
Holiday rentals with a pool in Simi Valley
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Top-rated rentals with a pool in Simi Valley
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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

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

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.

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.

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!

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!

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.

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.

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.

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!

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.

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
House rentals with a pool

Lake Balboa Ranch Home with Pool & indoor Jacuzzi

Stunning View Hollywood Hills Guest House

New Toluca Lake Private Pool House

Paradise Retreat | Private 3 Bedroom w/ Pool & Spa

Peace of Paradise

3 bdrm / 4 Bed / 2 bath Kitchen/Jacuzzi/Laundry

Serene Hillside Oasis with Pool & Stunning Views

Spacious LA Villa w/ Pool, Hot Tub & Parking
Condo rentals with a pool

Skyline view Condo, Free Parking, Jacuzzi

Modern, Spacious 1 Bd Loft in DTLA - FREE Parking

Stylish Modern industrial condo with Rooftop pool

Luxury Top Floor DTLA Condo w/Pool *Free Parking*

Luxury Resort Condo by Six Flags Magic Mountain

DTLA Elegance & Style (1 bdrm, Free Parking, Pool)

Designer | HighRise Condo | DTLA

Luxury Resort Style Condo Valencia!
Home rentals with a private pool

Plant Lover's Paradise: Jacuzzi/Pool, 420 Welcome

Contemporary Cottage - An Oasis with a Private Heated Pool.

Keep Cool in the Poolside Shade at a Charming Encino House

Serene Cozy Guesthouse Garden Oasis
101 Luxurious Home near Universal Studios Pool/Spa

Pool Oasis in Vintage Craftsman House

Designer’s Dream Oasis with Lap Pool & Hot Tub

Historical Swiss Chalet in Los Angeles (with pool)
When is the best time to visit Simi Valley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| 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 |
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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