Find Hotels with an Outdoor Pool in Winter Garden, FL

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Top Winter Garden Hotels with an Outdoor Pool

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

2.5 star property
Bay Lake
9.4 out of 10, Exceptional, (4310)
"Really good place to stay "
United States
Lians
$116 nightly
The price is $130
Jan 4 - Jan 5, 2026
Total with taxes and fees
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Home2 Suites by Hilton Orlando at Flamingo Crossings

3.0 star property
Bay Lake
9.2 out of 10, Wonderful, (5056)
"Great location nice breakfast and front desk people is amazing "
United States
Orlando
$103 nightly
The price is $116
Dec 16 - Dec 17
Total with taxes and fees
Home2 Suites by Hilton Orlando at Flamingo Crossings

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

3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2249)
"Great stay"
United States
Christopher
$114 nightly
The price is $128
Dec 11 - Dec 12
Total with taxes and fees
SpringHill 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
9.0 out of 10, Wonderful, (1643)
"Amazing! Will come back soon!"
United States
DeAndre
$118 nightly
The price is $133
Jan 4 - Jan 5, 2026
Total with taxes and fees
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (1969)
"Great stay"
United States
Windy Laine
$143 nightly
The price is $161
Dec 21 - Dec 22
Total with taxes and fees
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Hilton Vacation Club Aqua Sol Orlando West

4.0 star property
Winter Garden
8.8 out of 10, Excellent, (4070)
"Really nice place friendly staff. "
United States
Keith
$131 nightly
The price is $148
Dec 17 - Dec 18
Total with taxes and fees
Hilton Vacation Club Aqua Sol Orlando West

Homewood Suites by Hilton Orlando at Flamingo Crossings

3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (2129)
"Our stay was great and location was convenient when looking for food!"
United States
Sofia Alexia
$111 nightly
The price is $125
Dec 21 - Dec 22
Total with taxes and fees
Homewood Suites by Hilton Orlando at Flamingo Crossings

The Grove Resort & Water Park Orlando

4.0 star property
Winter Garden
8.0 out of 10, Very Good, (8779)
"Everything about it was excellent The staff , the rooms , the resort , very convenient location .We were very very pleased with everything very beautiful area "
United States
Ruben
$198 nightly
The price is $223
Dec 9 - Dec 10
Total with taxes and fees
The Grove Resort & Water Park Orlando

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

3.5 star property
Winter Garden
10.0 out of 10, Exceptional, (1)
"Room was very clean apartment has everything that you need all necessary things for stay like cops plates utensils host was very nice. Communication with him was very easy. Everything was ready when we arrive. We didn’t have to wait for anything. Highly recommended."
Canada
Ramiz
$204 nightly
The price is $230
Dec 9 - Dec 10
Total with taxes and fees
Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

The Oak View Place..

Oakland
9.2 out of 10, Wonderful, (10)
"The VRBO looked brand new and I only knew it was not because of the reviews from previous years. The live oak trees on the property added to the beauty of the surroundings."
United States
Libba F.
$260 nightly
The price is $289
Dec 9 - Dec 10
Total with taxes and fees
The Oak View Place..
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.

Find out more about Winter Garden

Discover top Winter Garden attractions

Winter Garden, Florida, is a charming locale that offers a delightful mix of relaxation and adventure, perfect for families seeking a rejuvenating getaway. Start your day with a stroll along the West Orange Trail, a scenic path ideal for biking or walking that winds through lush landscapes and quaint neighborhoods. You can then explore the vibrant downtown area, where you'll find the historic Winter Garden Theatre, hosting a range of live performances. For a touch of nature, visit the nearby Lake Apopka, where you can enjoy birdwatching or a peaceful picnic by the water's edge. Families can delight in the interactive exhibits at the Central Florida Railroad Museum, which offers a glimpse into the area’s history. Finally, unwind at one of the local spas or wellness centers, where you can indulge in a relaxing massage or a rejuvenating facial. Staying in hotels with pools in the heart of Winter Garden not only provides a refreshing escape after a day of exploration but also places you within easy reach of these attractions, allowing for quality family time and the ultimate in relaxation.

