Vacation Rentals By Owner In Healdsburg, CA

Showing 80 Of 170 Vacation Rentals

Exceptional(1)

$184.97

/ Nightly

Private Vacation Home

Downtown Healdsburg home very near the Plaza! 30 Day Minimum per law.

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(22)

$2391.73

/ Nightly

Private Vacation Home

The Quails Crossing-Healdsburg Vineyard Home

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(190)

$1127.25

/ Nightly

Private Vacation Home

Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(4)

$433.4

/ Nightly

Private Vacation Home

Beautifully appointed house and garden only 10 minutes walk from the plaza

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(1)

$700.99

/ Nightly

Private Vacation Home

Haven at Healdsburg, by Vinifera Homes

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(32)

$721.01

/ Nightly

Private Vacation Home

Heron House - Hot Tub and Wine Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(17)

$488.18

/ Nightly

Private Vacation Home

Wine country getaway; stay in a winery

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(5)

$517.83

/ Nightly

Private Vacation Home

Riverbend Retreat - Hot Tub and Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

$1177.5

/ Nightly

Private Vacation Home

Limerick Lane- 3B on 2.3 acres, Pool, Hot Tub and Tranquility

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(7)

$912.5

/ Nightly

Private Vacation Home

Right in the heart of Healdsburg lies this charming two-bedroom house

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(108)

$852.73

/ Nightly

Private Vacation Home

Hidden Pocket: Pool + Spa, 1.5 Fenced Acres, Healdsburg

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(5)

$377.53

/ Nightly

Private Vacation Home

Gorgeous Healdsburg house in town. Great location, fire pit, yard, huge kitchen!

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(7)

$1002.37

/ Nightly

Private Vacation Home

The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(42)

$905.98

/ Nightly

Apart-hotel

Three-Bedroom Hotel Suites in Downtown Healdsburg

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(25)

$701.6

/ Nightly

Private Vacation Home

Healdsburg Plaza Charmer + Hot Tub

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(136)

$2141.4

/ Nightly

Private Vacation Home

TandaTula, Wine Country Sanctuary with Pool, Hot Tub, Bocce, Fire Pits and More!

Healdsburg, California, United States

Bed

Bath

Sleeps

$219.52

/ Nightly

Private Vacation Home

Enchanting Wine Country Retreat ~ Hot Tub & Vineyard Views 3BD/2BA

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(1)

$999

/ Nightly

Private Vacation Home

Ivy House Downtown Healdsburg Plaza

Healdsburg, California, United States

Bed

Bath

Sleeps

$399.98

/ Nightly

Private Vacation Home

Wine & Dine Downtown Healdsburg | Walk Everywhere

Healdsburg, California, United States

Bed

Bath

Sleeps

$946.86

/ Nightly

Private Vacation Home

Dry Creek Valley Home and Vineyard

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

$633.61

/ Nightly

Private vacation home

Sonoma Wine Country Retreat: Private Pool

Healdsburg, California, United States

Bed

Bath

Sleeps

$725.89

/ Nightly

Private vacation home

Healdsburg 2BR Victorian vineyard cottage with mountain views

Healdsburg, California, United States

Bed

Bath

Sleeps

$710.00

/ Nightly

Private vacation home

Beautiful ArtHaus with Pool, Hot Tub, and Sauna!

Healdsburg, California, United States

Bed

Bath

Sleeps

$692.13

/ Nightly

Private vacation home

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

Healdsburg, California, United States

Bed

Bath

Sleeps

$690.74

/ Nightly

Private vacation home

Heron House - Hot Tub and Wine Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

$690.11

/ Nightly

Private vacation home

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

Healdsburg, California, United States

Bed

Bath

Sleeps

$623.98

/ Nightly

Cottage

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

Healdsburg, California, United States

Bed

Bath

Sleeps

$617.64

/ Nightly

Private vacation home

Wine country retreat

Healdsburg, California, United States

Bed

Bath

Sleeps

$620.69

/ Nightly

Private vacation home

Healdsburg Plaza Charmer + Hot Tub

Healdsburg, California, United States

Bed

Bath

Sleeps

$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

$184.97

$2391.73

$1127.25

$433.4

$700.99

$721.01

$488.18

$517.83

$1177.5

$912.5

$852.73

$377.53

$1002.37

$905.98

$701.6

$2141.4

$219.52

$999

$399.98

$946.86

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

Most Popular Cities in California