Search Hotels with Pool in Winter Park

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Check availability on Winter Park Hotels with Pool

Tonight
26 Feb - 27 Feb
Tomorrow
27 Feb - 28 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, (1,000 reviews)
  • cleanliness
    Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
The Alfond Inn
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, (1,006 reviews)
Calypso Cay Vacation Villas
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, (4,309 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 ฿3,557
฿4,042 total
includes taxes & fees
12 Mar - 13 Mar
Rosen Centre Hotel
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, (1,565 reviews)
  • cleanliness
    Sun-kissed relaxation awaits at this poolside oasis with loungers and shade umbrellas.
The price is ฿3,822
฿4,300 total
includes taxes & fees
22 Mar - 23 Mar
Hyatt House Orlando International Drive
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, (1,366 reviews)
  • cleanliness
    Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.
The price is ฿2,958
฿3,328 total
includes taxes & fees
3 Mar - 4 Mar
La Quinta Inn & Suites by Wyndham Orlando Airport
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, (953 reviews)
  • cleanliness
    Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.
The price is ฿2,948
฿3,317 total
includes taxes & fees
22 Mar - 23 Mar
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, a heated pool, pool umbrellas, pool loungers

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
Orlando
8.4 out of 10, Very good, (3,778 reviews)
  • cleanliness
    Splashy lakeside retreat with two hot tubs and a poolside tiki bar for carefree family fun in the Florida sun.
The price is ฿2,212
฿3,538 total
includes taxes & fees
2 Mar - 3 Mar
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Aerial view

Wyndham Garden Lake Buena Vista – Disney Springs® Area

Wyndham Garden Lake Buena Vista – Disney Springs® Area
3.5 star property
Lake Buena Vista
8.2 out of 10, Very good, (3,996 reviews)
  • cleanliness
    Splash into family-friendly fun with 2 outdoor pools and a poolside bar at this Disney Springs resort.
The price is ฿2,933
฿4,558 total
includes taxes & fees
1 Mar - 2 Mar
Wyndham Garden Lake Buena Vista – Disney Springs® Area
Outdoor pool

Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
3.0 star property
Airport North
9.4 out of 10, Exceptional, (2,538 reviews)
  • cleanliness
    Vibrant pool oasis near Orlando Airport beckons travellers to dive in after a day exploring nearby attractions.
The price is ฿4,051
฿4,558 total
includes taxes & fees
2 Mar - 3 Mar
Hampton Inn & Suites Orlando Airport @ Gateway Village
2 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas

Wyndham Lake Buena Vista – Disney Springs® Area

Wyndham Lake Buena Vista – Disney Springs® Area
4.0 star property
Lake Buena Vista
8.8 out of 10, Excellent, (2,801 reviews)
  • cleanliness
    Float in paradise with 2 dreamy outdoor pools offering sun-soaked fun and cabana luxury.
The price is ฿3,856
฿5,597 total
includes taxes & fees
2 Mar - 3 Mar
Wyndham Lake Buena Vista – Disney Springs® Area
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.
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Choose what matters most at hotels with a pool in Winter Park

Breakfast included
4 stars

Top Winter Park Hotel Reviews

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Amazing perfect location "
Sean 3-night trip
Posted 14 hours ago
Rosen Inn at Pointe 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.