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Family-friendly vacation rentals in Healdsburg

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Healdsburg

  • Total vacation rentals

    Explore 90 vacation rentals in Healdsburg

  • Nightly prices starting at

    Healdsburg vacation rentals start at ﺩ.ﺇ 367 per night before taxes and fees

  • Verified guest reviews

    Over 4,780 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Healdsburg vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Healdsburg rentals

  • 4.9 Average rating

    Healdsburg stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Healdsburg

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A cozy living area features a comfortable sofa adorned with decorative pillows. A plush blanket is draped over the seat. The kitchen is visible in the background, showcasing modern appliances. Glass doors open to an outdoor deck, allowing natural light to brighten the space.
Home in Healdsburg

Chic Wine Country Stay - Walk to River & Downtown

Discover our cozy two-bedroom retreat, just minutes from downtown. This charming space features top-quality cooking items, a bidet, and a heated towel rack. Enjoy seamless indoor-outdoor living with doors that open to a deck, complete with a BBQ and outdoor dining area. Located across from scenic walking trails and only four blocks from the Russian River, it's the perfect spot for nature lovers. Despite its small size, every detail is thoughtfully designed for your comfort. Book your stay today

4.92 out of 5 average rating, 134 reviews
Superhost
The exterior of the barn cottage is featured, showcasing a two-story structure with large windows illuminated in a warm glow. The entrance is adorned with wooden doors and a star accent. A spacious deck is visible above, providing an inviting outdoor space.
Cottage in Healdsburg

❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤

❤New! Welcome to the "The Elegant Barn", our newly built stylish Barn Cottage in the HEART of wine country! Our *INSTAWORTHY* barn cottage boasts a HOT TUB, panoramic vineyard VIEWS, comfy furnishings & convertible glass indoor/outdoor doors to bring the outdoors inside! LOCATION, LOCATION, LOCATION! Set on a historic vineyard property on Dry Creek Road, the location of Healdsburg's most famous wineries, and an easy walk, bike ride or drive to many of the best wineries in the area! PETS OK!❤

4.9 out of 5 average rating, 268 reviews
Top guest favorite
An airy living space is highlighted by high-beamed ceilings and large windows, allowing plenty of natural light. A gray sofa and two brown leather chairs are arranged around a round coffee table on a light-colored rug. The adjacent dining area features a wooden table, surrounded by various chairs.
Home in Healdsburg

Healdsburg House - Chiquita Road

Relax with the whole family at this peaceful and private home mins to the Healdsburg Square, Montage Resort, and Dry Creek/Alexander Valley Wineries. The updated home features an open concept kitchen, two family rooms, and a sparkling hot tub on 1.5 private acres surrounded by vineyards and oak trees. Cruise your bike to town or head directly out Chiquita Road to some of the world's greatest cycling. 2.4 miles to the Montage Resort. 2.5 miles to the Healdsburg Square. Welcome to Wine Country!

5.0 out of 5 average rating, 126 reviews
Superhost
An aerial view reveals a spacious property surrounded by lush vineyards. The main house is situated to the left, with a sparkling pool adjacent to it. A winding road leads through the greenery, while gentle hills stretch into the distance under a clear blue sky.
Home in Healdsburg

Dry Creek Ranch ~ (Tariff Discount) Hot Tub & Pool

Enjoy an idyllic wine tasting weekend for 3-4 couples, have fun with the whole family (pets welcome) or find adventure along the world famous Dry Creek Road. This property boasts a main house, pool house & Game barn. The main house sleeps 10. The pool house features a 70” flatscreen, a Live Edge tasting bar and Lanai. The property is only 1.4 miles from Healdsburg’s square. Take a gentle bike ride into town or stay put – pour wine, soak in the hot tub, and watch the sun set over the vineyards

4.89 out of 5 average rating, 109 reviews
Guest favorite
A modern living area showcases a comfortable gray sectional sofa and two accent chairs. A round wooden coffee table sits in the center, with a small plant adding a touch of greenery. Soft lighting is provided by a ceiling fixture and table lamps, enhancing the inviting atmosphere.
Home in Healdsburg

