Family-friendly holiday rentals in Healdsburg

5.0 out of 5 average rating, 222 reviews

Tiny home in Sebastopol

The Sonoma Spyglass | Incredible Views + Sauna

🏵️ Featured as one of “California’s Most Wishlisted Airbnbs!” 🏵️ 🌈 Come enjoy deep rest, romance & rejuvenation! ❤️ 🌺 Our Sonoma Spyglass is a gorgeous retreat, designed and built by Artistree Home, seamlessly blending sustainability with a deep connection to nature. 🍇 Tucked in the heart of Sonoma’s wine country, the space offers access to nearby walks and local wineries. Soak in the tub with incredible views or enjoy the detached barrel sauna for a perfectly relaxing stay. 🌺🙏 🌺

KitchenIndoor spacesHot tub

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.

5.0 out of 5 average rating, 122 reviews

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!

Indoor spacesFamilyDecor

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.

4.92 out of 5 average rating, 154 reviews

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

FamilyKitchenLocation

4.98 out of 5 average rating, 122 reviews

The backyard showcases a newly built pool surrounded by a spacious wood deck, featuring in-pool loungers. A picturesque sunset casts warm light on the landscape, while the home and outdoor seating areas are framed by tall trees, creating a serene country atmosphere.

Home in Sebastopol

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

Welcome to your private retreat on a fenced 1.3-acre property minutes from Sebastopol, Occidental and Russian River. Enjoy a heated, covered pool, hot tub, and large outdoor area with orchard, you-pick garden beds, and outdoor kitchen w/ pizza oven & grill. The game barn features a projector, air hockey, ping pong, darts, and cornhole. Pet & family-friendly, with a 2-car garage, EV charger, and fast WiFi. Minutes to top wineries. Spotless, designer-decorated home with a responsive host.

KitchenIndoor spacesCleanliness

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.

4.92 out of 5 average rating, 132 reviews

Vineyard Vista, Modern Farmhouse Cottage with Pool

Our architect remodeled (2021), five star, elegant Farmhouse with great room and fireplace, is simply perfect throughout. This unique wine country two-acre property, with heated swimming pool (for a fee), looks out to the beautiful Russian River vineyards and the never-ending Western panorama. Only minutes from award winning food and shopping in downtown Healdsburg, it’s within easy walking or bicycling distance of tasting rooms at J, Rodney Strong and other acclaimed Sonoma wineries.

FamilyIndoor spacesComfort

4.97 out of 5 average rating, 705 reviews

The exterior of a rustic winery building is featured, characterized by its earthy tones and distinctive red door accents. Lush greenery and blooming purple flowers surround the structure, enhancing its natural setting. The building's design includes terracotta roofing and large windows that invite an abundance of natural light.

Farm stay in Healdsburg

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

Indoor spacesFamilyLayout

4.99 out of 5 average rating, 178 reviews

Cottage in Geyserville

Country Carriage House 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 cottage is modern/rustic meets country-correct. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Goats, horses, dogs, one heifer 🐄 named Francis, and one farm cat named Leo on property. Fully fenced front yard and back patio!

FamilyIndoor spacesHospitality

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.

4.88 out of 5 average rating, 362 reviews

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.

KitchenFamilyPets

4.99 out of 5 average rating, 318 reviews

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

1083 Guest House is comfortable luxury in a spacious private cottage within walking distance of four-star restaurants, wineries, fabulous boutique shopping, and the Russian River. Your secluded cottage is nestled in the trees with views of a wooded area and is the perfect base for your Wine Country get away. There is no stove/oven due to zoning/licensing so the cottage has a microwave, small air fryer, toaster and bbq.

KitchenIndoor spacesWalkability

4.97 out of 5 average rating, 255 reviews

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

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

KitchenFamilyValue

5.0 out of 5 average rating, 228 reviews

A rustic cottage crafted from wood is nestled among trees, surrounded by a gravel yard. Outdoor seating is arranged at a table with light-colored chairs, providing a space to enjoy the serene surroundings. Potted plants enhance the natural ambiance.

Cottage in Healdsburg

Bee Haven Cottage

This unique property is located only 2.4 miles from Healdsburg Plaza. Situated on a historic 11-acre farm with 5 acres of Zinfandel grapes. This newly renovated Studio cottage was built in 1903. This creekside cottage is fully restored in an artist's handcrafted manner. All the furnishings are of the highest quality. Enjoy the natural surroundings while soaking in the private outdoor spa.

FamilyIndoor spacesQuiet

Holiday home in Healdsburg

A modern living room features two comfortable armchairs and a sleek sofa, complemented by a coffee table adorned with a globe. A flat-screen TV is mounted on the wall, and natural light fills the space through large windows. An inviting atmosphere is created by neutral tones.

4.96 out of 5 average rating, 112 reviews

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.

Indoor spacesKitchenDecor

Popular amenities for Healdsburg family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A spacious living room features large sliding glass doors that open to a patio, allowing natural light to fill the space. Comfortable sofas are arranged around a wooden coffee table on a patterned rug, with a television mounted on a wall unit. Lush greenery is visible beyond the windows.

