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Hotels with Swimming Pools in Winter Garden

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Check availability on Winter Garden Hotels with Swimming Pools

Tonight
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

Our top choices for Winter Garden hotels with a pool

A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
A Marriott Fairfield hotel sign with a landscaped garden in front.
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.

1. 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.
S$110
includes taxes & fees
31 Aug - 1 Sept
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

2. 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.
S$134
includes taxes & fees
1 Sept - 2 Sept
Home2 Suites by Hilton Orlando at Flamingo Crossings
A hotel pool area with lounge chairs, a fire pit, and a large pool.
A large hotel with multiple floors, a central courtyard, and a reflective water feature.
A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.

3. 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.
S$118
includes taxes & fees
7 Sept - 8 Sept
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A swimming pool with lounge chairs and a view of a building in the background.
An outdoor patio with round tables and chairs, a red umbrella, and a grill.
A hotel entrance with a sign reading "HOME 2 SUITES BY HILTON".
A hotel room with a kitchenette, a sofa, a desk, and a dining area.

4. 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.
S$152
includes taxes & fees
6 Sept - 7 Sept
Home2 Suites By Hilton Winter Garden
A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with a desk, chair, and bed.
A bar area with a long counter, multiple chairs, and a variety of bottles.

5. 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.
S$112
includes taxes & fees
30 Aug - 31 Aug
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.
A restaurant with outdoor seating, a fire feature, and a bar area.
A lounge area with a fire feature, wicker furniture, and a bar in the background.

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.
S$132
includes taxes & fees
30 Aug - 31 Aug
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
A modern kitchen with a large island, bar stools, pendant lighting, and a flat-screen TV.
A large hotel with a central entrance, multiple floors, and a sign indicating 'Homewood Suites by Hilton.'
A hotel room with a large window, a pool view, a chair, a table, a lamp, and a bed.

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.
S$151
includes taxes & fees
1 Sept - 2 Sept
Homewood Suites by Hilton Orlando at Flamingo Crossings
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A modern living room with a sofa, ottoman, and a TV on a stand.
A hotel with a blue roof, a reflection pool, and palm trees.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.

8. 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.
S$170
includes taxes & fees
13 Sept - 14 Sept
Hilton Vacation Club Aqua Sol Orlando West
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.
A modern lobby with a reception desk, seating area, and a bar.
A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.

9. 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.
S$311
includes taxes & fees
24 Aug - 25 Aug
The Grove Resort & Water Park Orlando
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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

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
A lobby with a central seating area, wooden ceiling, and patterned carpet.
A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.

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
S$110
includes taxes & fees
31 Aug - 1 Sept
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.
A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
S$134
includes taxes & fees
1 Sept - 2 Sept
Home2 Suites by Hilton Orlando at Flamingo Crossings
A large hotel with multiple floors, a central courtyard, and a reflective water feature.
A hotel pool area with lounge chairs, a fire pit, and a large pool.
A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
S$118
includes taxes & fees
7 Sept - 8 Sept
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with a desk, chair, and bed.
A bar area with a long counter, multiple chairs, and a variety of bottles.

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
S$112
includes taxes & fees
30 Aug - 31 Aug
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.
A restaurant with outdoor seating, a fire feature, and a bar area.
A lounge area with a fire feature, wicker furniture, and a bar in the background.

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
S$132
includes taxes & fees
30 Aug - 31 Aug
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
An outdoor patio with round tables and chairs, a red umbrella, and a grill.
A swimming pool with lounge chairs and a view of a building in the background.
A hotel entrance with a sign reading "HOME 2 SUITES BY HILTON".
A hotel room with a kitchenette, a sofa, a desk, and a dining area.

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
S$152
includes taxes & fees
6 Sept - 7 Sept
Home2 Suites By Hilton Winter Garden
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
A modern kitchen with a large island, bar stools, pendant lighting, and a flat-screen TV.
A large hotel with a central entrance, multiple floors, and a sign indicating 'Homewood Suites by Hilton.'
A hotel room with a large window, a pool view, a chair, a table, a lamp, and a bed.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
S$151
includes taxes & fees
1 Sept - 2 Sept
Homewood Suites by Hilton Orlando at Flamingo Crossings
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Hotels with pools and hot tubs in Winter Garden

A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with a desk, chair, and bed.
A bar area with a long counter, multiple chairs, and a variety of bottles.

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
S$112
includes taxes & fees
30 Aug - 31 Aug
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.
A restaurant with outdoor seating, a fire feature, and a bar area.
A lounge area with a fire feature, wicker furniture, and a bar in the background.

