Family-friendly holiday rentals in Healdsburg

A covered patio is framed by wooden beams, offering a view of expansive vineyard landscapes and distant hills. Outdoor seating, including a dining table and lounge chairs, is arranged on the deck, inviting relaxation amid the tranquil scenery.

4.99 out of 5 average rating, 133 reviews

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.

KitchenFamilyCondition

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

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.

KitchenIndoor spacesWalkability

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, 119 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 spacesFamilyOutdoor spaces

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, 152 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

KitchenIndoor spacesNearby

4.98 out of 5 average rating, 121 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.

Indoor spacesKitchenNearby

4.97 out of 5 average rating, 699 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

KitchenFamilyValue

4.99 out of 5 average rating, 177 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!

Indoor spacesFamilySleep quality

4.97 out of 5 average rating, 627 reviews

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.

KitchenFamilyQuiet

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.

4.99 out of 5 average rating, 315 reviews

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.

Indoor spacesKitchenBathroom

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.

4.97 out of 5 average rating, 254 reviews

Designer Cottage | Garden Oasis | Walk to Plaza

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

FamilyIndoor spacesValue

5.0 out of 5 average rating, 227 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.

Indoor spacesFamilyCondition

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.

4.97 out of 5 average rating, 110 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 spacesKitchenSleep quality

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 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.

5.0 out of 5 average rating, 167 reviews

Luxe Guest Suite in Dry Creek 5 mins From Town!

Indoor spacesKitchenView

4.93 out of 5 average rating, 177 reviews

Modern Healdsburg Retreat • Hot Tub, Bocce & Views

FamilyIndoor spacesAccuracy

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, 361 reviews

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

Indoor spacesKitchenRiver

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.

4.9 out of 5 average rating, 106 reviews

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

FamilyKitchenBathroom

5.0 out of 5 average rating, 121 reviews

Home in Sebastopol

Pixel Place - A Private Arcade + Outdoor Sanctuary

Indoor spacesFamilyCheckout

4.91 out of 5 average rating, 191 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

Indoor spacesKitchenGetting around

The exterior of a beautifully designed house is presented, showcasing a light-colored facade with decorative shutters and a newly paved pathway. A stone fountain serves as a focal point amidst landscaped greenery, highlighting the inviting entrance and two stories of windows.

4.97 out of 5 average rating, 106 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

Indoor spacesKitchenLocation

4.98 out of 5 average rating, 118 reviews

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

FamilyIndoor spacesLayout

Family- and pet-friendly home rentals

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

KitchenFamilyParks

4.93 out of 5 average rating, 653 reviews

Healdsburg Garden House

Indoor spacesFamilyBarbecue

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

4.91 out of 5 average rating, 258 reviews

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

KitchenIndoor spacesQuiet

4.97 out of 5 average rating, 231 reviews

Wine Country Retreat | Pool, Hot Tub + Vibes

FamilyIndoor spacesAmenities

4.95 out of 5 average rating, 233 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

FamilyKitchenNearby

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

FamilyIndoor spacesDecor

4.91 out of 5 average rating, 464 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

FamilyKitchenBiking

4.96 out of 5 average rating, 218 reviews

Home in Forestville

Hilltop Haven Retreat | Scenic Hydro-Spa + Sauna

FamilyIndoor spacesHot tub

Family-friendly home rentals with a pool

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

Indoor spacesFamilySleep quality

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, 479 reviews

Pony Ranch Vineyard Estate with Pool

Indoor spacesFamilyAir conditioning

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

KitchenIndoor spacesPool

4.98 out of 5 average rating, 132 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

Indoor spacesKitchenDecor

4.95 out of 5 average rating, 546 reviews

A modern home is showcased with large sliding glass doors that open to a spacious wooden deck. The inviting heated pool features a gentle curve, with sun loungers placed nearby. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.

Home in Sonoma

Designer Sonoma Getaway with Pool, Hot Tub & Bocce

Indoor spacesFamilyNearby

4.94 out of 5 average rating, 264 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

FamilyKitchenPets

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.

4.98 out of 5 average rating, 206 reviews

Pacific Gardens Retreat

Indoor spacesFamilyLayout