Family-friendly holiday rentals in St. Helena

4.95 out of 5 average rating, 132 reviews

A collection of blooming roses in various shades, including pink and red, is displayed in the foreground. In the background, a home with gray siding and a tall green tree is visible, complemented by sunlight illuminating the scene.

Guesthouse in St. Helena

Romantic Napa Valley Cottage

Looking for the perfect getaway? This modern studio nestled among California oaks is serene, private and gorgeous. Just minutes from downtown St Helena, enjoy easy access to Napa's best wineries and restaurants. With over 375+ wineries, you'll never be bored! Relax on the huge deck outside your door in between your adventures or get the green thumb going in the garden with more than 1,000 trees, flowers, and shrubs. Ask about host's insider tips to get the most out of your stay in Napa Valley!

A modern living space is displayed with a sectional sofa adorned with decorative pillows. A rectangular coffee table is centered on a subtle area rug, while a round mirror adds depth to the room. The open layout connects to a kitchen area featuring sleek cabinetry and bar seating.

5 out of 5 average rating, 115 reviews

Serene 1 BR Condo at Silverado Resort

Calming, relaxing, and stylish, this newly-remodeled 2nd floor condo at Silverado Resort is modern, serene, and peaceful. It’s perfect for a couple's celebration, a special birthday, or a quiet place to stay after enjoying one of the many events hosted at this famed property! Blending urban sophistication with Wine Country charm, this exquisite condo features upscale amenities, 100% bamboo linens, a posh sleeper sofa, two fireplaces, and a premium King size mattress for next level sleep bliss.

4.89 out of 5 average rating, 289 reviews

The entrance features a wooden deck with steps leading up to a door, surrounded by lush greenery. Decorative metal accents and potted plants add character, while wooden double doors below exhibit rustic charm. The overall setting is inviting and blends harmoniously with the natural surroundings.

Cabin in Calistoga

Wine Country Mountain Home

Whole house wine country luxury for 2 in a Private and secluded forested location. Starlink WiFi, Forest at your front door. Clean and Comfortable vintage cabin In the mountains. Mid way between Napa and Sonoma valleys: 7 miles to Calistoga; 10 miles to Santa Rosa. NO cleaning fee at check out. Self-check-in with lock box. Professionally cleaned and sanitized before all check ins. Monthly discounts of 50%, weekly discounts 25% for travelers looking to work from home. Inquire with host.

4.96 out of 5 average rating, 101 reviews

A modern living area features a large dark green sofa complemented by a cozy white chair and a stylish coffee table. Natural light streams through multiple windows, illuminating a patterned area rug. A dining area and kitchen are visible in the background.

Home in Calistoga

Calistoga Tejas Trails

Welcome to Tejas Trails, your country getaway nestled in Calistoga's mountain vistas, just 10 minutes from downtown. This new home (2023) is easy to share with friends or family. Enjoy refreshing mountain sunrises, dinners on the huge deck, watch sunsets sipping wine by the firepit, swing under a large oak tree, and take tranquil walks on the country road. This is the perfect place to leave the hustle and bustle behind, while still minutes from Napa Valley’s finest restaurants and wineries!

4.96 out of 5 average rating, 178 reviews

The exterior of the villa is adorned with lush greenery and shrubs, creating a serene atmosphere. The warm-toned facade features a tiled roof and wooden shutters. A gravel driveway leads to the entrance, framed by neatly arranged garden spaces and decorative pots.

Villa in Napa

An Italian Villa in the heart of Napa Valley!

Villa RayEl was inspired by the farmhouses and small villas of Italy. Located midway between downtown Napa and Yountville, this property sits on 2 acres providing great privacy. It sits next to a year-round creek with a view of a vineyard and nightly sunsets. It has a pool and an attached hot tub. Located 5 minutes off Highway 29, 8 minutes to Downtown Napa and 8 minutes to Yountville. It is convenient to great wineries, restaurants. Its the perfect getaway for families and friends!

