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Holiday Rentals with Pools in St. Helena

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    Travellers to St. Helena are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    26 Matching Rentals in the St. Helena AreaView all 55 rentals
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    St. Helena
    5 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    St. Helena
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Casa Cabernet1 / 18
    (1)Excellent
    St. Helena
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    St. Helena
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Stonehenge' depicts wine country living at it's best. You will enjoy the home as much as you'll love exploring Napa Valley. The home is professionally designed and furnished (mostly Restoration Hardware) and comes with a gorgeous pool, patio with fireplace, fire pit, BBQ, 1/2 outdoor basketball...
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    94574, St. Helena, Napa Valley
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    The following rentals are within 15 kilometres of St. Helena.
    Glen Ellen
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Grill
    • Hot Tub
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The charming house has two bedrooms: a very generous master bedroom suite with a private deck and a second bedroom with two beds that can be coverted into one queen size bed. Additionally, the living room has a comfortable pull-out couch suitable for sleeping two. The gourmet kitchen is fully...
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    95442, Glen Ellen, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Modern 3br Home W/Pool & Seasonal Creek in Sonoma.1 / 31
    (9)Excellent
    Kenwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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 27 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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    95452, Kenwood, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Glen Ellen
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Parking
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The charming house has two bedrooms: a very generous master bedroom suite with a private deck and a second bedroom with two beds that can be coverted into one queen size bed. Additionally, the living room has a comfortable pull-out couch suitable for sleeping two. The gourmet kitchen is fully...
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    95442, Glen Ellen, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Glen Ellen
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Hot Tub
    • Parking
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The charming house has two bedrooms: a very generous master bedroom suite with a private deck and a second bedroom with two beds that can be coverted into one queen size bed. Additionally, the living room has a comfortable pull-out couch suitable for sleeping two. The gourmet kitchen is fully...
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    95442, Glen Ellen, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Relaxing, Private Poolside Cottage for 2 in Sonoma Valley Wine Country1 / 18
    (19)Excellent
    Kenwood
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    We stayed here for the ironman santarosa 70.3, and it was perfect. Just 15-20 minutes from Santa Rosa nested in a perfect quiet place. Linda and Mike go out of there way to...
    Reviewed 27 June 2017
    Sonoma Rosso was the perfect cottage for our first visit to wine country. Linda was so helpful with recommendations before we arrived and she and Michael were fantastic hosts...
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    About this property
    Relax and unwind in a brand new, poolside guest cottage on a private compound just off the Highway 12 Wine Trail in Kenwood. The Sonoma Valley scenery is gorgeous - from vineyards and wide open fields studded with ancient oaks to rolling hills and dramatic mountains. Your home away from home...
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    95409, Kenwood, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Glen Ellen
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Washer
    • DVD Player
    • Housekeeping Included
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful villa three blocks to Glen Ellen restaurants. Furnishings and interior design focused on creating a sanctuary in the Valley of the Moon. Lovely pool, full kitchens, BBQ, laundry rooms make for a wonderful and relaxing place to experience the Sonoma lifestyle. Great for a get away in wine...
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    Location Information
    95442, Glen Ellen, Sonoma County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Calistoga
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Patio
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern luxury meets Napa Valley Wine Country ranch style in this beautifully 17 acre property nestled in a private valley in the Mayacamas Mountains 1,200 feet above Calistoga. We call it 'Mayastoga.' Learn more about 'Mayastoga' and 'Mayastoga Ranches' by searching the web. The home is an...
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    94515, Calistoga, Napa Valley
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Kenwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Grill
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous 3BR/2BA home in Kenwood features high ceilings and a chef’s kitchen, as well as vibrant hand-picked artwork and carefully selected furnishings. A wood-burning pot belly stove/fireplace in the dining room adds cozy ambiance on a cool evening. Set on a breathtaking 6.5-acre estate...
