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Kenwood Holiday Vacation with Pools

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    Travellers to Kenwood are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    26 Matching Rentals in the Kenwood AreaView all 78 rentals
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    Summer Midweek Special! Poolside Cottage in Best Wine Country Location1 / 18
    (17)Excellent
    Kenwood
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    Kenwood
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Kenwood
    4 Bedrooms, 4 Bathrooms, Sleeps 10 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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    Kenwood, Sonoma County 95452
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Kenwood
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • 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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    Kenwood, Sonoma County 95452
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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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
    • 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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    Kenwood, Sonoma County 95452
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kenwood
    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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    The following rentals are within 10 kilometres of Kenwood.
    Secluded Sonoma Country Retreat, Views, Pool-Spa1 / 26
    (1)Excellent
    Sonoma
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2015
    We stayed at Rancho Paradiso in Oct. 2014. This home was perfect for our three couples group as the layout has 3 master suites. It did not disappoint! It is spacious and well...
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    About this property
    RANCHO PARADISO 5 minutes from Historic Sonoma Plaza and 12 minutes from Napa, Rancho Paradiso is a private gated property on 4 acres, a wonderful mesmerizing place. Centrally located for exploring this beautiful world class wine tasting region. We are located in the heart of the Carneros...
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    Location Information
    Sonoma, Sonoma County 95476
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Glen Ellen
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    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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    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Sonoma
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sonoma Hideaway is a wine country gem that combines indoor outdoor living amongst the vines with the privacy of a 2 acre lot - Perfect for families! The Master Bedroom, 2 guest bedrooms (one with trundle bed), 1 kids bedroom (2 beds and trundle bed) sleep a total of 10 people (8 adults and two...
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    Sonoma, Sonoma County 95476
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Charming Country Cottage Minutes To  Plaza/TOT695N1 / 27
    (5)Excellent
    Sonoma
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • DVD Player
    • Grill
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2016
    The place was absolutely perfect! Karen and Pieter were gracious hosts who have literally thought of everything. Top notch kitchen appliances, with a kitchen stocked with all...
    Reviewed 15 March 2014
    My husband and I stayed here for the month of February. We wanted a quiet place to relax with everything we might need to feel at home for a month away, and this place provided...
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    About this property
    Alder Mews.... imagine your own private guest cottage nestled among mature oaks and rolling horse pasture on a beautiful 20 acre property in an exclusive area close to numerous wineries and 10 minutes from the historic and charming Sonoma Plaza shops and renown restaurants. After a day of...
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    Location Information
    Sonoma, Sonoma County 95476
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Glen Ellen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this 4BR, 2BA secluded country cottage your home-away-from-home while you explore wine country. Relax and unwind in a down-to-earth, shabby chic interior, and enjoy Sonoma Mountain views from the private pool and spacious outdoor seating area. Long Description: A charming wood bridge leads...
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    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Glen Ellen
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 3-bedroom, 3.5-bath house in Glen Ellen boasts jaw-dropping views of the valley and spectacular sunsets! Watch them from the solar-powered pool or the outdoor farm tables with combined seating for 10. With two master suites, two living areas and a high-end kitchen, this is the perfect vacation...
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    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Glen Ellen
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Patio
    • Air Conditioning
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breathtaking views of the Sonoma Valley steal the show at this magnificent California ranch-style home, nestled in the heart of Glen Ellen’s wine country. Featured on ABC's "The Bachelor", this 6BR/4BA private estate overlooks its own vineyard and features both a main house and guest house with...
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    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Runningwood Sonoma1 / 68
    (3)Excellent
    Sonoma
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2015
    This is a beautiful home on a great piece of property. Home has nice amenities, great view, and is comfortable. I'd recommend it. Rudy was a very polite host!
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    About this property
    The estate house was built in 1994 and has since enjoyed an elite group of guests beginning with Warner Brothers premier stars who stayed at Runningwood while filming a new Warner Brothers production. Since then the property has been used to host and entertain high profile wedding ceremonies and...
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    Sonoma, Sonoma County 95476
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sonoma
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful gated one-of-kind Wine Country Estate is situated within 10 minutes of the Sonoma Plaza. Retreat to a private world of your own that is minutes to everything the Wine Country has to offer. Lush landscaping, grapevines, waterfalls, flowers, gardens, amazing outdoor pool & spa,...
