Family-friendly holiday rentals in Healdsburg

Cosmo Beach: Riverfront Sanctuary

Riverfront dog friendly 1.5 acre oasis on the Russian River. The property is private, lush, serene & sunny, with access to a huge private beach. The house is modern yet rustic & is fully equipped. It has gorgeous river valley/redwood/bridge views, decks, spa, boats, fireplace, serious kitchen, fruit trees, grapevines & wildlife. Centrally located between Healdsburg, Sebastopol & the Sonoma Coast. Fantastic wineries, trails & redwoods are minutes away. 3 beaches & river park are only steps away

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.

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

The Wine Ranch

The Wine Ranch Just five minutes north of Healdsburg Plaza, The Wine Ranch is a beautifully remodeled ranch-style home, set on over a half acre of lush outdoor space. The property features a bocce ball court, ping-pong, an expansive deck and patio perfect for al fresco dining or tranquil relaxation. Designed to host gatherings, the spacious living room, dining area, and gourmet kitchen create an inviting atmosphere for couples, families, or groups of up to eight friends.

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.

Rustic Yet Luxurious Cabin in the Redwoods

This rustic yet luxurious cabin is the perfect place to unplug. Walk through the woods, relax by a fire, and enjoy the food and wine of the Russian River Valley. 10 minutes from the beach. Minutes from Occidental, Graton, Forestville, and Guerneville. House has a full bathroom, bedroom downstairs with a Cal King bed and one upstairs with two twin beds. 5 acres in the redwoods, trampoline, fire pit area, high-speed Internet.

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