Family-friendly holiday rentals in Simi Valley

Sparkling Pool/pickleball/ hot tub/ fire pit

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

Hotel California: Gated & secluded resort w/views

The Last Resort; poolside guest suite situated on 1.3+ hilly acres. The comforts and privacy of home with private bath, private sitting areas, pool, Jacuzzi & spectacular views Take a relaxing stroll through the grassy knoll or to the top of the property for a view of beautiful rolling hills as far as the eye can see. Right off the beaten path yet miles away. Solar and salt systems keeps this pool at the perfect temperature naturally and without chemicals! Peace and quiet or fun in the sun

Glamping in Luxury Covered Wagon w/ King Bed

Experience luxurious glamping comfort in a Pioneer Conestoga wagon w/ King Bed! With a plush bed & matching bunks, our wagon is perfect for a romantic weekend, family adventure, girl's/boy's trip, or just for a few days away! Nestled in the gorgeous Santa Monica mountains with beautiful views and oak trees, this stay is a full retreat! Next door sits Prospector Ranch with an authentic saloon, horses, & hiking & biking trails. LA, the 101 freeway, beaches, breweries & wineries are minutes away!

New Modern guesthouse with pool in Simi Valley

Welcome to this little gem. Our beautiful centrally located 1 bedroom guesthouse has vaulted ceilings, full size kitchen, spacious living room (optional additional queen bed) and a gorgeous bathroom. This modern 500 sq. ft. place is ALL yours to enjoy! Relax, have a cup of pour-over coffee, tea, or any of the Keurig varieties. Enjoy the many Roku selections like Disney+/Apple TV/Hulu/Amazon/Netflix/HBO Max and more. Short walk to the community pools/basketball/tennis/volleyball, and BBQ areas.

Adorable Studio With Private Entrance

Enjoy your stay in this cozy, Brand New Attached ADU with its own private entrance. Located in a Beautiful quiet neighborhood in Simi Valley with tons of Hiking Trails, Beautiful Parks, Shopping at the Simi Valley Town Center, and lots of Restaurants. This cozy unit is perfect for a weekend getaway or even a home away from home. The unit is to the left of the main house comes with its own Full Bathroom, Queen memory foam mattress, sitting area , 40" smart tv, dinning area, and a Full kitchen.

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.

Beautiful Guesthouse. Spacious 1,100 sqft, 2+1.

Spacious 1,100 sqft guest house has crown moldings throughout. It provides comfort, and privacy of a home away from home. Bedrooms are well appointed and have sufficient closet spaces. Cute cozy kitchen has granite counter top, refrigerator, stove & oven, cabinets. it is fully equipped with pots, pans, dishes, glasses, cups and all kitchen necessities. One bedroom and living area has laminate flooring. One bedroom has tile floor. The bathroom has granite flooring & a comfy shower .

Luxury Non-Toxic Stay•King Bed• Curated•30minto LA

Discover a designer 2 bed/1 bath, 750 sqft getaway where style meets sustainability. Every corner is intentionally curated with polished concrete floors, artisan stoneware, warm salt lamps, and green living essentials. The space feels light, open, and elevated—stocked with everything to make your stay effortless. A perfect hub for traveling professionals or families who want to explore Malibu’s beaches and Los Angeles highlights, while enjoying more space and value outside the city.

Mountain Views in Simi Valley....No Cleaning Fee!

Lovely one bedroom studio apartment. Amazing views, lemon trees and dozens of wild peacocks roam the yard. Very relaxing and peaceful, perfect for couples. Attached in-law suite with a private entrance. You have the entire space to yourself! 450 sq ft, full bath with washer/dryer. Kitchenette w/ fridge. HDTV with Amazon FireTV and free WiFi. Heating and A/C. There is a huge private deck w/ seating and a BBQ. One queen bed w/ down comforter and down mattress topper...very comfy!

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.

GREAT VIEWS Over 400-Yr Oaks • Stylish Whole Home

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 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!

Casa Rancho El Segundo - NO Cleaning Fees

No Cleaning Fees – Pets Welcome (Just Ask First!) Escape to our peaceful guest house in Thousand Oaks—your cozy ranch getaway with private entrance, parking, and a fenced side yard perfect for BBQs and evenings by the fire pit. Meet Larry the llama, Bob the alpaca, and their furry friends! Take the bikes for a neighborhood spin or bring along cut-up carrots and apples—they’ll love the treat. Book now and enjoy comfort, charm, and a sprinkle of countryside magic!