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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
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Winter Garden hotels with a pool

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.
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.

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.
₩130,783
₩147,131 total
includes taxes & fees
Oct 20 - Oct 21
Home2 Suites by Hilton Orlando at Flamingo Crossings
A hotel pool area with lounge chairs, a fire pit, and a large pool.
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.
A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.

2. 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.
₩115,061
₩129,443 total
includes taxes & fees
Oct 27 - Oct 28
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
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 lobby with a central seating area, wooden ceiling, and patterned carpet.

3. 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.
₩101,391
₩114,064 total
includes taxes & fees
Oct 27 - Oct 28
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
An outdoor patio with a barbecue grill, dining area, and umbrella.
A modern kitchen with a large island, bar stools, pendant lighting, and a flat-screen TV.
A hotel room with a large window, a pool view, a chair, a table, a lamp, and a bed.

4. 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.
₩152,763
₩171,859 total
includes taxes & fees
Oct 26 - Oct 27
Homewood Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with a desk, chair, and bed.
A restaurant with outdoor seating, a bar, and a fire feature.
Bar (on property)

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.
₩104,943
₩118,061 total
includes taxes & fees
Oct 26 - Oct 27
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 lounge area with a fire feature, wicker furniture, and a bar in the background.
A restaurant with outdoor seating, a fire feature, and a bar area.

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.
₩116,603
₩131,179 total
includes taxes & fees
Oct 26 - Oct 27
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with lounge chairs and a view of a building in the background.
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.
A modern hotel lobby with a central seating area, a kitchen in the background, and a television mounted on the wall.

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.
₩164,048
₩184,553 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites By Hilton Winter Garden
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A modern lobby with a reception desk, seating area, and a bar.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.

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.
₩227,912
₩330,282 total
includes taxes & fees
Nov 9 - Nov 10
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 hotel with a blue roof, a reflection pool, and palm trees.
A hotel room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.

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.
₩126,387
₩179,889 total
includes taxes & fees
Oct 19 - Oct 20
Hilton Vacation Club Aqua Sol Orlando West
A pool area with lounge chairs and a small pool.
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
Interior
A bathroom with two sinks, a large mirror, and a vanity with a light fixture.

10. Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
₩93,818
₩330,206 total
includes taxes & fees
Oct 12 - Oct 13
Upstay: Condo Near Disney w Pool, Sauna
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

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 Marriott Fairfield hotel sign with a landscaped garden in front.

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
₩101,391
₩114,064 total
includes taxes & fees
Oct 27 - Oct 28
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 pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.
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
₩130,783
₩147,131 total
includes taxes & fees
Oct 20 - Oct 21
Home2 Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.
A hotel room with a desk, chair, and bed.
A restaurant with outdoor seating, a bar, and a fire feature.
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
₩104,943
₩118,061 total
includes taxes & fees
Oct 26 - Oct 27
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
An outdoor patio with round tables and chairs, a red umbrella, and a grill.
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.
A modern hotel lobby with a central seating area, a kitchen in the background, and a television mounted on the wall.

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
₩164,048
₩184,553 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites By Hilton Winter Garden
A large hotel with multiple floors, a central courtyard, and a reflective water feature.
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.
A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
₩115,061
₩129,443 total
includes taxes & fees
Oct 27 - Oct 28
Residence Inn by Marriott Orlando Flamingo Crossing/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 lounge area with a fire feature, wicker furniture, and a bar in the background.
A restaurant with outdoor seating, a fire feature, and a bar area.

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
₩116,603
₩131,179 total
includes taxes & fees
Oct 26 - Oct 27
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
An outdoor patio with a barbecue grill, dining area, and umbrella.
A modern kitchen with a large island, bar stools, pendant lighting, and a flat-screen TV.
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
₩152,763
₩171,859 total
includes taxes & fees
Oct 26 - Oct 27
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 hotel room with a desk, chair, and bed.
A restaurant with outdoor seating, a bar, and a fire feature.
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
₩104,943
₩118,061 total
includes taxes & fees
Oct 26 - Oct 27
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 lounge area with a fire feature, wicker furniture, and a bar in the background.
A restaurant with outdoor seating, a fire feature, and a bar area.

