Seeking an upscale villa rental in Winnetka? Browse our curated index of private luxury estates, complete with spacious floorplans and premium amenities. Easily compare verified listings for a truly refined holiday escape.
Pool, Air Conditioner, View, Internet, Fireplace/Heating, Sports/Activities, Security/Safety
AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater
Exceptional
38 reviews
Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals
Superb
12 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub
Exceptional
22 reviews
Parking, Pool, Balcony/Terrace, View, Guest Services, Internet, Security/Safety
AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking
Exceptional
9 reviews
Pet Friendly, Kitchen, Laundry, Breakfast, Pool, Internet, Wheelchair Accessible
Exceptional
3 reviews
AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet
Review score
1 reviews
Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay
Exceptional
4 reviews
AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Laundry, No Smoking
Exceptional
1 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Onsen, Lodgings
AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet
Exceptional
21 reviews
Air Conditioner, Internet, Parking, Child Friendly
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen
Exceptional
1 reviews
Air Conditioner, Kitchen, Internet, Parking, Child Friendly
AC, Dryer, Fireplace, Heater, Kitchen, Laundry, No Smoking, Patio, Washer
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet
Exceptional
3 reviews
AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer
AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking
Exceptional
1 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
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 Villa Rentals 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 villa rentals stand out?
Every villa rentals 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 villa rentals 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 Villa Rentals in Winnetka
You can currently explore 44 verified villa rentals in Winnetka. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.
Villa prices in Winnetka vary depending on the season, location, and amenities. Rates typically start from around $212 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.
Many villas in Winnetka are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Winnetka.
Yes, Winnetka offers a wide range of villas ideal for group stays. Many properties include 6 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.
For popular travel periods, it’s generally recommended to book your Winnetka villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.
Villas in Winnetka often include highly sought-after amenities such as Fireplace/Heating, Laundry, and Balcony/Terrace. These features enhance comfort and convenience, making them especially popular among travelers visiting Winnetka.
To discover top-rated villas in Winnetka, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the 'Rating' filter above to start your search.