Family-friendly vacation rentals in Healdsburg

Russian River Luxury Escape | Private Hot Tub

Indulge in luxury at your new modern style home. Unwind in the elegant, open space interior with natural lighting and Forestville's scenery seeping through the windows. Craft culinary creations in the fully stocked kitchen with a spacious island, and relax on the large backyard deck or hot tub. Stay connected with fast Wi-Fi, the dedicated office space, and the electric car charging outlet. Conveniently located near the Russian River, enjoy your space designed for utmost comfort and tranquility.

Bucher Vineyard Cottage

Discover the Charm of Our Vineyard Cottage! Escape to the heart of wine country with a stay at our fantastic one-bedroom cottage, nestled on the renowned Bucher Vineyard. Large room with kitchen & cozy seating area. Enjoy a restful night in a comfy queen bed surrounded by a stunning Redwood wall. Covered patio with heaters and fan. Deck with spectacular views of our vineyard & the Russian River Valley. Gas fire pit near deck. Hosts John & Diane are farmers and winery owners live on the property.

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

Healdsburg 2br Cottage with Private Yard!

Relax at our renovated private guesthouse a 5 min drive (1 mi) from the Healdsburg Plaza. Updated 2 br/ 1 ba home with private yard and outdoor dining and lounge areas. Our layout is ideal for one family or close friends traveling together as the one bathroom is accessed through the primary bedroom. Perfect for a wine country getaway- convenient location just outside of Healdsburg city limits in a vineyard adjacent neighborhood. We love kids and welcome them! Permit #TVR22-0119

Updated Russian River Cabin (beach/river access!)

Escape to wine, water, nature, and cozy cabin comfort that's a short trip from SF (75 min) and only minutes to charming Healdsburg and Dry Creek Valley wineries. Right on the Russian River, our cabin is a great getaway for wine tasting, river fun (beach, canoe/kayak/SUPs), and Healdsburg (9 min). Built in 1949, we've kept the cabin's rustic charm (the antlers and the moose mount came with the place!), but updated it with modern design and conveniences. Perfect for couples or a family.

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.

Sonoma Retreat w/Pool/Spa/Barn/OD Kitchen/Orchard

- Luxurious west Sonoma oasis - Heated pool with large wooden deck - 6-person Private Hot Tub - Entertain and feast in the outdoor kitchen with BBQ, Neopolitan Wood-fired Pizza Oven and large outdoor tables. - Newly remodeled farmhouse kitchen - Epic Entertainment Barn: Air Hockey, 100" TV Projector, Darts & More - Expansive backyard with Apple Orchard - Pick Seasonal Vegetables from Garden Beds - Pet Friendly Home, Fenced

Country Barn in Downtown Geyserville

Linger over coffee on your quaint patio amongst 6 acres downtown in sweet Geyserville. An industrial loft vibe with wine country bones—the "barn" is a modern/rustic country-correct cottage. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Property rental supports Farm Sanctuary on site of rescue goats, horses, and one heifer named Francis.

Downtown Healdsburg Nest

You can't get any closer to all that Healdsburg has to offer. Just two blocks from the charming Plaza, this fully furnished, upstairs 2 bdr apartment has everything you need for a quick trip to Wine Country or longer-term stay. High-speed internet and all the comforts of home. Steps away from world-class restaurants, tasting rooms, shops, galleries, and music venues.

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Your perfect wine country escape awaits!

Dry Creek Valley Cottage

We live in a beautiful rural country setting but we are only a 5-7 minute easy drive into downtown Healdsburg where all the lovely shops, wineries and restaurants are. We invite you to enjoy our lovely garden and taste all the wonderful fruit when it is in season. We have apple, pear, peach, plum, pomegranate, persimmon and citrus trees.

Hilltop Villa with Sweeping Views & Trail Access

Perched above Fitch Mountain, this private hilltop villa offers sweeping wine-country views, direct access to scenic hiking trails, and peaceful seclusion just minutes from downtown Healdsburg. Bright interiors, high ceilings, and a fenced yard make it ideal for couples or small groups seeking a refined, nature-forward getaway.