Vacation Rentals By Owner In Healdsburg, CA

Showing 100 Of 170 Vacation Rentals

$1620.2

/ Nightly

Private Vacation Home

Country chic cottage and connected water tower next to Jordan winery

Healdsburg, California, United States

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Sleeps

Exceptional(5)

$1200.45

/ Nightly

Private Vacation Home

3 BR with Saltwater Pool | Pool House | Healdsburg | Sleeps 6 | Biking Trails

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(13)

$2041.8

/ Nightly

Private Vacation Home

Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(352)

$298

/ Nightly

Cabin

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

Healdsburg, California, United States

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Bath

Sleeps

$201.29

/ Nightly

Private Vacation Home

Mid-Century Healdsburg Bungalow meets Modern Contemporary 2BR/2BA, walk to town

Healdsburg, California, United States

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Exceptional(1)

$604.63

/ Nightly

Private Vacation Home

Stunning Sonoma 3BR, 3BA house w/view, lap pool, hot tub, Tesla chgr, Healdsburg

Healdsburg, California, United States

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Sleeps

Exceptional(3)

$463.65

/ Nightly

Private Vacation Home

Healdsburg 2BR riverfront home with private dock & river views

Healdsburg, California, United States

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Bath

Sleeps

$465.77

/ Nightly

Private Vacation Home

Healdsburg furnished 7BR monthly rental, two cottages, 30+ nights, hot tub

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(18)

$565.92

/ Nightly

Private Vacation Home

Healdsburg 3BR vineyard farmhouse with game barn & wood fireplace

Healdsburg, California, United States

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Bath

Sleeps

$201.19

/ Nightly

Private Vacation Home

Healdsburg furnished 2BR monthly rental, 30+ nights, hot tub, valley views

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(17)

$725.89

/ Nightly

Private Vacation Home

Healdsburg 2BR Victorian vineyard cottage with mountain views

Healdsburg, California, United States

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Bath

Sleeps

$247.23

/ Nightly

Private Vacation Home

Healdsburg furnished 5BR monthly rental, 30+ nights, river valley views

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(5)

$732.13

/ Nightly

Apartment

Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(1)

$633.61

/ Nightly

Private Vacation Home

Sonoma Wine Country Retreat: Private Pool

Healdsburg, California, United States

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Bath

Sleeps

$151.99

/ Nightly

Agritourism

Fully furnished ADU farmhouse in fabulous Healdsburg all utilities included

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(71)

Select Dates for Price

Cottage

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(55)

$1437.93

/ Nightly

Private Vacation Home

Luxury Home in Healdsburg with a Private Pool plus complimentary wine tastings.

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(41)

$627.6

/ Nightly

Private Vacation Home

Healdsburg Wine Country Retreat | Hot Tub, Bocce, Vineyard Views

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(4)

$275.33

/ Nightly

Private Vacation Home

Heavenly Hideaway - Wine Tastings Included

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(29)

$1102.43

/ Nightly

Private Vacation Home

Lux Wine Country Oasis with Hot Tub - Wine Tastings Included

Healdsburg, California, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 132 Private vacation home

Most popular vacation rentals in Healdsburg

Exceptional(29)

$633.61

/ Nightly

Private vacation home

Sonoma Wine Country Retreat: Private Pool

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(29)

$725.89

/ Nightly

Private vacation home

Healdsburg 2BR Victorian vineyard cottage with mountain views

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(29)

$710.00

/ Nightly

Private vacation home

Beautiful ArtHaus with Pool, Hot Tub, and Sauna!

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(29)

$692.13

/ Nightly

Private vacation home

Wine Country Retreat with Panoramic Views-5 min from downtown Healdsburg

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(29)

$690.74

/ Nightly

Private vacation home

Heron House - Hot Tub and Wine Tastings Included

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(29)

$690.11

/ Nightly

Private vacation home

Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(29)

$623.98

/ Nightly

Cottage

Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(29)

$617.64

/ Nightly

Private vacation home

Wine country retreat

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(29)

$620.69

/ Nightly

Private vacation home

Healdsburg Plaza Charmer + Hot Tub

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(29)

$732.13

/ Nightly

Apartment

Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting

Healdsburg, California, United States

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Bath

Sleeps

Vacation Rentals By Owner In Healdsburg, CA

$1620.2

$1200.45

$2041.8

$298

$201.29

$604.63

$463.65

$465.77

$565.92

$201.19

$725.89

$247.23

$732.13

$633.61

$151.99

$1437.93

$627.6

$275.33

$1102.43

Rent a place that suits your needs

Most popular vacation rentals in Healdsburg

$633.61

$725.89

$710.00

$692.13

$690.74

$690.11

$623.98

$617.64

$620.69

$732.13

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