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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 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Winter Garden hotels with a pool

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Free daily buffet breakfast
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Exterior

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.
￥13,671
￥15,380 total
includes taxes & fees
Sep 29 - Sep 30
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers
Exterior
42-inch flat-screen TV with satellite channels, TV
Exterior

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.
￥13,856
￥15,589 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, a heated pool
Bar (on property)
Bar (on property)
Suite, 1 King Bed with Sofa bed | Premium bedding, desk, laptop workspace, iron/ironing board

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.
￥12,028
￥13,531 total
includes taxes & fees
Sep 16 - Sep 17
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Shower, free toiletries, hair dryer, towels
Lobby
Suite, 1 Bedroom, Non Smoking | Pool | Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

4. 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.
￥14,900
￥16,764 total
includes taxes & fees
Sep 28 - Sep 29
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Outdoor pool, a heated pool
Premium bedding, desk, laptop workspace, soundproofing
Bar (on property)
Bar (on property)

5. 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.
￥14,231
￥16,009 total
includes taxes & fees
Sep 14 - Sep 15
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool
Interior
Exterior
Exterior

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.
￥17,508
￥19,698 total
includes taxes & fees
Sep 24 - Sep 25
Home2 Suites By Hilton Winter Garden
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
2 bars/lounges
Exterior
49-inch LED TV with cable channels, TV, Netflix

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.
￥20,028
￥22,530 total
includes taxes & fees
Sep 27 - Sep 28
Homewood Suites by Hilton Orlando at Flamingo Crossings
2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)
Premium bedding, in-room safe, iron/ironing board, WiFi (free)
Exterior
Lobby

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.
￥14,485
￥20,616 total
includes taxes & fees
Sep 22 - Sep 23
Hilton Vacation Club Aqua Sol Orlando West
Waterslide
Aerial view
3 restaurants; breakfast, lunch, and dinner served
Lobby

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.
￥29,040
￥41,139 total
includes taxes & fees
Oct 12 - Oct 13
The Grove Resort & Water Park Orlando
Pool
Exterior
Smart TV
Coffee/tea maker, fridge, microwave, oven

10. Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
Winter Garden
￥15,853
￥50,879 total
includes taxes & fees
Sep 28 - Sep 29
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
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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

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

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
￥13,856
￥15,589 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites by Hilton Orlando at Flamingo Crossings
Free daily buffet breakfast
Lobby
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
￥13,671
￥15,380 total
includes taxes & fees
Sep 29 - Sep 30
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Outdoor pool, a heated pool
Bar (on property)
Bar (on property)
Suite, 1 King Bed with Sofa bed | Premium bedding, desk, laptop workspace, iron/ironing board

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
￥12,028
￥13,531 total
includes taxes & fees
Sep 16 - Sep 17
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Exterior
Gazebo
Lobby
Suite, 1 Bedroom, Non Smoking | Pool | Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
￥14,900
￥16,764 total
includes taxes & fees
Sep 28 - Sep 29
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Outdoor pool, a heated pool
Premium bedding, desk, laptop workspace, soundproofing
Bar (on property)
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
￥14,231
￥16,009 total
includes taxes & fees
Sep 14 - Sep 15
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Exterior
Interior
Exterior
Outdoor pool

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
Winter Garden
￥17,508
￥19,698 total
includes taxes & fees
Sep 24 - Sep 25
Home2 Suites By Hilton Winter Garden
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
2 bars/lounges
Exterior
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
￥20,028
￥22,530 total
includes taxes & fees
Sep 27 - Sep 28
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
Bar (on property)
Bar (on property)
Suite, 1 King Bed with Sofa bed | Premium bedding, desk, laptop workspace, iron/ironing board

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Bay Lake
￥12,028
￥13,531 total
includes taxes & fees
Sep 16 - Sep 17
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool
Premium bedding, desk, laptop workspace, soundproofing
Bar (on property)
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
￥14,231
￥16,009 total
includes taxes & fees
Sep 14 - Sep 15
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)
Premium bedding, in-room safe, iron/ironing board, WiFi (free)
Flat-screen TV, DVD player
Lobby

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
￥14,485
￥20,616 total
includes taxes & fees
Sep 22 - Sep 23
Hilton Vacation Club Aqua Sol Orlando West
Waterslide
Aerial view
3 restaurants; breakfast, lunch, and dinner served
Lobby

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
￥29,040
￥41,139 total
includes taxes & fees
Oct 12 - Oct 13
The Grove Resort & Water Park Orlando
Pool
Interior
Coffee/tea maker, fridge, microwave, oven
TV, fireplace, video games, DVD player

