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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 190 Rentals in Healdsburg
    Stunning NEW Modern Farmhouse, Just 3 Blocks from Healdsburg Plaza1 / 27
    (6)Excellent
    3.5 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Remodeled, Spotless & Only 3 Blocks from the Plaza!1 / 18
    2.6 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Ultimate Romance on Dry Creek 5 mins From Town!1 / 30
    1.4 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Kenya's Kastle1 / 44
    2.8 kilometres from Simi Winery
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    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
    The Ultimate Wine Lover's Experience1 / 14
    6.4 kilometres from Simi Winery
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 10
    Enjoy a Slice Of Country--Two miles to Downtown Healdsburg1 / 30
    (41)Excellent
    1.3 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
    Breathtaking Dry Creek Estate - Modern, Spacious, Luxury!1 / 30
    (5)Excellent
    2.7 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
    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 30
    (40)Excellent
    8.2 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Secluded Luxury Vineyard Estate Guest House1 / 17
    (85)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
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 30
    (5)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
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    120-acres of peace and tranquility, 10 minutes from downtown Healdsburg1 / 30
    (22)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
    Healdsburg Downtown Condo1 / 18
    3.1 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Spectacular View Estate 5min Away1 / 30
    (17)Excellent
    2.3 kilometres from Simi Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Dry Creek Cottage - Healdsburg1 / 7
    (97)Excellent
    1.5 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Creek Front Vineyard, West Dry Creek Healdsburg CA1 / 30
    (11)Very good
    6.6 kilometres from Simi Winery
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    Private 3 Bed + Cottage Wine Country Estate With Pool And More1 / 23
    (10)Excellent
    5.5 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
    Updated cabin, right on Russian River, amazing river access & location!1 / 26
    (38)Excellent
    4.7 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
    Mountaintop Respite Overlooking Vineyards: Pool & Spa - 2-4 Guests1 / 30
    5.3 kilometres from Simi Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Modern Retreat - Spectacular View Home Above Dry Creek Valley1 / 25
    (18)Very good
    3.2 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
    Downtown Healdsburg Loft - (30 day minimum rentals only)1 / 19
    (4)Excellent
    2.5 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
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    Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.1 / 30
    (5)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
    A redwood retreat in the heart of Sonoma County wine country (w/ Fiber Internet)1 / 30
    (7)Very good
    5.7 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
    Spectacular view of Dry Creek Valley1 / 24
    (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
    Entire Resort Villa *Pool-Spa-Tennis-Wine-Dine*1 / 30
    (8)Excellent
    8.6 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
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 16
    (82)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
    Beautiful Studio Getaway in the Heart of Wine Country1 / 12
    (71)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
    luxuriously appointed new large guest suite in a landmark Victorian1 / 18
    (14)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
    The Cabin on Fitch Mountain1 / 30
    (40)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
    (7)Excellent
    7.0 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
    Mountain Cottage near Russian River, hiking & downtown, family and pet friendly1 / 27
    3.2 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 Wine Country Getaway with Panoramic Valley Views -Close 2 downtown1 / 24
    (155)Excellent
    3.8 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
    Morning Dew-A Riverfront Healdsburg Home1 / 30
    (26)Very good
    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 5BR/5.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza1 / 30
    (23)Excellent
    5.3 kilometres from Simi Winery
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Healdsburg Downtown Cottage1 / 6
    3.1 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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
    Stunning Retreat Overlooking Vineyards w/ Pool, Hot Tub & Guest Suite1 / 30
    5.4 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
    Lovely Mid Century Home in Healdsburg1 / 20
    2.4 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 4
    Modern Hilltop Healdsburg Residence With 360' Views1 / 30
    10.6 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
    Coppola by AvantStay | Explore The Wineries Near This Gorgeous Healdsburg Home!1 / 30
    8.2 kilometres from Simi Winery
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Modern Vineyard Farmhouse - Close to Downtown Healdsburg - 4 BD/4 Ensuite Baths1 / 14
    3.1 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
    Charming farmhouse amongst the vines1 / 30
    8.7 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
    Private Healdsburg Retreat, 1.5 walk to town Plaza, nearby bus shuttle1 / 19
    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
    Heavenly Hideaway on the Healdsburg Plaza1 / 30
    3.5 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
    Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball1 / 30
    6.8 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
    A Beautiful Vineyard Farmhouse1 / 26
    9.5 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
    Healdsburg Gem! 3BR Pool & Tennis Court1 / 30
    2.8 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
    5 BEDROOM 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE1 / 30
    (22)Excellent
    4.3 kilometres from Simi Winery
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Unheated)
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 12
    Stay surrounded by Fitch Mountain Park and Open Space Preserve.1 / 14
    (8)Very good
    4.5 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
    Great outdoor space, fire pit & gourmet kitchen minutes from downtown Healdsburg1 / 15
    2.6 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
    Stunning Healdsburg House with Vineyard Views1 / 22
    3.4 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!1 / 30
    (93)Excellent
    3.9 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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