Luxury Vacation Rentals in Winnetka

Luxury Vacation Rentals in Winnetka

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 3 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Winnetka

ৎ୭Glamour Home ৎ୭ Pool, Games, Jacuzzi & more property photo 1

ৎ୭Glamour Home ৎ୭ Pool, Games, Jacuzzi & more

3 bedrooms•2 baths
1,247 US dollars for 3 nights•

~$95 less than other sites

The Stagg Lane Retreat property photo 1

The Stagg Lane Retreat

5 bedrooms•4 baths
2,464 US dollars for 3 nights•
New

~$215 less than other sites

ৎ୭Bright & Gorgeous Canoga Park Guesthouseৎ୭ property photo 1

ৎ୭Bright & Gorgeous Canoga Park Guesthouseৎ୭

1 bedroom•1 bath
3,891 US dollars for 30 nights•

~$295 less than other sites

Welcome to Winnetka

Welcome to Winnetka

Experience the best of Los Angeles living with Wander’s luxury vacation rentals in Winnetka. Our handpicked collection showcases striking contemporary homes with sunlit living spaces, manicured backyards, and seamless indoor to outdoor flow for laid-back Valley days and sparkling evenings.
Expect thoughtful design at every turn. Think chef-ready kitchens, spa-style primary suites, refreshing pools or hot tubs, and dedicated work areas supported by ultra fast WiFi. Smart home features and premium linens elevate the everyday.
Every stay includes pristine cleaning and 24/7 concierge support, so you can settle in with confidence. When you book a Wander, you get hotel-grade consistency paired with the comfort and privacy of a beautiful home.

Destinations near Winnetka

Woodland Hills
North Hollywood
Beverly Hills
Los Angeles
Glendale
Altadena
Fullerton
Huntington Beach
Orange
Newport Beach
Laguna Beach
Montecito
Mission Viejo
Bakersfield
Lake Mathews
Crestline

Available soon in Winnetka

ৎ୭Glamour Home ৎ୭ Pool, Games, Jacuzzi & more property photo 1

ৎ୭Glamour Home ৎ୭ Pool, Games, Jacuzzi & more

3 bedrooms•2 baths
1,247 US dollars for 3 nights•

~$95 less than other sites

The Stagg Lane Retreat property photo 1

The Stagg Lane Retreat

5 bedrooms•4 baths
2,464 US dollars for 3 nights•
New

~$215 less than other sites

All homes in Winnetka

ৎ୭Glamour Home ৎ୭ Pool, Games, Jacuzzi & more property photo 1

ৎ୭Glamour Home ৎ୭ Pool, Games, Jacuzzi & more

3 bedrooms•2 baths
1,247 US dollars for 3 nights•

~$95 less than other sites

The Stagg Lane Retreat property photo 1

The Stagg Lane Retreat

5 bedrooms•4 baths
2,464 US dollars for 3 nights•
New

~$215 less than other sites

ৎ୭Bright & Gorgeous Canoga Park Guesthouseৎ୭ property photo 1

ৎ୭Bright & Gorgeous Canoga Park Guesthouseৎ୭

1 bedroom•1 bath
3,891 US dollars for 30 nights•

~$295 less than other sites

View all homes

Highlights in Winnetka

Discover the vibrant heart of the West San Fernando Valley, featuring lush parks, historic ranches, and premier shopping destinations.
Orcutt Ranch Horticulture Center
Westfield Topanga & The Village
Lake Balboa Park
Sepulveda Basin Wildlife Reserve
Santa Susana Pass State Historic Park
Los Encinos State Historic Park

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for vacation rentals in Winnetka

Jacuzzi (2)
Hot tub (2)
Outdoor pool (2)
Garden (2)
Ping pong table (1)
Fire pit (1)
Fire place (1)
Dryer (3)
Patio (1)
Balcony (1)
Bbq area (1)
Washer (3)
Oven (3)
Kitchen (3)
Tv (3)
Dishwasher (3)

Other popular amenities & vacation types in Winnetka

Family vacation rentals in Winnetka
Large group vacation rentals in Winnetka
Pet-friendly vacation rentals in Winnetka
Private pool vacation rentals in Winnetka
Discover more of Winnetka

Discover more of Winnetka

Tucked in the western San Fernando Valley, Winnetka blends a calm residential rhythm with easy access to the best of greater Los Angeles. Sunny skies and wide boulevards set a relaxed tone, while the Santa Monica Mountains rise nearby for scenic drives and fresh-air escapes.
Topanga Canyon, coastal routes, and major cultural hubs sit within convenient reach, making day plans effortless and evenings unhurried. You can explore studios, beaches, and galleries around the city, then return to a neighborhood that feels unpressured and welcoming.
This balance of serenity and connection is why Wander’s luxury vacation rentals in Winnetka are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Winnetka

Why should I book a Wander in Winnetka over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.
Every home in Winnetka delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Winnetka?

Some of our most popular vacation rentals in Winnetka include ৎ୭Glamour Home ৎ୭ Pool • Games• Jacuzzi & more, The Stagg Lane Retreat, and ৎ୭Bright & Gorgeous Canoga Park Guesthouseৎ୭. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Winnetka?

Wander offers 3 vacation rentals in Winnetka, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Winnetka?

You can check-in to Wander vacation rentals in Winnetka after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Winnetka have WiFi access?

Yes. Every Wander home in Winnetka has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.