Search for vacation rentals in Winnetka.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Winnetka area to find the perfect spot for your vacay.

7027 Keokuk Ave
	7027 Keokuk Ave Winnetka, CA $1,900 Vacation Rentals, Unknown ADU one bedroom, one bathroom, in a good quiet neighborhood. Washer and Dryer, stove, microwave, full size bathroom. Come see it!...

6739 Sunnybrae Ave
	6739 Sunnybrae Ave Winnetka, CA $2,695 Vacation Rentals, Unknown Welcome to this Charming 2BR 1 BA back house located on a cul-de-sac in a quiet family neighborhood. This cozy home features a fully equipped kitchen with a refrigerator, stove/oven and built-in......

7302 Lubao Ave
	7302 Lubao Ave Winnetka, CA $2,500 Vacation Rentals, Unknown Brand New 1 Bedroom ADU with brand new appliances, split unit A/C, high ceiling, separate entry. Utilities included. One parking space, close to public transportations, College, University, and......

20749 Stephanie Dr
	20749 Stephanie Dr Winnetka, CA $4,700 Vacation Rentals, Unknown Welcome to your ideal retreat in the heart of Winnetka! This beautifully upgraded home offers the perfect blend of comfort, convenience, and style. With 3 spacious bedrooms and 2 baths, including a......

6930 Sunny Brae Ave
	6930 Sunny Brae Ave Winnetka, CA $3,750 Vacation Rentals, Unknown Located near transportation, shopping and schools. Very large back and side yards. Located on cul de sac. Attached garage and laundry hookups. New kitchen, bathrooms, paint, laminates and......

8108 Sunny Brae Ave
	8108 Sunny Brae Ave Winnetka, CA $3,850 Vacation Rentals, Unknown This rental property has been newly painted and boasts hardwood floors. The kitchen is equipped with like-new appliances and there's a separate laundry room with a washer and dryer. The spacious......

7426 Irondale Ave
	7426 Irondale Ave Winnetka, CA $4,100 Vacation Rentals, Unknown New HVAC, New Roof, Large Kitchen, Upgraded kitchen counter, cabinets, new laminate flooring, large backyard and front yard...

7700 Penfield Ave
	7700 Penfield Ave Winnetka, CA $3,600 Vacation Rentals, Unknown GREAT 3BDRM 2BATH HOUSE IN QUITE CLEAN NEIGHBORHOOD New upgrades: - Professionally painted exterior and interior in warm, neutral, soft white. - Refinished ceilings; No popcorn! - Refinished......

6748 Stephanie Pl
	6748 Stephanie Pl Winnetka, CA $2,000 Vacation Rentals, Unknown The most beautiful , ,detach ADU you will see!with your own huge privet green back yard, with artificial grass. Designer bathroom and custom kitchen! Plenty of natural light, located on a quite col......

Penfield Ave
	Penfield Ave Winnetka, CA $3,750 Vacation Rentals, Unknown Newly painted interior and exterior, refinished ceilings. New toilets. Original Hardwood floors. Fireplace, Big backyard, game room with large pool table. Nice neighborhood near Pierce College, Cal......

6838 Winnetka Ave
	6838 Winnetka Ave Winnetka, CA $4,600 Vacation Rentals, Unknown 4 bdrm + 2 bath House plus a 1 bedroom 1 bath Guest House or Office 6 Ft high vinyl fence in the front No maintenance turf New paint inside and outside New vinyl flooring throughout New kitchen......

6971 Cozycroft Ave
	6971 Cozycroft Ave Winnetka, CA $3,798 Vacation Rentals, Unknown ** Open house 3 bed and 2 bath house in a beautiful street; close to pierce college and the new Woodland Hills Topanga mall. You need to see this house before making your decision. Walking distance......

7970 Sunny Brae Ave
	7970 Sunny Brae Ave Winnetka, CA $3,800 Vacation Rentals, Unknown AVAILABLE JUNE 1ST - Beautiful 3 bed 2 bath home ready for lease! This is the perfect home for a new family looking to be on a quiet street that is walking distance from Sunny Brae Elementary......

