Best Vacation Homes in Winnetka
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
607 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
AU $322/Night
7 Nights - AU $2,250
House
9.4(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
75.35 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Kitchen
AU $257/Night
7 Nights - AU $1,796
AU $251/Night
7 Nights - AU $1,755
House
10.0(1 Review)
3 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $877/Night
7 Nights - AU $6,138
House
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Parking
AU $177/Night
7 Nights - AU $1,241
House
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
Air Conditioner
Internet
Laundry
AU $401/Night
7 Nights - AU $2,810
Bed & Breakfast
1 Bedroom
1 Bath
3 Guests
Hot Tub- Fireplace/Heating
- Kitchen
- Parking
AU $228/Night
7 Nights - AU $1,599
Winnetka Luxury Rentals
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
7559 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
AU $1,125/Night
7 Nights - AU $7,875
House
3 Bedrooms
2 Baths
9 Guests
1216.32 ft²
Pool
Breakfast- Parking
- Air Conditioner
AU $911/Night
7 Nights - AU $6,374
House
9.6(50 Reviews)
4 Bedrooms
2 Baths
10 Guests
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $752/Night
7 Nights - AU $5,267
House
8.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $643/Night
7 Nights - AU $4,499
House
8.8(17 Reviews)
4 Bedrooms
2 Baths
16 Guests
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
AU $637/Night
7 Nights - AU $4,459
New
House
3 Bedrooms
2 Baths
6 Guests
1300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $616/Night
7 Nights - AU $4,312
House
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $603/Night
7 Nights - AU $4,223
House
1 Bedroom
2 Baths
10 Guests
1500 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $578/Night
7 Nights - AU $4,042
Winnetka Pet Friendly Vacation Rentals
House
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $202/Night
7 Nights - AU $1,411
New
House
1 Bedroom
2 Baths
10 Guests
1679.17 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
AU $430/Night
7 Nights - AU $3,007
House
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
AU $189/Night
7 Nights - AU $1,325
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $185/Night
7 Nights - AU $1,292
House
4 Bedrooms
3 Baths
8 Guests
2100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $443/Night
7 Nights - AU $3,101
House
4 Bedrooms
3 Baths
8 Guests
2100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $400/Night
7 Nights - AU $2,801
House
3 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $242/Night
7 Nights - AU $1,695
Apartment
8.0(1 Review)
1 Bedroom
1 Bath
4 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $203/Night
7 Nights - AU $1,422
Winnetka Large Vacation Homes
House
1.0(1 Review)
4 Bedrooms
2 Baths
12 Guests
1533 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
AU $607/Night
7 Nights - AU $4,252
House
5 Bedrooms
4 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
AU $828/Night
7 Nights - AU $5,799
Villa
3 Bedrooms
2 Baths
7 Guests
1800 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
AU $558/Night
7 Nights - AU $3,904
House
1 Bedroom
3 Baths
10 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $1,467/Night
7 Nights - AU $10,269
House
5 Bedrooms
3 Baths
14 Guests
- Private Pool
- Pool
- Pet Friendly
- Kitchen
AU $879/Night
7 Nights - AU $6,156
House
4 Bedrooms
2 Baths
10 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $539/Night
7 Nights - AU $3,776
Why Choose Rent By Owner for your Winnetka Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Winnetka
When should you plan your Vacation Rentals stay?
Finding the ideal time to visit here can enhance your experience, allowing you to enjoy this destination's best weather and local atmosphere during your stay.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you can enjoy longer daylight hours and pleasant weather in this destination, making it ideal for outdoor activities and exploring the area.
Average Temperature Daytime: around 85°F - Nighttime: around 60°F
Fall (September to November)
Fall offers a mild climate with comfortable temperatures, providing a great atmosphere for sightseeing and relaxing stays in the region's vacation rentals.
Average Temperature Daytime: around 75°F - Nighttime: around 55°F
Off-Season Highlights
Winter (December to February)
Winter is the quietest season here, with cooler temperatures that are perfect if you prefer a peaceful getaway away from the crowds in cozy vacation rentals.
Average Temperature Daytime: around 65°F - Nighttime: around 45°F
Spring (March to May)
Spring brings mild weather and blooming scenery, offering a less busy but equally beautiful time to visit and find excellent deals on vacation rentals.
Average Temperature Daytime: around 70°F - Nighttime: around 50°F
Weekly Weather Forecast for Winnetka
How to Book Your Winnetka Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winnetka
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- You can enjoy a private outdoor swimming pool to relax and unwind in the sunshine.
- Many properties feature spacious patios or decks, perfect for outdoor dining or entertaining guests.
- Look for units with lush, landscaped gardens that add natural beauty and privacy to your stay.
- Some rentals offer outdoor fire pits, ideal for cozy evenings under the stars.
- Impressive courtyard areas may provide inviting seating spaces for socializing or quiet reflection.
- Expect well-maintained backyard lawns suitable for outdoor activities or family games.
- Nearby outdoor amenities often include scenic walking paths or garden areas, enhancing your connection with nature during your visit here.
Top Attractions Around Winnetka
What attractions are nearby?
In this destination, you can enjoy outdoor activities such as hiking and nature walks in nearby parks, explore local community events, or experience the vibrant culture that the region has to offer, all conveniently accessible from your chosen vacation rentals.
Family Activities
- Woodley Park: You can enjoy a family picnic and open-air activities at this scenic park, perfect for relaxing outings in the area.
- Skirball Cultural Center: Explore engaging cultural exhibits and participate in educational programs suited for children and families seeking enriching experiences nearby.
