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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 November dates now. Secure your vacation rental today, and have the perfect trip.
    All 63 Rentals in Healdsburg
    2.0 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2.1 miles from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    2.2 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    1.7 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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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
    4.4 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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    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
    1.3 miles from Simi Winery
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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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
    Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg1 / 46
    (58)Excellent
    1.8 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    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
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    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 49
    (38)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
    (65)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
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 35
    (25)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
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (78)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
    Art and Wine Estate - Vineyards, Pool, Garden1 / 48
    (12)Very good
    8.2 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
    Beautiful Studio Getaway  in the Heart of Wine Country1 / 12
    (52)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
    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, 120 acres all to yourself with a lake and farm.1 / 47
    (18)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
    luxuriously appointed new large guest suite in a landmark Victorian1 / 21
    (37)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
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    1.7 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
    Dry Creek Cottage - Healdsburg1 / 6
    (69)Excellent
    0.9 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
    Private Wine Country Retreat-Luxury estate, pool, hot tub, 3 miles to town1 / 42
    (41)Excellent
    0.9 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
    The Cabin on Fitch Mountain1 / 37
    (26)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
    Tanda Tula, Wine Country Sanctuary1 / 28
    (100)Excellent
    4.3 miles from Simi Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Wine country getaway; stay in a winery1 / 12
    (14)Excellent
    2.1 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
    Updated cabin, right on Russian River, amazing views & location!1 / 23
    (24)Excellent
    2.8 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
    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 / 50
    (30)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
    Healdsburg River Front Oasis Retreat.1 / 28
    (76)Excellent
    2.6 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
    Morning Dew- A Riverfront Healdsburg Home1 / 27
    (18)Excellent
    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
    Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza1 / 23
    (21)Excellent
    3.3 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
    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Hilltop Hideaway:  Bright, Fresh, Modern, Views And Only 2 Miles To Plaza1 / 45
    (120)Excellent
    2.7 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
    Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!1 / 35
    (83)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
    Healdsburg Cottage  Walk to the Plaza, Workspace1 / 34
    (129)Excellent
    1.7 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
    Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.1 / 11
    (182)Excellent
    2.4 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
    Dog Friendly  Vineyard Estate Cottage with Lap Pool and Incredible Views1 / 18
    (46)Excellent
    5.2 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
    Modern, newly built 5 BR home with beautiful views and 50 acres of privacy1 / 46
    (16)Excellent
    5.7 miles from Simi Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly1 / 16
    (97)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
    Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg1 / 36
    (147)Very good
    5.2 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
    0.7 miles from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2.1 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Healdsburg - Chalk Hill Wine Country Cottage1 / 24
    (163)Excellent
    7.7 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
    Top Of The World Dry Creek Views With Hot Tub, POOL and new Tesla charger!1 / 25
    (63)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 home on 10 acres w/ hot tub, English garden & stunning patio!1 / 35
    (9)Excellent
    1.3 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
    Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets1 / 38
    (37)Excellent
    3.7 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    2.1 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards1 / 24
    (52)Very good
    2.1 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
    3.3 miles from Simi Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
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    Enjoy your own private retreat in the Wine Country at Lily Pad Ranch. Luxury 3 bedroom home with guest house on seven acres in the Heart of Wine Country. Relax under the oak trees on this serene and extremely private gated estate only 5 minutes from the Healdsburg Plaza. Sip a glass of wine by...
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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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