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
S$132
includes taxes & fees
30 Aug - 31 Aug
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A modern living room with a sofa, ottoman, and a TV on a stand.
A modern living room with a teal accent wall, a sofa, ottomans, a dining area with white chairs, and a balcony with a view.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
S$170
includes taxes & fees
13 Sept - 14 Sept
Hilton Vacation Club Aqua Sol Orlando West
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.
A modern lobby with a reception desk, seating area, and a bar.
A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
S$311
includes taxes & fees
24 Aug - 25 Aug
The Grove Resort & Water Park Orlando
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

Upstay Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
Winter Garden
S$336
includes taxes & fees
24 Aug - 25 Aug
Upstay Tropical Style Family Condo w Pool
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4-star hotels with pools in Winter Garden

A resort with a large pool, water slides, palm trees, and beach umbrellas.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.
A modern lobby with a reception desk, seating area, and a bar.
A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
S$311
includes taxes & fees
24 Aug - 25 Aug
The Grove Resort & Water Park Orlando
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A modern living room with a sofa, ottoman, and a TV on a stand.
A modern living room with a teal accent wall, a sofa, ottomans, a dining area with white chairs, and a balcony with a view.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
S$170
includes taxes & fees
13 Sept - 14 Sept
Hilton Vacation Club Aqua Sol Orlando West
A modern living room with a sofa, coffee table, and a ceiling fan.
A bedroom with a bed, a dresser, a ceiling fan, and a TV on the wall.
A balcony with two black chairs and a table, a ceiling fan, and a view of greenery.

Upstay 3BR Condo w Pool & Patio Near Disney

Upstay 3BR Condo w Pool & Patio Near Disney
Winter Garden
S$295
includes taxes & fees
24 Aug - 25 Aug
Upstay 3BR Condo w Pool & Patio Near Disney
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.

Upstay: 3BR Family Condo w Pool & Sauna

Upstay: 3BR Family Condo w Pool & Sauna
Winter Garden
Upstay: 3BR Family Condo w Pool & Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
S$324
includes taxes & fees
8 Sept - 9 Sept
Modern 3BR Resort Condo With Pool Near Disney
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
A modern kitchen with white cabinets, a stainless steel oven, and a microwave.

Family Fun Condo Pool and Sauna Near Disney

Family Fun Condo Pool and Sauna Near Disney
Winter Garden
Family Fun Condo Pool and Sauna Near Disney
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.
A bedroom with a large bed, a bathtub, and a balcony with curtains.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

Upstay Modern 2BR Condo Near Disney

Upstay Modern 2BR Condo Near Disney
Winter Garden
S$336
includes taxes & fees
24 Aug - 25 Aug
Upstay Modern 2BR Condo Near Disney
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A modern kitchen with white cabinets, a dishwasher, and a granite countertop.

Upstay - Pet-friendly Condo - Sauna, Pool

Upstay - Pet-friendly Condo - Sauna, Pool
Winter Garden
S$302
includes taxes & fees
24 Aug - 25 Aug
Upstay - Pet-friendly Condo - Sauna, Pool
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.
A spacious living area with a sofa, coffee table, and a view of the kitchen.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.
A modern kitchen with a dishwasher, a dining area with a table and chairs, and a view of the outside.

Upstay: Resort Style Condo w Pool, Sauna

Upstay: Resort Style Condo w Pool, Sauna
Winter Garden
S$304
includes taxes & fees
24 Aug - 25 Aug
Upstay: Resort Style Condo w Pool, Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A modern kitchen with granite countertops, a dining area with a gray sofa and a small round table, and a balcony with a view of the outdoors.
A spacious living area with a large sofa, a coffee table, and a TV mounted on the wall. There are large windows offering a view of the outdoors.

Upstay Condo w Pool & Sauna Sleeps 8

Upstay Condo w Pool & Sauna Sleeps 8
Winter Garden
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.
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Top Winter Garden Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8/10 Good
"I love the fact you can walk around freely to other areas of the resort"
Vonnita 4-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Need adult only pools and to service room more than once a week.also was not told of parking fee until I arrived."
Patricia 6-night trip
Posted 2 hours ago
Marriott's Grande Vista
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

10/10 Excellent
"Rooms are very clean and staff very friendly. Great location and free bus to Disney if booked ahead. Nice pool area and shop if not a little expensive."
Charlotte 4-night trip
Posted 9 hours ago
Wyndham I-Drive Avanti Resort & Conference Center

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 56 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 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 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 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 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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