20244 Hartland St
	20244 Hartland St Winnetka, CA $3,798 Vacation Rentals, Unknown Can also be rented short term, but we rather rent the house for a longer term renovated, this stunning 4bedroom/2 bath single-family house is in a sought after school district North of the Ventura......

7056 Lubao Ave
	7056 Lubao Ave Winnetka, CA $3,798 Vacation Rentals, Unknown few days in April rent is free. This Home is Beautiful, 3 bed 2 bath with back yard . Redone home with granite counters, stainless appliances, eat in kitchen, laundry area off kitchen, French doors......

20745 Ingomar St
	20745 Ingomar St Winnetka, CA $4,500 Vacation Rentals, Unknown TURN-KEY RENTAL WITH MODERN UPGRADES + POOL, SPA & SOLAR! Fully renovated two-story residence with a pristine pool, spa, and solar included! This stunning home was recently upgraded throughout! The......

19813 Welby Way
	19813 Welby Way Winnetka, CA $1,900 Vacation Rentals, Unknown Brand new ADU house with own address. Beautiful modern look, with private fence around the house, vinyl flooring throughout the house, air conditioning, heater, gas range, refrigerator, drinking......

20318 Blythe St
	20318 Blythe St Winnetka, CA $6,200 Vacation Rentals, Unknown GORGEOUS HOME, AMAZING COMMUNITY AND OPPORTUNITY THIS IS A MUST SEE HOME DON'T MISS IT This lovely home is located on a quiet cul-de-sac in an award winning elementary school district in the highly......

Oso Ave
	Oso Ave Winnetka, CA $2,996 Vacation Rentals, Unknown Dated 3 bedroom, 2 bathroom home with family room, and amazing yard!! Fruit trees!! Home needs some renovation.Appliances are on the property and available for tenants use. Fabulous neighborhood.......

20642 Londelius St
	20642 Londelius St Winnetka, CA $4,000 Vacation Rentals, Unknown Welcome to your fully remodeled retreat in the heart of Winnetka! This exquisite home seamlessly blends modern elegance with timeless comfort, offering a serene sanctuary for relaxation and......

7731 Mason Ave
	7731 Mason Ave Winnetka, CA $3,500 Vacation Rentals, Unknown Conveniently situated and accessible via Ventura Freeway, CA-118, and I-405, this residence is a few minutes away from Runnymede Park, Winnetka Recreation Center, several malls including Westfield......

Sunnybrae Ave
	Sunnybrae Ave Winnetka, CA $4,800 Vacation Rentals, Unknown Freshly Remodeled. New flooring, Roofing, Kitchen, Plumbing, HVAC, Backyard Patio(not pictured). Big and deep Pool. Big front & back yard. 2 car attached garage....

7457 Cozycroft Ave
	7457 Cozycroft Ave Winnetka, CA $3,799 Vacation Rentals, Unknown This house was recently remodeled one level single family with 3 bedroom and 2 bathroom and its own full back yard and parking. Best part of Winnetka near pierce collage and Topanga mall. The......

Fullbright Ave
	Fullbright Ave Winnetka, CA $3,795 Vacation Rentals, Unknown Very nice house in a great location. The house includes 4 bedrooms and 2 bathrooms with a big green front and backyard. This is your dream house. The house includes the following: - 4 good size......

20334 Bassett St
	20334 Bassett St Winnetka, CA $1,900 Vacation Rentals, Unknown New charming fully remodeled Junior ADU 1 bedroom and 1 bath, Guest house unit. Beautiful modern, with a private fenced front yard, appliances include: Microwave, refrigerator and stove. Vinyl......

8466 Quartz Ave
	8466 Quartz Ave Winnetka, CA $4,499 Vacation Rentals, Unknown Location, Location, Location, Very Safe neighborhood. (Brand New) Modern Style 3 bedroom, 2 (full bath) brand new remodeled house for rent. Lots of storage outside Brand new complete remodeled with......

