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Kenwood Holiday Homes

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    Travellers to Kenwood are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 15 Rentals in Kenwood
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    Relaxing, Private Poolside Cottage for 2 in Sonoma Valley Wine Country1 / 54
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Heiter House - the perfect getaway in Wine Country1 / 25
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    WALK to Wineries from this Gorgeous Designer Home!1 / 23
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to wine country with a stay at this exquisite 4BR/3BA Kenwood estate set on an acre of landscaped grounds with pool, fruit trees, and private vineyard. Easy walk to wineries or short drive to Sonoma and Napa Valley restaurants. Sleeps 8. ABOUT THE HOUSE This single-level country house...
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    Kenwood, Sonoma County 95452
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one of a kind stone lodge is located in a secluded location at the very heart of the Sonoma Valley, all 5 bedrooms are large and have a private, ensuite bath. We have a caretaker who lives just down the lane, so you can be assured of superior oversight and assistance. We now have access to a...
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    Kenwood, Sonoma County 95452
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfectly located in the heart of the Sonoma Wine Country, this one-acre property is set amongst surrounding vineyards and mountains and is just steps to the town of Kenwood with access to numerous wine tasting rooms, restaurants, and shopping. This Kenwood home is designed to maximize outdoor...
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    Kenwood, Sonoma County 95452
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2015
    I live locally and wanted to find a rental that my family could gather at and decided on this Kenwood property mainly as the pool looked like the perfect place to relax and...
    Reviewed 28 March 2015
    Wow this place was so tranquil and beautiful. It was exactly what I needed to recharge my batteries. The drive up there was so relaxing and beautiful. It's in the perfect area...
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    About this property
    Escape to this 2 acre, 3-bedroom retreat in the heart of Sonoma Wine Country, nestled among Oak and Fir trees along a calming seasonal creek. Located in Adobe Canyon, off the Valley of the Moon Highway, the quintessential Wine Country Hamlet of Kenwood is just a short 5-minute drive as is the...
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    Kenwood, Sonoma County 95452
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Spa, Bocce, Bbq Kitchen, Walk or Bike to Wineries1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Hot Tub
    • Central Heating
    • Satellite TV
    • Grill
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2016
    I booked this property for 4 adults. We ended up with a Newborn as our 5th!!! This house has been transformed by the Owner Peter into a great oasis in the middle of an old...
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    About this property
    Hello and welcome to Casa Orinda, our newly renovated wine country home in Kenwood, in the heart of the Valley of the Moon.<BR><BR>Our 2 bedroom, 2 bathroom home features an open kitchen-living floor plan perfect for enjoying a good time with family and friends. <BR><BR>The kitchen is fully...
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    Kenwood, Sonoma County 95452
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Kenwood Cottage - Canyon Setting on Sonoma Creek1 / 17
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Washer
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 September 2012
    Stayed here with 2 friends....all middle-aged ladies enjoying Northern California. The Cottage was spotlessly clean, well maintained, restfull, and centrally located. From...
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    About this property
    Kenwood Cottage is located in the heart of Sonoma's wine country and the charming town of Kenwood. This two bedroom home (over 1300 square feet of living space) is walking or biking distance to Sugarloaf Ridge State Park and major wineries. This idyllic cottage rests on a year round creek in the...
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    Kenwood, Sonoma County 95452
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The decision to spend time outdoors or indoors will be difficult as this luxury vacation home features gorgeous and well appointed living areas both inside and out. Upon arrival you will notice that the architecture of the luxurious Estate in the Vines was designed to complement its wine country...
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    Location Information
    Kenwood, Sonoma County 95409
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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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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    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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    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
    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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