Hotels with a Pool in Winter Park

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
Feb 25 - Feb 26
Tomorrow
Feb 26 - Feb 27
This weekend
Feb 28 - Mar 2
Next weekend
Mar 7 - Mar 9

Hotels with a Pool in Winter Park

Silverado II Resort & Event Center
Indoor spa tub

Silverado II Resort & Event Center

3.5 star property
8.2 out of 10, Very Good, (150)
Silverado II Resort & Event Center
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 neighborhoods in Winter Park

Get a lay of the land and find the perfect place to stay
Default Image

Bear Crossing

The Bear Crossing neighborhood offers attractions such as Winter Park Ski Resort and Saint Mary's Glacier.

See properties in Bear Crossing
Bear Crossing

Top landmarks in Winter Park

Winter Park Ski Resort featuring snow skiing, forests and snow

Winter Park Ski Resort

Skiers and snowboarders might want to test out the slopes at Winter Park Ski Resort, a top skiing spot located 3.7 mi (5.9 km) from central Winter Park. It also offers winter sports like snowboarding and is great for fun activities like horseback riding.

See properties in Winter Park Ski Resort
Winter Park Ski Resort

Frequently asked questions

What are the best hotels with a pool in Winter Park?
With a dining venue, WiFi and the perfect setting for lounging by the water, The Vintage Hotel is recommended by travelers. Winter Park Mountain Lodge is another highly rated Winter Park hotel with a pool.
What are the cheapest hotels with a pool in Winter Park?
Choose one of the cheap hotels in Winter Park with a pool and have more fun for less. Just sort by “Price: low to high,” then fine-tune your search by setting the maximum amount you want to pay. To earn discounts on future trips, be sure to join One Key™, our rewards program.
What is the best time to stay in a hotel with a pool in Winter Park?
July is the warmest month, with temperatures ranging from 45ºF (7ºC) to 72ºF (22ºC). December has the coolest weather. It’s usually between 7ºF (-14ºC) and 25ºF (-4ºC) then. May is the ideal month to enjoy a more relaxed pace and potentially find cheaper Winter Park hotels with a pool.
What hotels with a pool are closest to Trestle Bike Park?
Do some sightseeing and then lounge poolside at The Vintage Hotel. Offering a dining venue and a picnic area, this property is a quick drive from Trestle Bike Park. Winter Park Mountain Lodge is another option nearby. Browse the range of hotels in Winter Park with a pool that’ll put you near this popular attraction.
Are there any hotels with a pool in Winter Park with parking?
There are 2,334 Winter Park hotels with a pool and parking. Book a room at The Vintage Hotel, which has a dining venue and a picnic area. Winter Park Mountain Lodge also combines the ease of parking with the perks of a pool.