The Best Hotels with a Pool in Winter Park, FL from ₩117,546 in 2026

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando : Aparthotel located near Orlando Vineland Premium Outlets. Features 6 outdoor pools, a children's pool, and 3 restaurants. Universal's Cabana Bay Beach Resort : Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, and 2 restaurants. Avanti International Resort : Hotel, 11-minute walk from The Orlando Eye. Provides a children's pool, a seasonal outdoor pool, and a snack bar/deli. Rosen Inn Lake Buena Vista : Hotel located near Disney Springs™. Features 2 outdoor pools, a children's pool, and a snack bar/deli. Hyatt Regency Orlando International Airport : Offers 2 restaurants, an outdoor pool, and complimentary wireless internet access.

A two-story house with a balcony, surrounded by lush greenery and trees.

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Our top choices for Winter Park hotels with a pool

Outdoor pool, open 9:00 AM to 9:00 PM, sun loungers

Palazzo Lakeside Hotel

Kissimmee

Splash into lakeside bliss with an inviting outdoor pool surrounded by sun loungers and scenic views.

₩92,354 total

includes taxes & fees

Jul 19 - Jul 20

Outdoor pool, open 9 AM to 10 PM, sun loungers

Orlando Palms Hotel

Orlando

Dive into the cool waters of this Florida oasis, just steps from your comfy poolside lounger.

₩80,686 total

includes taxes & fees

Aug 11 - Aug 12

Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room

Universal's Cabana Bay Beach Resort

Florida Center

Dive into double the fun with 2 outdoor pools, hot tubs, and a lazy river paradise.

₩252,933 total

includes taxes & fees

Jul 20 - Jul 21

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.

₩195,601 total

includes taxes & fees

Jul 20 - Jul 21

Outdoor pool, pool umbrellas, sun loungers

La Quinta Inn & Suites by Wyndham Orlando Airport

Airport North

Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.

₩117,546 total

includes taxes & fees

Jul 16 - Jul 17

Hyatt Regency Orlando International Airport

Orlando

Tropical poolside oasis at an airport hotel offers relaxing moments surrounded by sunshine, just steps away from departure gates.

₩315,330 total

includes taxes & fees

Aug 3 - Aug 4

Ramada by Wyndham Suites Orlando Airport

Airport North

Poolside paradise awaits with sun loungers, umbrellas, and a refreshing outdoor oasis.

₩133,549 total

includes taxes & fees

Jul 13 - Jul 14

Wingate by Wyndham - Orlando International Airport

Airport North

Refreshing outdoor pool oasis with sun loungers offers relaxation after exploring nearby shopping and dining options.

₩135,078 total

includes taxes & fees

Jul 13 - Jul 14

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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

Hyatt Regency Orlando International Airport

10/10 Excellent

"So clean, I really enjoyed my stay!!"

Lake Buena Vista Resort Village & Spa

10/10 Excellent

"Loved the condo and spa services. Did have to talk with a lady trying to sell time shares. She was nice until I declined and had to decline multiple times, she was very pushy. After about the 4th time I politely declined the time share meeting she became very rude and short. I was no longer anyone she wanted to have in her presence. I’m just glad I didn’t have to deal with her long, I probably would have looked for another place to stay had that been the case."

Frequently asked questions

What are some accommodations with pools in Winter Park?

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel located near Orlando Vineland Premium Outlets. Features 6 outdoor pools, a children's pool, and 3 restaurants. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, and 2 restaurants. Avanti International Resort: Hotel, 11-minute walk from The Orlando Eye. Provides a children's pool, a seasonal outdoor pool, and a snack bar/deli. Rosen Inn Lake Buena Vista: Hotel located near Disney Springs™. Features 2 outdoor pools, a children's pool, and a snack bar/deli. Hyatt Regency Orlando International Airport: Offers 2 restaurants, an outdoor pool, and complimentary wireless internet access.

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 Albin Polasek Museum and Sculpture Gardens and Kraft Azalea 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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