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Vacation Rentals nearby Simi Winery

16275 Healdsburg Ave, Healdsburg, California 95448-9075
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    Travellers to Healdsburg are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    All 119 Rentals in Healdsburg
    Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome1 / 20
    (29)Excellent
    1.5 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 43
    (33)Excellent
    8.2 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    9 minutes to Healdsburg Plaza: 1.6 Acres of Privacy at End of Country Road1 / 36
    (76)Excellent
    7.8 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Wooded Restful Retreat, with broad scenic views, outdoor dining1 / 22
    (123)Excellent
    4.5 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
    Hilltop Hideaway:  Bright, Fresh, Modern, Views And Only 2 Miles To Plaza1 / 50
    (90)Excellent
    4.5 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 in Historic Downtown - Walk to the Plaza1 / 25
    (100)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
    Dry Creek Valley Home and Vineyard1 / 24
    (27)Excellent
    3.5 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Healdsburg - Chalk Hill Wine Country Cottage1 / 24
    (143)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
    Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets1 / 38
    (31)Excellent
    6.0 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Creekside Cottage-Style Home, 4 Bedrooms, 2.5 Bath w/Hot Tub and Spacious Lawn1 / 24
    (45)Excellent
    7.6 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Healdsburg River Front Oasis with Views and Hot Tub.1 / 28
    (41)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
    Modern View Home - Pool, hot tub, large deck, BBQ - 1 mile to Healdsburg Plaza1 / 24
    (32)Excellent
    4.0 kilometres from Simi Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    luxuriously appointed new large guest suite in a landmark Victorian1 / 21
    (23)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
    Crossroads Vineyard:  In the Heart of Healdsburg Wine Country1 / 23
    (82)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
    Dog Friendly  Vineyard Estate Cottage with Lap Pool and Incredible Views1 / 18
    (25)Excellent
    8.4 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
    4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views1 / 23
    (86)Excellent
    4.3 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Secluded Valley Retreat1 / 21
    (27)Excellent
    7.9 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
    Enjoy the Sunset from Upscale Home Among the Vineyards — short walk to Healdsbur1 / 48
    (44)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
    Private Wine Country Retreat-Luxury estate, pool, hot tub, 3 miles to town1 / 42
    (38)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
    Luxury Vineyard Estate Guest House1 / 19
    (71)Excellent
    8.5 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
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    Modern Sophisticated Private Luxurious W/Views & Hot Tub1 / 20
    (121)Excellent
    4.9 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Fitch Mountain Cottage with Private Beach Access and River Views1 / 24
    (18)Excellent
    3.6 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    New Contemporary Home in the Heart of Sonoma Wine Country.1 / 24
    (13)Excellent
    3.3 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 / 24
    (73)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
    Modern Home: Private Hilltop, Views, Pool & Spa  ~  2-6 Guests1 / 38
    (62)Excellent
    5.0 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Incredible view, peaceful family rental overlooking Dry Creek Valley1 / 33
    (26)Very good
    3.4 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball1 / 49
    (53)Excellent
    6.3 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards1 / 24
    (52)Very good
    3.4 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
    2.1 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
    Updated cabin, right on Russian River, amazing views & location!1 / 23
    (8)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
    Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg1 / 46
    (40)Excellent
    2.9 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Stunning Mountain Top Estate with View Over Dry Creek Vineyards1 / 26
    (13)Excellent
    8.6 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
    Great Outdoor Kitchen, Large Pool/Hot Tub, Firepit, Views, 8 mins to Plaza1 / 43
    (79)Excellent
    3.4 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
    Dry Creek Farm--Vineyard, Pool and Spa with Stunning View, Dog friendly1 / 50
    (65)Excellent
    6.7 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
    ArtHAUS - Private Retreat, Contemporary Design1 / 33
    (48)Excellent
    1.2 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
    Modern Wine Country Cottage in Historic Healdsburg, Premiere Location1 / 24
    (72)Excellent
    4.0 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
    Elegant - Peaceful - Romantic - Private1 / 24
    (129)Very good
    2.7 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
    Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8 guests, children welcome)1 / 25
    (25)Excellent
    1.8 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
    Stunning, quiet, contemporary, single-level, eco-friendly home on 2.5 acres1 / 25
    (21)Excellent
    7.0 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    *LImited Time Discount*  Healdsburg Riverside Cottage - Beautiful River Views1 / 24
    (20)Excellent
    4.5 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
    Redwood River House- Peaceful Riverfront Cottage minutes from Downtown1 / 23
    (29)Very good
    3.2 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Modern Retreat - Spectacular View Home Above Dry Creek Valley1 / 24
    (16)Excellent
    3.3 kilometres from Simi Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    House with Beautiful Wine Country Views1 / 25
    (35)Excellent
    3.6 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
    Top Of The World Dry Creek Views With Hot Tub and NEW POOL and Bocce Ball Court!1 / 24
    (49)Excellent
    7.8 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
    Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town1 / 44
    (50)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
    River View - Riverfront Getaway in Healdsburg - Hot Tub, Kayaks, River Access1 / 26
    (48)Excellent
    3.2 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 / 24
    (134)Very good
    8.3 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    *New Home* 3 Blocks from Downtown Healdsburg Plaza!1 / 15
    (10)Excellent
    2.7 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Alexander Valley/ Spa, & Newly Planted Vineyard/  3 miles to town1 / 23
    (16)Excellent
    2.1 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
    Gorgeous Views and Great Wine Tasting Minutes Away1 / 23
    (22)Very good
    4.5 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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