Guest house holiday rentals in Simi Valley

4.98 out of 5 average rating, 272 reviews

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.

Guest house in Malibu

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

4.99 out of 5 average rating, 653 reviews

A vibrant cluster of orange poppies is set against lush greenery and rolling mountains. The landscape is characterized by a mix of wildflowers and shrubs under a cloudy sky, presenting a natural and serene environment.

Guest house in Calabasas

Monte Nido Retreat, minutes to Malibu/Pepperdine

Monte Nido is nestled in the Santa Monica Mountains between Calabasas and Malibu, 5 minutes away from Pepperdine University in Malibu. You can walk to the Backbone trail head from our yard. The guest house has a private entrance, full kitchen, bath and french doors that open up to a private patio with a fountain. There is also a private deck for star gazing and afternoon naps. Perfect for hiking, biking, surfing, and relaxation. There are no streetlights or sidewalks. It is truly paradise.

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.

4.98 out of 5 average rating, 116 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

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.

4.99 out of 5 average rating, 112 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.

4.94 out of 5 average rating, 264 reviews

An outdoor clawfoot tub is positioned on a wooden deck, surrounded by greenery and a wooden fence. Soft lighting is provided by overhead string lights. A person is seated in the tub, wrapped in a pink towel, reading a newspaper, creating a relaxed atmosphere.

Guest house in Topanga

Outdoor Clawfoot, Hot Tub, Deck

Welcome to the Farmhouse, a cozy studio retreat nestled in the Topanga hills. This cozy space features a comfy queen canopy bed, en-suite bath, and a kitchenette for light meals. The room opens onto a private deck and patio, perfect for waking up with the singing birds, small pond, and an outdoor clawfoot tub for a relaxing soak under the trees. Enjoy easy access to local attractions including cafes and restaurants, village shops, hiking trails with breathtaking views, and Malibu beaches.l

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.

4.94 out of 5 average rating, 145 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 house in Chatsworth

The studio features a comfortable queen bed against a backdrop of soft blue walls. A kitchenette area is visible, equipped with a microwave and small refrigerator. Natural light illuminates the space, highlighting a cozy seating area with a stylish coffee table and a wall-mounted television.

4.92 out of 5 average rating, 292 reviews

Comfortable Private Studio - near hiking

Come get away to a slower pace at our thoughtfully appointed studio in the beautiful hills of Lake Manor! When staying at our place you will be a short drive to West Hills, Canoga Park, Calabasas, Northridge, and more. We are in a quiet neighborhood in the "country." Our studio setup allows traveling workers and getaway seekers to find the work-life balance they need with: ✧Comfy work desk ✧ High-speed Wi-Fi ✧Close by fun hiking trails ✧Roku TV ✧Shared outdoor space ✧ parking - free

Guest house in Thousand Oaks

A serene bedroom features a spacious bed adorned with soft linens and multiple pillows. Natural light filters through a window dressed with sheer curtains. A decorative pendant light hangs from the ceiling, while a woven rug adds texture to the concrete floor.

4.95 out of 5 average rating, 129 reviews

Luxury Stay•2/1•King Bed•Private•WD•30 mins to 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.

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.

4.97 out of 5 average rating, 150 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.

4.96 out of 5 average rating, 146 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.

4.95 out of 5 average rating, 160 reviews

A spacious kitchen area features light wood cabinetry, a large island with seating, and modern appliances. Natural light pours in through large windows, illuminating the open living space that includes a cozy sitting area and a staircase leading to the loft above.

Guest house in Topanga

The Hideaway Retreat - Mountain Loft with Sauna

Experience this unique mountain loft, designed by a local Topanga artist, with 16' ceilings and views of the surrounding epic mountains. Enjoy a complimentary bottle of wine, our outdoor barrel steam sauna, and bring the kids or pets for hikes right outside the front door. Book an on-site massage or do a yoga session, watch movies on TVs in every room, or simply relax. Medley Ln offers some of the best views in all of Topanga.

A spacious bedroom features a queen bed with a crisp white comforter and blue accents. Mirrored sliding doors reflect the room's design, enhancing the light from the large window. Two bedside lamps and a textured area rug add warmth to the modern decor.