Holiday houses in Simi Valley

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Top-rated holiday rentals in Simi Valley

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A scenic view captures the mountains enveloped in delicate marine layer clouds at sunrise. Soft hues of pink, orange, and purple blend seamlessly in the sky, while the foreground features lush greenery, adding depth to the tranquil atmosphere.
Tiny home in Topanga
4.98 out of 5 average rating, 160 reviews

The Tiny Surfer's Ocean-Inspired Mountain Cabana

A healing retreat, in mountainous cloud forest setting, just above the Pacific Ocean. Hugged by marine layer clouds and mountains, our tiny cabana and sauna offers the healing serenity of nature. A quiet resting place for all; tiny house living removes distractions. With little more than what you truly need, you can reconnect to your heart and find balance. A respite for surfers, spiritual seekers, nature lovers, and city folks, our aim is for you to connect with that which matters most to you.

Guest favourite
A spacious private deck overlooks scenic hills and rock formations. Lush greenery and trees surround the area, enhancing the natural beauty. The deck features a metal railing and a seating area, inviting relaxation outdoors. A grill is also visible, perfect for outdoor meals.
Guest suite in Simi Valley
4.92 out of 5 average rating, 1,004 reviews

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/ full size fridge. HDTV with Amazon FireTV stick 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!

Top Guest favourite
A cozy living room features a dark blue sofa adorned with a yellow throw blanket. A round coffee table sits in the center, accompanied by colorful poufs and a decorative plant. Natural light enters through a nearby door, highlighting the warm wooden flooring.
Guesthouse in Simi Valley
4.99 out of 5 average rating, 103 reviews

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.

Top Guest favourite
Tiny home in Thousand Oaks
4.89 out of 5 average rating, 157 reviews

Fun stay! in teeny tiny home, lit yard, parking

Interested in a unique, affordable and sustainable stay to explore So Cal from a safe, quiet home base? Then this bright, high-end resort coach upcycled to a teeny tiny home is for you. She's not a standard house or stale hotel, she's special, private and has a twinkling yard space & parking for you. Full size fridge, stove top, microwave, cookware, coffee maker, cream/sugar, fast wifi, washer/dryer, large TV with Firestick, desk area, queen size bed, deluxe sofa and tree shaded picnic table.

Guest favourite
The kitchen features sleek white cabinetry complemented by a granite countertop. A stainless steel gas stove and microwave are positioned above. Kitchen utensils are neatly arranged beside the stove, with additional appliances visible, including a coffee maker. A waste basket is located to the left.
Guesthouse in Simi Valley
4.95 out of 5 average rating, 132 reviews

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.

Top Guest favourite
A private outdoor area features a sparkling pool accompanied by a spa, surrounded by lounge chairs and umbrellas. A covered patio with a barbecue grill and outdoor seating is visible, while colorful drinks are placed on a black table, enhancing the inviting atmosphere.
Home in Simi Valley
5 out of 5 average rating, 18 reviews

Paradise Retreat | Private 3 Bedroom w/ Pool & Spa

Welcome to Paradise Retreat! This rustic 3BR/2.5BA home features a private sparkling pool, spa, and outdoor dining patio and plenty of space to lounge in the sun—perfect for couples, families and friends. Located on the east end of Simi Valley near parks, hiking, and Ventura beaches, it's a peaceful getaway with cozy interiors and sunset views. Minutes from restaurants, shopping, Corriganville Park, and the Reagan Library. Unwind, relax, and make lasting memories at your home away from home.

Guest favourite
A cozy sleeping area features a spacious bed adorned with various pillows and a textured blanket. On either side of the bed, minimalist nightstands with lamps provide lighting. Three abstract artworks are displayed above the headboard, enhancing the serene ambiance.
Guesthouse in Simi Valley
4.91 out of 5 average rating, 168 reviews

Central Studio | Modern Touches & Natural Light

Modern studio centrally located to everything the Simi Valley area has to offer. Just a few minutes from the freeway, shopping and restaurants. This recently renovated, private studio is fully equipped for your stay. A combination of modern and natural tones gives this studio a warm feeling of style and comfort. Just right for couples or solo travelers looking for a snug place to rest. Please note the studio is attached to the main home and a train passes nearby. Possible noise may be heard.

