Winnetka rentals with pool

We found 397 rentals with pool — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a holiday home with a pool in Winnetka?
A number of factors will influence the price of a holiday home with a pool in Winnetka, such as the size of the property and when and how long you plan to stay. All you have to do is enter your holiday dates and any preferences to find a house where you can have a splashing great time.
When is the best time to book a holiday home with a pool in Winnetka?
Our holiday homes with a pool in Winnetka experience the highest number of bookings in May. Expect average temperatures of between 10 ºC (10ºC) and 17 ºC (17ºC) if you want to visit this corner of North Suburbs then. If availability is limited in May, explore possibilities in the months before and after.
What holiday homes with a pool in Winnetka have nice views?
Relaxing is effortless at our holiday homes with a pool in Winnetka. Take a dip in the water or just take in the outlooks. Tailor your search by "Guest rating" or "Recommended" to discover exceptional properties where you can lose yourself in the incredible scenery as your worries float away.