- The Village at Topanga: Discover a variety of family-friendly dining, shopping, and entertainment options just a short drive from your vacation rental here.
- Topanga State Park: Embark on hiking adventures amidst natural beauty that offers breathtaking views and outdoor fun for all ages within the region.
Adult Activities
- Hiking at Topanga State Park: Explore scenic trails that offer breathtaking views and a chance to connect with nature, all within easy reach of your vacation rentals in the region.
- Visiting the Skirball Cultural Center: Immerse yourself in diverse exhibits and cultural experiences that highlight the area's rich history and artistic heritage.
- Relaxing at Malibu Beaches: Enjoy a day by the ocean soaking up the sun or strolling along the shoreline near this popular coastal destination.
- Discovering Local Wineries and Tasting Rooms: Sample regional wines and enjoy guided tours that showcase the area's vibrant viticulture scene.
Winnetka Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shops: Take advantage of the area's charming cafes and boutiques to experience authentic regional flavors and unique shopping opportunities during your stay.
- Plan Outdoor Activities: Make the most of the pleasant climate by visiting nearby parks and outdoor spaces, perfect for relaxing or engaging in recreational pursuits.
- Discover Nearby Attractions: While here, consider exploring local points of interest that highlight the region's cultural and natural beauty for a well-rounded visit.
- Choose the Ideal Vacation Rentals: Select thoughtfully curated accommodations that offer comfort and convenience, ensuring a seamless and enjoyable stay in this destination.
Transportation Options
- Los Angeles International Airport (LAX): This major airport offers convenient international and domestic flights, making it easy to access the region's amenities and attractions.
- Metrolink Train Service: Connecting you swiftly to downtown Los Angeles and neighboring cities, this commuter rail provides a reliable transportation option within the area.
- Local Bus Services: Local bus routes serve the region comprehensively, offering an economical way to explore nearby neighborhoods and points of interest.
- Rideshare Services: Companies like Uber and Lyft operate extensively here, providing flexible and on-demand transportation options for your stay.
Local Customs Options
- Respect for Local Aesthetics: When visiting this area, it’s customary to maintain a respectful attitude towards the neighborhood's well-kept properties and natural surroundings.
- Community Engagement: Participating in local events and supporting neighborhood initiatives is appreciated by residents here, fostering a sense of community.
- Environmental Consciousness: Recycling and conserving water are important customs in this region, reflecting its commitment to sustainability.
- Politeness and Greetings: Greeting neighbors with a friendly nod or smile aligns with the polite social norms typical of this destination.
Frequently Asked Questions About Winnetka?
1. What are the top vacation rentals in Winnetka?
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 in Winnetka:
- Relaxing Getaway w/Game Room, Pickleball & More
- Private Guest House in Winnetka - 2bd/1ba Private Entrance and Yard Area
- ৎ୭Glamour Home ৎ୭ Pool Games Jacuzzi & more
- Cozy BRAND NEW 2 bed/2 Bath Private House Close to Everything
- *Peaceful & Beautiful! Pool, Firepit, BBQ, Central
- Modern cozy family friendly
- Casa One
- Best Western Canoga Park Motor Inn
- Modern Style 4-Bedroom Home with Jacuzzi
- Best Western Canoga Park Motor Inn
2. Which vacation homes in Winnetka are best for families?
If you are looking for a family-friendly vacation home in Winnetka, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winnetka:
3. How many Rentbyowner vacation rentals are available in Winnetka?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 52 in the Winnetka area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winnetka.
4. What is the cancellation policy for vacation rentals in Winnetka, California?
The cancellation policy varies by listing, so it's important to review the specific terms and conditions provided in the listing details. For definitive information, contact the property owner directly.
5. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning fees, service charges, or security deposits are typically outlined in the listing. To ensure transparency, review all fee details carefully before confirming your booking.
6. How do I confirm the availability of a vacation rental in Winnetka during my travel dates?
Availability depends on current bookings and can change frequently. Use the booking platform’s calendar to check real-time availability or reach out to the property owner for confirmation.
7. What amenities are usually included with vacation rentals in the region?
Most listings feature essential amenities for a comfortable stay, such as Wi-Fi, parking, and kitchen facilities. Specific amenities are detailed in each listing, so reviewing those will give you a clear picture of what to expect.
8. What should I know about the check-in and check-out process for vacation rentals here?
Check-in and check-out procedures vary by property. Details including key collection, entry times, and departure instructions are provided in the listing or communicated by the host. Contact the owner directly if you have any specific questions.
Winnetka Top Rated Vacation Rentals
Hotel
8.3(143 Reviews)
1 Bath
279.86 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $244/Night
7 Nights - AU $1,705
House
10.0(4 Reviews)
1 Bedroom
2 Baths
4 Guests
600 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $242/Night
7 Nights - AU $1,691
House
1.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
AU $690/Night
7 Nights - AU $4,832
House
3 Bedrooms
2 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
AU $785/Night
7 Nights - AU $5,495
House
4 Bedrooms
2 Baths
8 Guests
1800 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
AU $649/Night
7 Nights - AU $4,542
House
3 Bedrooms
2 Baths
6 Guests
2300 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
AU $522/Night
7 Nights - AU $3,653
House
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $358/Night
7 Nights - AU $2,503
House
1 Bedroom
1 Bath
2 Guests
- Pool
- Kitchen
- Air Conditioner
- Laundry
AU $126/Night
7 Nights - AU $879
