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 cozy seating area is set on a wooden deck, framed by a canvas canopy. Soft cushions adorn the light-colored sofas, while a small table holds a plant and decorative items. The view showcases rolling hills and a sunset sky, blending warm colors.
Guesthouse in Malibu
4.98 out of 5 average rating, 240 reviews

Views along the Malibu, private, tiny-guesthouse

NOT FIRE AREA & MALIBU is OPEN! ❤️Best views in Malibu! Nestled in the mountainside, this tiny guest-house, has unobstructed, spectacular views of the Santa Monica Mountains and the Pacific Ocean. Clean cozy comfortable modern tiny home tucked behind Malibu’s iconic steel and glass house, Blu Space. The tiny guest-house is best for couples or solo travelers. property borders Solstice Canyon National Park-centrally located to beaches, restaurants and shops ❤️ Must climb stairs- pls read house rules

Top Guest favourite
Home in Moorpark
4.96 out of 5 average rating, 134 reviews

Amazing grounds/ Bunnies/ Peaceful/ Hot Tub

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

Top Guest favourite
An aerial view captures the expansive property featuring a spacious guest suite, inviting pool area, and various outdoor sitting spaces. Lush greenery and palm trees surround the layout, while colorful umbrellas and seating arrangements provide relaxation options in the sun. Scenic walking paths are visible throughout.
Guesthouse in Simi Valley
4.98 out of 5 average rating, 115 reviews

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

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, 108 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.

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
4.94 out of 5 average rating, 139 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.

Guest favourite
A modern home exterior is showcased at sunset, highlighting a spacious hot tub with colorful LED lighting. Large glass windows reveal glimpses of the interior, while surrounding planters add greenery to the welcoming atmosphere.
Home in Chatsworth
4.9 out of 5 average rating, 91 reviews

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.

Guest favourite
A light-filled living area features a dark coffee table centered on a decorative area rug. Two black chairs with yellow-accented cushions sit adjacent to the modern entertainment unit, which displays a flat-screen TV. Large windows offer views of the outdoors.
Home in Thousand Oaks
4.93 out of 5 average rating, 235 reviews

GREAT VIEWS - Stylish - Whole Home - Over the Oaks

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, and a convertible full couch to sleep up to six. Also included is a full kitchen, AC, heater, desk, Smart TV, deck with a view, and very fast WIFI! Over the Oaks! VIEW!

Top Guest favourite
Home in Simi Valley
4.93 out of 5 average rating, 163 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 serene pool area features a curved pool surrounded by lush greenery. A large pot with an agave plant accentuates the scene. The patio area is paved and includes comfortable seating, creating an inviting atmosphere for relaxation.
Guesthouse in Simi Valley
5 out of 5 average rating, 310 reviews

Resort Oasis

This private bedroom suite is part of the main house, but completely secluded from the rest of the home (you will not share any common spaces or have access to the home nor will we enter unit without prior notification). The space is bright & airy thanks to the vaulted ceilings, defused sky lights and large windows & sliding door. Kitchenette in unit and BBQ grill in the garden. There is also a large outdoor kitchen police. There are many unique garden areas for you to enjoy.

Top 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, 1,045 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/ 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!

Guest favourite
A front view of the house showcases a covered porch with white railings. Flower beds and planters filled with greenery frame the entrance. The concrete pathway leads to the steps of the porch, which are bordered by a landscaped yard. Light rain creates a subtle sheen on the pavement.
Home in Camarillo
4.91 out of 5 average rating, 213 reviews

Private Guest House in an Orchard, Private Entry,

Relax and live (or work) in this very private, quiet and secluded one bedroom house. If you are here for business, shopping, conferences or just on a vacation, this is a perfect home away from home. Recently remodeled, very Clean, one bedroom one bathroom house is close to Moorpark, Thousand Oaks, Simi Valley and Camarillo. It is close to Reagan Library, Moorpark College, Amgen, T.O. Civic Arts Plaza and Camarillo Outlets. Driving distance to Ventura and Malibu beaches.

Top Guest favourite
Double French doors open to an inviting interior, revealing a spacious living area complemented by wooden ceiling beams and modern decor. Natural light fills the room, enhancing the cozy atmosphere with a plush rug, stylized furniture, and a vibrant artwork accenting the wall.
Guest suite in Thousand Oaks
4.97 out of 5 average rating, 190 reviews

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!

Popular amenities for Simi Valley holiday rentals

When is the best time to visit Simi Valley?

