Search Hotels with Pool in Windermere

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Check availability on Windermere Hotels with Pool

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Windermere hotels with a pool

Property amenity
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
8.6 out of 10, Excellent, (748)
"What a wonderful stay! "
United States
Lucia
The price is Rp1.409.092
Rp1.585.229 total
includes taxes & fees
26 Jan - 27 Jan 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
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, (1402)
"Good location, good breakfast "
United States
Andrea
The price is Rp1.975.910
Rp2.222.899 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt House Orlando International Drive
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, (2102)
"Very nice place to stay in, we love it!!"
United States
Basim
The price is Rp1.155.907
Rp1.976.915 total
includes taxes & fees
6 Jan - 7 Jan 2026
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, (3314)
"clean rooms friendly staff great location "
United States
Greg
The price is Rp1.054.935
Rp1.197.351 total
includes taxes & fees
4 Jan - 5 Jan 2026
Seasons Florida Resort
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, (4385)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is Rp1.996.004
Rp2.245.504 total
includes taxes & fees
23 Jan - 24 Jan 2026
Rosen Shingle Creek
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, (1921)
"Good place to stay "
United States
victor
The price is Rp1.306.110
Rp1.469.374 total
includes taxes & fees
4 Jan - 5 Jan 2026
Aloft Orlando Lake Buena Vista
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, (3936)
"Excellent room and the beds were very comfortable, also very clean "
United States
Daisy
The price is Rp1.043.381
Rp1.512.889 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wyndham I-Drive Avanti Resort & Conference Center
Outdoor pool, open 9:00 AM to 9:00 PM, pool loungers
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
Kissimmee
8.2 out of 10, Very good, (5148)
"Beautiful place to stay."
United States
Mohammad
The price is Rp652.382
Rp1.310.317 total
includes taxes & fees
7 Jan - 8 Jan 2026
Palazzo Lakeside Hotel
View from room
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista
3.5 star property
Orlando
8.6 out of 10, Excellent, (5646)
"Great property to stay"
United States
Deepankar
The price is Rp1.371.248
Rp1.542.549 total
includes taxes & fees
23 Jan - 24 Jan 2026
Rosen Inn Lake Buena Vista
Outdoor pool
Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
Florida Center
9.0 out of 10, Wonderful, (489)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is Rp1.442.582
Rp1.622.906 total
includes taxes & fees
26 Jan - 27 Jan 2026
Spark by Hilton Orlando near Universal
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 Windermere Hotel Reviews

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent
"Great experience. Buffet was elaborate. "
Olakunle 3-night trip
Posted 15 hours ago
DoubleTree by Hilton Hotel Orlando at SeaWorld

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. Wyndham I-Drive Avanti Resort & Conference Center: Hotel, 7-minute walk from CoCo Key Water Resort. Offers a children's pool, an outdoor pool and 2 bars. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Provides 2 coffee shops/cafes, 3 outdoor swimming pools and complimentary wireless Internet access. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 2-minute walk from Universal Orlando Resort. Features a children's pool, an outdoor pool and 2 restaurants. Avanti International Resort: Hotel, 9-minute walk from Pointe Orlando. Offers a children's pool, a seasonal outdoor pool and a snack bar/deli.
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.