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

4.92 out of 5 average rating, 157 reviews
Top guest favorite
Home in Healdsburg

Modern Healdsburg Retreat • Hot Tub, Bocce & Views

Vineyard views + hot tub under the stars—modern Healdsburg, 5 min to the Plaza. Set in Dry Creek Valley, this design-forward retreat feels a world away—yet you’re minutes from top wineries, tasting rooms, and dining. Slow mornings with coffee overlooking the vines. Golden-hour dinners outside. Evenings in the hot tub with sunset views and total privacy. Designed for relaxed Wine Country living with bocce, outdoor lounge spaces, and seamless indoor-outdoor flow.

4.93 out of 5 average rating, 181 reviews
Superhost
Two modern, white structures stand beneath a large green tree against a clear blue sky. The buildings feature large glass windows, allowing for natural light. The area is surrounded by open grass, contributing to a relaxed and spacious atmosphere.
Home in Healdsburg

Three-Building Healdsburg Homestead with Wine Barn

Your humble Healdsburg Homestead for launching wine country adventure! Three buildings on a 1/2 acre property, including a barn with a winetasting bar & game room! Great for families and groups. Perfectly located for cycling on the legendary Eastside/Westside loop. For wine lovers, we are across the street from Rodney Strong Vineyard and the amazing sparkling wines of the beautiful J Vineyard. Best of all, Healdsburg Plaza is just a short hop away!

4.84 out of 5 average rating, 159 reviews
Guest favorite
A pathway leads to a welcoming front porch, flanked by greenery and blooming flowers. The light-colored home is partially shaded by surrounding trees, creating a serene approach. The yard features fresh landscaping with mulch and various plants, enhancing the inviting entrance.
Home in Healdsburg

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.

4.89 out of 5 average rating, 366 reviews
Top guest favorite
A rustic cabin is nestled among towering redwood trees, featuring wooden shingles and large windows. A wooden deck, adorned with string lights, enhances the inviting exterior, while the natural landscape provides a serene backdrop. A gravel path leads to the entrance.
Cabin in Occidental

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.

4.97 out of 5 average rating, 640 reviews
Top guest favorite
A bright living area features a spacious white sectional couch and a wooden coffee table. An expansive bookshelf holds various items, with a television and fireplace being focal points. Large glass doors open to a garden, bringing in natural light and outdoor views.
Guesthouse in Healdsburg

Designer Cottage | Garden Oasis | Walk to Plaza

✓ Fully equipped kitchen. ✓ On-site EV charger. ✓ Lush, private garden. ✓ Dedicated workspace. ✓ Comfortably accommodates 2 guests. ✓ Close to world-class wineries and dining. ✓ Private, architect-designed cottage for two. ✓ Seamless indoor-outdoor living. ✓ Stylish retreat created especially for couples. ✓ Comfortable Queen Bed with Hotel pressed Sheets. ✓ Just a 4-minute walk to Healdsburg Plaza.

4.97 out of 5 average rating, 262 reviews
Top guest favorite
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg

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!

5.0 out of 5 average rating, 277 reviews
Top guest favorite
The exterior of a charming cottage is framed by lush greenery and features a welcoming entrance with wooden doors. A stone pathway leads to the home, which is complemented by vibrant foliage and a pergola adorned with vines.
Home in Healdsburg

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.

4.96 out of 5 average rating, 497 reviews

Popular amenities for Healdsburg family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A spacious outdoor deck is furnished with a large sectional sofa and several lounge chairs, all adorned with blue cushions. A wooden coffee table sits in the center, surrounded by lush greenery and trees, creating a serene and private atmosphere.
Guesthouse in Healdsburg

Luxurious, Private, Healdsburg Guest Cottage

4.99 out of 5 average rating, 321 reviews
Guest favorite
Aerial view of a modern farmhouse villa surrounded by lush, rolling hills. Vibrant flowering trees line the property, alongside a grassy landscape that slopes gently upward. The natural setting offers a sense of seclusion, with trees creating a backdrop against clear blue skies.
Villa in Santa Rosa

Farmhouse Villa w/ Captivating Views & Hot Tub

4.98 out of 5 average rating, 132 reviews
Top guest favorite
A covered hot tub is surrounded by curtain drapes and string lights, providing a cozy ambiance. The tub is filled with water that displays a soothing green hue, inviting relaxation in a tranquil outdoor setting.
Home in Geyserville

Updated 5 BR house w/ hot tub - walk to downtown!

