Family-friendly holiday rentals in Kenwood

4.98 out of 5 average rating, 329 reviews

A stunning sunset casts warm hues over the rolling hills of Sonoma County, blending shades of orange and purple in the sky. The valley below is highlighted by patches of greenery and the silhouette of distant hills, creating a serene, panoramic view.

Guest suite in Penngrove

Sunset View - Sonoma Mountain Terrace

Take your wine country visit to a new level with a unique agri-tourism stay on a luxurious, non-traditional dairy farm. Nestled in the foothills of Sonoma County, Sonoma Mountain provides a farm experience like none other, with the opportunity to feed a baby calf, observe milking our show cows, or just enjoy "being unplugged." Take a stroll through our extensive gardens or enjoy our million-dollar sunsets each night overlooking Santa Rosa. Lots of opportunity for privacy and outdoor relaxation.

4.94 out of 5 average rating, 113 reviews

The exterior of a charming single-story home is featured, with a covered porch framed by white columns. A well-maintained garden surrounds the house, showcasing colorful flowers and neatly arranged stepping stones leading to the entrance.

Home in Kenwood

Modern Luxury in Sonoma's Valley of the Moon

Go for a long visit in this luxury vacation rental with hardwood floors, custom high end furnishings, stone counter tops and much more. Ideally suited for the sophisticated traveler who desires high quality modern accommodations. Relax in a private backyard with a deck overlooking our vineyard and seasonal creek. Enjoy dinner at the large grapevine covered picnic table. Stroll through the Zinfandel & Petite Syrah vineyard. Every detail is taken into consideration to insure your maximum comfort.

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, 274 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, 284 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.

Guesthouse 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

4.93 out of 5 average rating, 122 reviews

A solar-heated pool is set within a spacious patio of brick pavers. Two white lounge chairs sit beside the pool, accompanied by large umbrellas providing shade. Lush greenery and a wooden fence are visible in the background, enhancing the serene atmosphere.

Cottage in Sonoma

Farm Cottage With Private Pool

*NOTE: the pool is solar heated and is only open JUNE 1- OCTOBER 31. Private, quiet, peaceful family or couple-friendly rustic farm cottage, wine country retreat with a private pool minutes away from wineries, like Schug, Gloria Ferrar, Viansa, Ram's Gate and Sonoma town square. Solar-heated pool is open June-October. We are locked in by three dead-end roads, so it's very quiet. Large deck, large pool patio, kids' play structure, and more. Horses are our neighbors and life slows down here.

4.97 out of 5 average rating, 140 reviews

A serene backyard setting features a stone patio with four wooden Adirondack chairs arranged around a central fire pit. Lush greenery, including ferns and flowering plants, surrounds the area, creating a cozy atmosphere for relaxation.

Home in Kenwood

The Kenwood House, A Place to Stay

The Kenwood House, is a newly renovated turn of the century craftsman cottage, one of the most charming in Kenwood! Walking distance to wineries, vineyards and restaurants! You’ll love our cozy farmhouse style, relax on the front porch with views of the Kenwood Plaza Park. Enjoy the HOT TUB and fire pit under the stars in the magical backyard! Wine country serenity reminiscent of a New England landscape. Tesla Battery protection. $30 per extra guest over 4 per night. Sonoma County TOT #373

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.

4.89 out of 5 average rating, 530 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

A spacious wooden cottage is framed by vibrant autumn foliage. The exterior showcases large windows and a wraparound deck with seating. A natural path leads through landscaped greenery, enhancing the serene ambiance of the surrounding environment.

4.94 out of 5 average rating, 110 reviews

Artist inspired retreat in the best part of Sonoma

Find natural beauty in the Redwood as this Cedarfield Forest home shelters you in stylish Sonoma cottage. As you open the privacy Gates you are greeted with a quintessential English garden the scent of fresh rosemary and lavender. Miles of vineyards and wineries are moments away. Sonoma is known for state parks as well as Hot Springs an abundance of eateries and the charming Glen Ellen saloon are less than 3 miles away. Just steps away from natural Sonoma warm springs open seasonally.

