Family-friendly holiday rentals in Kenwood

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.

4.99 out of 5 average rating, 257 reviews

Quiet Wine County Retreat with Bocce and Hot tub!

Central wine country location Close to wineries, tasting rooms, gourmet market, french bakery & restaurants New luxury 3-BR, 2.5 bath Hot tub & bocce ball We can host 5 adults + 2-3 kids Quiet spacious home nestled in the redwoods on 1/2 acre Complimentary pastries from local bakery Linens, towels, spa robes & toiletries provided Complimentary coffee, tea & sugar Huge outdoor decks with 3 seating areas, dining table, fire-pit Corn-hole, giant jenga & board games Kids’ books, games & baby items

4.95 out of 5 average rating, 274 reviews

A spacious bedroom features a comfortable, well-dressed bed with neutral-toned linens and decorative pillows. Floor-to-ceiling windows offer a view of the garden patio, while artwork adorns the walls. A bedside table displays a lamp, adding functionality to the inviting space.

Guest house in Kenwood

Casa de Vincenzi

Beautiful, immaculate private studio, situated in Kenwood village with separate entrance and garden patio offers a quiet retreat in the heart of Sonoma Valley. Walking distance to world class tasting rooms and restaurants. Close to Sonoma, Glen Ellen and fave parks. Enjoy your ensuite bathroom with fluffy towels and toiletries. Indoor or outdoor dining to enjoy wine, tea, conversation, TV or wifi. Sleep in the quiet of your comfy King size bed. TOT (Transient Occupancy Tax) included. TOT #3720N

4.92 out of 5 average rating, 287 reviews

A spacious living room features a dark sofa adorned with decorative cushions, complemented by a round coffee table. Natural light filters in through a nearby door, enhancing the neutral tones of the room. A simple wall mirror and a floor lamp add subtle decor elements.

Flat in Santa Rosa

Getaway At The Grove- 1,400 sq ft unit

Located in the heart of Sonoma Valley is a historic property on 1.11 acres that boasts several gardens and an olive orchard. The 1,400 sq ft unit is located directly below the host's main residence and features a large bedroom, bathroom, and living room with a wet bar, fridge, microwave, Nespresso coffeemaker and water kettle. It is also equipped with WiFi & AC/heating. The property is located across the street from beautiful St. Francis Winery and hiking trails at Hood Mountain Regional Park.

4.99 out of 5 average rating, 265 reviews

A serene outdoor space features a sparkling saltwater pool surrounded by lush greenery and colorful landscaping. A cozy cottage is positioned in the background, with a gray roof and welcoming entrance. Comfortable lounge chairs are arranged neatly beside the pool, inviting relaxation.

Cottage in Kenwood

Private Charming Poolside 1 BD/BA in Sonoma Valley

Escape to your home-away-from-home on a private residential compound: the perfect getaway spot in the heart of beautiful Sonoma Valley! 🏡 Why You’ll Love It: ✔️ Minutes to 25+ wineries & great restaurants ✔️ Easy drives to Sonoma, Calistoga, Healdsburg, Napa & the Coast ✔️ Great hiking in nearby parks ✔️ Birdwatching in the garden ✔️ Saltwater pool & bocce court ✔️ Stunning Mountain views ✔️ Private patio with gas grill & outdoor dining ✔️ Full kitchen, separate bedroom with ensuite bath

A welcoming home is nestled among large oak trees, featuring a spacious deck and multiple steps leading up to the entrance. Lush greenery and a variety of plants frame the path, enhancing the natural surroundings. Bright sunlight casts a warm glow on the scene.

4.88 out of 5 average rating, 514 reviews

The Oak Haven - a relaxing sanctuary w/spa!

Welcome to The Valley Of The Moon! Glen Ellen, a hidden gem in the heart of the rolling hills of wine country, is only 20 minutes from downtown Sonoma and prides itself on offering something amazing for everyone. Many beautiful state parks and famous vineyards are just a few minutes away. Enjoy wilderness and fine wine at your doorstep in a beautiful, private home away from home at The Oak Haven. Relax, take a load off, you deserve it! License Number: LIC24-0319 TOT Certificate No: 1387N

4.96 out of 5 average rating, 189 reviews

Vineyard Retreat • Steps to Tastings • Press Pick

WHY YOU'LL LOVE IT -Stroll through your own private vineyard -Pool, hot tub & bocce in a stunning serene setting -Minutes to top wineries, restaurants spas & towns -Complimentary tastings at the Estate Winery next door -Stylish interior with thoughtful touches -Chef-ready fully stocked kitchen -Helpful host and quick communication AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | The Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

Guest suite in Junior College

A cozy guest suite features a queen-size bed with a textured blanket and decorative pillows. A small desk with a chair and a mini fridge are positioned nearby. Soft lighting and wall art enhance the ambiance, while a ceiling fan provides comfort.