4.99 out of 5 average rating, 143 reviews
Top guest favorite
A spacious deck features comfortable seating arrangements with wicker chairs and side tables. A large dining table is positioned under an umbrella, providing a shaded area for meals. Lush greenery and vineyards are visible in the background, enhancing the serene environment.
Home in Healdsburg

Vineyard views, hot tub, sauna, cinema

4.98 out of 5 average rating, 124 reviews
Guest favorite
A bright kitchen features sleek white cabinetry and a spacious island with a light marble countertop. Pendant lights hang above the island, while large windows allow natural light to fill the space. Stainless steel appliances add a modern touch to the overall design.
Home in Windsor

Gourmet Kitchen in Wine Country w/Hot Tub + Office

4.95 out of 5 average rating, 116 reviews
Guest favorite
An expansive backyard is shown, featuring a sparkling pool surrounded by a stone patio. A gazebo offers shaded seating, while a cozy fire pit creates an inviting gathering space. Lush greenery and trees frame the scene, enhancing the tranquil setting of the home.
Home in Santa Rosa

5-Bedroom Creekside Wine Country Retreat

4.96 out of 5 average rating, 102 reviews
Top guest favorite
A large glass door opens to a private lanai, revealing expansive views of lush vineyards and rolling hills. Comfortable seating is arranged on the deck, surrounded by greenery, while natural light enhances the serene atmosphere.
Guesthouse in Healdsburg

Luxe Guest Suite in Dry Creek 5 mins From Town!

5.0 out of 5 average rating, 169 reviews
Top guest favorite
A serene outdoor space is showcased, featuring a sparkling pool surrounded by neatly arranged white lounge chairs. Lush greenery and blooming shrubs create a natural border, enhancing the tranquil atmosphere.
Home in Geyserville

Historic Home; Walk to Cyrus, Diavola, Catelli's

4.98 out of 5 average rating, 122 reviews

Family- and pet-friendly home rentals

Top guest favorite
Home in Healdsburg

Healdsburg Garden House

4.93 out of 5 average rating, 659 reviews
Superhost
A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.
Treehouse in Bodega Bay

Eagle's Nest Treehouse Farm Stay

4.95 out of 5 average rating, 240 reviews
Top guest favorite
Cottage in Geyserville

Country Carriage House in Downtown Geyserville

4.99 out of 5 average rating, 186 reviews
Guest favorite
The bedroom features a spacious bed with white linens accentuated by a decorative pillow. A ceiling fan is present, and natural light enters through a window. Artwork adorns the walls, including a map and framed prints. A small desk and a television stand complete the space.
Home in Healdsburg

Wine Country Cottage in Healdsburg

4.89 out of 5 average rating, 429 reviews
Top guest favorite
A bright and welcoming living space features a mix of modern and cozy elements. Wooden beams enhance the ceiling above various seating arrangements, including a plush sofa and a round dining table. Natural light filters through large windows, highlighting framed art on the walls.
Cottage in Sebastopol

Designer Wine Country Cottage in Perfect Location

4.99 out of 5 average rating, 273 reviews
Top guest favorite
Home in Forestville

Hilltop Haven Retreat | Scenic Hydro-Spa + Sauna

4.97 out of 5 average rating, 230 reviews
Guest favorite
A well-appointed bedroom features a spacious bed with a light-colored upholstered headboard, draped in soft linens and a textured throw. Two nightstands flank the bed, each with a lamp and decorative items. Large windows allow natural light to illuminate the room, while soft curtains frame the view.
Home in Santa Rosa

