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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 September dates now. Secure your vacation rental today, and have the perfect trip.
    All 69 Rentals in Healdsburg
    VineHaven / Spa, Gardens, & Spectacular Vineyard Views1 / 21
    (5)Excellent
    2.0 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views1 / 32
    (16)Very good
    2.0 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Maison du Soleil / Stunning One-Story 4br/3ba home w.Spa, and Ping Pong Table!1 / 25
    (5)Excellent
    1.0 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly1 / 25
    (3)Excellent
    4.3 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Reviewed October 16, 2016
    the house is fabulous and the location is perfect.minutes to town and lots of wineriespeaceful setting and cool clean house
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    About this property
    Location, location location! Perfectly situated only 3 miles (a 5-7 minute drive) from the charming and historic Healdsburg Plaza, this fabulous, custom three-bedroom home abounds with special eco-friendly features. You will be wowed by this modern home’s beautiful open-beamed cathedral ceiling,...
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.5 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Beautifully located, perched just above the Russian River, on S. Fitch Mountain, this vintage 1927 river home has been beautifully renovated and modernized with central heat/AC, new dual-paned windows, high open-beamed ceilings, and all the modern conveniences while still maintaining its vintage...
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful mountain top wine retreat in Healdsburg!1 / 26
    (1)Excellent
    2.4 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
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    Pet friendly
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    Reviewed June 9, 2015
    I would definitely recommend this property. My wife and I stayed there with friends for a wine country holiday. The house seems recently remodeled with many seating areas both...
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    About this property
    Our home is a perfect starting point to Alexander Valley and Dry Creek wineries and a short walk to the banks of Russian River where you can float, kayak, paddle board or just lay in the sun. Nested on Fitch Mountain, our home is in the heart of nature. You are close enough to downtown Healdsburg...
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.0 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Waterfront
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    Pet friendly
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    About this property
    River View Lodge appeals to guests with its spectacular riverfront setting, spacious river view deck, charming décor, exceptionally comfortable beds and linens, outstanding cleanliness, and quality amenities. River View features private river access, and includes kayaks, paddles and life jackets....
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!1 / 25
    (4)Excellent
    1.2 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Shaded by a 100-year-old oak tree, this very special home ‘lives’ on 30 vineyard acres and is off Dry Creek Road, just one mile west of the north end of charming, upscale, historic, Healdsburg in the heart of Sonoma County’s Wine Country. Newly renovated, this 3 bedroom/2 bath, Ranch House with...
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.1 miles from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Cozy Riverfront Home with Peace and Seclusion awaits you in the heart of Healdsburg. Tucked into one of the best locations on Healdsburg's Riverfront awaits this upscale cottage. Open Floor Plan with lots of Natural Light and Large Expansive Deck. Redwood River House is a well maintained 2...
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1.8 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Spend your vacation in the heart of Healdsburg, CA at the Moorish-inspired Cypress House. Beautiful tiles, an interior courtyard, and an incredible view of downtown and beyond from the top floor terrace make this property unique to wine country. Located at the edge of a small shopping center, it...
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Healdsburg Contemporary Cottage1 / 8
    (2)Excellent
    1.8 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed September 23, 2019
    As we travel for 6 months of the year we are experts at holiday rentals and know that gaining access to the property is usually the most difficult thing to accomplish. In this...
    Reviewed August 21, 2017
    This was the best money I have ever spent on a vacation property. Where do I start? This quaint, tastefully decorated cottage is perfectly located. It is close enough to the...
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    About this property
    The Space The perfect home away from home. Makes this your personal sanctuary wether you are staying for the weekend or for the whole month while looking for the perfect home to buy. Well appointed, decorated with international contemporary art with just enough touches that take you beyond the...
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    2.6 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Welcome to heavenly Healdsburg and Hilltop's Vista Villa! This gated 2-bedroom, 2-bath luxury Tuscan inspired villa is located only 3 miles from the historic Healdsburg plaza on one hillside acre near the top of the east side of Fitch mountain and is the only home this close to the top! This...
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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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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * TurnKey photo-verifies this home is professionally cleaned with products approved by the EPA for use against COVID-19. * PROPERTY OVERVIEW A lavish retreat for the ultimate group getaway, this stunning 3BR/3BA home with a guest suite is hedged by expansive vineyards and mature trees. Spend an...
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1.1 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    This stunning gated modern ranch house is nestled on one acre among the vineyards, and very well located at the north end of Healdsburg on Alexander Valley Road. Just remodeled, professionally decorated and furnished, this single story, 2000 sq. ft., 3 bedroom, 2.5 bath home sits under the shade of...
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    0.7 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This newly remodeled vacation rental home is wonderfully located less than 8 minutes north of downtown Healdsburg. It is nestled on the rolling hills of Dry Creek Valley with views looking towards Alexander Valley. Recently refreshed with stylish furnishings, fixtures and lighting system, the home...
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.2 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    1.7 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
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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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.0 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
    4.4 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.8 miles 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.3 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Sauna
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    About this property
    Hello wonderful Guests! We are happy to share our beautiful home that we have built from scratch 8 years ago. We have put much thought and consideration into each aspect of the home. We have children, so we have made this home very family friendly. Children simply love the home and grounds with...
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    1.3 miles from Simi Winery
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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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
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    1.7 miles from Simi Winery
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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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
    Dry Creek Valley Vineyard Home1 / 36
    (29)Excellent
    4.8 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 Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg1 / 46
    (45)Excellent
    1.8 miles 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Crossroads Vineyard:  In the Heart of Healdsburg Wine Country1 / 23
    (88)Excellent
    1.6 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
    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 / 33
    (5)Excellent
    1.5 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    0.5 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
    Spectacular view of Dry Creek Valley1 / 26
    (1)Excellent
    1.1 miles from Simi Winery
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Dry Creek Valley Home and Vineyard1 / 24
    (27)Excellent
    2.1 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
    Peaceful Estate With Views, Incredible Outdoor Space & Only 4 Minutes to Town1 / 23
    (22)Excellent
    1.0 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 49
    (34)Excellent
    5.1 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town1 / 44
    (50)Very good
    2.7 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
    Enchanting Wine Country Villa1 / 24
    (3)Excellent
    5.4 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
    Luxury Vineyard Estate House and Guest House1 / 45
    (73)Excellent
    5.3 miles from Simi Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 4
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (62)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
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 35
    (11)Excellent
    4.4 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
    Beautiful Studio Getaway  in the Heart of Wine Country1 / 12
    (36)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
    8.2 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Vineyard Guest House1 / 31
    (17)Excellent
    4.6 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
    4,700 ft 4 bed & 4 bath ranch, Summer 2020, fully catered plant based retreats1 / 47
    (14)Excellent
    4.0 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Housekeeping Included
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    • Private Outdoor Pool (Unheated)
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    luxuriously appointed new large guest suite in a landmark Victorian1 / 21
    (29)Excellent
    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
    1.7 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Spectacular View Estate 5min Away1 / 45
    (17)Excellent
    1.4 miles from Simi Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg1 / 48
    (49)Excellent
    2.1 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Stunning Mountain Top Estate with View Over Dry Creek Vineyards1 / 28
    (17)Excellent
    5.4 miles from Simi Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    River View - Riverfront Getaway in Healdsburg - Hot Tub, Kayaks, River Access1 / 32
    (51)Excellent
    2.0 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Dry Creek Cottage - Healdsburg1 / 6
    (48)Excellent
    0.9 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Redwood River House- Peaceful Riverfront Cottage minutes from Downtown1 / 29
    (31)Very good
    2.0 miles from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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