TOP Hotels with Pool in Winter Park, FL for 2026

Q: What are some accommodation options with pools in Winter Park?

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando : Aparthotel located near Orlando Vineland Premium Outlets. Features 6 outdoor swimming 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 swimming 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 swimming 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

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

The Alfond Inn

Winter Park

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

฿11,090 total

includes taxes & fees

15 Jul - 16 Jul

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.

฿7,004 total

includes taxes & fees

3 Aug - 4 Aug

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.

฿5,618 total

includes taxes & fees

20 Jul - 21 Jul

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.

฿4,345 total

includes taxes & fees

20 Jul - 21 Jul

Wyndham Grand Orlando Resort Bonnet Creek

Orlando

Splash into aquatic bliss at this resort with 5 outdoor pools, a lazy river, and poolside cabanas.

฿6,937 total

includes taxes & fees

19 Jul - 20 Jul

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

Dive into a cool-down oasis with a spacious outdoor pool, hot tub, and poolside bar service.

฿5,253 total

includes taxes & fees

6 Aug - 7 Aug

Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

Vibrant pool oasis near Orlando Airport beckons travellers to dive in after a day exploring nearby attractions.

฿3,501 total

includes taxes & fees

19 Jul - 20 Jul

Outdoor pool, pool umbrellas, pool 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.

฿2,767 total

includes taxes & fees

20 Jul - 21 Jul

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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 accommodation options with pools in Winter Park?

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel located near Orlando Vineland Premium Outlets. Features 6 outdoor swimming 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 swimming 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 swimming 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 such as 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. Travellers 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 the local weather in Winter Park into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 28°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Park are August, September, July and June, with each month seeing an average of 185 mm 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. If you want to venture outside the area, take a train from Winter Park Station. Winter Park might not have many public transport options, so consider renting a car to explore more.

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