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Find Hotels with a Pool in Winter Garden, FL

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Check availability on Winter Garden Hotels with a Pool

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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 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.
A Marriott Fairfield hotel sign with a landscaped garden in front.

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.
NT$2,833
NT$3,187 total
includes taxes & fees
Oct 13 - Oct 14
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 restaurant with a bar area, seating, and a view of greenery outside.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.

2. 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$3,096
NT$3,483 total
includes taxes & fees
Oct 4 - Oct 5
Home2 Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
A bar area with a long counter, multiple chairs, and a variety of bottles.
A hotel room with a desk, chair, and bed.

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.
NT$2,607
NT$2,933 total
includes taxes & fees
Sep 27 - Sep 28
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.
A lounge area with a fire feature, wicker furniture, and a bar in the background.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

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.
NT$2,769
NT$3,115 total
includes taxes & fees
Oct 26 - Oct 27
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A hotel pool area with lounge chairs, a fire pit, and a large pool.
A modern bathroom with a large mirror, two sinks, and a glass-enclosed shower area.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.
A large hotel with multiple floors, a central courtyard, and a reflective water feature.

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$3,501
NT$3,939 total
includes taxes & fees
Oct 26 - Oct 27
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A swimming pool with lounge chairs and a view of a building in the background.
A modern hotel lobby with a central seating area, a kitchen in the background, and a television mounted on the wall.
A hotel room with a kitchenette, a sofa, a desk, and a dining area.
An outdoor patio with round tables and chairs, a red umbrella, and a grill.

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.
NT$4,137
NT$4,654 total
includes taxes & fees
Oct 8 - Oct 9
Home2 Suites By Hilton Winter Garden
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
A large hotel with a central entrance, multiple floors, and a sign indicating 'Homewood Suites by Hilton.'
A modern kitchen with a large island, bar stools, pendant lighting, and a flat-screen TV.
An outdoor patio with a barbecue grill, dining area, and umbrella.

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.
NT$3,279
NT$3,689 total
includes taxes & fees
Oct 4 - Oct 5
Homewood Suites by Hilton Orlando at Flamingo Crossings
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.
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.

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.
NT$2,992
NT$4,258 total
includes taxes & fees
Oct 2 - Oct 3
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.
NT$5,679
NT$8,138 total
includes taxes & fees
Sep 27 - Sep 28
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 Marriott Fairfield hotel sign with a landscaped garden in front.
A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.
A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.

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$2,833
NT$3,187 total
includes taxes & fees
Oct 13 - Oct 14
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 restaurant with a bar area, seating, and a view of greenery outside.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
NT$3,096
NT$3,483 total
includes taxes & fees
Oct 4 - Oct 5
Home2 Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
A bar area with a long counter, multiple chairs, and a variety of bottles.
A hotel room with a desk, chair, and bed.

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
NT$2,607
NT$2,933 total
includes taxes & fees
Sep 27 - Sep 28
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.
A lounge area with a fire feature, wicker furniture, and a bar in the background.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
NT$2,769
NT$3,115 total
includes taxes & fees
Oct 26 - Oct 27
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 modern hotel lobby with a central seating area, a kitchen in the background, and a television mounted on the wall.
A hotel room with a kitchenette, a sofa, a desk, and a dining area.
A swimming pool with lounge chairs and a view of a building in the background.

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
NT$4,137
NT$4,654 total
includes taxes & fees
Oct 8 - Oct 9
Home2 Suites By Hilton Winter Garden
A large hotel with multiple floors, a central courtyard, and a reflective water feature.
A covered outdoor seating area with tables and chairs, a ceiling fan, and a view of a pool and buildings in the background.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.
A hotel pool area with lounge chairs, a fire pit, and a large pool.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
NT$3,501
NT$3,939 total
includes taxes & fees
Oct 26 - Oct 27
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
A large hotel with a central entrance, multiple floors, and a sign indicating 'Homewood Suites by Hilton.'
A modern kitchen with a large island, bar stools, pendant lighting, and a flat-screen TV.
An outdoor patio with a barbecue grill, dining area, and umbrella.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
NT$3,279
NT$3,689 total
includes taxes & fees
Oct 4 - Oct 5
Homewood Suites by Hilton Orlando at Flamingo Crossings
View all properties

Hotels with pools and hot tubs in Winter Garden

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

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
NT$2,607
NT$2,933 total
includes taxes & fees
Sep 27 - Sep 28
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.
A lounge area with a fire feature, wicker furniture, and a bar in the background.
A modern kitchen with stainless steel appliances, a dishwasher, and a dining area with a sofa and a TV.

