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Check prices for these dates

Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13
In one month
Apr 25 - Apr 27
In two months
May 23 - May 25

Browse Select Winnetka Villas

Beverly Hills Luxury 5BR Villa with Pool, Hot Tub, Rooftop Patio & Parking!
Onsite parking

Beverly Hills Luxury 5BR Villa with Pool, Hot Tub, Rooftop Patio & Parking!

8.8 out of 10, Excellent, (16)
"We had 10 people aged 4-80, and we all had a great time. There was plenty of room to be able to do our own thing, but also room for gathering. "
Beverly Hills Luxury 5BR Villa with Pool, Hot Tub, Rooftop Patio & Parking!
The Beverly Hills Tree House
Pool

The Beverly Hills Tree House

The Beverly Hills Tree House
Hollywood Hills Designer Villa/Duplex with Authentic Charm
Smart TV, books, offices

Hollywood Hills Designer Villa/Duplex with Authentic Charm

9.6 out of 10, Exceptional, (45)
"This is a great place. Perfect location. Easy check in. Thank you. "
Hollywood Hills Designer Villa/Duplex with Authentic Charm
STUNNING private Designer villa/duplex in the top of Hollywood Hills.
Terrace/patio

STUNNING private Designer villa/duplex in the top of Hollywood Hills.

9.4 out of 10, Exceptional, (69)
"Perfect house for the two of us, secluded in the hills but close to everything. Very clean, safe neighborhood. Beautiful outdoor space with fantastic views. Easy parking. "
STUNNING private Designer villa/duplex in the top of Hollywood Hills.
Beautifully Remodeled 4BR Home-Outdoor Dining BBQ
Private kitchen

Beautifully Remodeled 4BR Home-Outdoor Dining BBQ

9.6 out of 10, Exceptional, (16)
"House was just as described. Ample room for us all. Only suggestion would be to have bigger pans for this size of our party. The neighborhood was nice and quiet."
Beautifully Remodeled 4BR Home-Outdoor Dining BBQ
The Modern Serenity Retreat
Dining

The Modern Serenity Retreat

10.0 out of 10, Exceptional, (2)
"From beginning to what I didn’t want to end was so effortlessly awesome! The pictures on the site is very nice, but once you open the door, #boom omg it was so beautiful, huge, clean and fresh! Neighborhood was a plus. I celebrated my birthday with a nice gathering of family and close friends with a birthday dinner party and it was amazing! A time I will never forget. The host made sure I was satisfied from the beginning to end of my stay. Available with a quick response ready to help and assist...
The Modern Serenity Retreat
Your Own Private RESORT!🏝9BR/10BA Gated Compound✰ HUGE Pool, Gym, Yard, Parking
A heated pool

Your Own Private RESORT!🏝9BR/10BA Gated Compound✰ HUGE Pool, Gym, Yard, Parking

10.0 out of 10, Exceptional, (42)
"By far, one of the top vacation rentals we have had the pleasure to enjoy. Beautiful private oasis with a magical outdoor area. Everyone in our traveling party was beyond pleased. The location is perfect and the communication with the manager/hosts was outstanding! Thank you for everything!! "
Your Own Private RESORT!🏝9BR/10BA Gated Compound✰ HUGE Pool, Gym, Yard, Parking
Incredible white water ocean view
Outdoor dining

Incredible white water ocean view

10.0 out of 10, Exceptional, (287)
"Loved everything about the stay. The place was clean, having a washer and dryer is a must with kids. The view and location to the beach is amazing. Would stay here again. "
Incredible white water ocean view
Mediterranean Villa Pool & Jacuzzi & BBQ Malibu & Hollywood Bliss
Outdoor spa tub

Mediterranean Villa Pool & Jacuzzi & BBQ Malibu & Hollywood Bliss

9.6 out of 10, Exceptional, (5)
"Everything was great. Loved having so many places within walking distance, including the Pickwick Pub right next to the property. "
Mediterranean Villa Pool & Jacuzzi & BBQ Malibu & Hollywood Bliss
The Beverly Grand Villa @ Bel Air, Los Angeles
Outdoor pool, a heated pool

The Beverly Grand Villa @ Bel Air, Los Angeles

9.6 out of 10, Exceptional, (23)
"Our family members range in ages 18-83. We enjoyed our time together in this beautiful home! The house is a spacious, elegant, clean home. There were a few issues that the owner and property manager properly addressed. We appreciated their concern for our comfort and prompt efforts to meet our needs. We felt welcomed by the gift for us and the ease of communication with the owner and manager. The house is as described and pictured. The kitchen is very large with two extra large refrigerators,...
The Beverly Grand Villa @ Bel Air, Los Angeles
Beautiful Hollywood Hills Villa - Heat Pool, BBQ, Hollywood Sign, Prime Location
Outdoor pool, a heated pool

Beautiful Hollywood Hills Villa - Heat Pool, BBQ, Hollywood Sign, Prime Location

10.0 out of 10, Exceptional, (35)
"Amazing location close to all the big attractions. Home was so beautiful and comfortable. "
Beautiful Hollywood Hills Villa - Heat Pool, BBQ, Hollywood Sign, Prime Location
Villa Outpost in the Hollywood Hills.
Interior

Villa Outpost in the Hollywood Hills.