4.94 out of 5 average rating, 226 reviews

Cozy Private Guest Suite Centrally Located

This recently remodeled guest suite in Santa Rosa’s Junior College neighborhood offers a cozy retreat for 1-2 guests. It features a queen-size bed with a natural latex mattress, Smart TV, WiFi, mini fridge, microwave, Keurig coffee maker, and electric kettle. Relax in the shared garden courtyard with Adirondack chairs, a bistro table, and a propane grill. On-street parking is plentiful, and with a Walk Score of 85, you’re close to shops, dining, and the college.

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.

Flat 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

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.

4.97 out of 5 average rating, 735 reviews

A rustic cabin interior features wooden walls and ceiling, showcasing a spacious bed with red and black plaid bedding. A cozy seating area includes a leather couch and a patterned throw pillow. A small dining table rests nearby, complemented by large windows allowing natural light.

Cabin in Glen Ellen

Wine Country Cabin in the Woods

Enjoy our family owned historic cabin and the beautiful area. Our gas fireplace, hot spa, fine bedding, and high speed wi-fi await. We're 5-10 min from wineries/dining in Kenwood and Glen Ellen in the heart of Sonoma Valley, adjacent to Napa Valley, with fantastic wineries, restaurants, breweries and 4 state parks with a free pass! We welcome friendly people of all backgrounds!

4.89 out of 5 average rating, 496 reviews

A bright living area features high ceilings and wooden beams. A comfortable cream sofa is positioned between two armchairs, accompanied by small round tables with decorative plants. Natural light enters through the windows, illuminating the cozy atmosphere.

Home in Kenwood

Vineyard Cottage • Hot Tub + Wine Tasting Included

🍷✨ Vineyard Cottage Getaway | Hot Tub + Wine Tasting + Views Escape to your private wine country retreat in the heart of Sonoma Valley! Located on our family’s working vineyard at Hamilton Family Wines, your stay offers the perfect balance of cozy charm and modern comforts — just steps from tasting rooms, shops, and dining in the village of Kenwood.

4.97 out of 5 average rating, 852 reviews

A hand-painted welcome sign is displayed on a white oval background. Red cursive lettering spells 'Welcome,' surrounded by colorful flowers and green leaves, creating an inviting entry point.

Flat in Santa Rosa

Private Getaway in West Santa Rosa

This is the perfect place to spend your Wine Country vacation or just a weekend getaway. A 500-square foot private 1 bedroom granny in a quiet safe neighborhood. We want very much for this to feel like your home away from home when visiting Sonoma County. Thanks, Rhonda & Jeanine.

Popular amenities for Kenwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 504 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

4.97 out of 5 average rating, 287 reviews

The kitchen and dining area features a large wooden dining table surrounded by four chairs, adorned with greenery. A modern kitchen is equipped with stainless steel appliances, and a hand-drawn chalk mural of hummingbirds adds a vibrant touch to the wall.

Home in Sebastopol

Vino & Views, Artisan Hues |Spa, Eggs & Equine Too

4.97 out of 5 average rating, 128 reviews

Villa in Santa Rosa

Private 1+ acre, Bocce, New Heated Pool & Hot Tub

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.

5 out of 5 average rating, 340 reviews

Sonoma Farmhouse Tree Top Guest Studio

A bright and airy living space features large windows with views of the outdoors. Comfortable seating includes a green sofa and two armchairs. A round marble coffee table sits in front of the sofa, while a dining table is situated nearby. Natural light enhances the welcoming atmosphere.

4.99 out of 5 average rating, 146 reviews

GlenEllenHaven/HotTub/YogaYurt/EvCHGR/Pet Friendly

Superhost

A spacious outdoor seating area features a comfortable sofa with plush cushions facing the ocean. The scene captures the soothing waves and rugged coastline, complemented by a fire feature at the center, all under a beautiful sky transitioning from day to evening.