4.99 out of 5 average rating, 230 reviews

A cozy living area showcases a rustic brick fireplace, producing a warm glow. Two armchairs with colorful striped blankets sit beside a small round table. A television is mounted above the mantelpiece, contributing to the inviting ambiance.

Cabin in Glen Ellen

Unique Historic Getaway w/Hot Tub and Fireplace

Hosmer House is a vintage gem, well preserved yet well appointed. Fully curated decor fills our families historic cabin. Close to wine tasting, fine dining and 3 state parks w/pass in historic Glen Ellen and Kenwood. Large always hot spa, fireplace, full kitchen, big TV, propane fire pit, screened in dining porch and 2 sets of french doors off the living room so you can enjoy nature or just curl up by the fire. Host next door for wine/food tips! We welcome people of all backgrounds!

A beautifully landscaped garden features a pathway bordered by gravel and decorative plants. White wicker chairs surround a small table, inviting relaxation. The wooden deck and spa pool are visible in the background, complementing the modern home adorned with solar panels.

4.92 out of 5 average rating, 204 reviews

Luxury home, heated spa tub, walk to restaurants

Luna Lodge, a 3 bedroom 2 bath Glen Ellen village luxury home in the heart of Sonoma wine country. The home has a beautiful garden with spa pool by a peaceful creek. Everything you need for a great vacation is at your fingertips. Situated on a quiet lane, 5 min walk to wine tasting rooms, top restaurants, food markets. Enjoy a gourmet private chef dinner while at the home. Let us know if you are interested and we will help you arrange a very special dining experience.

Superhost

A spacious backyard is showcased, featuring a hot tub surrounded by greenery. Comfortable patio furniture is arranged under a sunshade, with a hammock and additional seating visible. A manicured lawn extends, bordered by flowering shrubs and trees, creating a tranquil outdoor space.

Home in Roseland

4.82 out of 5 average rating, 127 reviews

Sonoma Valley Vacation Home

This home is located in the Sonoma Valley in the heart of the Wine Country. You will be minutes away from dining, shopping and wineries. The newly updated home features 3 bedrooms, 2 bathrooms plus a queen sofa sleeper in the living room. Enjoy the beautiful backyard with a Hot Tub, Fire Pit, BBQ, hammock and patio seating. The home features all amenities to make your trip perfect to Wine Country and enjoy all that it has to offer! SVR22-001 TOT:3583

4.91 out of 5 average rating, 334 reviews

The cottage exterior is softly illuminated by string lights, enhancing its inviting atmosphere. A bicycle hangs decoratively beside the door. Lush greenery and decorative plants are present along the pathway, leading to a porch that welcomes guests into the charming space.

Cottage in Glen Ellen

Creekside Retreat Cottage – Wine Country Haven

Wake up beside the gentle creek in your own cottage escape! •Queen bed & cozy fireplace •Peaceful waterfront deck •Fully stocked kitchen & coffee bar •Fast Wi-Fi plus workspace •Backyard with creek access Minutes to Sonoma Plaza, wineries and trails, our 800-sq-ft hideaway is perfect for couples or solo travelers seeking nature and convenience. Washer/dryer, board games and parking included. Book your Wine Country Haven today!

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, 525 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

4.97 out of 5 average rating, 655 reviews

A serene hot tub is situated in the foreground, surrounded by lush greenery. In the background, a cabin with vibrant orange walls is elevated among tall redwood trees, with a wooden staircase leading to its entrance. Natural light filters through the leaves, creating a peaceful setting.

