condo w Pool Sauna
View all properties

4-star hotels with pools in Winter Garden

2 outdoor pools, cabanas (surcharge), pool umbrellas
Flat-screen TV, DVD player
Lobby
Flat-screen TV, DVD player

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
NT$3,302
NT$4,622 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Vacation Club Aqua Sol Orlando West
Waterslide
Lake
Lobby
Aerial view

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
NT$5,445
NT$7,902 total
includes taxes & fees
Aug 25 - Aug 26
The Grove Resort & Water Park Orlando
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
NT$2,223
NT$7,902 total
includes taxes & fees
Aug 23 - Aug 24
Upstay: Condo Near Disney w Pool, Sauna
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Front of property

Upstay - 3BR Condo w Pool and Sauna

Upstay - 3BR Condo w Pool and Sauna
Winter Garden
NT$2,610
NT$8,337 total
includes taxes & fees
Aug 12 - Aug 13
Upstay - 3BR Condo w Pool and Sauna
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

Upstay Condo With Pool Near Disney & Pet Friendly

Upstay Condo With Pool Near Disney & Pet Friendly
Winter Garden
NT$4,350
NT$9,569 total
includes taxes & fees
Aug 15 - Aug 16
Upstay Condo With Pool Near Disney & Pet Friendly
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

Upstay Disney Pet Friendly Condo w Pool Spa Games

Upstay Disney Pet Friendly Condo w Pool Spa Games
Winter Garden
NT$2,481
NT$7,467 total
includes taxes & fees
Aug 17 - Aug 18
Upstay Disney Pet Friendly Condo w Pool Spa Games
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Pet-friendly Condo Pool, Saunanear Disney

Pet-friendly Condo Pool, Saunanear Disney
Winter Garden
NT$2,610
NT$8,337 total
includes taxes & fees
Aug 16 - Aug 17
Pet-friendly Condo Pool, Saunanear Disney
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Upstay - Large Condo Near Disney w Pool and Gym

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
NT$2,294
NT$7,995 total
includes taxes & fees
Aug 12 - Aug 13
Upstay - Large Condo Near Disney w Pool and Gym
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

Upstay Modern 2BR Condo Near Disney

Upstay Modern 2BR Condo Near Disney
Winter Garden
NT$2,610
NT$7,612 total
includes taxes & fees
Aug 12 - Aug 13
Upstay Modern 2BR Condo Near Disney
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Beautiful Condo w Outdoor Pool and Sauna

Beautiful Condo w Outdoor Pool and Sauna
Winter Garden
NT$2,288
NT$7,974 total
includes taxes & fees
Aug 12 - Aug 13
Beautiful Condo w Outdoor Pool and Sauna
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Great place to stay clean and we had a great view"
Tracy 7-night trip
Posted 2 hours ago
Universal's Cabana Bay Beach Resort
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

8/10 Good
"Todo bien limpio"
Gilberto 6-night trip
Posted 2 hours ago
Rosen Inn Lake Buena Vista
Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"We love the dolphin! We always stay there. It’s a wonderful place."
Sheryl L 2-night trip
Posted 2 hours ago
Walt Disney World Dolphin
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Resort was great fun trip would recommend"
Tasia 2-night trip
Posted 3 hours ago
Westgate Lakes Resort & Spa Universal Studios Area
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Excellent stay all around, comfort, location, amenities, staff all was perfect!"
Melissa 3-night trip
Posted 3 hours ago
Hilton Vacation Club Aqua Sol Orlando West
Walt Disney World Swan

Walt Disney World Swan

10/10 Excellent
"Loved walking to the parks."
JEREMY 3-night trip
Posted 4 hours ago
Walt Disney World Swan
Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Is great"
Giselli 2-night trip
Posted 4 hours ago
Marriott's Grande Vista
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"hotel it self was wonderful everything u need is right there. however the darn toilet would not flush kept clogging. keep in mind we was there for about 4 nights. ice cream area could use a makeover. but loved this place would come back when in orlando"
kendal 2-night trip
Posted 6 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Beautiful. So simple to check in and everything is was great. Best find for a place to stay."
Heather 1-night trip
Posted 6 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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 56 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, 1-minute walk 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, 4-minute walk from Flamingo Crossings Town Center. Features a snack bar/deli, a pool, and buffet.
How many pool hotels are there in Winter Garden?
Expedia's 56 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 Universal's Volcano Bay while you're in the area. Make a point to visit attractions like Lake Louisa State Park and Winter Garden Art Association. 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.

Explore a world of travel with Expedia