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Holiday Rentals with Pools in Kenwood

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    Travellers to Kenwood are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    9 Matching Rentals in KenwoodView all 17 rentals
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    Relaxing, Private Poolside Cottage for 2 in Sonoma Valley Wine Country1 / 18
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Modern 3br Home W/Pool & Seasonal Creek in Sonoma.1 / 31
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Grill
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enter through a private gate--up a small driveway -- relax and enjoy this quiet, modern cottage and loft with all the amenities needed for a peaceful time away. Explore the Valley of the Moon in Kenwood and surrounding wineries, restaurants, and regional parks. Several award winning wineries are at...
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    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This secluded home is nestled on the hillside on over 7 acres of century old oak trees in Sonoma wine country. The sweeping driveway takes you up the property to the house and 2 car garage. Along the way, you may be greeted by a family of deer resting under the large fig tree in the field. Before...
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    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Satellite TV
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a gracious, two story home. The dining room has seating for 8. The master suite and bathroom is located on the main level of the house. The second floor has a work space at the top of the landing. The two guestrooms on this level share a bathroom. One bedroom has a king size bed. The other...
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    Location Information
    Kenwood, Sonoma County 95409
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Panoramic vineyard views anchor this expansive 4-bed, 3.5-bath rental with a main house and separate guest house. This place has it all: an ideal location in the center of wine country, a gorgeous outdoor space with pool and patio, and a light-washed, modern interior. Ready for relaxation? Drive...
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    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Poolside 3BR in Wine Country w/ Cabana, Hot Tub, Bocce Court & Orchards1 / 24
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Been traveling to wine country for over 25 years. Of course when we are accompanied by friends, they always want to visit Napa. Who doesn't like Disneyland? On this most recent...
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    About this property
    Surrounded by wineries in the darling area of Kenwood, this elegant 3BR/3.5BA home offers an upscale stay central to Napa and Sonoma. Enjoy the sweeping backyard, where a pool, spa, bocce court, and fire pit offer an extraordinary outdoor experience. Modern décor intermingles with fine...
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    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Porch
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded two-story mansion in Kenwood is perfect for a luxurious, private getaway. Regal, columned home is situated on 20 acres of land, accessed via cul-de-sac private drive with security gate. The grounds include a pool with bath house, guest house, and children's playground. You can sit at a...
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    Location Information
    Kenwood, Sonoma County 95452
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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