Search Hotels with Pool in Windermere

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windermere Hotels with Pool

Our top choices for Windermere hotels with a pool

3 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas

Caribe Royale Orlando

Caribe Royale Orlando
4.5 star property
Orlando
9.2 out of 10, Wonderful, (4,587 reviews)
"Awesome resort, we visit at least 3 times a year. "
United States
Eric
The price is ฿4,231
฿6,106 total
includes taxes & fees
16 Jan - 17 Jan
Caribe Royale Orlando
Outdoor pool, pool umbrellas, pool loungers

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1,461 reviews)
"Great place to stay and great amenities"
United States
Darshan
The price is ฿3,432
฿3,860 total
includes taxes & fees
26 Jan - 27 Jan
Hyatt House Orlando International Drive
Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
3.5 star property
Florida Center
9.0 out of 10, Wonderful, (6,030 reviews)
"Great place to stay"
United States
Peggy
The price is ฿4,187
฿4,711 total
includes taxes & fees
25 Jan - 26 Jan
Universal's Cabana Bay Beach Resort
6 outdoor pools, free pool cabanas, pool umbrellas

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
Orlando
9.4 out of 10, Exceptional, (4,323 reviews)
"Great stay!"
Canada
Sylvie
The price is ฿3,753
฿4,222 total
includes taxes & fees
8 Feb - 9 Feb
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers

Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL
3.5 star property
International Drive District
9.0 out of 10, Wonderful, (3,734 reviews)
"Great location and hotel for the price "
United States
Rose Marie
The price is ฿2,814
฿3,166 total
includes taxes & fees
25 Jan - 26 Jan
Tru By Hilton Orlando Convention Center Area, FL
Water park

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area
4.0 star property
Orlando
8.2 out of 10, Very good, (5,662 reviews)
"Very good hotel and location"
United States
Diego
The price is ฿3,070
฿4,516 total
includes taxes & fees
19 Jan - 20 Jan
Westgate Lakes Resort & Spa Universal Studios Area
Outdoor pool, pool umbrellas, pool loungers

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
Orlando
8.8 out of 10, Excellent, (1,939 reviews)
"Super nice hotel at a great price."
United States
Terry
The price is ฿2,582
฿2,904 total
includes taxes & fees
25 Jan - 26 Jan
Aloft Orlando Lake Buena Vista
Outdoor pool

Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
Airport North
9.6 out of 10, Exceptional, (2,893 reviews)
"Perfect location, the staff here is super friendly and always willing to assist, totally enjoyed our stay"
United States
RUSSELL
The price is ฿4,785
฿5,383 total
includes taxes & fees
25 Jan - 26 Jan
Hyatt House 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, (2,481 reviews)
"Great stay "
United States
Nancy
The price is ฿4,105
฿4,618 total
includes taxes & fees
26 Jan - 27 Jan
Hampton Inn & Suites Orlando Airport @ Gateway Village
Exterior

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (3,628 reviews)
"Great , great hotel great location "
United States
Adrian
The price is ฿4,150
฿6,425 total
includes taxes & fees
19 Jan - 20 Jan
Margaritaville Resort Orlando with H2O Waterpark
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
"El estacionamiento es demasiado caro $40 por noche "
Jose 1-night trip
Posted 15 hours ago
DoubleTree by Hilton Hotel Orlando at SeaWorld

Frequently asked questions

What are some hotels with pools in Windermere?
Wyndham I-Drive Avanti Resort & Conference Center: Hotel, 7-minute walk from CoCo Key Water Resort. Features a children's pool, an outdoor pool and 2 bars. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor swimming pools and 2 restaurants. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Provides 6 outdoor swimming pools, a children's pool and 3 restaurants. Rosen Inn at Pointe Orlando: Hotel, 14-minute walk from Orange County Convention Center. Features 2 coffee shops/cafes, 3 outdoor swimming pools and complimentary wireless Internet access. The Grove Resort & Water Park Orlando: Resort located near Flamingo Crossings Town Center. Offers 6 outdoor swimming pools, a children's pool and free water park access.
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.