Hotels with Swimming Pools in Winter Park

  • 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
6 Feb - 7 Feb
Tomorrow
7 Feb - 8 Feb
This weekend
6 Feb - 8 Feb
Next weekend
13 Feb - 15 Feb

Our top choices for Winter Park hotels with a pool

Exterior

gorgeous property at winter park -118

gorgeous property at winter park -118
2.0 star property
Winter Park
The price is S$389
includes taxes & fees
3 Mar - 4 Mar
gorgeous property at winter park -118
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, (1,001 reviews)
  • cleanliness
    Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
The Alfond Inn
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, (1,509 reviews)
  • cleanliness
    Sun-kissed relaxation awaits at this poolside oasis with loungers and shade umbrellas.
The price is S$170
includes taxes & fees
8 Feb - 9 Feb
Hyatt House Orlando International Drive
Outdoor pool, open 8:00 AM to 9:00 PM, pool cabanas (surcharge)

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
International Drive District
8.4 out of 10, Very good, (902 reviews)
  • cleanliness
    Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.
The price is S$147
includes taxes & fees
22 Feb - 23 Feb
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas

Caribe Royale Orlando

Caribe Royale Orlando
4.5 star property
Orlando
9.2 out of 10, Wonderful, (4,692 reviews)
  • cleanliness
    Dive into serene luxury with 3 refreshing outdoor pools, cabana service, and a water slide in a family-friendly resort oasis.
The price is S$234
includes taxes & fees
8 Feb - 9 Feb
Caribe Royale Orlando
4 outdoor pools, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)

Marriott's Grande Vista

Marriott's Grande Vista
4.0 star property
Orlando
9.0 out of 10, Wonderful, (3,858 reviews)
The price is S$205
includes taxes & fees
4 Mar - 5 Mar
Marriott's Grande Vista
Outdoor pool, pool umbrellas, pool loungers

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
Orlando
8.8 out of 10, Excellent, (1,962 reviews)
  • cleanliness
    Splash into a sun-drenched poolside paradise at this Disney-adjacent hotel with lounger service.
The price is S$129
includes taxes & fees
8 Feb - 9 Feb
Aloft Orlando 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

Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Excellent ⭐️⭐️⭐️⭐️⭐️"
Sharlyn 3-night trip
Posted 1 day ago
Marriott's Grande Vista

Frequently asked questions

What are some accommodation options with pools in Winter Park?
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Features 6 outdoor swimming pools, a children's pool and 3 restaurants. DoubleTree by Hilton Orlando Theme Park Resort: Resort, 8-minute walk from Aquatica. Offers 2 outdoor swimming pools, a children's pool and 2 restaurants. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 3-minute walk from Universal Orlando Resort. Provides a children's pool, an outdoor pool and 2 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. Wyndham I-Drive Avanti Resort & Conference Center: Hotel, 7-minute walk from CoCo Key Water Resort. Offers a children's pool, an outdoor pool and 2 bars.
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