4.86 out of 5 average rating, 244 reviews

A light yellow house features a welcoming front porch with white railings and a staircase leading to the entrance. Windows along the upper level allow natural light, and the well-kept yard includes shrubs. A mailbox is positioned at the foot of the stairs.

Home in St. Helena

The Dollhouse in Saint Helena

Charming remodeled Victorian 2 bdrm/2 bath - Light & spacious home. WD- Fireplace- Walking distance to downtown St. Helena,, several wineries and vineyards. 3 min walk to Farmstead, Charter Oak, Gott's and NV Health Spa. Plenty of HOT water in the bathrooms. Modern fully stocked kitchen/All linens and towels provided. Upstairs: Living Room/Dining Room/Kitchen/Guest Bdrm/Full Bath Downstairs: Den with Smart TV/Master Suite Great backyard for dining. Legal short term rental permit.

4.98 out of 5 average rating, 447 reviews

An inviting outdoor space is surrounded by lush greenery and blooming lavender. Two wooden chairs are positioned to overlook sweeping views of the valley and vineyards below. A stone fire pit adds to the serene atmosphere of this natural setting.

Cottage in Penngrove

Sonoma Mountain Artist's Retreat

Enjoy the perched feeling of Sonoma Mountain's setting with sweeping views and nature. The slightly tamed wilderness with an olive orchard and gardens sets the tone as you chill on the redwood deck. This is a studio cottage with expansive views to the western valley and Marin. Mount Tam appears through the windows from your super comfy bed. This is a beautiful and unique space adjacent to a mellow artist's studio. NOTE: Well behaved and Pre-Approved dogs available for a nightly fee.

4.97 out of 5 average rating, 566 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.

The spacious bathroom features a modern dual-sink vanity with a large circular mirror above. A freestanding bathtub is positioned beside a natural light-filled window, with greenery adding a touch of nature. A glass shower enclosure is visible, complemented by stylish overhead lighting.

4.96 out of 5 average rating, 508 reviews

A Private Guesthouse Studio – The Otter

the Otter studio - a peaceful standalone studio in the heart of Napa Valley wine country. the Otter studio is less than one mile from Downtown Napa but far enough away from the hustle and bustle to provide a tranquil retreat while retaining every thoughtful amenity. Enjoy our cozy living space. We are legally permitted to rent to Napa Valley visitors. Ask about our other Napa listings if the dates here are booked.

4.99 out of 5 average rating, 304 reviews

A bright living area features a cozy twin size daybed with patterned pillows. Two upholstered chairs with a cow print design sit across from each other on a colorful area rug. Natural light streams through the windows adorned with shutters, creating a welcoming atmosphere.

Apartment in Santa Rosa

Robin's Nest

Your second home is above our 2-car garage, a 1 bedroom, 1 bath, living room, full kitchen and dining area. A twin size daybed is in the living room. Local grocery stores are within a mile, a 10-minute drive to downtown Santa Rosa, 45-minute drive to the coast and little over an hour to San Francisco. We are centrally located to explore Sonoma and Napa County wineries, breweries and hiking trails. Permit #SVR23-170

A spacious living area features a light-colored sofa adorned with decorative pillows. Large windows allow natural light to fill the space, while a wooden dining table sits nearby. The adjacent doorway leads to an outdoor area, enhancing the connection with nature.

4.96 out of 5 average rating, 918 reviews

Carriage House at Main Street Farmhouse!

Clean, comfortable, space on this Farmhouse property dating back to 1880. Enter exact number of guests for correct pricing $60 per person after 2. Studio with queen bed, full bathroom, kitchen with stove/oven, microwave, sauté pan, toaster, coffee and tea, dinette, tv area and IKEA queen sofa/sleeper. Beautiful patio with fire pit, several nice seating areas. Not suitable for children under the age of 12.

Guest suite in Santa Rosa

A private patio area is depicted, featuring wooden decking and surrounding foliage. A small metal chair is positioned on the patio, providing a peaceful spot to enjoy the outdoor scenery. In the background, a green landscape with distant hills is visible under a cloudy sky.

