
Vacation rentals with a pool in Simi Valley
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Simi Valley

Total vacation rentals
Explore 80 vacation rentals in Simi Valley

Verified guest reviews
Over 2,120 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
70 of Simi Valley vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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
Top-rated rentals with a pool in Simi Valley
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Secluded Oasis Estate
A Writer's Hideaway and Private Escape for the Hollywood Elite. This 3,500 Sq. Ft. oasis features a huge pool and spa, complete with a BBQ and outdoor fire-pit. Enjoy the viewfrom the hillside deck. A long driveway with ample parking leads to this stunning 4.5 bedroom/3 bath home. Large Master Suite includes fireplace, deck, and huge master bath with huge shower and tub with a view. Kitchen fully equipped. Property backs up to the best mountain biking trails in SoCal. Parties/Events Not allowed

Pickleball/ Hot Tub/Heated Pool/Tennis
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

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.

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

Heated Pool+Spa +Kids Fun Paradise-Near LA Beaches
BUILT FOR FAMILIES, Los Angeles (EV Car Chargers FREE) Less than 25 min from Malibu, Downtown, Hollywood, Venice, Pasadena, Universal City, Beverly Hills, Santa Monica. This home has been Newly Furnished and Completely Remodeled. Heated Salt Water Pool, Fitness Equipment, Full Kitchen, BBQ, Big Screen TVs indoors and outdoors by the Pool. Study Work Desk. Jacuzzi, Cable, Wi-Fi, Office Work Space, Private Parking, Ping Pong tables, Corn Hole, Floating beds for the pool and Jungle Gym.

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.

Tuscan Villa Guest House
Lovely, private guest house in the middle of an avocado orchard with swimming pool & hot tub & spectacular views of the Channel Islands. Sunsets are unbelievable! Feels like you're in the Tuscan hills of Italy with an ocean view in the distance. Tranquil & secluded yet only 10 minutes from Camarillo Airport & the Camarillo Outlet stores, 20 minutes to beaches, 30 minutes to Malibu, 45 minutes to Santa Barbara, 1 hour North of Los Angeles. Cal State University Channel Islands is 15 minutes away.

Plant Lover's Paradise: Jacuzzi/Pool, 420 Welcome
A plant lover's paradise tucked into a private backyard studio guesthouse, your own escape w/ a cal king bed, large pool, hot tub, cabana, and massage chair, not shared, all yours to enjoy! Surrounded by tropical fruit trees, an organic garden, and an aquaponics system, a true botanical hidden oasis. Cannabis-friendly (outdoors only). Mention "420" for complimentary organically grown pre-rolls (subject to availability). Max 2 guests. Please confirm you've reviewed the house rules when booking.

Island Style Oasis Home- Island in the Sky
Welcome to Island Style Oasis– your very own private paradise! Our luxurious retreat is the perfect place to escape the hustle and bustle of everyday life and indulge in some much-needed relaxation. Nestled in a peaceful and serene valley our stunning property offers everything you need to rejuvenate your body and mind. Whether you want to take a dip in our sparkling pool, soak in one of our Jacuzzi tubs, or unwind in our steam showers and dry sauna, we've got you covered.

Amazing private guest suite w /pool in Chatsworth
HOME SHARING #HSR20-000438 Hi everyone! We're close to restaurants, parks, great views, 15 minutes from Magic Mountain, 20 minutes from Hollywood, Close to Porter Ranch plaza, 10 Minutes from Northridge Mall & great hiking trails at Santa Susana Historic Park. We have it all Location, quiet neighborhood, the outdoors space, a pool and tennis court! Amenities! Pets and kids welcome! The guest suite is GREAT! Private entrance, Lots of light and great energy!

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.

Hillside Oasis: Hot Tub, Grotto, View
Welcome to our little slice of heaven in Thousand Oaks, CA. Serene retreat, situated on a hillside, with pool, grotto, and a hot tub. The house features astonishing views of the entire Conejo Valley. Great for family reunions, large groups, and pool days. Wake up to the birds singing and fall asleep to city lights. Your oasis awaits you!
Popular amenities for Simi Valley rentals with a pool
House rentals with a pool

Spacious Home With Pool and Spa in Thousand Oaks

A Happy Home w/Sparkling Pool

Midcentury Modern home with tons of Natural light!

Modern Family Farmhouse pool&spa, treehouse, bocce

Cali Luxury Dream Pool Hideaway + Guest Suite

Luxurious villa King Beds Pool & Spa

The Paradise Hot-Tub Treehouse

Magical sanctuary - hot tub/pool
Condo rentals with a pool

Stylish Modern industrial condo with Rooftop pool

Modern, Spacious 1 Bd Loft in DTLA - FREE Parking

Skyline view Condo, Free Parking, Jacuzzi

⁎ArtDeco ⁎ Condo⁎ pool⁎ Gym⁎Free Parking⁎Jacuzzi

Brand-New, Deluxe Hollywood Studio

Pool | Hottub | King Bed | WD | Walk to Shops

Updated 2 Bed 2 Bath Condo Westlake Village

The Lofts: Rooftop Pool & Spa, Free Parking, DTLA
Home rentals with a private pool

2 BR Mediterranean Oasis Sleeps 6!

Contemporary Cottage - An Oasis with a Private Heated Pool.
Beautiful Guest Cottage with Private Pool (Rancho)

Serene Cozy Guesthouse Garden Oasis

Keep Cool in the Poolside Shade at a Charming Encino House

Pool Oasis in Vintage Craftsman House

Designer’s Dream Oasis with Lap Pool & Hot Tub

Pool and Historical Swiss Chalet in Los Angeles
When is the best time to visit Simi Valley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 922 | ﺩ.ﺇ 900 | ﺩ.ﺇ 720 | ﺩ.ﺇ 606 | ﺩ.ﺇ 701 | ﺩ.ﺇ 760 | ﺩ.ﺇ 874 | ﺩ.ﺇ 790 | ﺩ.ﺇ 760 | ﺩ.ﺇ 643 | ﺩ.ﺇ 698 | ﺩ.ﺇ 977 |
| Avg. temp | 13°C | 13°C | 14°C | 14°C | 15°C | 17°C | 19°C | 19°C | 18°C | 18°C | 15°C | 13°C |
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- Venice Beach
- Universal Studios Hollywood
- Beach House
- SoFi Stadium
- Santa Monica Beach
- University of California - Los Angeles
- Los Angeles Convention Center
- University of Southern California
- Crypto.com Arena
- Six Flags Magic Mountain
- Dodger Stadium
- Rose Bowl Stadium
- Long Beach Convention & Entertainment Center
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- The Queen Mary
- Hollywood Walk of Fame
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- Hollywood Bowl
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- La Brea Tar Pits and Museum
- Dockweiler State Beach