Centrally Located Modern Wine Country Home

4.94 out of 5 average rating, 126 reviews
Guest favorite
A spacious great room features a high wood-beamed ceiling and natural light pouring in through skylights. Comfortable lounge seating is arranged near a fireplace, with a large dining table designed to accommodate multiple guests, creating an inviting space for gatherings.
Cabin in Forestville

The Black Sheep - Wine Country • Hot Tub • Theater

4.94 out of 5 average rating, 166 reviews

Family-friendly home rentals with a pool

Guest favorite
A heated swimming pool reflects the early evening sky, surrounded by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a shaded umbrella. The vineyard is visible in the background, enhancing the peaceful atmosphere of this outdoor space.
Home in Healdsburg

Vineyard Vista, Modern Farmhouse Cottage with Pool

4.93 out of 5 average rating, 134 reviews
Guest favorite
A spacious outdoor area features a large pool surrounded by natural stone walls. Comfortable lounge chairs are positioned for relaxation, and green umbrellas provide shade. Lush landscaping enhances the serene environment, with trees and plants framing the scene.
Home in Sebastopol

Private Resort with Pool, Pool House, View and Spa

4.92 out of 5 average rating, 136 reviews
Guest favorite
The image displays a sunny outdoor pool area surrounded by comfortable lounge chairs. Two shaded cabanas offer shelter, while vibrant orange and red canopies provide additional shade. Lush green hills are visible in the background, contributing to a serene atmosphere.
Home in Cloverdale

Woodhawk Manor of Alexander Valley

4.87 out of 5 average rating, 126 reviews
Top guest favorite
A spacious guest house is set within a picturesque vineyard estate, featuring a distinct architectural style with multiple gabled rooftops. The driveway leads to a well-maintained entrance, surrounded by lush landscaping and mature trees, providing a serene and welcoming arrival experience.
Guest suite in Healdsburg

Pony Ranch Vineyard Estate with Pool

4.93 out of 5 average rating, 484 reviews
Guest favorite
The serene pool area is surrounded by lush greenery, featuring modern lounge chairs and large umbrellas for shade. The sparkling water invites relaxation, while a covered outdoor space extends from the home, providing a seamless transition to the tranquil outdoor retreat.
Home in Sebastopol

Serene Wine Country Retreat with Pool & Hot Tub

4.89 out of 5 average rating, 119 reviews
Top guest favorite
A spacious pool area is framed by greenery and a white fence, featuring a large, clear swimming pool. Lounge chairs are positioned nearby on the grass, with a cozy seating area visible to the right. The sky above displays colorful clouds at sunset.
Home in Santa Rosa

Heated Pool, Hot Tub & Fire Pit in Wine Country

5.0 out of 5 average rating, 139 reviews
Guest favorite
Home in Santa Rosa

Wine Country Escape: Pool & Hot Tub. Fast WiFi

4.93 out of 5 average rating, 193 reviews
Top guest favorite
A Mediterranean-inspired house is set amidst lush gardens and rolling hills. The round swimming pool is surrounded by colorful landscaping and lounge chairs, inviting relaxation. The exterior features warm stucco walls and a tiled roof, showcasing a harmonious blend with the natural surroundings.
Home in Santa Rosa

Wine Country Luxury Retreat - Pool Sauna Spa Views

4.99 out of 5 average rating, 142 reviews

When is the best time to visit Healdsburg?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,623ﺩ.ﺇ 1,653ﺩ.ﺇ 1,656ﺩ.ﺇ 1,726ﺩ.ﺇ 2,031ﺩ.ﺇ 1,866ﺩ.ﺇ 1,770ﺩ.ﺇ 1,594ﺩ.ﺇ 1,638ﺩ.ﺇ 1,664ﺩ.ﺇ 1,946ﺩ.ﺇ 1,667
Avg. temp10°C10°C11°C11°C12°C13°C14°C14°C15°C13°C12°C10°C

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