4.9 out of 5 average rating, 743 reviews

Wine Country guest house

This large private studio apartment is modern and cozy. You are next to beautiful country side while you are in the city. There is a large patio for you to relax and enjoy the beautiful wine country view. You can drive or ride your bike to Sonoma Wine Country at HWY 12 or to Russian River Brewery. The Listing excludes Tax. The unit has short term permit form Santa Rosa SVR24-056.

Popular amenities for St. Helena family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 503 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

Luxe WineCountry getaway with Pool, hottub & Bocce

4.96 out of 5 average rating, 575 reviews

The cabin is nestled among lush greenery, showcasing multiple levels and large windows that reflect warm indoor light. A hot tub sits on the expansive lower deck, complemented by a bright red umbrella, creating an inviting outdoor space as dusk settles over the surroundings.

Cabin in Guerneville

Unique Modern Mountain Getaway

4.91 out of 5 average rating, 379 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

4.98 out of 5 average rating, 282 reviews

The Spyglass Treehouse is nestled among towering redwoods, showcasing a unique, curved design. A spacious deck wraps around the structure, offering views of the surrounding foliage. Natural grasses frame the foreground, enhancing the connection with the tranquil, forested environment.

Treehouse in Occidental

The Spectacular Spyglass Treehouse

4.99 out of 5 average rating, 255 reviews

The spacious outdoor deck is illuminated in the evening glow, featuring multiple seating areas, a dining table, and a hot tub. Large glass doors provide a view into the inviting interior, framed by tall redwood trees, creating a serene ambiance.

Home in Glen Ellen

Quiet Wine County Retreat with Bocce and Hot tub!

5 out of 5 average rating, 339 reviews

An outdoor seating area is illuminated by string lights, creating a relaxed ambiance. A fire pit is positioned nearby, inviting conversation. The two-story building features a staircase leading to a private entrance, surrounded by greenery and colorful flowers.

Guest suite in Sonoma

Sonoma Farmhouse Tree Top Guest Studio

4.92 out of 5 average rating, 104 reviews

The villa stands nestled among the trees, featuring a spacious driveway leading to a tri-garage. Its exterior combines warm tones with charming shutters. The picturesque hillside setting offers a blend of greenery and distant trees, contributing to a serene ambiance.

Home in Santa Rosa

Wine Country Opulent Villa-Brush Creek

5 out of 5 average rating, 186 reviews

The modern container home is surrounded by lush greenery and grapevines. Floor-to-ceiling windows reflect the natural light, offering unobstructed views of the landscape. The structure is elevated, enhancing the connection to the surrounding redwoods and vineyards.

Guesthouse in Sebastopol

Modern Container Home with Vineyard Views [NEW]

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 587 reviews

A cozy bedroom features a spacious bed with a light-colored duvet and decorative green pillow. Natural light enters through the window with wooden blinds. A small TV is positioned on a nearby barrel, and a sliding door leads to a closet with hanging space.

Guesthouse in Napa

Kats Place Napa Valley Walk Downtown VR-16-0044

4.96 out of 5 average rating, 499 reviews

A spacious interior features a queen bed with a light blue quilt, complemented by a cozy seating area. Large windows offer views of surrounding greenery, while a small dining table is positioned nearby. Natural light enhances the welcoming atmosphere of the room.

Guesthouse in Sonoma

Tranquil Wine Country Guest Cottage

4.93 out of 5 average rating, 799 reviews

A bright living area features a leather couch with orange cushions, complemented by a comfortable armchair. Natural light enters through large windows, illuminating a wooden coffee table stacked with magazines. A fan hangs from the ceiling, and a flat-screen TV is mounted on the wall.

Guesthouse in Sebastopol

Sun Drenched Flat

4.92 out of 5 average rating, 554 reviews

A spacious bedroom is furnished with a king-size bed layered in white linens and accented with plush yellow pillows. Sunlight filters through two windows dressed with white curtains, illuminating the warm tones of the room. A wooden chair and nightstand complement the inviting decor.

