Hotels with Pool & Resorts in Winter Park

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Winter Park Hotels with Pool

Tonight
26 Jul - 27 Jul
Tomorrow
27 Jul - 28 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Best Winter Park Hotels with Pool

The Alfond Inn
Outdoor pool, open 10:00 AM to 5:00 PM, pool umbrellas, pool loungers

The Alfond Inn

4.0 star property
9.4 out of 10, Exceptional, (1012)
"Hotel was great location was great. The only thing I recommend is the lack of chairs by the
pool
. "
Erik
The Alfond Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Winter Park Hotel Reviews

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Close to restaurants and bars within walking distance!"
John 1-night trip
Posted 15 hours ago
Rosen Inn at Pointe Orlando

Frequently asked questions

What's it like visiting Winter Park?
If lounging by a pool is your idea of the perfect getaway, you may want to consider Winter Park, which has 8 places to stay with pools. During your trip, you can explore sights such as Universal Studios Florida and Universal Orlando Resort, and then take it easy poolside at one of the accommodation options in Winter Park that guests like for their pools.
What are some accommodation options with pools in Winter Park?
Hyatt Regency Orlando International Airport: Features 2 restaurants, an outdoor pool and complimentary wireless Internet access. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 2-minute walk from Universal Orlando Resort. Offers a children's pool, an outdoor pool and 2 restaurants. Marriott's Grande Vista: Hotel located near Aquatica. Provides 4 outdoor swimming pools, a children's pool and 3 restaurants. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor swimming pools and 2 restaurants. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Offers 6 outdoor swimming pools, a children's pool and 3 restaurants.
How many pool hotels can I expect to find in Winter Park?
Expedia has 8 hotels in Winter Park for your poolside break.
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 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.