Winter Park Hotels with Swimming Pool

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Park Hotels with Swimming Pools

Tonight
24 Feb - 25 Feb
Tomorrow
25 Feb - 26 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

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

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1,002 reviews)
  • cleanliness
    Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
The Alfond Inn
Water park

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area
4.0 star property
Orlando
8.2 out of 10, Very good, (5,912 reviews)
  • cleanliness
    Splash into aquatic paradise with 7 pools, a lazy river, and waterslides at this family resort.
The price is RM470
RM660 total
includes taxes & fees
25 Feb - 26 Feb
Westgate Lakes Resort & Spa Universal Studios Area
Outdoor pool, pool umbrellas, pool loungers

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1,562 reviews)
  • cleanliness
    Sun-kissed relaxation awaits at this poolside oasis with loungers and shade umbrellas.
The price is RM424
RM477 total
includes taxes & fees
25 Feb - 26 Feb
Hyatt House Orlando International Drive
3 outdoor pools, pool umbrellas, pool loungers

Calypso Cay Vacation Villas

Calypso Cay Vacation Villas
3.5 star property
Kissimmee
8.2 out of 10, Very good, (1,012 reviews)
Calypso Cay Vacation Villas
Outdoor pool, pool umbrellas, pool loungers

La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport
3.0 star property
Airport North
7.4 out of 10, Good, (1,351 reviews)
  • cleanliness
    Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.
The price is RM372
RM418 total
includes taxes & fees
2 Mar - 3 Mar
La Quinta Inn & Suites by Wyndham Orlando Airport
Outdoor pool, a heated pool, pool umbrellas, pool loungers

Universal's Endless Summer Resort - Surfside Inn and Suites

Universal's Endless Summer Resort - Surfside Inn and Suites
3.0 star property
International Drive District
9.4 out of 10, Exceptional, (2,370 reviews)
The price is RM549
RM617 total
includes taxes & fees
3 Mar - 4 Mar
Universal's Endless Summer Resort - Surfside Inn and Suites
Outdoor pool, open 6:00 AM to midnight, pool umbrellas, pool loungers

Rosen Centre Hotel

Rosen Centre Hotel
4.0 star property
International Drive District
9.0 out of 10, Wonderful, (4,311 reviews)
  • cleanliness
    Dive into poolside bliss at this luxury resort with 2 hot tubs and full-service spa to rejuvenate your senses.
The price is RM445
RM506 total
includes taxes & fees
4 Mar - 5 Mar
Rosen Centre Hotel
Outdoor pool, open 8:00 AM to 7:30 PM, pool umbrellas, pool loungers

Pestana Orlando Suites - Lake Buena Vista

Pestana Orlando Suites - Lake Buena Vista
4.0 star property
Orlando
9.4 out of 10, Exceptional, (2,145 reviews)
  • cleanliness
    Cool splash of paradise near Orlando theme parks, complete with sun loungers for the perfect pool day.
The price is RM401
RM499 total
includes taxes & fees
22 Mar - 23 Mar
Pestana Orlando Suites - Lake Buena Vista
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.
View all properties

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

Breakfast included
4 stars

Top Winter Park Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Staff was all really nice and helpful!!!"
Margarita 4-night trip
Posted 1 day ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Frequently asked questions

What are some accommodation options with pools in Winter Park?
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Condo resort located near Disney Springs™. Features 6 outdoor swimming pools, a children's pool and 3 restaurants. 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. DoubleTree by Hilton Orlando Theme Park Resort: Resort, 8-minute walk from Aquatica. Provides 2 outdoor swimming pools, a children's pool and 2 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. Marriott's Grande Vista: Condo resort located near Orange County Convention Center. Offers 4 outdoor swimming pools, a children's pool and 3 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.

Explore a world of travel with Expedia