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
NT$2,769
NT$3,115 total
includes taxes & fees
Oct 26 - Oct 27
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.
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.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
NT$2,992
NT$4,258 total
includes taxes & fees
Oct 2 - Oct 3
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
NT$5,679
NT$8,138 total
includes taxes & fees
Sep 27 - Sep 28
The Grove Resort & Water Park Orlando
A covered balcony with wicker chairs, a ceiling fan, and a view of trees.

Upstay Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
Winter Garden
NT$1,934
NT$7,759 total
includes taxes & fees
Sep 27 - Sep 28
Upstay Tropical Style Family Condo w Pool
View all properties

4-star hotels with pools in Winter Garden

A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.
A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.
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.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
NT$2,992
NT$4,258 total
includes taxes & fees
Oct 2 - Oct 3
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
NT$5,679
NT$8,138 total
includes taxes & fees
Sep 27 - Sep 28
The Grove Resort & Water Park Orlando
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.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A spacious living area with a sofa, coffee table, and a view of the kitchen.

Upstay Disney Pet Friendly Condo w Pool Spa Games

Upstay Disney Pet Friendly Condo w Pool Spa Games
Winter Garden
NT$2,578
NT$7,520 total
includes taxes & fees
Sep 28 - Sep 29
Upstay Disney Pet Friendly Condo w Pool Spa Games
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
NT$2,196
NT$7,806 total
includes taxes & fees
Sep 28 - Sep 29
Modern 3BR Resort Condo With Pool Near Disney
A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.
A spacious living room with a sofa, a coffee table, and a TV. There is a balcony with a view of trees and buildings.

Upstay - 3BR Condo w Pool and Sauna

Upstay - 3BR Condo w Pool and Sauna
Winter Garden
Upstay - 3BR Condo w Pool and Sauna
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 bathroom with a bathtub, a circular wall decoration, and a ceiling fan.
A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.

Upstay: Condo w Pool, Sauna for 6 Guests

Upstay: Condo w Pool, Sauna for 6 Guests
Winter Garden
Upstay: Condo w Pool, Sauna for 6 Guests
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.

Upstay Condo With Pool Near Disney & Pet Friendly

Upstay Condo With Pool Near Disney & Pet Friendly
Winter Garden
NT$2,578
NT$7,520 total
includes taxes & fees
Sep 28 - Sep 29
Upstay Condo With Pool Near Disney & Pet Friendly
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 hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.
A spacious living area with a sofa, coffee table, and a view of the kitchen.

Upstay: Resort Style Condo w Pool, Sauna

Upstay: Resort Style Condo w Pool, Sauna
Winter Garden
NT$2,578
NT$7,520 total
includes taxes & fees
Sep 28 - Sep 29
Upstay: Resort Style Condo w Pool, Sauna
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.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

Upstay - Large Condo w Pool, Sauna, Gym

Upstay - Large Condo w Pool, Sauna, Gym
Winter Garden
Upstay - Large Condo w Pool, Sauna, Gym
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A bedroom with a large bed, a bathroom with a bathtub, and a balcony with a view.

Bright Family Escape With Game Room and Sauna

Bright Family Escape With Game Room and Sauna
Winter Garden
NT$2,706
NT$7,663 total
includes taxes & fees
Sep 27 - Sep 28
Bright Family Escape With Game Room 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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"This was our second stay here and everything was great. It’s very convenient to Disney. Maybe next time we can explore the resort"
Candace 2-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
"Clean ,great area and will go there again"
Jose 6-night trip
Posted 1 hour ago
Marriott's Grande Vista
Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"Excelente como siempre!"
Juan 3-night trip
Posted 2 hours ago
Walt Disney World Dolphin
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"This was our 2nd time staying it was again an amazing stay the room was amazing the staff were awesome we would recommend others to stay and will come back again"
Glen 3-night trip
Posted 3 hours ago
The Grove Resort & Water Park Orlando
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Amazing! The staff is so awesome friendly and over the top!!!"
Angela 2-night trip
Posted 18 hours ago
Westgate Lakes Resort & Spa Universal Studios Area

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 53 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 53 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 Magic Kingdom® Park while you're in the area. Make a point to visit attractions like 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 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.

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