Find the best hotels with an outdoor pool in Winter Garden

For travelers seeking a refreshing escape in Winter Garden, Florida, these hotels offer fantastic outdoor pool amenities perfect for relaxation and fun under the sun.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

  • Why it's great for poolside lounging: Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance is a fantastic option for travelers looking to enjoy an outdoor pool experience, an exceptional review rating of 9.6. The hotel features an outdoor pool complete with sun loungers and a poolside bar, ideal for soaking up the Florida sun while enjoying refreshing drinks.
  • Other amenities: Other noteworthy amenities include a complimentary buffet breakfast, free self-parking, and a 24-hour fitness center. Guests can also benefit from well-equipped kitchenettes in their suites, making it easy to prepare meals during their stay. Additionally, the hotel offers a rooftop garden and easy access to local attractions, enhancing the overall experience.
  • Neighborhood: Bay Lake
  • Nearby attractions: Orange Lake Golf - 3.65 miles, Island H2O Live! - 3.76 miles, Flamingo Crossings Town Center - 0.19 miles

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

  • Why it's great for poolside lounging: Travelers seeking a budget-friendly hotel with outstanding outdoor pool facilities will find Fairfield by Marriott Inn & Suites Orlando at Flamingo Crossings to be an excellent choice, a superb review rating of 9.4. The hotel features an inviting outdoor pool complete with accessible features, sun loungers, and a poolside bar, perfect for unwinding after a day of exploring.
  • Other amenities: Beyond the outdoor pool, guests can enjoy a complimentary breakfast buffet, self-parking, and a rooftop garden for a bit of tranquility. Additional amenities include a fitness center available around the clock, concierge services, and easy access to local attractions, making it a convenient base for any adventure.
  • Neighborhood: Bay Lake
  • Nearby attractions: Orange Lake Golf - 3.81 miles, Island H2O Live! - 3.92 miles, Flamingo Crossings Town Center - 0.17 miles

Home2 Suites by Hilton Orlando at Flamingo Crossings

  • Why it's great for poolside lounging: Ideal for guests looking to enjoy a vibrant outdoor pool experience, Home2 Suites by Hilton Orlando at Flamingo Crossings shines with a high review rating of 9.2. The hotel features an accessible outdoor pool equipped with sun loungers and a thrilling waterslide, ensuring a delightful poolside retreat for guests of all ages.
  • Other amenities: In addition to its impressive pool area, guests can relish in various amenities including complimentary buffet breakfast, self-parking options, and a fitness center available 24 hours a day. The hotel also offers a kitchenette in each suite, perfect for those who enjoy cooking during their stay, and electric car charging stations for eco-conscious travelers.
  • Neighborhood: Bay Lake
  • Nearby attractions: Orange Lake Golf - 3.62 miles, Island H2O Live! - 3.73 miles, Flamingo Crossings Town Center - 0.15 miles

Hilton Vacation Club Aqua Sol Orlando West

  • Why it's great for poolside lounging: For a luxurious outdoor pool experience, Hilton Vacation Club Aqua Sol Orlando West is a top choice for travelers, reflected in its commendable review rating of 8.8. The resort features an expansive outdoor pool area with a waterslide and a poolside bar, creating a perfect setting for relaxation and leisure.
  • Other amenities: Guests can also take advantage of a variety of additional amenities such as onsite tennis courts, a hot tub, and mini-golf. The hotel includes a concierge service, self-parking, and family-friendly amenities like a playground, ensuring a memorable stay for all. With premium bedding and spacious rooms, guests will find comfort in every corner of this resort.
  • Nearby attractions: Orange Lake Golf - 2.59 miles, Surfari Water Park - 1.78 miles, Lake Davenport - 1.18 miles

The Grove Resort & Water Park Orlando

  • Why it's great for poolside lounging: The Grove Resort & Water Park Orlando is an excellent choice for travelers seeking an exciting outdoor pool experience, featuring a review rating of 8.0. With a vast outdoor pool area that includes a lazy river, waterslides, and private cabanas, guests can truly unwind in a tropical oasis.
  • Other amenities: In addition to its impressive pool facilities, guests have access to a hot tub, a nearby fishing area, and a variety of dining options, including a poolside restaurant. The resort also offers a range of amenities such as arcade games, a children's club, and complimentary self-parking, ensuring a fun-filled stay for guests of all ages.
  • Nearby attractions: Orange Lake Golf - 3.11 miles, Surfari Water Park - 0.35 miles, Lake Davenport - 2.55 miles

Top Winter Garden Hotel Reviews

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