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Winter Garden
￥45,008
￥81,510 total
includes taxes & fees
Sep 14 - Sep 15
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
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 Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
Winter Garden
￥10,254
￥38,573 total
includes taxes & fees
Sep 20 - Sep 21
Upstay Tropical Style Family Condo w Pool
Lobby
Interior
Exterior
Pool

Family-Friendly 2BR Condo w Resort Pool & Sauna

Family-Friendly 2BR Condo w Resort Pool & Sauna
Winter Garden
￥11,214
￥39,060 total
includes taxes & fees
Sep 28 - Sep 29
Family-Friendly 2BR Condo w Resort Pool & Sauna
A heated pool
Dining
Outdoor dining
Bar (on property)

1-Bedroom Villa Near Disney w/ Pool & Lazy River

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
￥24,731
￥37,039 total
includes taxes & fees
Sep 16 - Sep 17
1-Bedroom Villa Near Disney w/ Pool & Lazy River
A heated pool
Dining
Bar (on property)
Outdoor dining

Studio Near Disney World

Studio Near Disney World
Kissimmee
￥18,894
￥30,012 total
includes taxes & fees
Sep 16 - Sep 17
Studio Near Disney World
Interior
TV
Exterior
Pool

Upstay: Stylish Resort Getaway w/ Pool near Disney

Upstay: Stylish Resort Getaway w/ Pool near Disney
Winter Garden
￥9,524
￥40,782 total
includes taxes & fees
Sep 21 - Sep 22
Upstay: Stylish Resort Getaway w/ Pool near Disney
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4-star hotels with pools in Winter Garden

Waterslide
Aerial view
3 restaurants; breakfast, lunch, and dinner served
Lobby

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
￥29,040
￥41,139 total
includes taxes & fees
Oct 12 - Oct 13
The Grove Resort & Water Park Orlando
2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)
Premium bedding, in-room safe, iron/ironing board, WiFi (free)
Flat-screen TV, DVD player
Lobby

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
￥14,485
￥20,616 total
includes taxes & fees
Sep 22 - Sep 23
Hilton Vacation Club Aqua Sol Orlando West
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Front of property
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Spacious 3BR Family Getaway w Pool Near Disney

Spacious 3BR Family Getaway w Pool Near Disney
Winter Garden
Spacious 3BR Family Getaway w Pool Near Disney
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Front of property

Upstay Condo w Pool & Sauna Sleeps 8

Upstay Condo w Pool & Sauna Sleeps 8
Winter Garden
￥17,226
￥45,127 total
includes taxes & fees
Sep 19 - Sep 20
Upstay Condo w Pool & Sauna Sleeps 8
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
Winter Garden
￥11,591
￥38,788 total
includes taxes & fees
Sep 21 - Sep 22
Modern 3BR Resort Condo With Pool Near Disney
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
￥10,949
￥38,065 total
includes taxes & fees
Sep 14 - Sep 15
Upstay - 3BR Condo w Pool and Sauna
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Front of property
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Upstay: 3BR Family Condo w Pool & Sauna

Upstay: 3BR Family Condo w Pool & Sauna
Winter Garden
￥10,618
￥37,693 total
includes taxes & fees
Sep 14 - Sep 15
Upstay: 3BR Family Condo w Pool & Sauna
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
￥12,829
￥40,182 total
includes taxes & fees
Sep 20 - Sep 21
Upstay Pet-friendly Condo With Pool
Apartment (3 Bedrooms) | Front of property
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

Upstay 3BR Condo w Pool & Patio Near Disney

Upstay 3BR Condo w Pool & Patio Near Disney
Winter Garden
￥9,217
￥36,117 total
includes taxes & fees
Sep 21 - Sep 22
Upstay 3BR Condo w Pool & Patio Near Disney
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
￥11,060
￥34,735 total
includes taxes & fees
Sep 14 - Sep 15
Upstay Condo With Outdoor Pool & 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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"We enjoyed our time way which felt like our home away from home."
Bonnie 3-night trip
Posted 7 hours ago
The Grove Resort & Water Park Orlando
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Friendly helpful staff. Room was clean with lots of towels and linens."
William 1-night trip
Posted 9 hours ago
Rosen Inn Lake Buena Vista
Walt Disney World Dolphin

Walt Disney World Dolphin

8/10 Good
"Appreciated the daily room cleaning."
Cathy 3-night trip
Posted 13 hours ago
Walt Disney World Dolphin
Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Love it"
Amanda 3-night trip
Posted 14 hours ago
Marriott's Grande Vista
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"The shower door needs repair. It would not stay closed. Other than that it was really nice. The entrances are a little confusing , but the staff and maps were very helpful."
Soo-Ling 2-night trip
Posted 15 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 58 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 58 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 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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