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Vacation Rentals near Simi Winery

16275 Healdsburg Ave, Healdsburg, California 95448-9075
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    Travelers to Healdsburg are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    Stunning NEW Modern Farmhouse, Just 3 Blocks from Healdsburg Plaza1 / 27
    (6)Excellent
    2.2 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    1.6 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    0.9 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    1.7 miles from Simi Winery
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Mountain Views
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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
    Rental Home - 3 Bedrooms, 6 Bathrooms, Sleeps 8
    4.0 miles from Simi Winery
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 5 Bathrooms, Sleeps 10
    Breathtaking Dry Creek Estate - Modern, Spacious, Luxury!1 / 30
    (5)Excellent
    1.7 miles from Simi Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Secluded Luxury Vineyard Estate Guest House1 / 17
    (85)Excellent
    5.3 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 30
    (4)Excellent
    4.4 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    120-acres of peace and tranquility, 10 minutes from downtown Healdsburg1 / 30
    (5)Excellent
    4.0 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    1.9 miles 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
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    Spectacular View Estate 5min Away1 / 30
    (17)Excellent
    1.4 miles from Simi Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Dry Creek Cottage - Healdsburg1 / 7
    (17)Very good
    0.9 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    4.1 miles from Simi Winery
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    • Waterfront
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    Healdsburg, Sonoma County
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    3.4 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Updated cabin, right on Russian River, amazing river access & location!1 / 26
    (38)Excellent
    2.9 miles from Simi Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    3.2 miles from Simi Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Modern Retreat - Spectacular View Home Above Dry Creek Valley1 / 25
    (18)Very good
    1.9 miles from Simi Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Downtown Healdsburg Loft - (30 day minimum rentals only)1 / 19
    (4)Excellent
    1.5 miles 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 / 30
    (4)Excellent
    2.2 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    3.5 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Entire Resort Villa *Pool-Spa-Tennis-Wine-Dine*1 / 30
    (2)Excellent
    5.3 miles from Simi Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 16
    (82)Excellent
    3.5 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful Studio Getaway  in the Heart of Wine Country1 / 12
    (71)Excellent
    3.6 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    3.4 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    The Cabin on Fitch Mountain1 / 30
    (8)Very good
    2.7 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    4.3 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    2.0 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Healdsburg Wine Country Getaway with Panoramic Valley Views -Close 2 downtown1 / 24
    (155)Excellent
    2.4 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Morning Dew-A Riverfront Healdsburg Home1 / 30
    (6)Very good
    2.7 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    5BR/5.5BA 17 Acre Estate/Pickleball Court/Pool/Hot Tub/5 mins to Hburg Plaza1 / 30
    (7)Excellent
    3.3 miles from Simi Winery
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    1.9 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Yard
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3.4 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1.5 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 4
    6.6 miles from Simi Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    1.9 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5.4 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    2.5 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.1 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    4.2 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.9 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1.7 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    5 BEDROOM 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE1 / 30
    (12)Excellent
    2.6 miles from Simi Winery
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 12
    Stay surrounded by Fitch Mountain Park and Open Space Preserve.1 / 14
    (6)Very good
    2.8 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.1 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.6 miles from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.5 miles from Simi Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!1 / 30
    (93)Excellent
    2.4 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.7 miles from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2.7 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2.1 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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