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    Location Information
    95452, Kenwood, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Calistoga
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This rental is available on a long-term basis in addition to short-term. Please call in to speak directly with our team to facilitate a long-term rental. Please note: Long-term rentals longer than 30 nights require bi-monthly housekeeping at the guest’s expense and a monthly homeowner required...
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    Location Information
    94515, Calistoga, Napa Valley
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Kenwood
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • Air Conditioning
    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
    95452, Kenwood, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Glen Ellen
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breathtaking views of the Sonoma Valley steal the show at this ranch-style home in the heart of Glen Ellen’s wine country. Featured on ABC's 'The Bachelor,' this 6BR/4BA estate overlooks its own vineyard and features a main house and guest house with comfortable sleeping for 12. The home also has...
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    Location Information
    95442, Glen Ellen, Sonoma County
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Calistoga
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Napa Valley Wine Country home is located on 6.7 acres on the valley floor between Calistoga and St. Helena. Offering flexible length of stays. Amidst a 4.3 acre top quality organic cab vineyard with 100 year old oaks, this property is a very special wine country escape. Four night minimum....
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    Location Information
    94515, Calistoga, Napa Valley
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    Kenwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All originally built or restored by owners for friends and family - this elegant home sits on an acre with over 300 feet of rare Sonoma Creek frontage in Kenwood. Behind the stone wall and gated circular driveway there's a 16' x 33' solar heated saline pool with a child safe automatic cover that's...
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    Location Information
    95452, Kenwood, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lawndale Sonoma County
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a sunlit ridge high above the Sonoma Valley and Napa Valley. Alpicella Vineyard and Villa combines a romantic retreat that is country yet sophisticated. The private cottage is part of a 6,000 acre pristine wilderness. The cottage has views that overlook our award winning, organic estate...
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    Location Information
    95409, Lawndale Sonoma County, California
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kenwood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled along a quiet country road overlooking Sonoma Valley vineyards and mountain panoramas, this 2BR/2BA cottage offers an ideal setup for couples vacationing together. Enjoy spacious communal living areas and a private upstairs loft with separate entrance. You’ll have all the comforts of home...
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    95452, Kenwood, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Kenwood
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Mountain Views
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rose cottage is a serene and charming retreat within minutes to world class wineries along the famed 'Wine Highway', restaurants, outdoor activities and shopping in gorgeous Sonoma. Your stand alone private ~1000 square foot 1 bedroom cottage is located on an exclusive, private country lane...
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    95442, Kenwood, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Kenwood
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/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
    95409, Kenwood, Sonoma County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Calistoga
    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Mountain Views
    • Wi-Fi
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the best of Napa Valley at this luxury 7-bedroom, 7.5-bathroom Calistoga vacation rental house which sleeps 14. With a spacious, lovely interior and a picturesque, entertaining exterior, this beautiful home is an ideal size for families, friends or couples traveling together. With a daily...
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    Location Information
    94515, Calistoga, Napa Valley
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    Poolside 3BR/4.5BA in Wine Country w/ Spa, Fitness Cabana & Bocce Court1 / 24
    (1)Excellent
    Kenwood
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2017
    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/4.5BA home offers an upscale stay central to Napa and Sonoma. Enjoy the manicured backyard, where a pool, spa, bocce court, dining patio, and fire pit offer an extraordinary outdoor experience. Modern decor intermingles with...
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    Location Information
    95452, Kenwood, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Kenwood
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    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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    95452, Kenwood, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Glen Ellen
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Vista is a one-of-kind, private estate in the heart of Sonoma wine country. Beautifully furnished, this 2BR/2BA compound sits behind a gated entry on a verdant hillside. The home’s abundant windows showcase the stunning views. Swim in the solar-heated pool and enjoy relaxing soaks in the hot...
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    Location Information
    95442, Glen Ellen, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Kenwood
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled under the giant oaks at the end of this country road overlooking Napa Valley vineyards and mountain panoramas, this 1BR cottage sits on a stunning 6.5-acre estate. The cottage has a spacious living area, well-equipped kitchen, and large deck with a private hot tub overlooking the scenic...
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    Location Information
    95452, Kenwood, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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