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Frequently Asked Questions

  • What are the best places to stay in Simi Valley?

    Simi Valley has relaxing neighborhoods with quiet streets and welcoming local cafes. Many travelers frequently choose stays near central parks or around the foothills to enjoy green spaces and convenient access to local sights.

  • What are the best things to do in Simi Valley with kids?

    Simi Valley has interactive exhibits at the Skateboarding Hall of Fame, outdoor adventures along Rocky Peak Park trails, and history to explore at Strathearn Historical Park and Museum. Families often enjoy blending education and nature throughout the area.

  • What are some of the best things to do in Simi Valley?

    Wander the exhibits at the Ronald Reagan Presidential Library, hike scenic trails in Rocky Peak Park, or experience local performance at the Simi Valley Cultural Arts Center. Outdoor activities and historical sites are frequently suggested.

  • How is the weather in Simi Valley?

    Simi Valley has mild winters, usually between 44–66°F (7–19°C), with more rain in February and December, and dry, warm summers near 58–74°F (15–23°C). Layers and sun protection help for seasonal shifts and sunny days.

  • When is the best time to visit Simi Valley?

    Late spring and early autumn are often recommended for milder temperatures around 65–73°F (18–23°C) and lower rainfall. These seasons are popular for outdoor activities and local celebrations.

  • What are the best places to visit in Simi Valley?

    Explore the Ronald Reagan Presidential Library, wander gardens at Strathearn Historical Park and Museum, or stroll Corriganville Park with its film history and scenic trails. Simi Valley has a mix of cultural landmarks and outdoor sites for visitors.

  • What are some hiking trails in Simi Valley?

    Explore the trails at Rocky Peak Park and Corriganville Park for scenic views and wildlife spotting. Oak Park has quieter paths suited for shorter strolls and family adventures.

  • What are some family activities we can do in Simi Valley?

    Families frequently explore nature at Rocky Peak Park, participate in hands-on history at Strathearn Historical Park and Museum, or enjoy a show at the Simi Valley Cultural Arts Center. Parks and indoor spaces suit many interests.

  • What are some of the best day trip ideas from Simi Valley?

    Locals often suggest visits to nearby beaches, mountain parks, or arts districts in surrounding cities. Wine country excursions and nature preserves are also frequently recommended for travelers seeking variety.

  • Are there any pet friendly accommodations available in Simi Valley?

    Pet friendly stays are available in several neighborhoods throughout Simi Valley, with easy access to local parks and trails. Many hosts welcome guests traveling with pets, and amenities can include enclosed yards or nearby walking paths.

  • What are some local tips for visiting Simi Valley?

    Layers are useful for the changing temperatures, especially if you plan outdoor excursions. Locals appreciate early morning hikes and often suggest reserving ahead for museums or community events during weekends.

  • What is Simi Valley known for?

    Simi Valley is widely recognized for its presidential library, scenic foothills, and links to the film industry. The area blends suburban parks with cultural heritage sites.

  • What are the best hidden gems to explore in Simi Valley?

    Explore the quiet paths at Oak Park, discover local art at the Simi Valley Cultural Arts Center, or visit small, family-owned antique shops throughout town. These often-recommended spots highlight community character and creativity.

  • What are the best foods to try in Simi Valley?

    Simi Valley’s diners and family-run restaurants are frequently suggested for classic American comfort food, fresh tacos, and locally rooted Mediterranean dishes. Bakeries around town are known for seasonal fruit pies.

  • What should I bring for a trip to Simi Valley?

    Pack layers for shifting temperatures and a hat or sunscreen for sunny afternoons. Comfortable shoes help for exploring trails, parks, and museums around town.

  • What is the nightlife in Simi Valley like?

    Simi Valley has cozy pubs, family-friendly bowling, and community theater performances at the Simi Valley Cultural Arts Center. Nightlife often features relaxed gatherings and live local music.

  • What are the most popular events or festivals in Simi Valley?

    The Happy Face Music Festival, seasonal harvest celebrations, and community art fairs are frequently suggested events in Simi Valley. These bring together music, local food, and arts for residents and visitors throughout the year.

  • Are there family friendly vacation rentals in Simi Valley?

    Many vacation rentals in Simi Valley are family friendly, with spacious layouts, nearby parks, and quiet residential areas. Listings often include outdoor areas and flexible amenities for group stays.

Quick stats about holiday rentals in Simi Valley

  • Total holiday rentals

    Explore 240 holiday rentals in Simi Valley

  • Verified guest reviews

    Over 10,030 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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