Holiday rentals with a pool in Simi Valley

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Simi Valley

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
Home in Moorpark
4.95 out of 5 average rating, 118 reviews

Pool House on the Ranch/ seasonal heated pool

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, 113 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 clear swimming pool reflects the sky, with a colorful beach ball gently floating on the water's surface. Comfortable lounge chairs and an umbrella provide shaded seating nearby, while green hills rise in the background, creating a serene outdoor space.
Guest suite in West Hills
4.99 out of 5 average rating, 734 reviews

LA, Top of the Hills, Views, Pool, Private Suite

We would like to offer people from all over the world visiting Los Angeles a place to relax after intense sightseeing tours or after a long work day. We created a little suite that has a separate bedroom, a separate living room, and a private bathroom with amazing views of the valley hills and the city right by the pool. Just have a glass of wine at the end of our back yard on top of the hill and watch the moon and stars, do a few laps in the pool, or just watch a movie in your own living room.

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.

Guest favourite
A spacious open-plan living area features large glass doors leading to the outdoor space. A modern dining table is complemented by a stylish pendant light. A comfortable seating arrangement is visible beside a fireplace, with a television mounted on the wall.
Home in West Hills
4.98 out of 5 average rating, 110 reviews

Lux Resort Gorgeous Views & Pool

Wake up to a breathtaking view of the sunrise at this newly renovated 5BDR luxurious home, located in the most peaceful area in West Hills. Comes with a pool, 6bd (1 king, 1 queen) ping pong table, theater/game room & balcony access for 4 rooms. Next to the 118 and 101 freeways makes it a less than 20 minutes drive to most entertainment places in Los Angeles like Hollywood, Malibu, Santa Monica, Universal Studios, a 5 min drive to essential markets & 1 of southern Cali’s biggest shopping malls!

Guest favourite
A modern travel trailer is displayed beside the property, showcasing a smooth exterior with distinctive branding. The trailer is positioned under an awning, providing coverage from the elements. A patio area with furniture can be seen in the background, contributing to the inviting outdoor space.
Campervan/RV in Castaic
4.96 out of 5 average rating, 611 reviews

Newer Tiny House Comfy Cozy/ Six Flags/CalArts

Newer "Tiny House" in a very private and relaxing setting. Great for couples and kids. Beautiful amenities, private entrance with parking on property. Enjoy the mountain and canyon views of the Castaic and surrounding valleys below! Only minutes from Six Flags and Cal Arts. Luxurious Master suite, complete kitchen with large counter space, beautiful bathroom with skylight! All amenities provided for your enjoyment and stay. Coffee, Tea, WiFi, TV included. All the comforts of being at Home!

Guest favourite
A serene pool area is surrounded by a paved patio and greenery, showcasing a clear blue pool reflecting the colors of a vibrant sunset sky. A gentle slope leads to the back of the house, enhancing the outdoor space's appeal.
Home in Chatsworth
4.94 out of 5 average rating, 107 reviews

Address: 22428 Napa St, West Hills, CA

ATTENTION TO ALL GUESTS : This unit is located in 22428 Napa St, West Hills, CA Please make sure to read this and check on the maps if that's good make your reservation. Welcome to our stunning newly constructed 2 bed, 2 bath home with an open floor plan that will take your breath away! The contemporary design boasts luxurious finishes and high-end appliances. Enjoy the beautifully landscaped yard and private patio area for an intimate evening under the stars.

Guest favourite
The exterior of the mid-century modern home is showcased at dusk, highlighting a pool in the foreground. A dining set sits beside the pool, with large windows revealing the interior space. Architectural elements include a stone chimney and surrounding greenery.
Home in Thousand Oaks
4.98 out of 5 average rating, 199 reviews

Eichler -Private- Oasis: Pool & Spa Escape

Welcome to the Eichler House in Thousand Oaks! This mid-century modern home features a pool, jacuzzi, fireplace, and built-in BBQ—perfect for entertaining or relaxing. Fully remodeled with modern amenities, it boasts an atrium, open floor plan, and floor-to-ceiling windows for seamless indoor-outdoor living. Nestled on a private lot backing to open space, it offers tranquility while being minutes from hiking trails, shopping, and 30 minutes from the beach.

Guest favourite
A spacious living area is presented, featuring a modern sectional sofa and a coffee table. A small kitchenette with a microwave and refrigerator is visible to the left. Dark curtains frame the window, and the room is well-lit by overhead lighting, enhancing the clean, comfortable atmosphere.
Guesthouse in Thousand Oaks
4.95 out of 5 average rating, 614 reviews

Comfortable, Suite Close to Everything

Welcome! Our place is close to Malibu, Camarillo Outlets, Ronald Reagan Library, Amgen, Hiking, Ventura, Parks, 25mins from various Beaches, Halfway point between Los Angeles and Santa Barbara, 40mins or so to Los Angeles/Hollywood and 1hr drive to Santa Barbara. You’ll love it because of the quiet neighborhood, a private suite and space all to yourself. Our place is good for couples, solo adventurers, & business travelers. *Heater and A/C inside unit.

Top Guest favourite
A modern kitchen features sleek countertops and dark cabinetry, complemented by a stylish tile backsplash. High-end stainless steel appliances are integrated, with a spacious open layout that allows for easy movement. Natural light streams in through the window, illuminating the inviting cooking space.
Home in Thousand Oaks
4.98 out of 5 average rating, 140 reviews

A Happy Home

Celebrate your time off in our happy, family-friendly home. This four-bedroom single-story house boasts an AMAZING kitchen, an expansive pet-friendly backyard, a refreshing swimming pool, and beautifully decorated living room and bedroom spaces. The water pressure in both of the home's walk-in showers will blow your mind and everyone will want to try out the remote-controlled bidet in the Master Bathroom. We look forward to hosting you and yours!

Guest favourite
Apartment in Calabasas
4.92 out of 5 average rating, 141 reviews

Luxury 2 King Master Bdrm Woodland Hills

Relax and feel at home in this luxury apartment with a cozy touch. The apartment is located in Woodland Hills/Canoga Park, 5 minutes away from the Topanga Mall. There is plentiful shopping, dining, movie theaters and family activities within a few miles. Nearby cities include Calabasas, Tarzana, Studio City, Sherman Oaks, and Encino. Easy freeway access. Apartment is complete with in unit laundry. Building includes resort style amenities.

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, 295 reviews

Resort Oasis

This is a gorgeous 500 sq foot pool house with chef’s kitchen. Full access to pool, spa, outdoor kitchen and all the various garden areas on 1/3 of an acre. It is a large detached studio great for up to 2 guests. It’s located on a quiet cul de sac. If you’d like to have a special event or film on the property, we charge on a hourly basis depending on the number of guests and event type.

Popular amenities for Simi Valley rentals with a pool

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Avg. price$267 AUD$246 AUD$275 AUD$253 AUD$293 AUD$318 AUD$366 AUD$330 AUD$318 AUD$318 AUD$286 AUD$273 AUD
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Quick stats about holiday rentals with a pool in Simi Valley

  • Total holiday rentals

    Explore 70 holiday rentals in Simi Valley

  • Verified guest reviews

    Over 1,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Simi Valley holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Simi Valley rentals

  • 4.7 Average rating

    Simi Valley stays receive an average rating of 4.7 out of 5 from guests

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