Find Hotels with a Pool in Winter Garden, FL

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Check availability on Winter Garden Hotels with a Pool

Tonight
Nov 22 - Nov 23
Tomorrow
Nov 23 - Nov 24
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Top Winter Garden Hotels with a Pool

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

2.5 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.4 out of 10, Exceptional, (4255)
Vibrant pool area welcomes families with comfortable loungers, refreshing drinks, and attentive bar service just minutes from Disney parks. Sports enthusiasts appreciate the basketball court while parents value the shallow pool section perfect for young swimmers.
$112 nightly
The price is $126
Dec 9 - Dec 10
Total with taxes and fees
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Outdoor pool, a heated pool
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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

3.5 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Hot tub
9.0 out of 10, Wonderful, (2244)
Sparkling waters beckon at this hotel's expansive outdoor pool area, complete with a relaxing hot tub and convenient poolside bar. A complimentary shuttle whisks guests to theme parks while the freshly remodeled spaces provide a comfortable respite.
$102 nightly
The price is $115
Dec 10 - Dec 11
Total with taxes and fees
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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

3.5 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Hot tub
9.0 out of 10, Wonderful, (1633)
Swimmers splash in the spacious outdoor pool while others relax in the steaming hot tub nearby. A poolside bar serves cold drinks, creating a perfect retreat after park adventures. The hotel's complimentary Disney shuttle, breakfast buffet, and fitness center complete this family escape.
$106 nightly
The price is $119
Dec 15 - Dec 16
Total with taxes and fees
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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

3.0 star property
Bay Lake
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (4980)
Spacious rooms with full kitchens welcome families after exciting pool adventures with waterslides and sun loungers. Beyond the sparkling waters, guests enjoy firepit gatherings, a 24-hour fitness center with Peloton bikes, and complimentary theme park shuttles.
$103 nightly
The price is $116
Nov 30 - Dec 1
Total with taxes and fees
Home2 Suites by Hilton Orlando at Flamingo Crossings
Exterior
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4.0 star property
Winter Garden
  • 2 outdoor pools
  • Poolside bar
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (4071)
Splash into aquatic bliss at a resort boasting multiple swimming options, from thrilling waterslides to tranquil pool loungers. Beyond water adventures, guests enjoy tennis courts, mini golf, paddle boats, and convenient poolside dining.
$131 nightly
The price is $148
Dec 1 - Dec 2
Total with taxes and fees
Hilton Vacation Club Aqua Sol Orlando West
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

3.0 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.6 out of 10, Exceptional, (1964)
Sparkling waters beckon at this family-friendly retreat featuring an inviting outdoor pool complete with sun loungers and refreshing poolside bar service. Located just 10-15 minutes from Disney theme parks, this spotless hotel offers spacious accommodations with fully equipped kitchens.
$125 nightly
The price is $141
Dec 8 - Dec 9
Total with taxes and fees
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings

3.0 star property
Bay Lake
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (2090)
Splash into vacation bliss at the outdoor pool featuring an exciting waterslide and sun loungers for post-swim relaxation. Families appreciate the nearby theme park shuttle, on-site dining, and spacious suites with full kitchenettes.
$111 nightly
The price is $125
Dec 18 - Dec 19
Total with taxes and fees
Homewood Suites by Hilton Orlando at Flamingo Crossings
Aerial view
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4.0 star property
Winter Garden
  • 6 outdoor pools
  • 3 poolside bars
  • Pool loungers
  • 2 hot tubs
8.0 out of 10, Very Good, (8769)
Flowing waters beckon from six outdoor pools, including a free water park with waterslide and lazy river. Cabanas provide shade while three poolside bars serve refreshing drinks between fishing excursions and arcade games.
$198 nightly
The price is $223
Nov 23 - Nov 24
Total with taxes and fees
The Grove Resort & Water Park Orlando
Outdoor pool
Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden

3.0 star property
Winter Garden
  • Outdoor pool
9.4 out of 10, Exceptional, (351)
Fitness enthusiasts appreciate this hotel's well-maintained outdoor pool and fully equipped fitness center. Spotlessly clean rooms with designer toiletries offer a peaceful retreat after enjoying the complimentary breakfast praised by travelers.
$114 nightly
The price is $128
Dec 18 - Dec 19
Total with taxes and fees
Home2 Suites By Hilton Winter Garden
Outdoor pool
Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

3.5 star property
Winter Garden
  • Outdoor pool
$204 nightly
The price is $230
Nov 23 - Nov 24
Total with taxes and fees
Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
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 Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"One of the best resorts I’ve stayed at. Everything was perfect. "
Tabitha 3-night trip
Posted 19 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/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 25 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 steps 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, 1-minute walk from Flamingo Crossings Town Center. Features a snack bar/deli, a pool, and buffet. Orange Lake Holiday Inn Resort 2 Bedroom Villa In Beautiful Orlando/Kissimmee: Resort located near Walt Disney World® Resort. Offers complimentary wireless internet access, a pool, and kitchens.
How many pool hotels are there in Winter Garden?
Expedia's 25 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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