Vacation Rentals & House Rentals in Healdsburg

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96 house rentals

Healdsburg, 4BR/3BA, Hot tub, Fire pit, Vineyard views

Healdsburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,030

Healdsburg, 4BR/4BA, Pool, Internet, Fireplace

Healdsburg house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,601

Healdsburg, 4BR/2.5BA, hot tub, Fire pit, Bocce Ball, BBQ

Healdsburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,030

Healdsburg, 5BR/5.5BA Estate, Pool, Hot tub, Fire pit, Games

Healdsburg house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$3,317

Kenya's Kastle

Healdsburg house

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

Price per night from

$210

Healdsburg Downtown Cottage

Healdsburg cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$286

Healdsburg, Jimtown, 3BR/2BA, hot tub, Internet, BBQ, Gardens

Healdsburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Difficult to reserve, but beautiful property” We recently stayed at the Jimtown house with 2 other couples. We had a great time enjoying the lovely house. The hard work came before when trying to make the reservations. We found the property management to be polite, but irritating. They sent a 12 page contract with an ridiculous amount to signatures required. They didn't answer repeated questions and the payment process was very unprofessional. They asked for my credit card information through email. They require you to open a special account to pay for the security deposit. It has been 2 weeks and I haven't seen my deposit returned yet. They require you to pay a cleaning fee of $200 and then ask you to clean the house before you leave. We had to empty waste baskets, sweep and remove linens from the bed. The house itself is beautifully furnished and very clean. It is close to the road so there is road noise, but we loved the surrounding and the gardens. The irrigation to the garden in back was out of order so we hand watered the trees and veggies because they were literally dying. Hopefully the owners were alerted and fixed it because the garden is great If the management company were different, I would have given 5 stars, but they need to revamp their system to make it easier for their clients to rent the house!

Price per night from

$744

Hidden Oasis ~ a Private Luxury Home in Healdsburg

Healdsburg house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$1,764

Great rentals within 20 miles that match your search

Spacious Studio in Sonoma wine country

Santa Rosa studio

  • Studio
  • 1 bathroom
  • sleeps 3

Price per night from

$218

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$132

The TreeHouse- Charming Cabin in the Redwoods

Monte Rio house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$189

Downtown B&B close to Arts, Food, Wine great beer

Santa Rosa house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$478

Superbowl 50; February 3-10

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$572

Enchanted Forest Estate

Guerneville house

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 28

“Best place to stay with a large group” We had the best time staying at the two side-by-side houses in Russian river. We have 6 families and way too many kids =) The layout and set up of the houses was perfect. The downstairs play rooms for the kids was ideal. The park-like backyard and easy access to the river made this place one of the best we have ever stayed at. In addition, they have everything you could ever need during your stay from the Bbq's, well stocked kitchens to the canoe and kayak's. We will definitely come back.

Price per night from

$1,824

The Ranch Above St Helena ~ 5 bedroom 8 1/2 bath Overlooking St. Helena

St. Helena house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 12

Price per night from

$6,861

Big Canyon RD

Middletown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$285

Mandala A-Frame House

Cobb house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$285

Bohemian Creekside Cottage minutes from Occidental and Sebastopol

Occidental house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$342

Alexander Valley Lodge on 54 acres with Pool and Hot Tub

Geyserville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$1,030

Sonoma Wine Nest - Location! Location! Location!

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$372

Wine Country Redwood Estate

Santa Rosa villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 15

Price per night from

$1,596

Beautiful Forest Villa Retreat in Sonoma County

Cazadero villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

Price per night from

$1,373

Grand Riverfront Estate with Dock, Minutes from the Beach

Monte Rio house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$258

Stunning Mid-Century Modern Retreat

Guerneville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$315

Luxury secluded redwood retreat in Green Valley

Forestville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$229

Wine Country Getaway in Napa/Sonoma, Hot Tub, Redwoods and Creek Views

Santa Rosa house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$515

The Cottage

Santa Rosa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$342

Wine Country Luxury Home-Pool, Hot Tub, Brush Creek

Santa Rosa house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,373

Tranquil vineyard retreat

Windsor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$189

Wine Country apartment

Larkfield-Wikiup house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$343

Modern 2BR Condo at The Meadows at Fountaingrove

Fulton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$237

Secluded Hillside Hideaway Offers Elegance/Comfort

Forestville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$257

A Perfect Getaway in The Wine Country

Santa Rosa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$365

Romantic Wine Country Cottage with View, Hot Tub & Pool

Sebastopol guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$188

Price per night from

$681

Chalk Hill Cottage - 1 BR w/ Sleeper Sofa

Windsor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$172

Casa Tranquilo

Forestville house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$1,258

Gorgeous Country Home

Sebastopol house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$566

Viewing 38 of 96
rentals in Healdsburg

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About Healdsburg

Located along the Russian River at the center of Sonoma County wine country, Healdsburg offers a perfect vacation paradise, especially for wine lovers and outdoor enthusiasts. Every year, visitors come here from all over the world to experience tours through the rolling hillsides covered with vineyards and olive groves. Some of the finest award winning olive oils, wines, and champagnes in the world are produced right here. The mountains lie within easy reach of downtown Healdsburg, offering endless outdoor activities against a backdrop of rugged natural beauty. Stay in your own private vacation rental and enjoy a cup of coffee on your deck as the sun rises. Head into town for shopping, art galleries, craft studios, and seasonal festivals. When you're ready to explore the wilderness, there are miles of scenic trails and picnic areas here offering beautiful overlooks and wildlife spotting opportunities. At night, come home to your vacation rental in Healdsburg. Pool and luxury gourmet kitchens are features that many rentals offer, which can make your private condo or vacation home a great place for relaxing in style or hosting dinner for your family and friends.

Here are a few additional suggestions for your trip:

  • Tour wine country: A vineyard tour is an indispensible part of the Healdsburg Experience.
  • Go biking: Explore the steep back country trails by bicycle or rent a bike and peddle around town and have a freewheeling afternoon on a bicycle wine tour.
  • Take a balloon ride: Experience the majestic beauty of Sonoma from the sky. Take a ride in a colorful balloon at sunrise and follow it up with a romantic champagne brunch.
  • Go boating and fishing: Head out onto Healdsburg's tranquil lakes and waterways for some of the best fly fishing opportunities in the state.
  • Spend an afternoon in the spa: Healdsburg spa venues are truly world class. After a few days of mountain biking and rock climbing, indulge in an afternoon of serious pampering.
  • Go bird watching and wildlife spotting: The Healdsburg area is home to some of California's most elusive bird and wildlife species. Come here to see eagles, hawks, otters, foxes, and black bears.

Sonoma country is becoming increasingly popular for weekend getaways, family reunions, and Healdsburg wedding locations. Bring your friends and family, rent a luxury vacation home or seasonal condo, and let the vacation memories begin.

Top Destination reviews

Healdsburg, Jimtown, 3BR/2BA, hot tub, Internet, BBQ, Gardens
Most Excellent!

We just celebrated a girls get togther at the Jimstown house and it was excellent. The house is in a great location, is artfully decorated and very comfortable. There were 4 women on our trip and the house can easily accomodate 6 guests. The bonus of an orchard, ripe blackberries, and a garden was icing on the cake. Being next door to the Jimstown Store was a treat and it was a short walk to a great tasting room. The short drive to Healdsburg was very easy. We are thinking this needs to be an annual trip!see more

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