The Best Hotels with a Pool in Winter Park, FL from NT$2,812 in 2026

Q: What are some accommodations with pools in Winter Park?

Hyatt Regency Orlando International Airport : Features 2 restaurants, an outdoor pool, and complimentary wireless internet access. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando : Aparthotel located near Orlando Vineland Premium Outlets. Offers 6 outdoor pools, a children's pool, and 3 restaurants. DoubleTree by Hilton at the Entrance to Universal Orlando : Hotel, 3-minute walk from Universal Orlando Resort. Provides a children's pool, an outdoor pool, and 2 restaurants. Rosen Inn Lake Buena Vista : Hotel located near Disney Springs™. Features 2 outdoor pools, a children's pool, and a snack bar/deli. Universal's Cabana Bay Beach Resort : Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, and 2 restaurants.

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Our top choices for Winter Park hotels with a pool

The Alfond Inn

Winter Park

Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.

NT$10,756 total

includes taxes & fees

Aug 3 - Aug 4

Outdoor pool, open 6:00 AM to 11:00 PM, pool umbrellas, sun loungers

Courtyard by Marriott Orlando Downtown

Ivanhoe Village

Float in sunshine at downtown Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.

NT$4,446 total

includes taxes & fees

Jul 31 - Aug 1

Comfort Suites Downtown

Ivanhoe Village

Make a splash in downtown Orlando with this hotel's seasonal outdoor pool and relaxing hot tub for post-exploration recovery.

NT$4,054 total

includes taxes & fees

Aug 16 - Aug 17

Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers

Hilton Orlando/Altamonte Springs

Altamonte Springs

Sink into pure bliss at this outdoor pool with loungers for a refreshing Florida getaway.

NT$4,132 total

includes taxes & fees

Aug 2 - Aug 3

La Quinta Inn & Suites by Wyndham Orlando UCF

Orlando

Sun-soaked outdoor pool offers refreshing escapes and hot tub relaxation near the University of Central Florida campus.

NT$3,233 total

includes taxes & fees

Aug 2 - Aug 3

Hyatt House Orlando Airport

Airport North

Refreshing outdoor pool sanctuary awaits near Florida Mall, with a firepit and poolside lounging for a sunny getaway experience.

NT$4,141 total

includes taxes & fees

Aug 11 - Aug 12

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Choose what matters most at hotels with a pool in Winter Park

Breakfast included

4 stars

Top Winter Park Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Nice hotel very clean."

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"I was quite impressed with the service, location, amenities and shuttle service provided by this hotel. First time staying at a Drury hotel and won't be my last. Front desk was very helpful checking us in and getting room connected to the Disney app for early entry, enjoyed the snack hour and especially appreciated the convenient shuttle service, even one of the drivers provided me water while I waited for the other shuttle to arrive....THANK YOU. Great stay overall."

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent

"We had a great stay and would definitely come back! For the price, this resort was a great value. We weren’t expecting a luxury five-star resort, so the minor cosmetic issues in our room, like scratches on the floor and a loose bathroom vanity door, didn’t affect our stay. Everything worked as it should. One of the elevators in our building was out of service, so we had to use the one at the other end of the building. It was a little inconvenient but not a dealbreaker. The amenities were definitely the highlight. There was so much to do that we could have easily spent another day just enjoying the resort. Overall, it’s a fun, family-friendly place with plenty to offer. If you come with realistic expectations for the price, I think you’ll be pleasantly surprised. We’d definitely stay here again!"

Frequently asked questions

What are some accommodations with pools in Winter Park?

Hyatt Regency Orlando International Airport: Features 2 restaurants, an outdoor pool, and complimentary wireless internet access. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel located near Orlando Vineland Premium Outlets. Offers 6 outdoor pools, a children's pool, and 3 restaurants. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 3-minute walk from Universal Orlando Resort. Provides a children's pool, an outdoor pool, and 2 restaurants. Rosen Inn Lake Buena Vista: Hotel located near Disney Springs™. Features 2 outdoor pools, a children's pool, and a snack bar/deli. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, and 2 restaurants.

What is there to see and do in Winter Park?

Explore places like Kia Center, Universal Studios Florida, and Universal Orlando Resort while you're in the area. Spend some time experiencing the great outdoors at Lake Virginia and Albin Polasek Museum and Sculpture Gardens. 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.

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