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Search Hotels with Swimming Pool in Winter Garden

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Check availability on Winter Garden Hotels with Swimming Pool

Tonight
5 Sept - 6 Sept
Tomorrow
6 Sept - 7 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Our top choices for Winter Garden hotels with a pool

Outdoor pool
Exterior
Living area
Bar (on property)

1. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Splash into holiday mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
₹8,523
₹9,589 total
includes taxes & fees
28 Sept - 29 Sept
Home2 Suites by Hilton Orlando at Flamingo Crossings
Pool
Pool
Exterior
Breakfast meal

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.
₹10,394
₹11,694 total
includes taxes & fees
13 Sept - 14 Sept
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Pool
Bar (on property)
Bar (on property)
Bar (on property)

3. 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.
₹7,399
₹8,324 total
includes taxes & fees
23 Sept - 24 Sept
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Pool
Bar (on property)
Bar (on property)
Room

4. 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.
₹8,755
₹9,849 total
includes taxes & fees
30 Sept - 1 Oct
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Pool
Lobby
Bathroom
Suite, 1 Bedroom, Non Smoking | Pool

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 holiday escape in a serene setting.
₹8,788
₹9,887 total
includes taxes & fees
29 Sept - 30 Sept
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Pool
Interior
Exterior
Suite, 1 Bedroom

6. 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.
₹11,158
₹12,553 total
includes taxes & fees
13 Sept - 14 Sept
Home2 Suites By Hilton Winter Garden
Pool
Exterior
Living area
Bar (on property)

7. 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.
₹11,903
₹13,390 total
includes taxes & fees
8 Sept - 9 Sept
Homewood Suites by Hilton Orlando at Flamingo Crossings
Waterslide
Outdoor dining
Aerial view
Lobby

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.
₹16,518
₹23,791 total
includes taxes & fees
5 Oct - 6 Oct
The Grove Resort & Water Park Orlando
Pool
Exterior
Lobby
Living area

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.
₹8,911
₹12,683 total
includes taxes & fees
13 Sept - 14 Sept
Hilton Vacation Club Aqua Sol Orlando West
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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

Breakfast meal
Pool
Pool
Lobby

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
₹10,394
₹11,694 total
includes taxes & fees
13 Sept - 14 Sept
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Exterior
Outdoor pool
Living area
Bar (on property)

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
₹8,523
₹9,589 total
includes taxes & fees
28 Sept - 29 Sept
Home2 Suites by Hilton Orlando at Flamingo Crossings
Pool
Exterior
Living area
Bar (on property)

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
₹11,903
₹13,390 total
includes taxes & fees
8 Sept - 9 Sept
Homewood Suites by Hilton Orlando at Flamingo Crossings
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
₹7,399
₹8,324 total
includes taxes & fees
23 Sept - 24 Sept
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Exterior
Lobby
Gazebo
Suite, 1 Bedroom, Non Smoking | Pool

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
₹8,788
₹9,887 total
includes taxes & fees
29 Sept - 30 Sept
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Pool
Bar (on property)
Bar (on property)
Room

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
₹8,755
₹9,849 total
includes taxes & fees
30 Sept - 1 Oct
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Exterior
Interior
Exterior
Suite, 1 Bedroom

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
₹11,158
₹12,553 total
includes taxes & fees
13 Sept - 14 Sept
Home2 Suites By Hilton Winter Garden
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Hotels with pools and hot tubs in Winter Garden

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
₹7,399
₹8,324 total
includes taxes & fees
23 Sept - 24 Sept
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Pool
Bar (on property)
Bar (on property)
Room

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
₹8,755
₹9,849 total
includes taxes & fees
30 Sept - 1 Oct
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Waterslide
Outdoor dining
Aerial view
Lobby

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
₹16,518
₹23,791 total
includes taxes & fees
5 Oct - 6 Oct
The Grove Resort & Water Park Orlando
Pool
Living area
Lobby
Living area

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
₹8,911
₹12,683 total
includes taxes & fees
13 Sept - 14 Sept
Hilton Vacation Club Aqua Sol Orlando West
House
House
House
House

Upstay Modern 2BR Condo Near Disney

Upstay Modern 2BR Condo Near Disney
Winter Garden
₹7,652
₹23,008 total
includes taxes & fees
9 Sept - 10 Sept
Upstay Modern 2BR Condo Near Disney
Room
Room
Room
Room

Upstay - Condo w Hot Tub and Pool - Near Disney

Upstay - Condo w Hot Tub and Pool - Near Disney
Winter Garden
₹7,096
₹21,880 total
includes taxes & fees
7 Sept - 8 Sept
Upstay - Condo w Hot Tub and Pool - Near Disney
Room
Room
Room
Room

Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna
Winter Garden
₹7,096
₹21,880 total
includes taxes & fees
9 Sept - 10 Sept
Upstay - Condo Near Disney w Pool Hot tub Sauna
Room
Room
Room
Room

Modern 3BR Condo Near Disney- Pool and Hot Tub

Modern 3BR Condo Near Disney- Pool and Hot Tub
Winter Garden
₹7,607
₹22,390 total
includes taxes & fees
21 Sept - 22 Sept
Modern 3BR Condo Near Disney- Pool and Hot Tub
House
House
House
House

Upstay - Condo Near Disney w Pool-spa-sauna-games

Upstay - Condo Near Disney w Pool-spa-sauna-games
Winter Garden
₹5,760
₹20,879 total
includes taxes & fees
8 Sept - 9 Sept
Upstay - Condo Near Disney w Pool-spa-sauna-games
House
House
House
House

Upstay Large Family Condo w Pool Sauna

Upstay Large Family Condo w Pool Sauna
Winter Garden
Upstay Large Family Condo w Pool Sauna
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4-star hotels with pools in Winter Garden

Waterslide
Outdoor dining
Aerial view
Lobby

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
₹16,518
₹23,791 total
includes taxes & fees
5 Oct - 6 Oct
The Grove Resort & Water Park Orlando
Pool
Living area
Lobby
Living area

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
₹8,911
₹12,683 total
includes taxes & fees
13 Sept - 14 Sept
Hilton Vacation Club Aqua Sol Orlando West
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

Upstay - Pet-friendly Suite w Pool, Sauna

Upstay - Pet-friendly Suite w Pool, Sauna
Winter Garden
₹9,922
₹24,876 total
includes taxes & fees
16 Sept - 17 Sept
Upstay - Pet-friendly Suite w Pool, Sauna
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Front of property
Apartment (3 Bedrooms) | Interior

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
₹6,923
₹23,628 total
includes taxes & fees
8 Sept - 9 Sept
Modern 3BR Resort Condo With Pool Near Disney
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Upstay: Modern Condo w Outdoor Pool - Near Disney!

Upstay: Modern Condo w Outdoor Pool - Near Disney!
Winter Garden
Upstay: Modern Condo w Outdoor Pool - Near Disney!
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Upstay 3BR Suite w Pool, Sauna & Gamesnear Disney

Upstay 3BR Suite w Pool, Sauna & Gamesnear Disney
Winter Garden
₹6,174
₹22,786 total
includes taxes & fees
8 Sept - 9 Sept
Upstay 3BR Suite w Pool, Sauna & Gamesnear Disney
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Upstay Pet-friendly Condo With Pool

Upstay Pet-friendly Condo With Pool
Winter Garden
Upstay Pet-friendly Condo With Pool
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

Upstay Condo With Outdoor Pool & Sauna

Upstay Condo With Outdoor Pool & Sauna
Winter Garden
₹8,883
₹23,706 total
includes taxes & fees
7 Sept - 8 Sept
Upstay Condo With Outdoor Pool & Sauna
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Front of property

Upstay Disney Pet Friendly Condo w Pool Spa Games

Upstay Disney Pet Friendly Condo w Pool Spa Games
Winter Garden
₹6,331
₹20,836 total
includes taxes & fees
9 Sept - 10 Sept
Upstay Disney Pet Friendly Condo w Pool Spa Games
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

Pet-friendly Resort Getaway With Patio and Pool

Pet-friendly Resort Getaway With Patio and Pool
Winter Garden
₹7,964
₹22,673 total
includes taxes & fees
21 Sept - 22 Sept
Pet-friendly Resort Getaway With Patio and Pool
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

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

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

10/10 Excellent
"Can’t fault this place. Staff were extremely helpful especially Laura who assisted my husband and I when we had to leave early due to a family emergency. She organized everything with Expedia. So very grateful. The room was amazing! Will stay here again"
Jane 6-night trip
Posted 1 hour ago
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"If I could give 10 stats I would"
Crystal 3-night trip
Posted 1 hour ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Easy access to universal. EV chargers were a bonus."
Lillian 1-night trip
Posted 2 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"Check in staff very courteous and helpful"
Donna 6-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
"Muy lindo y espectacular para pasar un fin de semana en pareja o en familia"
Osmany 2-night trip
Posted 2 hours ago
Westgate Lakes Resort & Spa Universal Studios Area
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Every thing was great"
Ruben 1-night trip
Posted 4 hours ago
Rosen Inn Lake Buena Vista
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"All was awesome! Great for a long or short layover."
John 1-night trip
Posted 6 hours ago
Hyatt Regency Orlando International Airport

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 59 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. 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, 4-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 59 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 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.

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