Find Hotels with a Pool in Windermere, FL

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Check availability on Windermere Hotels with a Pool

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

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, (744)
"What a wonderful stay! "
United States
Lucia
The price is ￥13,139
￥14,782 total
includes taxes & fees
Jan 26 - Jan 27, 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, sun 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, (1401)
"Good location, good breakfast "
United States
Andrea
The price is ￥18,425
￥20,728 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hyatt House Orlando International Drive
Outdoor pool, pool umbrellas, sun 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, (2097)
"Very nice place to stay in, we love it!!"
United States
Basim
The price is ￥10,778
￥18,433 total
includes taxes & fees
Jan 6 - Jan 7, 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, (3313)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is ￥8,461
￥9,603 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Seasons Florida Resort
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4378)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is ￥18,426
￥20,728 total
includes taxes & fees
Jan 23 - Jan 24, 2026
Rosen Shingle Creek
Outdoor pool, pool umbrellas, sun 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, (1919)
"Good place to stay "
United States
victor
The price is ￥12,179
￥13,702 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Aloft Orlando Lake Buena Vista
Outdoor pool, pool umbrellas, sun 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, (3935)
"Excellent room and the beds were very comfortable, also very clean "
United States
Daisy
The price is ￥9,729
￥14,108 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wyndham I-Drive Avanti Resort & Conference Center
Outdoor pool, open 9:00 AM to 9:00 PM, sun loungers
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
Kissimmee
8.2 out of 10, Very Good, (5145)
"Beautiful place to stay."
United States
Mohammad
The price is ￥6,085
￥12,221 total
includes taxes & fees
Jan 4 - Jan 5, 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 ￥12,522
￥14,088 total
includes taxes & fees
Jan 24 - Jan 25, 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, (486)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is ￥13,470
￥15,153 total
includes taxes & fees
Jan 26 - Jan 27, 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.
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Top Windermere Hotel Reviews

Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"Good clean room Convenient location for Epcot and Hollywood Disney "
johnny 4-night trip
Posted 1 day ago
Walt Disney World Dolphin

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 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 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 like 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 an accommodation with an outdoor pool if you're planning to visit Windermere in the driest months of November, February, or December when the average rainfall is 2 inches. Lodging 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 8 inches.