Cottage in Bodega Bay

4.84 out of 5 average rating, 302 reviews

Surfscape Beach House, Beach & Ocean views

A private deck features a luxury spa overlooking expansive views of Sonoma Mountain and Sonoma Valley. Two wicker chairs are placed around a glass table, inviting relaxation and enjoyment of the scenic landscape. The surrounding trees enhance the serene atmosphere.

4.99 out of 5 average rating, 323 reviews

Sonoma Valley Terrace- Great Views!! Private Spa!!

Family- and pet-friendly home rentals

A bright living area features a blue tufted sofa positioned opposite a wooden coffee table. A brick accent wall provides texture, while a large window allows natural light to illuminate the space. A small plant adds a touch of greenery.

4.77 out of 5 average rating, 131 reviews

2 Queen Beds • Dog Friendly • Just 3 mins to town

Guest house in Sebastopol

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.

4.93 out of 5 average rating, 799 reviews

Sun Drenched Flat

4.96 out of 5 average rating, 176 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

4.92 out of 5 average rating, 556 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

4.94 out of 5 average rating, 216 reviews

A pathway of wooden planks meanders through lush greenery, leading towards a studio cottage nestled among trees. The exterior of the cottage features warm earth tones, blending with the natural surroundings. Sunlight filters through the foliage, casting dappled light on the ground.

Cabin in Sebastopol

Country Studio Cottage Sanctuary

4.97 out of 5 average rating, 209 reviews

Home in Santa Rosa

Happy House Getaway - Pool, Hot Tub & Wine Country

An outdoor eating area features a round table covered with a patterned tablecloth, surrounded by four chairs. A large green umbrella provides shade, with vineyard views in the background. A gravel path and flowerbeds enhance the peaceful, landscaped setting.

4.96 out of 5 average rating, 381 reviews

Vineyard View Studio near Wineries, Dining, Hiking

A cozy living room features a light-colored sofa, a comfortable armchair, and a wooden coffee table. Natural light filters through windows adorned with bamboo shades, illuminating a vibrant area rug and greenery from potted plants. Colorful wall art adds a touch of personality to the space.

4.93 out of 5 average rating, 151 reviews

Valley of the Moon Vintage Guest Cottage

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 115 reviews

The spacious farmhouse is set amidst lush greenery, showcasing a serene pool surrounded by a patio. The exterior glows softly in the evening light, accentuating the property's inviting architecture and tranquil atmosphere.

Home in Santa Rosa

Farmhouse at Sonoma Oaks: Hot Tub · Pool · Bocce!

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, 269 reviews

A modern cottage is set against a backdrop of vibrant landscaping, showcasing a large, clear salt-water pool. Various outdoor seating areas are visible, complemented by lush trees and greenery that enhance the serene environment.

Guest house in Sonoma

Wine Country Gem - Sonoma Cottage with Pool Oasis

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.

4.95 out of 5 average rating, 447 reviews

Las Palmas Cottage

Guest suite in San Rafael

A circular wooden table is surrounded by four stylish chairs under a large umbrella, with a scenic view of the landscape in the background. The inviting pool glistens in the soft light, complemented by lounge chairs positioned nearby and greenery adding a natural touch.

4.91 out of 5 average rating, 341 reviews

Mountaintop poolside suite, sauna, views!

Guest house in Santa Rosa

A refreshing pool is surrounded by lush greenery and vibrant potted plants. Two chairs are positioned nearby, offering a serene space for relaxation. The cottage, featuring a light exterior and classic window design, rests under the shade of large trees, enhancing the tranquil atmosphere.

4.9 out of 5 average rating, 103 reviews

Tranquil Private Cottage / Pool-house

4.91 out of 5 average rating, 322 reviews

A tranquil pool reflects the vibrant hues of a sunset, bordered by lush greenery and palm trees. Comfortable seating areas are visible under shaded structures, enhancing an inviting outdoor space surrounded by colorful landscaping.

Guest house in Sonoma

Romantic Tropical Garden Casita

A spacious studio apartment features a king size bed with a colorful patterned quilt. Nightstands with lamps are positioned on either side. A kitchenette area is visible with open shelving and a small dining cart. Light wood flooring complements the bright, neutral walls.