Holiday houses in Simi Valley

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Top-rated holiday rentals in Simi Valley

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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 spacious living area features high-vaulted ceilings and natural wood beams. A comfortable sofa and coffee table are positioned around a 65-inch Smart 4K TV. A work station and coffee bar are visible alongside a granite island, with light flooding in through large windows.
Cottage in West Hills
4.99 out of 5 average rating, 260 reviews

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.

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, 109 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, 142 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
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, 223 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
Home in Simi Valley
4.99 out of 5 average rating, 80 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!

Top 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
4.94 out of 5 average rating, 78 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.

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, 1,054 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!

Top Guest favourite
A spacious outdoor deck features two wooden lounge chairs positioned for relaxation, with potted plants and natural greenery framing the area. Large windows of the house reflect sunlight, showcasing a blend of wood and modern architecture against the backdrop of surrounding hills.
Home in Topanga
4.93 out of 5 average rating, 416 reviews

Modern tree house in the heart of Topanga canyon

The house sits beautifully in the canyon, its organic feel and yet modern design transcends the idea of California living by blending indoor/outdoor through massive windows, incredible ceiling heights and stunning views. Nestled in the canyon, but only 5 min from Topanga town with its shops and restaurants and 10 min from the beach. You can now enjoy our new cedar wooden hot tub after a relaxing yoga session in the studio. Featured in the NYTimes, Dwell, Vogue...

Top Guest favourite
A tranquil garden setting features vibrant flowers and greenery surrounding a flowing fountain. Umbrellas provide shade over seating areas, and scenic mountains rise in the background under a clear blue sky. The landscape is designed for relaxation and outdoor enjoyment.
Guesthouse in Simi Valley
4.97 out of 5 average rating, 144 reviews

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.

Top Guest favourite
Guesthouse in Simi Valley
4.96 out of 5 average rating, 136 reviews

Rustic Ranch Retreat: Guesthouse with Nature Views

Escape to the tranquility of our picturesque working ranch, where you can experience the rustic charm of farm life like never before. Welcome to our one-of-a-kind Airbnb. Ranch Getaway: Unplug and unwind in our cozy guesthouse, nestled amidst the rolling hills of our working ranch. Here, you'll find a true escape from the hustle and bustle of city life, while only being one mile from the freeway. Parties are not allowed at The Ranch.

Guest favourite
Home in Simi Valley
4.89 out of 5 average rating, 228 reviews

Lovely, full function guest house with privacy.

Lovely guest house shows light and bright with crown moldings throughout. Granite flooring in family room, kitchen & bathrooms. All bed rooms have new beautiful laminated wood like flooring. It is a stand alone building, very quiet & provide privacy. For your convenience there is a courtesy EV charger available. A reservation in advance required. Bring your own cable. WiFi ready for working from home guests!

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 10,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    240 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