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
₩116,603
₩131,179 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 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 hotel room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
₩126,387
₩179,889 total
includes taxes & fees
Oct 19 - Oct 20
Hilton Vacation Club Aqua Sol Orlando West
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A modern lobby with a reception desk, seating area, and a bar.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
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
₩227,912
₩330,282 total
includes taxes & fees
Nov 9 - Nov 10
The Grove Resort & Water Park Orlando
Room
Room
Room
Room

Upstay Stylish 3BR Condo w Patio Near Disney

Upstay Stylish 3BR Condo w Patio Near Disney
Winter Garden
₩112,927
₩363,278 total
includes taxes & fees
Oct 14 - Oct 15
Upstay Stylish 3BR Condo w Patio Near Disney
View all properties

4-star hotels with pools in Winter Garden

A resort with a large pool, water slides, palm trees, and beach umbrellas.
A modern lobby with a reception desk, seating area, and a bar.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
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
₩227,912
₩330,282 total
includes taxes & fees
Nov 9 - Nov 10
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 hotel room with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
₩126,387
₩179,889 total
includes taxes & fees
Oct 19 - Oct 20
Hilton Vacation Club Aqua Sol Orlando West
Interior
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 lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
Interior

Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
₩93,818
₩330,206 total
includes taxes & fees
Oct 12 - Oct 13
Upstay: Condo Near Disney 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.
Interior
Front of property

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
₩104,540
₩342,267 total
includes taxes & fees
Nov 2 - Nov 3
Modern 3BR Resort Condo With Pool Near Disney
Interior
Interior
Interior
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
₩96,638
₩333,704 total
includes taxes & fees
Oct 13 - Oct 14
Upstay: 3BR Family Condo w Pool & Sauna
A modern kitchen with a granite countertop, a built-in dishwasher, and a large window.
Interior
Interior
Interior

Upstay - Pet-friendly Suite w Pool, Sauna

Upstay - Pet-friendly Suite w Pool, Sauna
Winter Garden
₩108,561
₩316,637 total
includes taxes & fees
Nov 2 - Nov 3
Upstay - Pet-friendly Suite w Pool, Sauna
A spacious living room with a sofa, a coffee table, and a TV. There are large windows with curtains, a balcony, and a ceiling fan.
A modern living room with a grey sofa, a round coffee table, and a flat-screen TV mounted on the wall.
A modern kitchen with a central island, bar stools, and built-in appliances.
A hallway with a round mirror, a console table, and a tiled floor.

Condo w Pool, Games Room - Pet Friendly

Condo w Pool, Games Room - Pet Friendly
Winter Garden
₩108,561
₩316,637 total
includes taxes & fees
Nov 2 - Nov 3
Condo w Pool, Games Room - Pet Friendly
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A modern living room with a grey sofa, a coffee table, and two armchairs. There is a kitchen area with white cabinets and a bar stool.
A bedroom with a bed, a large window, a ceiling fan, and a bathroom with a bathtub and a framed picture on the wall.
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.

Upstay Disney Area Condo w Pool Pet Friendly

Upstay Disney Area Condo w Pool Pet Friendly
Winter Garden
₩123,304
₩363,379 total
includes taxes & fees
Oct 12 - Oct 13
Upstay Disney Area Condo w Pool Pet Friendly
Interior
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A modern living room with a sectional sofa, a coffee table, and a painting on the wall. There is a kitchen area with a refrigerator, a microwave, and a dining table with chairs.
Front of property

Upstay 3BR Suite w Pool, Sauna & Gamesnear Disney

Upstay 3BR Suite w Pool, Sauna & Gamesnear Disney
Winter Garden
₩88,457
₩324,175 total
includes taxes & fees
Oct 12 - Oct 13
Upstay 3BR Suite w Pool, Sauna & Gamesnear Disney
A modern dining area with a glass table, white chairs, and decorative plates.
Interior
A hotel with a sign reading 'PALISADES' surrounded by landscaped gardens and palm trees.
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop. There are two bar stools under the counter.

Beautiful Condo w Outdoor Pool and Sauna

Beautiful Condo w Outdoor Pool and Sauna
Winter Garden
₩112,582
₩351,315 total
includes taxes & fees
Oct 19 - Oct 20
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

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Love this hotel! The location, staff, safety, and cleanliness are all top notch! I stay here frequently and this is why. They have never disappointed"
Lorie 2-night trip
Posted 1 hour ago
Rosen Inn Lake Buena Vista
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"The property and room were beautiful and well maintained. The kids had a great time. So much for them to do. The pools are amazing."
PATRICIA DENISE 3-night trip
Posted 7 hours ago
The Grove Resort & Water Park Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Room was very clean. Front desk staff were great! Will definitely return!"
Allison 5-night trip
Posted 11 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"A wonderful property. The amenities were fantastic. Daily buffet breakfast and evening diner included was a pleasant surprise. Evening beverages as well. Salt water pool and hot tub were nice, but the shuttle buses to and from the parks were a great savings on gas and parking fees. No resort fees as well make the property a must stay and full value for families!"
Rick 6-night trip
Posted 12 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"."
Kaitlin 3-night trip
Posted 16 hours ago
Walt Disney World Dolphin
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Great Staff and amenities."
Keith 2-night trip
Posted 17 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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