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, 255 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.

4.91 out of 5 average rating, 162 reviews

A cozy treehouse retreat is surrounded by towering redwoods, resting on stilts above the forest floor. Large windows illuminate the structure, allowing natural light to flood the interior. A wooden deck extends outdoors, providing a relaxing space to enjoy the serene woodland environment.

Treehouse in Camp Meeker

Redwood Treehouse Retreat - Hot tub, fire pit

Welcome to our Redwood Treehouse Retreat, where cozy meets luxury in the heart of nature. Nestled in the ancient trees, this romantic escape offers privacy and indulgence. Relax in the hot tub, cozy up by the fire, recharge your EV, and explore. We’re centrally located: 5 min from Occidental, 10 min to Russian River/Monte Rio beach, 20 min to coast/Sebastopol, and 30 min to Healdsburg. A perfect base to discover all the wonders of this captivating region. Your dreamy, secluded getaway awaits.

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

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

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.

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, 222 reviews

A spacious guest studio is illuminated by natural light from skylights above. A comfortable dark sofa and ottoman are situated near a wooden media console. A large artwork is displayed on one wall, while lush green plants enhance the tranquil ambiance.

Guest house in Petaluma

Spacious West Side Garden Studio

Find peace and quiet right in town. Our guest house is located at the end of a long property, far from the street, yet just a 5 block walk to the heart of downtown. It's a perfect place to spend evenings after exploring Point Reyes, wine country, or the Sonoma Coast.

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, 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

4.97 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

4.96 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

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

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

4.97 out of 5 average rating, 209 reviews

Home in Santa Rosa

Happy House Getaway - Pool, Hot Tub & Wine Country

4.98 out of 5 average rating, 217 reviews

A solar-heated pool glistens under sunlight, surrounded by a grassy lawn and majestic oak trees providing shade. Lounge chairs are positioned neatly along the pool's edge, while a covered terrace is visible in the background, enhancing the outdoor relaxation space.

Villa in Sonoma

Twin Oaks • Pool, Garden, Terrace, Bocce & Hot tub

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

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

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.

Guest house in Sonoma

Tranquil Wine Country Guest Cottage

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, 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

4.92 out of 5 average rating, 555 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

4.91 out of 5 average rating, 312 reviews

A cozy living area is filled with natural light, featuring a blue sectional sofa and a round coffee table topped with a neutral-colored book. Sheer curtains frame the window, and a plant adds a touch of greenery. A framed image is displayed on the wall.

Cottage in Glen Ellen

Private Creekside Cottage Retreat, Wine Country

4.99 out of 5 average rating, 450 reviews

A spacious studio guest cottage is displayed, featuring a queen-sized bed with a light-colored blanket. The room includes a blue dresser, a television, and a cozy seating area. Natural light enters through multiple windows, highlighting the wooden beams of the ceiling.

Guest house in Petaluma

Cozy Studio Guest Cottage in Old Downtown Petaluma

4.97 out of 5 average rating, 143 reviews

An outdoor dining area is presented with a large table surrounded by several woven chairs, all shaded by a large umbrella. The scenic backdrop reveals rolling hills and trees, creating a serene atmosphere for meals and relaxation.

Home in Santa Rosa

Cozy Autumn Escape – Yard, Games & Hill Views

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

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

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!

5 out of 5 average rating, 153 reviews

A vibrant living area is illuminated by natural light from multiple windows, showcasing a spacious sectional sofa adorned with colorful pillows. A low table sits at the center, surrounded by decorative poufs. The space features a warm area rug and tropical plants, creating an inviting atmosphere.

Bungalow in Rio Nido

BungalowTerrace-HotTub/Arcade/MassageChair/Gym

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