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Holiday Rentals with Pools in Simi Valley

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    Don't let other travellers get your favourite Simi Valley area holiday rental. You're so close to securing your perfect getaway. Book today.
    21 Matching Rentals in the Simi Valley AreaView all 53 rentals
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    Simi Valley
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Tuscan Villa Estate for Vacations  & Film Location1 / 12
    (2)Terrible
    Simi Valley
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    The following rentals are within 25 kilometers of Simi Valley.
    Beautiful Remodeled Home!!1 / 12
    (2)Average
    Bell Canyon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Recreational Paradise1 / 56
    (2)Excellent
    Westlake Village
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2017
    Our holiday was absolutely wonderful. Recreational Paradise is a delightful property in a fantastic location. We found everything we needed close by. The home is beautifully...
    Reviewed 18 July 2016
    My husband and I rented this home for us and our bridal party for the weekend of our wedding in Camarillo. Not only was the house absolutely gorgeous (the pictures do it no...
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    About this property
    Beautiful Ranch Style Home in Westlake Village with a Pool, Spa, Tennis Court, Basketball Court Ping Pong and Pool . A 4 bedroom, 4 bath home. Three of the rooms have their own private bath attached to bedroom. The 4th bedroom has a 1/2 bath close by. Living area includes: Living Room, Family...
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    Westlake Village, California 91362
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Bell Canyon
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Washer
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best Encino has to offer from this stylish 2BR/2.5BA split-level vacation rental, only 20 minutes from Universal Studies and iconic Beverly Hills. With two living areas, a game area and office space and a chef’s kitchen stocked and ready for the demands of your party, living in the...
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    Location Information
    Bell Canyon, California 91316
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Saddle Peak Buddha House - Malibu1 / 24
    (1)Excellent
    Topanga
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • Balcony
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    The location is amazing, with views of the ocean and the hills, sunrise and sunset! A spiritual aura pervades this home, which is very comfortable and welcoming. A huge deck...
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    About this property
    The Saddle Peak Buddha House is locally known for its breathtaking views, comfortable atmosphere and amazing energy. It is situated in the Santa Monica Mountains and overlooks the Pacific Ocean. Enjoy all the comforts of home at our relaxing retreat. The space has a very unique history involving...
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    Location Information
    Topanga, California 90290
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Agoura Hills
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spectacular ranch sits on over six acres of natural perfection, surrounded by the Santa Monica Mountains. Upon entering the hand-carved gate, guests will walk through a stone and brick tower, through a series of arches, and into the massive central lounge spaces. The great room, dining room,...
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    Location Information
    Agoura Hills, California 91301
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Hidden Hills
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful Colonial Home with a large backyard with a pool, spa, nice covered patio, basketball area, and partial views! Featuring 5 bedrooms (1 down and 4 up), plus a large bonus room upstairs perfect for theater, game room, etc., the possibilities are endless! Surrounded with charm and...
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    Hidden Hills, California 91302
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Thousand Oaks
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An entertainers delight! Large living space outdoors. A single story home featuring a dramatic view of the canyons and Malibu mountains. Large open living and eating areas, outside patio and sofas and TV adds another family room to lounge in. Built in BBQ and fire pit for relaxing in the evening....
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    Thousand Oaks, California 91360
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Calabasas
    6 Bedrooms, 9 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Privately Gated Country English Estate, sited on 1.8 acres with stunning city lights views. Spectacular property in all regards. Floor plan includes 6 bedrooms, 9 bathrooms, formal living & dining rooms, gym with full bath (can be 7th bedroom), large game room with wet bar and one of six...
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    Calabasas, California 91302
    Holiday Rental House - 6 Bedrooms, 9 Bathrooms, Sleeps 12
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    Agoura Hills
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Balcony
    • Washer
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Countryside views from every room! The gated 4-acre Malibu Hills home is nestled in the vineyard filled hills between the cities of Malibu and Agoura, in the midst of wedding venues, wine tasting venues, and just minutes to the beaches-- and with a sparkling pool! Breathe the fresh mountain air...
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    Location Information
    Agoura Hills, California 91301
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Topanga
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stop and smell the citrus In the urban jungle of Los Angeles, few neighbourhoods offer the peace and tranquility that Pacific Palisades does. And nestled at the base of the Santa Monica Mountains, wrapped in its own verdant garden, Passiflora House is a retreat within a retreat – a place to...
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    Topanga, California 90272
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Agoura Hills
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Washer
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning 4BR/3BA hillside estate offers breathtaking panoramic valley and mountain views. A 15-minute drive to Malibu, spend sun-drenched afternoons at the beach, or enjoy a shopping spree at the Shoppes at Westlake Village. After a day of exploring, unwind in the private infinity pool, then...
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    Location Information
    Agoura Hills, California 91301
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Topanga
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Grill
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the peaceful neighborhood of Encino, this private Los Angeles vacation rental home offers a serene retreat to discerning travelers visiting the City of Stars. Equipped with an abundance of contemporary creature comforts and an ADT Security system with 24-hour patrol protection, guests of...
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    Location Information
    Topanga, California 91316
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Westlake Village
    3 Bedrooms, 3 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My home is located in Westlake Village a upscale town that’s close to Restaurants, shops Bars and Markets Easy accces to the 101 freeway as well as Close to beaches .Westlake Hyatt , Westlake Four Seasons Hotel. Trader Joe’s Thousand Civic Crnter as well as the Thousand Oaks Mall.The condo...
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    Location Information
    Westlake Village, California 91362
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 2
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    Topanga
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dip in Nestled in the mountains, Duende Lane is a large bungalow home with a stunning backyard where there’s a large heated pool and canyon views. You’ll find a private wraparound garden behind the gate, all of which is worth exploring. But first, through the front door, you’ll find two sitting...
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    Location Information
    Topanga, California 90272
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Topanga
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Posetano Road is a two bedroom, two bathroom home in Pacific Palisades. This home’s soft-coloured sitting room is elegantly furnished and hung with black-and-white pictures, and gives straight onto the garden, where there’s a pool with a beautiful view. Both bedrooms are similarly low-key, with...
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    Location Information
    Topanga, California 90272
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Topanga
    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fast lane Nestled near the peak of the Santa Monica Mountains, Palisades Drive is high-end in every sense. Inside this newly built home, the hallway leads right to a staircase, then up to the cinema room and a courtyard with a fountain. The master bedroom (with a marbled ensuite, an...
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    Location Information
    Topanga, California 90272 2824
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    Westlake Village
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sun, sea and sand Situated right on the beach, this home is as idyllic inside too. First on the right is a hallway, which leads to the second bedroom (with a queen-size bed), with its whitewashed walls and wooden ceiling. Also here is the blue-and-white third bedroom, and a bathroom with a bath and...
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    Location Information
    Westlake Village, California 90265
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Westlake Village
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Nestled up on a hillside, this palatial 4BR/3BA offers expansive Santa Monica Mountain views. Your two-story getaway seamlessly combines 3,293 square-feet of upscale indoor/outdoor living space with a private backyard oasis that feels like royalty. After a morning hike, cool off...
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    Location Information
    Westlake Village, California 91361
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Calabasas
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Balcony
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Extraordinary gated estate with extreme privacy & incredible panoramic city views. Situated on 1.8 acres, this is a dream home. Includes theater room and gym. Featuring 6 bedrooms, 9 bathrooms, 6 fireplaces, hardwood & stone tile floors, two full bars, chef’s kitchen, full pantry, formal living,...
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    Location Information
    Calabasas, California 91302
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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