Search Hotels with Swimming Pool in Windermere

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Check availability on Windermere Hotels with Swimming Pool

Our top choices for Windermere hotels with a pool

Outdoor pool, pool umbrellas, pool loungers
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1351)
"Room, Breakfast, location AAAA+ "
United States
Ahmed Gabriel
The price is ₹8,825
₹9,928 total
includes taxes & fees
14 Dec - 15 Dec
Hyatt House Orlando International Drive
Outdoor pool, open 8:00 AM to 9:00 PM, pool cabanas (surcharge)
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
International Drive District
8.8 out of 10, Excellent, (673)
"Hospitable staff and nice rooms."
United States
Iryna
The price is ₹6,800
₹7,650 total
includes taxes & fees
8 Jan - 9 Jan 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, pool loungers
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1952)
"Beautiful resort with very friendly staff. "
United States
kristie
The price is ₹5,493
₹9,807 total
includes taxes & fees
14 Dec - 15 Dec
Kompose Boutique Resort at Theme Parks
Outdoor pool
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
Kissimmee
8.8 out of 10, Excellent, (3282)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is ₹5,385
₹6,111 total
includes taxes & fees
8 Jan - 9 Jan 2026
Seasons Florida Resort
Outdoor pool, pool umbrellas, pool loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
International Drive District
7.4 out of 10, Good, (3883)
"Room was good hotel was nice and clean"
United States
Amy
The price is ₹5,606
₹8,128 total
includes taxes & fees
14 Dec - 15 Dec
Wyndham I-Drive Avanti Resort & Conference Center
Outdoor pool, pool umbrellas, pool loungers
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
Orlando
8.8 out of 10, Excellent, (1902)
"Great rooms, staff, and property!"
United States
Cindy
The price is ₹6,657
₹7,489 total
includes taxes & fees
14 Dec - 15 Dec
Aloft Orlando Lake Buena Vista
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4348)
"Great resort "
United States
Camille
The price is ₹9,405
₹10,580 total
includes taxes & fees
14 Dec - 15 Dec
Rosen Shingle Creek
Terrace/patio
Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1234)
"Nice place very good"
United States
Hugo
The price is ₹7,524
₹8,540 total
includes taxes & fees
22 Dec - 23 Dec
Embassy Suites by Hilton Orlando Lake Buena Vista South
Outdoor pool, pool loungers
Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport
3.0 star property
Airport North
8.8 out of 10, Excellent, (3736)
"Good room, good breakfast and convenient to the airport."
United States
Mark
The price is ₹7,206
₹8,107 total
includes taxes & fees
15 Dec - 16 Dec
Wingate by Wyndham - Orlando International Airport
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 Windermere Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Staff was very helpful "
Sarah 1-night trip
Posted 10 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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Frequently asked questions

What are some hotels with pools in Windermere?
Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor swimming pools and 2 restaurants. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 2-minute walk from Universal Orlando Resort. Offers a children's pool, an outdoor pool and 2 restaurants. Avanti International Resort: Hotel, 9-minute walk from Pointe Orlando. Provides a children's pool, a seasonal outdoor pool and a snack bar/deli. La Quinta Inn & Suites by Wyndham Orlando Airport North: Features daily, an outdoor pool and complimentary high-speed (wired) Internet access. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Offers 6 outdoor swimming pools, a children's pool and 3 restaurants.
What is there to see and do in Windermere?
Explore places such as Universal Studios Florida, Universal Orlando Resort and Magic Kingdom® Park while you're in the area. Spend some time experiencing the great outdoors at Lake Butler and Tibet Butler Preserve.
When is the best time to book a hotel with a pool in Windermere?
You may want to consider accommodation that has an outdoor pool if you're planning to visit Windermere in the driest months of November, February or December, when the average rainfall is 49 mm. Accommodation with an indoor pool may be what you want if you come to town during the rainiest months of August, July and September when the average rainfall is 194 mm.