Guest suite in Petaluma

Fair Street Retreat A Historical Petaluma Studio

4.96 out of 5 average rating, 175 reviews

A spacious sleeping area features a large bed adorned with a patterned blanket and decorative pillows. Natural wood walls and ceiling add warmth, while large windows provide forest views. Nightstands are placed on either side of the bed, each with a lamp for soft lighting.

Treehouse in Bodega Bay

Eagle's Nest Treehouse Farm Stay

A comfortable living area features a light-colored sofa adjacent to a modern coffee table. Large glass doors lead to an outdoor space with views of the golf course, allowing natural light to fill the room. A fireplace adds a cozy touch.

4.91 out of 5 average rating, 151 reviews

Napa relaxation at its finest at Silverado Resort

Superhost

An open living area features a black leather sofa and bar-style seating at a wooden counter. Large windows allow natural light to fill the space, highlighting the wooden beams and flooring. The area connects to a lofted space, providing an airy atmosphere.

Guesthouse in Glen Ellen

4.84 out of 5 average rating, 970 reviews

Casa Relaxo: Mt top getaway with beautiful views

4.91 out of 5 average rating, 270 reviews

A craftsman cottage is set atop a gentle hill, featuring a welcoming porch framed by blue trim. Low stone steps lead to the entrance, and the pathway is suitable for vehicle access. Lush greenery surrounds the structure, enhancing its peaceful country setting.

Home in Calistoga

Cozy Craftsman Cottage

Family-friendly home rentals with a pool

The image showcases a scenic view of the Silverado Resort grounds, featuring well-maintained grassy areas and a sparkling pool surrounded by trees. The backdrop includes distant mountains and a clear blue sky, providing a tranquil outdoor setting.

4.99 out of 5 average rating, 472 reviews

Silverado! Luxe 1BR King Suite This View! Balcony

4.98 out of 5 average rating, 415 reviews

A cozy studio space features vaulted beam ceilings and warm wooden accents. A spacious bed sits against a backdrop of art, while a massage chair and a wall-mounted TV are visible. The area is complemented by decorative lighting and a welcoming atmosphere.

Guest suite in Petaluma

Petaluma Wine Country relaxing get away w/pool/spa

4.95 out of 5 average rating, 447 reviews

A private outdoor seating area is showcased, featuring a textured rug under a wicker table surrounded by comfortable chairs. Lush greenery and colorful potted plants create a serene garden atmosphere, while a bright green umbrella provides shade.

Guest suite in Sonoma

Casita de las Palmas

A serene view of a golf course is framed by large oak trees, showcasing lush green grass and a clear blue sky. The landscape features rolling hills and scattered trees, offering a tranquil outdoor space in the Napa Valley area.

4.89 out of 5 average rating, 290 reviews

Immaculate 2 bd 2 bath at Silverado Country Club

Superhost

The exterior of a private cottage is displayed, featuring a inviting entrance framed by shrubs and trees. Sunlight filters through the branches, casting a warm glow on the cottage dimensions. A pathway leads to the door, complementing the landscaped surroundings.

4.95 out of 5 average rating, 116 reviews

Casa Vina at Silverado Resort and Spa | Fireplace

Superhost

The entrance to a cave spa is framed by lush blooming plants, with stone walls and a wooden door. A sign announces 'Estate Cave - Spa Terra - Trinitas Tasting Room' above an arched entrance, complemented by a bench and vibrant flowers in the foreground.

4.82 out of 5 average rating, 102 reviews

Getaway in Napa! Bowling, Spa and More all Open!

The open-concept kitchen features modern appliances, including a microwave and oven, complemented by a large island with seating. Natural light floods the space, which seamlessly connects to the living area, revealing views of the outdoor patio through oversized windows.

4.93 out of 5 average rating, 134 reviews

Fairways Silverado Golf and Country