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    Location Information
    Sonoma, Sonoma County 95476
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Walk to Sonoma Plaza from this private, idyllic creak side retreat with a pool1 / 18
    (4)Very good
    Sonoma
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2014
    We visit the area every year for the Napa2Sonoma Half Marathon. We rent a house every time we come, and this was by far the most conveniently located for the race. It was quite...
    Reviewed 16 June 2014
    I stayed at the Inn Wine Country with my husband, his parents, his sister and brother -in-law, and their two little girls. The fourth bedroom was a pullout futon which was...
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    About this property
    Inn Wine Country is a unique, stylish light filled two story contemporary creek side oasis located within walking distance of historic Sonoma Plaza. Cross a charming bridge over Nathanson Creek to reach this perfectly situated one-of-a-kind retreat. You will enter a retreat totally removed from...
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    Location Information
    Sonoma, Sonoma County 95476
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sonoma
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new home custom designed by a prominent San Francisco Interior Designer and a North Carolina architect. The home is situated on 4+ acres in one of the most distinguished Sonoma neighborhoods and on the grounds of the former Spreckels Estate. The home looks east over Sonoma Valley with views...
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    Location Information
    Sonoma, Sonoma County 95476
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Glen Ellen
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    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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    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Glen Ellen
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Satellite TV
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The wine country oasis you've been dreaming of, complete with a bocce court. Newly remodeled and with high-end touches at every turn, this modern 2BR/2BA home is nestled between Sonoma, Santa Rosa, and Healdsburg. Ideal for 2 couples. Sleeps 4. ABOUT THE HOUSE Let the sound of Sonoma Creek lull...
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    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beautiful Estate on 3.5 Acres, Pool, Putting Green1 / 36
    (7)Excellent
    Sonoma
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Patio
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous secluded property offers great views, spacious living areas and solar heated pool. It is a perfect getaway for families or friends traveling together. And would be an excellent choice for corporate retreats and small weddings. The property is located in the Valley of the Moon on...
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    Location Information
    Sonoma, Sonoma County 95476
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sonoma
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience classic and easy California wine country indoor/outdoor living in this gorgeously renovated modern 2-bedroom, 1-bath property with expansive yard and pool in the scenic Sonoma Valley! Lounge poolside in the impressive and fenced backyard, or drive 6 minutes to the heart of the Carneros...
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    Location Information
    Sonoma, Sonoma County 95476
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    LAS PALMAS - Sonoma Resort-Like Home1 / 15
    (7)Excellent
    Sonoma
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Central Heating
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    My husband and I stayed at this house for a long weekend with 2 other couples to celebrate my 40th birthday in Sonoma. This house was perfect for it! Each couple had their own...
    Reviewed 23 January 2015
    This was our 2nd year staying at Las Palmas, and we have already booked for 2015. This is an exceptional property with all the amenities to make it a fun, relaxing and optimal...
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    About this property
    FOR THOSE LOOKING FOR A QUIET RELAXING RESORT-LIKE HOME. ***Given the setting of this property, the place is suited for quiet and relaxing enjoyment. Occupancy is limited to 6 people and parties and gatherings are not allowed. If you are looking for more of a party type house, our property manager...
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    Location Information
    Sonoma, Sonoma County 95476
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Glen Ellen
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Patio
    • Washer
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great for a multi-family getaway, this spacious 4BR/2BA Glen Ellen home lets you enjoy quality time together with its own private pool, outdoor dining area, hot tub, basketball court, and game room. And when you feel like quiet time, you can relax in the house library. In the surrounding region,...
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    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Glen Ellen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Grill
    • Satellite TV
    • Wi-Fi
    • Hot Tub
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Vista is a one-of-kind, completely private estate for discerning couples, families and friends. 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...
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    Location Information
    Glen Ellen, Sonoma County 95442
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sonoma
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the privacy of a redwood forest. Newly constructed, modern design comfortably sleeps 8 with 4BR, 4BA. Bright, spacious interiors are perfect for entertaining on a family retreat or friendly getaway. Spend your days poolside or touring wine country. You’ve never seen a vacation home quite...
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    Location Information
    Sonoma, Sonoma County 95476
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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