Find Hotels with a Pool in Winter Park, FL

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Check availability on Winter Park Hotels with a Pool

Our top choices for Winter Park hotels with a pool

2 outdoor pools, open 10:00 AM to 5:00 PM, cabanas (surcharge)
The Alfond Inn

The Alfond Inn

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1,000 reviews)
"Location was great, friendly staff, beautiful hotel."
United States
Jessica
The Alfond Inn
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, (1,461 reviews)
"Great place to stay and great amenities"
United States
Darshan
The price is ₩217,366
₩244,537 total
includes taxes & fees
Jan 26 - Jan 27
Hyatt House Orlando International Drive
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

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
International Drive District
8.6 out of 10, Excellent, (827 reviews)
"Location cannot be better; very clean place; helpful staff; substantial breakfast "
Canada
Leonid
The price is ₩135,927
₩152,918 total
includes taxes & fees
Feb 9 - Feb 10
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
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, (1,944 reviews)
"Super nice hotel at a great price."
United States
Terry
The price is ₩120,433
₩135,488 total
includes taxes & fees
Jan 25 - Jan 26
Aloft Orlando Lake Buena Vista
3 outdoor pools, a heated pool, cabanas (surcharge), pool umbrellas
Caribe Royale Orlando

Caribe Royale Orlando

Caribe Royale Orlando
4.5 star property
Orlando
9.2 out of 10, Wonderful, (4,590 reviews)
"Awesome resort, we visit at least 3 times a year. "
United States
Eric
The price is ₩178,005
₩263,042 total
includes taxes & fees
Jan 16 - Jan 17
Caribe Royale Orlando
Outdoor banquet area
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4,378 reviews)
"Very nice place to stay with family. "
United States
Anick
The price is ₩176,131
₩198,147 total
includes taxes & fees
Jan 23 - Jan 24
Rosen Shingle Creek
6 outdoor pools, free cabanas, pool umbrellas
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
Orlando
9.2 out of 10, Wonderful, (4,317 reviews)
"Great stay!"
Canada
Sylvie
The price is ₩175,068
₩196,951 total
includes taxes & fees
Feb 3 - Feb 4
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 Winter Park Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Great property for the holidays"
Francesca 1-night trip
Posted 10 hours ago
Universal's Cabana Bay Beach Resort

Frequently asked questions

What are some accommodations with pools in Winter Park?
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, 14-minute walk from Orange County Convention Center. Provides 2 coffee shops/cafes, 3 outdoor pools, and complimentary wireless internet access. DoubleTree by Hilton Hotel Orlando at SeaWorld: Resort, 8-minute walk from Aquatica. Features 2 outdoor pools, a children's pool, and 2 restaurants. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Offers 6 outdoor pools, a children's pool, and 3 restaurants.
What is there to see and do in Winter Park?
Explore places like Universal Studios Florida, Universal Orlando Resort, and Walt Disney World® Resort while you're in the area. Spend some time experiencing the great outdoors at Kraft Azalea Gardens and Lake Virginia. Travelers love Winter Park for its array of dining options.
When is the best time to book a hotel with a pool in Winter Park?
Taking into account the local weather in Winter Park can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Park are August, September, July, and June, with each month seeing an average of 7 inches of rainfall.
What's the best way to travel around Winter Park?
Knowing the transportation options in Winter Park can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Winter Park Station. Winter Park might not have very many public transit choices so consider renting a car to explore more.