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 Disney Springs™. Features 6 outdoor swimming pools, a children's pool and 3 restaurants. Hyatt Regency Orlando International Airport : Offers 2 restaurants, an outdoor pool and complimentary wireless Internet access. Universal's Cabana Bay Beach Resort : Hotel, 5-minute walk from Universal Orlando Resort. Provides a lazy river, 2 outdoor swimming pools and 2 restaurants. Westgate Lakes Resort & Spa Universal Studios Area : Hotel located near The Orlando Eye. Features 7 outdoor swimming pools, a children's pool and a water park. Rosen Inn at Pointe Orlando : Hotel, 14-minute walk from Orange County Convention Center. Offers 2 coffee shops/cafes, 3 outdoor swimming pools and complimentary wireless Internet access.

Check availability on Winter Park Hotels with Pool

Tonight

Tomorrow

This weekend

Next weekend

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.

Rp5.791.705 total

includes taxes & fees

18 May - 19 May

Outdoor pool, open 8:00 AM to 9:00 PM, pool cabanas (surcharge)

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

International Drive District

Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.

Rp1.298.521 total

includes taxes & fees

13 May - 14 May

2 outdoor pools, pool umbrellas, pool loungers

Universal's Endless Summer Resort - Dockside Inn and Suites

Florida Center

Splash into a family adventure at Universal's Endless Summer Resort with 2 outdoor pools, loungers, and a refreshing poolside bar.

Rp2.629.917 total

includes taxes & fees

27 Apr - 28 Apr

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.

Rp3.369.388 total

includes taxes & fees

27 Apr - 28 Apr

Westgate Lakes Resort & Spa Universal Studios Area

Orlando

Splash into aquatic paradise with 7 pools, a lazy river, and waterslides at this family resort.

Rp2.465.472 total

includes taxes & fees

26 Apr - 27 Apr

Outdoor pool, pool umbrellas, pool loungers

Hyatt House Orlando International Drive

International Drive District

Sun-kissed relaxation awaits at this poolside oasis with loungers and shade umbrellas.

Rp2.127.138 total

includes taxes & fees

26 Apr - 27 Apr

Wyndham Garden Lake Buena Vista – Disney Springs® Area

Lake Buena Vista

Splash into family-friendly fun with 2 outdoor pools and a poolside bar at this Disney Springs resort.

Rp2.413.336 total

includes taxes & fees

21 Apr - 22 Apr

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.

Rp2.045.533 total

includes taxes & fees

27 Apr - 28 Apr

View all properties

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

Breakfast included

4 stars

Top Winter Park Hotel Reviews

Ramada by Wyndham Suites Orlando Airport

8/10 Good

"Room was big, comfortable and quiet. Restaurants are walking distance. Airport shuttle was great. No complaints for a one night stay."

Westgate Lakes Resort & Spa Universal Studios Area

4/10 Poor

"The staff was extremely friendly and courteous when I arrived and remained very helpful throughout my stay. The facility I found to be very old in decor and in need of serious upgrade. The room had torn and very worn out furniture, but the bathroom and shower were clearly updated and very nice. The elevator was very dirty and remained so throughout. The adult only pool was nice until a ton of kids came and the adult only was never enforced. I did like the boardwalk to the small island hut and I spent my mornings there enjoying the beautiful view and the lake view. The facility is a member owned facility and not nearly as nice as others I have stayed out. Again, cleanliness has a lot to be desired and it badly needs a refresh."

Drury Plaza Hotel Orlando - Disney Springs Area

8/10 Good

"First time staying at the drury inn and it was a great experience! Pros it offers a happy hour with food and feee drinks! Pool is very nice and offers towels for use. The staff was very nice and answered all our questions. They offer free bus to Disney and early entry as well! A great experience!"

Frequently asked questions

What are some accommodation options with pools in Winter Park?

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel located near Disney Springs™. Features 6 outdoor swimming pools, a children's pool and 3 restaurants. Hyatt Regency Orlando International Airport: Offers 2 restaurants, an outdoor pool and complimentary wireless Internet access. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Provides a lazy river, 2 outdoor swimming pools and 2 restaurants. Westgate Lakes Resort & Spa Universal Studios Area: Hotel located near The Orlando Eye. Features 7 outdoor swimming pools, a children's pool and a water park. Rosen Inn at Pointe Orlando: Hotel, 14-minute walk from Orange County Convention Center. Offers 2 coffee shops/cafes, 3 outdoor swimming pools and complimentary wireless Internet access.

What is there to see and do in Winter Park?

Explore places such as Universal Studios Florida, Universal Orlando Resort and Universal's Volcano Bay while you're in the area. Spend some time experiencing the great outdoors at Kraft Azalea Gardens and Lake Virginia. 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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Winter Park Hotels with Pool