TOP Hotels with Pool in Winter Park, FL for 2026

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

Wyndham I-Drive Avanti Resort & Conference Center : Hotel, 7-minute walk from CoCo Key Water Resort. Features a children's pool, an outdoor pool and 2 bars. 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. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando : Hotel located near Disney Springs™. Provides 6 outdoor swimming pools, a children's pool and 3 restaurants. Rosen Inn at Pointe Orlando : Hotel, 14-minute walk from Orange County Convention Center. Features 2 coffee shops/cafes, 3 outdoor swimming pools and complimentary wireless Internet access. DoubleTree by Hilton at the Entrance to Universal Orlando : Hotel, 3-minute walk from Universal Orlando Resort. Offers a children's pool, an outdoor pool and 2 restaurants.

Kraft Azalea Gardens showing a fountain, a park and a pond

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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

Jessica

Rp6.760.664 total

includes taxes & fees

29 Jan - 30 Jan

Outdoor pool, pool umbrellas, pool loungers

Hyatt House Orlando International Drive

International Drive District

Darshan

Rp2.260.747 total

includes taxes & fees

25 Jan - 26 Jan

3 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas

Caribe Royale Orlando

Orlando

Matthew

Rp3.275.065 total

includes taxes & fees

23 Jan - 24 Jan

Aloft Orlando Lake Buena Vista

Orlando

Terry

Rp1.557.827 total

includes taxes & fees

25 Jan - 26 Jan

Rosen Shingle Creek

Orlando

Anick

Rp2.264.547 total

includes taxes & fees

23 Jan - 24 Jan

Red Lion Hotel Orlando Lake Buena Vista South

Kissimmee

Raymond

Rp1.435.779 total

includes taxes & fees

20 Jan - 21 Jan

6 outdoor pools, free pool cabanas, pool umbrellas

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Orlando

Sylvie

Rp2.188.554 total

includes taxes & fees

9 Feb - 10 Feb

View all properties

Top Winter Park Hotel Reviews

Rosen Inn at Pointe Orlando

10/10 Excellent

"They were always accommodating "

Hyatt Regency Orlando

10/10 Excellent

"The woman at the check in counter was super friendly. The room was super clean. I stayed in tower Two and had one of my best nights of sleep I have ever had in a hotel. The bed was amazing and the bathroom was large and spacious. The lady that cleaned the room on my floor was so nice and kind and wished me a good morning. I was so impressed with everything "

Universal's Cabana Bay Beach Resort

10/10 Excellent

"Great shrimp tacos and chicken tenders, family enjoyed their quesadillas too. Stayed in Americana building 6 with Volcano Bay view, beautiful and clean. Facilities gates were hard to open with hotel key, family could not get several gates open throughout stay which was frustrating. Others also having issues. Walking path to city walk convenient. Housekeeping came every other day to just make beds and give more towels and coffee. Didn’t get more wash cloths second time they came. Poolside great, lots of towels too out there and chairs. "

Frequently asked questions

What are some accommodation options with pools in Winter Park?

Wyndham I-Drive Avanti Resort & Conference Center: Hotel, 7-minute walk from CoCo Key Water Resort. Features a children's pool, an outdoor pool and 2 bars. 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. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Provides 6 outdoor swimming pools, a children's pool and 3 restaurants. Rosen Inn at Pointe Orlando: Hotel, 14-minute walk from Orange County Convention Center. Features 2 coffee shops/cafes, 3 outdoor swimming pools and complimentary wireless Internet access. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 3-minute walk from Universal Orlando Resort. Offers a children's pool, an outdoor pool and 2 restaurants.

What is there to see and do in Winter Park?

Explore places such as 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. 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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