20342 Baltar St
	20342 Baltar St Winnetka, CA $3,950 Vacation Rentals, Unknown Charming, 3/bedrooms, 2/bath one story home available for lease in Winnetka. It was recently remodeled with many upgrades including, kitchen, bathrooms, laundry room and a new A/C system which was......

20743 Chase St
	20743 Chase St Winnetka, CA $3,650 Vacation Rentals, Unknown House for rent in Winnetka 03 bedrooms-02 bathrooms - 01 spacious playroom. Quiet neighborhood. Freshly painted house. New hardwood floor. Newly remodeled master bathroom. Large living room, dining......

20340 Schoenborn St
	20340 Schoenborn St Winnetka, CA $3,885 Vacation Rentals, Unknown Recently painted and remodeled with new wood flooring, recessed light, granite counter top in the kitchen and new plumbing and AC system. Close to 101, 118 and 405 freeway. Close to the new huge......

20608 Cohasset St
	20608 Cohasset St Winnetka, CA $2,498 Vacation Rentals, Unknown Let us know if you prefer a 2 bedroom house. This is a new large open floor space one bed one bath house with a large living room and open kitchen. It has big backyard with large trees, 2 parking......

Gilmore St
	Gilmore St Winnetka, CA $1,900 Vacation Rentals, Unknown $1,900/mo which includes utilities, internet, pest control for one bedroom, private bathroom, and shared guest room. One room and private bathroom in a fully-furnished house, with a backyard that......

7308 Madora Ave
	7308 Madora Ave Winnetka, CA $4,500 Vacation Rentals, Unknown Welcome to your dream rental home at 7308 Madora Ave, Winnetka CA 91306. This beautifully remodeled house is ready to become your sanctuary in the heart of Winnetka. Features: 3 spacious bedrooms 3......

20207 Parthenia St
	20207 Parthenia St Winnetka, CA $2,100 Vacation Rentals, Unknown Located in a nice area of Winnetka. This an outstanding residence, it is almost new construction, new Kitchen with Stainless Steel Sink, Tiles, White color cabinets, Gas Range, tile and laminate......

20527 Londelius St
	20527 Londelius St Winnetka, CA $3,935 Vacation Rentals, Unknown Welcome to 20527 Londelius St, Canoga Park, CA 91306! Don't miss this chance to make this your new home! This home has an inviting, living space filled with natural light and lined with hardwood......

19711 Blythe St
	19711 Blythe St Winnetka, CA $4,700 Vacation Rentals, Unknown This 4-bedroom, 3-full-bath residence features hardwood floors and an updated kitchen that features state-of-the-art appliances, granite countertops, and ample storage space. The four bedrooms are......

6824 Lubao Ave
	6824 Lubao Ave Winnetka, CA $2,400 Vacation Rentals, Unknown Open House Saturday and Sunday 1-4pmThis charming back house for rent in the family friendly, Winnetka is a cozy living space perfect for someone looking for a peaceful retreat. The unit features 2......

20656 Covello St
	20656 Covello St Winnetka, CA $3,500 Vacation Rentals, Unknown 3 bed two bath completely renovated with new floors and bathrooms. Fresh paint exterior and interior and complete make over of backyard. A nice and quite cul de sac in a very nice neighborhood.......

6752 Stephanie Pl
	6752 Stephanie Pl Winnetka, CA $3,900 Vacation Rentals, Unknown Charming 3bed 2bath Winnetka /Woodland Hills Adjacent Home Located on a Huge Lot. Beautiful Light & Bright Kitchen with Large Built-In Refrigerator, 5 Burner Gas Stove, and White Quartz Countertops......

20607 Londelius St
	20607 Londelius St Winnetka, CA $4,000 Vacation Rentals, Unknown Solar system designed to cover 80-90% of average usage of home, huge savings in electric! Pool with diving board! Fenced in for animals, grass area in back, upgraded kitchen, two bathroom, 4......

8213 Quartz Ave
	8213 Quartz Ave Winnetka, CA $8,995 Vacation Rentals, Unknown Welcome to your dream home! This stunning single-family residence, completed in 2020, embodies modern luxury and timeless craftsmanship. Nestled in a serene neighborhood in the heart of the San......