Find Hotels with a Pool in Windermere, FL

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Top Windermere Hotels with a Pool

Fridge, microwave, oven, stovetop
Last Minute Disney Getaway! Private patio & Themed Bedrooms. Book Now! #115909

Last Minute Disney Getaway! Private patio & Themed Bedrooms. Book Now! #115909

Orlando
$492 nightly
The price is $546
Dec 11 - Dec 12
Total with taxes and fees
Last Minute Disney Getaway! Private patio & Themed Bedrooms. Book Now! #115909
Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)
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, (657)
"Hospitable staff and nice rooms."
United States
Iryna
$71 nightly
The price is $80
Dec 14 - Dec 15
Total with taxes and fees
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

4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1337)
"Room, Breakfast, location AAAA+ "
United States
Ahmed Gabriel
$116 nightly
The price is $131
Dec 9 - Dec 10
Total with taxes and fees
Hyatt House Orlando International Drive
Outdoor pool, pool umbrellas, sun loungers
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1919)
"Beautiful resort with very friendly staff. "
United States
kristie
$96 nightly
The price is $109
Dec 11 - Dec 12
Total with taxes and fees
Kompose Boutique Resort at Theme Parks
Outdoor pool
Seasons Florida Resort

Seasons Florida Resort

2.0 star property
Kissimmee
8.8 out of 10, Excellent, (3277)
"Staff nice , nice room for price ! "
United States
Paris
$49 nightly
The price is $56
Jan 5 - Jan 6, 2026
Total with taxes and fees
Seasons Florida Resort
Outdoor pool, pool umbrellas, sun loungers
La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North

3.0 star property
Airport North
7.4 out of 10, Good, (793)
"Near the beach , very nice people at the reception. "
United States
Leonie
$79 nightly
The price is $89
Dec 15 - Dec 16
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando Airport North
Royal Room, 2 Queen Beds, Pool View | Pool | Outdoor pool, a heated pool, open 9 AM to 9:00 PM, free cabanas
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

3.0 star property
Kissimmee
8.4 out of 10, Very Good, (2686)
"Very nice , clean and friendly place to stay with friends and family "
United States
Ariana
$72 nightly
The price is $82
Dec 9 - Dec 10
Total with taxes and fees
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
Outdoor pool, sun loungers
Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport

3.0 star property
Belle Isle
9.0 out of 10, Wonderful, (3988)
"Would stay again! "
United States
Matthew
$84 nightly
The price is $95
Dec 15 - Dec 16
Total with taxes and fees
Wyndham Garden Orlando Airport
Outdoor pool
Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village

3.0 star property
Airport North
9.4 out of 10, Exceptional, (2436)
"Great location to airport and food choices. "
United States
Aliza
$99 nightly
The price is $112
Dec 22 - Dec 23
Total with taxes and fees
Hampton Inn & Suites Orlando Airport @ Gateway Village
Outdoor pool, pool umbrellas, sun loungers
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
$74 nightly
The price is $83
Dec 14 - Dec 15
Total with taxes and fees
Aloft Orlando Lake Buena Vista
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

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent
"Friendly and helpful staff; proximity to attractions. "
Kristy 4-night trip
Posted 20 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 pools, and 2 restaurants. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Offers 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. Provides a children's pool, an outdoor pool, and 2 restaurants. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Features 6 outdoor pools, a children's pool, and 3 restaurants. Hyatt Regency Orlando: Hotel, 2-minute walk from Orange County Convention Center. Offers a children's pool, an outdoor pool, and 3 restaurants.
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.

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