Top Guest favourite
The exterior of a cottage-style home is shown, featuring a green facade with stone accents and a welcoming front porch. Lush shrubs and colorful flowers frame the entrance, while a paved driveway leads to a two-car garage, providing easy access to the property.
Home in Simi Valley
4.89 out of 5 average rating, 215 reviews

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.

Top Guest favourite
The speakeasy lounge features a custom-built bar area with a wooden countertop and seating options. A foosball table is positioned nearby, while a large television is mounted on the wall. Ambient lighting from decorative fixtures illuminates the space, complemented by vibrant orange curtains.
Home in Simi Valley
4.98 out of 5 average rating, 49 reviews

Calm oasis w/ spa, speakeasy, luxury resort vibes!

Welcome to Hacienda Madera, an oasis of calm in the foothills of Simi Valley. Slip into the backyard spa and soak in the majestic views. Then, head over to the speakeasy to mix yourself a cocktail or explore California's wine regions with picks from our in-house sommelier. Less than an hour from Los Angeles and Santa Barbara, our location makes us perfect for a weekend (or mid-week) escape. Or come stay with us when you're in the area for a wedding at one of our many local wedding venues!

Guest favourite
A comfortable king-sized platform bed is adorned with textured bedding and multiple decorative pillows. Brass wall sconces provide subtle lighting beside the bed, while a small nightstand holds a decorative vase with greenery. Soft natural light enters through the nearby window, illuminating the space.
Guesthouse in Simi Valley
4.93 out of 5 average rating, 60 reviews

Secluded Simi Sensation

A sensational & secluded guest house offering comfort & luxury in Simi Valley! Brand new build with no expenses spared boasting quartz countertops, stainless steel appliances, gas range, LG washer/dryer, high end fixtures & a KING-sized bed! Central location- shopping/dining & 118 FWY are 5-10 min away. 15 min to Hummingbird Nest Ranch, 10 min to Ronald Reagan Library, 7 min to Adventist Health, 30 min to BUR airport & close to Thousand Oaks, Canoga Park, Moorpark & Santa Monica Mtns.

Top Guest favourite
A spacious outdoor area is highlighted by a paved patio, framed by lush greenery and flowering plants. The exterior of the guest house features a tiled roof and multiple windows, allowing natural light to fill the interior. A few seating options are visible, enhancing the inviting atmosphere.
Home in Simi Valley
4.92 out of 5 average rating, 156 reviews

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 .

Top Guest favourite
A sparkling heated pool glistens under the sun, surrounded by a paved area featuring comfortable lounge chairs and a built-in BBQ grill. An inviting spa is positioned adjacent to the pool, while lush greenery can be noticed in the background, creating a peaceful outdoor atmosphere.
Home in Simi Valley
5 out of 5 average rating, 21 reviews

Peace of Paradise

Relax at this peaceful place to stay. Enjoy all the amenities this Peace of Paradise has to offer. Featuring 4 bedrooms, 3 bathrooms. Inside you are greeted with a tastefully remodeled kitchen that opens to the dining room, entertainment room provides a pool table. upstairs are 4 bedrooms, primary bedroom has a bathroom with walk-in closet. Secondary bedrooms are spacious. The backyard is perfect to swim in the refreshing pool or relax in the spa while BBQing some delicious food.

Popular amenities for Simi Valley holiday rentals

When is the best time to visit Simi Valley?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$250 NZD$264 NZD$261 NZD$273 NZD$284 NZD$303 NZD$289 NZD$292 NZD$287 NZD$261 NZD$266 NZD$255 NZD
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Quick stats about holiday rentals in Simi Valley

  • Total holiday rentals

    Explore 240 holiday rentals in Simi Valley

  • Verified guest reviews

    Over 9,770 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Simi Valley holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Simi Valley rentals

  • 4.8 Average rating

    Simi Valley stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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  4. Ventura County
  5. Simi Valley