House holiday rentals in Simi Valley

Tennis and Pickleball, Heated Pool, Peaceful View

Experience Olive Hill Ranch! This 5 plus acre estate is an escape from daily life. Have a dreamy sleep in the double queen beds. Cook in the kitchenette, on the Traeger or dine at nearby delicious cuisine. Enjoy our resort-like amenities, including pool (heated summer months) hot tub, tennis, pickle ball, and putting green. We are local to multiple golf courses and a fantastic driving range. Underwood family farm and equestrian centers are within walking distance. Just 30 miles from Hollywood

Family · Location · Long stay

Relaxing Mid-Century Modern under the oaks

Enjoy our restored mid century gem with high ceilings and walls of glass opening to a private garden under heritage oaks. Peaceful and serene, modern stocked kitchen, birch floors and designer finishes. Cal King and Queen beds plus large couch if needed, also a pack and play. Venture to nearby beaches from Ventura (20 min away) to Santa Barbara, discovery Old California in citrus and avocado groves of Heritage Valley and Ojai, explore historic Santa Paula. yet only aprx 1 hour from LA.

Value · Location · Quiet

Encinal Mountain Malibu - Gated Retreat EV charger

Located in Malibu, and unaffected by fires. Encinal Mountain is a private gated retreat featuring two King bedrooms, central A/C, spa bathrooms, and luxurious soaking tub. Fully fenced yard is safe for pets and children. Located 2 minutes up from the Pacific Coast Hwy and El Matador State Beach sits an architectural gem on 5 acres, designed by architects Buff & Hensman. Fully renovated down to the studs it has been restored to retain the midcentury history, yet upgraded with modern luxuries.

Value · Family · Comfort

GREAT VIEWS • Over 400-Yr Oaks • Near Hiking

If you're looking for an entire STYLISH residential home with a GREAT VIEW, this is it! Enjoy a relaxing stay tucked amongst a tightly knit series of homes with a nice view above the city's 400-YEAR-OLD OAK TREES. Includes a full kitchen, 2 separate bedrooms, 1.5 bathrooms, in a 2-story home. One queen bed, a queen pullout, & a bunk bed. Also included is a full kitchen, AC, heater, desk, Smart TV, deck with a view, and very fast WIFI! Over the Oaks! VIEW! Perfect for families or small groups!

Family · Location · Quiet

HOT TUB / Chic / Firepit / Rocky Peak / Beautiful!

Welcome to The Skyline at Rocky Peak, a rural 3-bedroom, 2-bath mountain retreat with HOT TUB and peekaboo views of the San Fernando Valley. Blending mid-century modern design with comfort, this peaceful hideaway features custom furnishings, a luxurious master suite, a home office, and an incredible backyard OASIS, FIREPIT, and built-in BBQ. Bifold patio doors. Guests rave about the serene vibe, thoughtful details, and a central and private location, everything you need for a relaxing escape.

Family · Location · Kitchen

Newly Remodeled Cozy Studio. King bed, Disinfected

Enjoy Your stay at this cozy studio located in West Hills California! This studio is centrally located in the premier West Hills neighborhood, a short drive from Calabasas, Malibu, Santa Monica, Warner Center. Wifi and street parking are included. Close to groceries, restaurants, shopping malls. Easy access to freeways. Brand new furniture and mattress bedding. Has its own heater and AC, not shared with the rest of the building. Shares a wall with the rest of the house where my family lives.

Value · Family · Solo travel

Crystal Island, Where Dreams Come True

Entertainers, paradise. Enhance your serenity while enjoying the spectacular views of the golf course and mountains surrounding this modern, comfortable, large 5 bedroom, 3 bath home. Just moments off the freeway but yet peaceful surroundings in the Sunset Hills area of Thousand Oaks. Soak in our new hot tub!! Kick back watching views of sunrise thru sunset. Gorgeous open kitchen, huge dining room, three social/den/living areas. Each Bedroom has a queen bed for a comfortable nights rest!

Location · Value · Checkout

Magnolia Cottage- a tranquil and inviting home.

Magnolia cottage is a charming family home located in a peaceful neighborhood, close to all that our beautiful area has to offer. Minutes from California Lutheran University, Moorpark College & the Ronald Reagan Library . With quick access to freeways, our cottage is 40 minutes to Malibu beaches or breathtaking drives into the canyons and Ojai . There are wonderful hiking/biking trails surrounding the property and shops and restaurants all within comfortable walking distance of the cottage.

Family · Value · Quiet

Editor's Choice*LA #1*4BR*Spa*Arcade*Ping Pong

This stylish, ground-level getaway offers modern furnishings & premium amenities in a central location. The open-concept layout features a fully equipped kitchen, dining area, & a cozy living room with a fireplace & arcade games. With 4 comfortable bedrooms, a floor mattress, & 3 sleek full bathrooms, it comfortably sleeps up to 10 guests. Step outside to a dream backyard to enjoy the hot tub, fire pits, ping pong table, or alfresco dining—your perfect Hollywood family retreat!

Location · Family · Accuracy

Island Style Oasis Home- Island in the Sky

Welcome to Island Style Oasis– your very own private paradise! Our luxurious retreat is the perfect place to escape the hustle and bustle of everyday life and indulge in some much-needed relaxation. Nestled in a peaceful and serene valley our stunning property offers everything you need to rejuvenate your body and mind. Whether you want to take a dip in our sparkling pool, soak in one of our Jacuzzi tubs, or unwind in our steam showers and dry sauna, we've got you covered.

Family · Location · Check-in

Eichler -Private- Oasis: Pool & Spa Escape

Welcome to the Eichler House in Thousand Oaks! This mid-century modern home features a pool, jacuzzi, fireplace, and built-in BBQ—perfect for entertaining or relaxing. Fully remodeled with modern amenities, it boasts an atrium, open floor plan, and floor-to-ceiling windows for seamless indoor-outdoor living. Nestled on a private lot backing to open space, it offers tranquility while being minutes from hiking trails, shopping, and 30 minutes from the beach.

Value · Family · Layout

Sweeping Ocean & Mountain Views, Private

Located Mid-Malibu, (not near fire zone) a 5 minute breathtaking drive up the canyon from Malibu Seafood Cafe, Solstice Canyon Trails, and Corral Beach, this 1 bedroom guest house is surrounded by the Santa Monica mountains, overlooking L.A., and sweeping ocean views. Enjoy a trailhead right on the property with views of Catalina Islands, surf at the beach below, ride nearby trails, or just relax in the backyard overlooking Pt Dume. Private & romantic.

Family · Location · Solo travel