Villa Outpost in the Hollywood Hills.
The Jetliner | Private Spa! by Colby & Conrad
4 bedrooms, desk, iron/ironing board, travel crib

The Jetliner | Private Spa! by Colby & Conrad

The Jetliner | Private Spa! by Colby & Conrad
Exquisite Hollywood Hills Retreat
3 bedrooms, iron/ironing board, WiFi, bed sheets

Exquisite Hollywood Hills Retreat

10.0 out of 10, Exceptional, (9)
"Wonderfully home with excellent accommodations and well stocked. Will consider next time we visit Los Angeles"
Exquisite Hollywood Hills Retreat
Staycation Home private pool - close to Malibu Beach
Outdoor pool, a waterfall pool

Staycation Home private pool - close to Malibu Beach

8.8 out of 10, Excellent, (3)
"We enjoyed our stay in Agoura Hills. The house location is ideal, close to the 101, shopping and restaurants. We were impressed by both the cleanliness of the house and the communication with the owner. There was plenty of room for us and enjoyed the backyard which included a pool, hot tub and gas grill. One suggestion would be to have a king size bed in the master bedroom. The room is large enough for it and we would have enjoyed that. Overall, we would stay again when in the Conejo Valley...
Staycation Home private pool - close to Malibu Beach
Mt Malibu Mansion w/ Amazing Ocean Views, Guest House, 2+ Acres, Hot Tub!
Beach nearby, sun loungers, beach towels

Mt Malibu Mansion w/ Amazing Ocean Views, Guest House, 2+ Acres, Hot Tub!

10.0 out of 10, Exceptional, (8)
"We had a fantastic stay at this beautiful villa in Malibu. The property itself is stunning, well-maintained, and offers breathtaking views. The owner was incredibly responsive, and any minor issues we encountered were quickly and efficiently resolved.However, the road leading to the villa can be a bit nerve-wracking. The guardrails were damaged by the January fires, making the drive feel less secure. If you're not comfortable with steep, winding roads, this may be something to consider, or wait...
Mt Malibu Mansion w/ Amazing Ocean Views, Guest House, 2+ Acres, Hot Tub!
Cheerful four bedroom house with charming view!
Outdoor pool, a heated pool

Cheerful four bedroom house with charming view!

9.0 out of 10, Wonderful, (28)
"We had such a great time! Host was really nice and was great at responding! Would definitely book again!"
Cheerful four bedroom house with charming view!
West Hollywood 5 BR Villa; Pool, Hot Tub, Rooftop Patio, Free Parking, Central
Onsite parking

West Hollywood 5 BR Villa; Pool, Hot Tub, Rooftop Patio, Free Parking, Central

9.0 out of 10, Wonderful, (13)
"This property stood out because of the outdoor living area, including pool, spa and grill. We paid extra ( $399) to have the pool heated for one day and it was perfect. The rooms and en suites were very nice and comfortable, plenty of space for us. We did request the property manager come over and show us how things worked because the appliances and faucets, etc. are all pretty high tech. The dishwasher was not stable, and did not work, but the manager sent repairmen over right away and they...
West Hollywood 5 BR Villa; Pool, Hot Tub, Rooftop Patio, Free Parking, Central
Beverly Grove Spanish Oasis 5 BR Villa with Pool, Hot tub, Parking
Onsite parking

Beverly Grove Spanish Oasis 5 BR Villa with Pool, Hot tub, Parking

9.4 out of 10, Exceptional, (6)
"Large space just home with great layout. Pool and Jacuzzi were definitely perks for the kids to keep them busy before venturing out during the days guest suite was perfect for sister-in-law to be able to get away. Awesome neighborhood to be in walking distance to target and other shopping stores. Overall, excellent place to stay if visiting LA. Down the street from Melrose place lol"
Beverly Grove Spanish Oasis 5 BR Villa with Pool, Hot tub, Parking
London Dream
Luxury Villa, Multiple Beds, Pool Access, Pool View (London Dream)

London Dream

4.5 star property
London Dream
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winnetka

Venice Breeze Suites
Property amenity

Venice Breeze Suites

3.5 star property
8.4 out of 10, Very good, (1631)
"We liked the kitchen in the unit which was very well equipped, even having a dishwasher. The large windows which let in lots of sunlight was a big bonus. The hotel also has a beautiful roof top patio which has a fabulous view of the Venice Beach board walk and ocean. You can also use the BBQ up there. Staff is very accomodating and the desk is serviced 24/7,"
The price is CA $334
CA $381 total
includes taxes & fees
Apr 13 - Apr 14
Venice Breeze Suites
Venice Suites
Exterior

Venice Suites

3.0 star property
8.2 out of 10, Very good, (1237)
"Excellent location right opposite the beach. Nice views from top floor terrace. A lot of activity in the area. "
The price is CA $299
CA $342 total
includes taxes & fees
Mar 31 - Apr 1
Venice Suites
The Crescent powered by Sonder
Interior

The Crescent powered by Sonder

4.0 star property
7.8 out of 10, Good, (1080)
"Room size was great and location was amazing!"
The price is CA $236
CA $269 total
includes taxes & fees
Apr 23 - Apr 24
The Crescent powered by Sonder
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do villas in Winnetka cost?
Villas in Winnetka range between and per night. These escapes give you the privacy to enjoy your own space at a price that’s gentle to your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Winnetka?
Pack your suitcase and choose from 246 villas in Winnetka. For a family vacation, a romantic break and everything in between, Expedia can help you find the perfect space in just a click or two.
Why book your villa in Winnetka with Expedia?
Booking a villa in Winnetka is as easy as deciding on your travel dates and selecting an option suited to your needs. Searching for something affordable or upmarket, or a property that also has a kitchen? Use Expedia’s search filters to narrow your results and find your dream fit.
How can I find cheap villas in Winnetka?
With Expedia’s user-friendly filter tool, reserving cheap villas in Winnetka is a breeze. To find accommodations that won’t break the bank, fine-tune your search by amenities, budget and star rating.