Family-friendly holiday rentals in Healdsburg

Private Entrance Suite in Heart of Wine Country

Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.

Ocean View Spa House

Beautiful Sea Ranch stylistic home in quiet residential cul-de-sac with sweeping ocean and hillside views in the Bodega Bay. Perfect for a quiet relaxing spa-like experience. Fitted with a hot tub, sauna and BBQ, beach access, this home makes for a perfect vacation escape with friends or family! Walk to short tail gultch trail head (Sonoma Parks) to get to the beach! Family amenities! Bodega Bay is only 1 hour and 25 minutes from San Francisco with lots of wonderful activities. EV charger!

Healdsburg Garden House

Enjoy a real Sonoma County Experience Best Value in the Valley Organic grapes, hops, flower and vegetable gardens Centrally located home away from home Large Covered Redwood Deck with Gas Grill NEW A/C and Heating (controls in each bedroom) Super clean and sanitized Private, spacious & comfortable Fully Stocked Kitchen w/ Dishwasher 50” HDTV’s in each room (HBO, Showtime, Netflix, YouTube…) 1 GB High Speed Ethernet Level Walk to Town Square and Russian River Beach TOT # 798N

Healdsburg Cottage-Workspace, Walk to Plaza

This light-filled cottage is a comfortable, easy to access hide-away in a friendly, historic neighborhood just 5 blocks from the Healdsburg Plaza. Have a glass of wine or dine at your own picnic table in the private, garden setting. Relax in the adirondack chairs. Build a fire in the fire pit (weather permitting). It's an easy stroll into town for wine tasting, shopping or dinner. Transient Occupancy Tax (TOT) of 16% is included in the price.

Sonoma Berry Blossom Farm

Modern and spacious with glass enclosed porch, high ceilings and lots of French doors, skylights and windows. Close to town in the very nicest area within a mile of downtown, walkable, or bikeable with my cruiser bikes. You’ll love the views, the location, the goats, quail running around and delicious cafe next door. We just lost our mini horse 7/27 :( we had 16 years, sorry if you had planned on meeting him, it was a sad loss for us.

Peaceful location, hot tub, fire pit, game room!

Feel your stress melt away as you wind your way down a country road to our little piece of heaven in wine country. Our cozy home is a great starting place for your Healdsburg adventures! Private yard, super comfortable beds, well equipped kitchen, cozy living room with fireplace, free wifi and cable, game room with pool table, poker, Skee-ball plus a wonderful outdoor dining area. Just a 5 minute drive to downtown Healdsburg.

Dry Creek Retreat- Bocce, Hot Tub, EV Charger

Ideally located 5 minutes from the Healdsburg Square on Dry Creek Road, this home has it all! Newly renovated home has spectacular vineyard views on a magical 1/2 acre lot, a hot tub, Bocce ball court, large deck, and a fully stocked kitchen. We pride ourselves on keeping the house fully stocked with everything our guests may need & spotlessly clean! World class food, wine, cycling, and nature are at your fingertips here!

Cozy Hisorical Home Walking Distance to Downtown!

Our newly renovated, historic yet modern vacation home is perfectly located in the heart of Sonoma County Wine Country! Featuring three bedrooms and two full bathrooms it is perfect for your family vacation, your wedding party or a getaway with a group of friends. World class dining and wineries galore! The Main Street House Team

The Roost - Sun Room

The Sun Room is a licensed guest room that is located 2 blocks from the central plaza of Healdsburg in a quiet residential neighborhood. The Roost occupies a corner of an historic 1860s farmhouse with a separate secluded porch and private entrance.