4.97 out of 5 average rating, 104 reviews

Casa Chiquita - Coziest in town!

KitchenFamilyView

5.0 out of 5 average rating, 167 reviews

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!

Indoor spacesFamilyLaundry

4.96 out of 5 average rating, 113 reviews

An open-concept kitchen and dining area features a large wooden dining table and modern kitchen appliances. A spacious island with bar seating is included, and the bi-fold patio doors lead to a deck with lounge seating surrounded by greenery.

Home in Forestville

Russian River Luxury Escape | Private Hot Tub

Indoor spacesFamilyDecor

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.

4.9 out of 5 average rating, 106 reviews

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

KitchenIndoor spacesOutdoor spaces

5.0 out of 5 average rating, 122 reviews

Home in Sebastopol

Pixel Place - A Private Arcade + Outdoor Sanctuary

KitchenIndoor spacesTV

4.91 out of 5 average rating, 261 reviews

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!❤

FamilyIndoor spacesPets

4.93 out of 5 average rating, 178 reviews

Modern Healdsburg Retreat • Hot Tub, Bocce & Views

Indoor spacesKitchenGetting around

4.91 out of 5 average rating, 193 reviews

The villa is set against a colorful sunset, highlighting its two-story structure. A large pool reflects the warm hues of the sky, while well-maintained landscaping surrounds the outdoor area. Soft lighting from the home creates an inviting ambiance.

Villa in Santa Rosa

Villa Annadel - Stunning 5 Bedroom with a Pool

FamilyKitchenBathroom

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 655 reviews

Healdsburg Garden House

Indoor spacesFamilyQuiet

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.

4.86 out of 5 average rating, 156 reviews

Three-Building Healdsburg Homestead with Wine Barn

FamilyIndoor spacesAir conditioning

4.94 out of 5 average rating, 234 reviews

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

KitchenIndoor spacesBiking

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.

4.89 out of 5 average rating, 425 reviews

Wine Country Cottage in Healdsburg

Indoor spacesKitchenBathroom

4.94 out of 5 average rating, 266 reviews

A Tuscan-inspired villa is set among rolling hills and vineyards. The property features a well-maintained front yard with a gravel drive, surrounded by lush grapevines. Elegant seating options are visible near the entrance, framed by vibrant trees and a scenic backdrop of the mountainous landscape.

Guesthouse in Cloverdale

Wing in Tuscan Villa with Vineyard and two bedrms

FamilyKitchenBathroom

4.96 out of 5 average rating, 223 reviews

Home in Forestville

Hilltop Haven Retreat | Scenic Hydro-Spa + Sauna

Indoor spacesFamilyBiking

4.95 out of 5 average rating, 114 reviews

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

KitchenIndoor spacesBarbecue

4.91 out of 5 average rating, 469 reviews

An outdoor fire pit surrounded by four wooden chairs offers a welcoming gathering space. The stone patio extends outward, framed by lush greenery and the vibrant hues of sunset. A vineyard is visible in the background, enhancing the natural setting.

Cottage in Sebastopol

Stunning Sauna Cottage Retreat on Private Vineyard

FamilyIndoor spacesSolo travel

Family-friendly home rentals with a pool

Guest suite in Healdsburg

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.

4.92 out of 5 average rating, 480 reviews

Pony Ranch Vineyard Estate with Pool

Indoor spacesKitchenLayout

4.97 out of 5 average rating, 233 reviews

Wine Country Retreat | Pool, Hot Tub + Vibes

Indoor spacesFamilyWalkability

4.97 out of 5 average rating, 158 reviews

Villa in Santa Rosa

Private 1+ acre, Bocce, Waterfall, Free Pool Heat

FamilyKitchenPets

4.96 out of 5 average rating, 125 reviews

A modern kitchen features a spacious island with three woven bar stools. Hexagon-tiled walls in a soothing grey tone complement open shelving displaying dishware. Large windows allow natural light to fill the space, with greenery visible outside.

Home in Sonoma

Modern wine country stunner with pool & pickleball

KitchenIndoor spacesParks

4.87 out of 5 average rating, 125 reviews

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

FamilyIndoor spacesPool

The outdoor area features a large swimming pool surrounded by lounge chairs and umbrellas. A spacious barn-like structure is visible in the background, nestled among trees, while a hot tub is situated adjacent to the pool, creating a serene and functional outdoor retreat.

4.98 out of 5 average rating, 122 reviews

Luxury Wine Country Barn Retreat on 25 Acres

KitchenFamilyCheckout

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.

4.99 out of 5 average rating, 139 reviews

Wine Country Luxury Retreat - Pool Sauna Spa Views

FamilyIndoor spacesCondition

A private outdoor area features a hot tub adjacent to a wooden deck. A white dining table is positioned for meals, surrounded by lush greenery. Soft lighting hangs above, adding to the relaxed setting. A window on the house offers natural light to the space.