Family-friendly 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

Hidden Gem by Nature Preserve + Private Parking

A gem in the area of boulders, trails and nature preserve on a private street with plenty of parking! The guesthouse offers a cozy setup with spacious living area; high-vaulted ceilings in all rooms; a 65 inch Smart 4K TV with FREE streaming apps (Netflix in 4K and more) plus local news. Located in a rural neighborhood, yet 5-10 minutes to the nearest dining, groceries, theaters, shopping and a 30-minute scenic drive away to the beach and major Los Angeles & Simi-Valley tourist attractions.

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.

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.

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 .

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.

Rose Garden Home, Thousand Oaks

The Rose Garden House, situated in Thousand Oaks on the border of Los Angeles and Ventura counties, is conveniently located near the 101 and PCH. It's an ideal stop for a group road trip through beautiful Southern California. It also provides proximity to serene hiking trails, golf courses, and horse riding clubs, ensuring a balanced blend of convenience and tranquility for your stay. There are Tesla superchargers and EV charging stations 5-7 min driving distances.

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!

Casita del Sol

Welcome to Casita del Sol, a charming two-bedroom, two-bathroom standalone guest house on the West-end of Simi Valley, a quaint and peaceful town. A short distance to local restaurants + shopping, and the Ronald Reagan Library and just 45 minutes from Los Angeles, Ventura or Malibu, Casita del Sol is a modern contemporary home perfect for a mini staycation or a long vacation. Relax, unwind and dine al fresco on your very own deck with garden views.