Guesthouse in Monte Rio

The Henhouse

4.96 out of 5 average rating, 275 reviews

Sonoma- Glen Ellen Getaway Shaded Garden & Spa

4.98 out of 5 average rating, 146 reviews

Cottage in Sonoma

Idyllic Sonoma Vineyard Farmhouse With Pool

4.89 out of 5 average rating, 234 reviews

A deck with a glass table and four woven chairs overlooks the river and surrounding greenery. A vase of flowers sits at the center of the table. The expansive lawn and white loungers are visible in the background, framed by lush trees.

Cottage in Monte Rio

Riverwood Cottage - Hot Tub, Direct River Access!

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, 155 reviews

GlenEllenHaven/HotTub/YogaYurt/EvCHGR/Pet Friendly

4.98 out of 5 average rating, 550 reviews

A bright dining room features a large wooden table surrounded by six chairs. A wood-burning stove is positioned in the corner, with greenery from potted plants enhancing the space. Skylights above allow natural light to flood the room, creating an inviting atmosphere.

Home in Sonoma

Wine Country Nest • Hot Tub Retreat • Sonoma

Cabin in Point Reyes Station

The exterior of a modern handmade home is surrounded by lush greenery and mature gardens. The structure features wooden siding, large windows, and a spacious deck. Stone steps lead up to the entrance, guiding visitors through blossoming flower beds.

4.9 out of 5 average rating, 819 reviews

Point Reyes Unique Creekside Home with Hot Tub

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 422 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

Guest suite in Santa Rosa

A spacious private deck is seen with views overlooking the rolling hills and valleys. Comfortable green lounge chairs are positioned for relaxation. The deck features wooden railing and steps leading down, while a doorway connects to the guest suite.

4.96 out of 5 average rating, 368 reviews

Wikiup lookout retreat

4.93 out of 5 average rating, 817 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

4.88 out of 5 average rating, 299 reviews

A single-story granny unit is presented with a beige exterior and a red door. Two windows flank the entrance, allowing natural light into the space. A small patio area with a table and chairs is visible to the side, surrounded by landscaping that adds privacy.

Home in Santa Rosa

Sunshine cottage

The charming exterior of a spacious house is framed by leafy trees, featuring large glass windows and a welcoming porch area. Comfortable seating options are arranged outside on a paved patio, providing an inviting space for relaxation amidst the surrounding natural landscape.

4.85 out of 5 average rating, 202 reviews

Quiet Glen Ellen Home with a View

4.9 out of 5 average rating, 204 reviews

Home in Guerneville

Riverfront Home with Private Dock on Russian River

4.94 out of 5 average rating, 793 reviews

An outdoor deck surrounded by lush greenery features a fire pit at its center, surrounded by seating options. A claw foot tub is positioned against the railing, while a small round table and folding chairs provide additional seating. Bright green cushions add color to the wooden lounge chairs.

Cottage in Occidental

The Perch - Outdoor Clawfoot Tub

4.84 out of 5 average rating, 990 reviews

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

Casa Relaxo: Mt top getaway with beautiful views

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 121 reviews

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.

Home in Healdsburg

Vineyard Vista, Modern Farmhouse Cottage with Pool

4.95 out of 5 average rating, 275 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.

Guesthouse in Sonoma

Wine Country Gem - Sonoma Cottage with Pool Oasis

4.98 out of 5 average rating, 433 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, 449 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

4.99 out of 5 average rating, 268 reviews

A cozy living area is furnished with a light-colored sectional sofa adorned with colorful accent pillows. A wooden coffee table holds snacks and glasses, while a lamp illuminates the space. Natural light enters through shutters, creating a warm ambiance.

Cottage in Kenwood

Spring getaway in beautiful Sonoma Valley!

4.97 out of 5 average rating, 109 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

5 out of 5 average rating, 166 reviews

A neon sign displays the name 'Bungalow Terrace' in bright pink lettering, creating a vibrant focal point against the background. The sign softly illuminates its surroundings, contributing to the playful ambiance of the space.

Bungalow in Guerneville

BungalowTerrace-HotTub/Arcade/MassageChair/Gym