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Holiday Rentals near Simi Winery

16275 Healdsburg Ave, Healdsburg, California 95448-9075
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    Travellers to Healdsburg are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    All 65 Rentals in Healdsburg
    3.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3.4 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    3.5 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    2.7 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
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    About this property
    The cottage is a well-appointed, stand-alone unit with a private gate and entrance which provides an ideal retreat for touring the Sonoma and Napa wine country. Located in a garden setting 5 blocks from the Healdsburg Plaza in the central, historic district, it is adjacent to a 2-story, 1880's...
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    7.1 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    Xanadu Healdsburg Luxury Vacation home in Healdsburg. In the Heart of Sonoma County Wine Country, Healdsburg is the hub of the Dry Creek, Alexander Valley and Russian River Wine Regions. The home is just Five minutes from the Healdsburg Plaza Square with dozens of Winery Tasting Rooms, Award...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    2.9 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    This Charming 2 bedroom 1880's Cottage is the perfect wine country getaway for 4. Just 2 blocks from the historic Downtown Plaza, Restaurants, Boutiques and Wine Tasting. The newly remodeled contemporary furnished interior is well appointed for you getaway needs. Living Loom, Dining area, Kitchen...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2.2 kilometres from Simi Winery
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Hot Tub
    • Grill
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    • Terrace
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    About this property
    The Residence at Comstock Wines is located on our 17 acre Estate Vineyards and was completed in 2016. The Residence boasts four stunning Master Suites, each offering private entrance, vineyard view terrace, gas fireplace, OrganicPedic beds, 1500 thread count linens, shower with vineyard view window...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    2.8 kilometres from Simi Winery
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    • Mountain Views
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    • Porch
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    Pet friendly
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    Smoking allowed
    About this property
    2nd floor: 11 foot ceilings. Beautiful, gourmet kitchen with stunning views. Kitchen is equipped with a Thermador 6 burner (and grill) gas stove top and double electric oven. Butcher block counter tops. Dishwasher, Professional quality knives and cookware. Large microwave. Spacious walk-in pantry....
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
    Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg1 / 46
    (58)Excellent
    2.9 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Crossroads Vineyard:  In the Heart of Healdsburg Wine Country1 / 23
    (88)Excellent
    2.6 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Spectacular view of Dry Creek Valley1 / 26
    (1)Excellent
    1.7 kilometres from Simi Winery
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 49
    (38)Excellent
    8.2 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town1 / 44
    (65)Very good
    4.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Enchanting Wine Country Villa1 / 24
    (3)Excellent
    8.7 kilometres from Simi Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 35
    (25)Excellent
    7.1 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (78)Excellent
    5.7 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Art and Wine Estate - Vineyards, Pool, Garden1 / 48
    (12)Very good
    13.2 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautiful Studio Getaway  in the Heart of Wine Country1 / 12
    (52)Excellent
    5.9 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Vineyard Guest House1 / 31
    (17)Excellent
    7.5 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    4,700 ft 4 bed & 4 bath ranch, 120 acres all to yourself with a lake and farm.1 / 47
    (18)Excellent
    6.4 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    luxuriously appointed new large guest suite in a landmark Victorian1 / 21
    (37)Excellent
    5.6 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.8 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg1 / 48
    (57)Excellent
    3.4 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Dry Creek Cottage - Healdsburg1 / 6
    (69)Excellent
    1.5 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Private Wine Country Retreat-Luxury estate, pool, hot tub, 3 miles to town1 / 42
    (41)Excellent
    1.5 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    The Cabin on Fitch Mountain1 / 37
    (25)Very good
    4.3 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Tanda Tula, Wine Country Sanctuary1 / 28
    (100)Excellent
    7.0 kilometres from Simi Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Wine country getaway; stay in a winery1 / 12
    (14)Excellent
    3.4 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Updated cabin, right on Russian River, amazing views & location!1 / 23
    (24)Excellent
    4.5 kilometres from Simi Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Downtown Healdsburg Loft - (30 day minimum rentals only)1 / 19
    (4)Excellent
    2.4 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.1 / 50
    (27)Excellent
    3.6 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Healdsburg River Front Oasis Retreat.1 / 28
    (76)Excellent
    4.3 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Morning Dew- A Riverfront Healdsburg Home1 / 27
    (18)Excellent
    4.4 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza1 / 23
    (21)Excellent
    5.3 kilometres from Simi Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    3.1 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Downtown Healdsburg Victorian Cottage: recently remodeled, one story, open floor plan, chefs kitchen, indoor-outdoor living, covered porch, and hot tub. Easy walk to Plaza, restaurants, wine tasting lounges, movies, performing arts theater, art galleries, and boutique shops. At the Center of Dry...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Hilltop Hideaway:  Bright, Fresh, Modern, Views And Only 2 Miles To Plaza1 / 45
    (118)Excellent
    4.4 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!1 / 35
    (82)Excellent
    3.9 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Healdsburg Cottage  Walk to the Plaza, Workspace1 / 34
    (127)Excellent
    2.7 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.1 / 11
    (179)Excellent
    3.8 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Dog Friendly  Vineyard Estate Cottage with Lap Pool and Incredible Views1 / 18
    (46)Excellent
    8.4 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Unheated)
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Modern, newly built 5 BR home with beautiful views and 50 acres of privacy1 / 46
    (16)Excellent
    9.2 kilometres from Simi Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly1 / 16
    (97)Very good
    4.5 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg1 / 36
    (147)Very good
    8.3 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1.2 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Enjoy the seclusion of this cottage on a privates drive in Dry Creek Valley just five minutes from the Healdsburg Plaza Square - the home of over 20 Wine Tasting Room, Award Winning Restaurants and Boutique Shops. The perfect Wine Country getaway for 2 couples with a queen sleeper in the Living...
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    3.5 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Just 2 blocks from the historic Downtown Plaza, Restaurants, Boutiques and Wine Tasting. Designer touches, high end finishes inspire. The setting lends the air of calm you seek when you visit Wine Country. An open concept chef's kitchen w/stainless appliances and sleek surfaces has ample storage...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Healdsburg - Chalk Hill Wine Country Cottage1 / 24
    (163)Excellent
    12.5 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Top Of The World Dry Creek Views With Hot Tub, POOL and new Tesla charger!1 / 25
    (63)Excellent
    7.8 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful home on 10 acres w/ hot tub, English garden & stunning patio!1 / 35
    (9)Excellent
    2.1 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets1 / 38
    (37)Excellent
    6.0 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3.5 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy your own private Wine Country retreat just minutes from Dry Creek and Alexander Valley wineries and 10min to Healdsburg Plaza. This home features an open concept floor plan on the main floor that opens up to a very large entertaining deck overlooking the property. The kitchen, complete with...
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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