Enjoy an upgraded stay with total privacy in Winnetka. Browse exclusive villas and vacation homes equipped with individual, private swimming facilities. Compare verified options on Owner Direct for a peaceful, secluded getaway.
Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals
Superb
12 reviews
AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet
Good
4 reviews
Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis
Fabulous
3 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
AC, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry
Exceptional
13 reviews
AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater
Exceptional
38 reviews
AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
10 reviews
AC, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area
Exceptional
7 reviews
AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave
Superb
15 reviews
AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet
Exceptional
26 reviews
AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave
AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
13 reviews
AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking
AC, Arcade, Balcony, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Kitchen
Exceptional
1 reviews
AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub
Exceptional
22 reviews
AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry
Exceptional
1 reviews
AC, Dryer, Laundry, Patio, Pool, Washer
AC, Balcony, Barbecue, Dryer, Heater, Hot Tub, Internet, Laundry, Living Area
Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Winnetka.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our vacation rentals with private pool stand out?
Every vacation rentals with private pool shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best vacation rentals with private pool in Winnetka are:
There are a lot of options in Winnetka. If you plan on staying in the Winnetka area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals wint Private Pool in Winnetka
You can explore 103 verified vacation rentals with a private pool in Winnetka. These include standalone villas and private homes where the pool is reserved exclusively for your group.
Prices for rentals with a private pool in Winnetka vary depending on the property size, location, and travel season. Rates typically start from around $175 per night, with higher prices for larger homes, prime locations, or peak travel periods.
Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.
Yes, some vacation rentals with private pools in Winnetka also welcome pets. Currently, 33 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.
Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.
Vacation rentals with private pools in Winnetka often include additional features such as Pool, Private Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.
Some family-friendly vacation rentals in Winnetka include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.