Family-friendly vacation rentals in Kenwood

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, 121 reviews

Artist retreat/Hot Tub/2B/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, a 5 person private hot tub. Miles of vineyards and wineries are moments away. Sonoma is known for state parks as well as Hot Springs an abundance of eateries a lovely 3 miles to Glen Ellen town center. Just steps away from natural Sonoma warm springs open seasonally.

FamilyIndoor spacesParks

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, 303 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

FamilyIndoor spacesLocation

4.96 out of 5 average rating, 114 reviews

The home is framed by lush greenery and vibrant plants, with a patio featuring outdoor furniture. Warm light spills from the windows, hinting at a cozy interior. A barbecue grill is positioned nearby, providing an inviting space for outdoor gatherings.

Home in Kenwood

Vineyard Haven: Pool, Hot Tub & Wine Country Charm

Property is managed by Inspired in Sonoma. Welcome to your private wine-country vineyard haven, nestled on an acre of quiet woodland in the heart of Kenwood, California—a serene pocket of Sonoma Valley where golden light filters through oak trees, and every day feels like a celebration of good living. This spacious elegantly appointed 3-bedroom house, swimming pool and Hot Tub invites up to eight guests to unwind, reconnect, and savor the beauty of Kenwood’s vineyards, tasting rooms, and parks.

FamilyKitchenCheck-in

4.95 out of 5 average rating, 308 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

KitchenIndoor spacesView

5 out of 5 average rating, 222 reviews

Tiny home in Sebastopol

The Sonoma Spyglass | Incredible Views + Sauna

🏵️ Featured as one of “California’s Most Wishlisted Airbnbs!” 🏵️ 🌈 Come enjoy deep rest, romance & rejuvenation! ❤️ 🌺 Our Sonoma Spyglass is a gorgeous retreat, designed and built by Artistree Home, seamlessly blending sustainability with a deep connection to nature. 🍇 Tucked in the heart of Sonoma’s wine country, the space offers access to nearby walks and local wineries. Soak in the tub with incredible views or enjoy the detached barrel sauna for a perfectly relaxing stay. 🌺🙏 🌺

KitchenIndoor spacesAccess

A comfortable living room is displayed, featuring a leather sectional couch complemented by decorative cushions. A television is positioned nearby, with a stylish wooden coffee table in front. Warm light filters through a large window, illuminating the open kitchen area with modern appliances.

4.97 out of 5 average rating, 127 reviews

Fireside Sips & Oak Dreams in Sonoma Valley

Ultimate wine country escape! Stylish 3-bedroom, 1-bathroom oasis nestled in serene Sonoma Valley. Charming getaway features an equipped kitchen, inviting outdoor patios, BBQ grill, outdoor games, and cozy fire pit, perfect for enjoying stunning wooded backdrop. Unwind on the Peloton bike or indulge in board games. Ideal destination! Downtown Glen Ellen and Kenwood wineries are just a five-minute drive away. A perfect balance of seclusion and convenience await you. Pets are allowed, with fee.

Indoor spacesKitchenDecor

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, 168 reviews

GlenEllenHaven/HotTub/YogaYurt/EvCHGR/Pet Friendly

*5 min Glen Ellen/Kenwood. *20 min to Sonoma/Santa Rosa *45 min Napa Welcome to Glen Ellen Haven, a private 2 bd 1 bath cottage surrounded by organic cabernet vineyards offering views of Sonoma Mountain from expansive deck. We invite you to relax in the hot tub after a day of wine tasting or hiking, practice your daily yoga habit in the 300 sq ft yurt (ask about Sound Healing/Yoga Instructor recommendations), or relax and enjoy the views from our deck. One dog allowed max 25lbs, $150 pet fee.

FamilyIndoor spacesCheck-in

4.99 out of 5 average rating, 272 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

Pool & garden getaway in beautiful 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

Indoor spacesKitchenDecor

Superhost

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

4.94 out of 5 average rating, 234 reviews

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

KitchenFamilyHospitality

4.99 out of 5 average rating, 255 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!

Indoor spacesKitchenCheckout

4.93 out of 5 average rating, 121 reviews

Home in Kenwood

Modern Luxury in Sonoma's Valley of the Moon

Experience an amazing visit in this luxury vacation rental with hardwood floors, custom high end furnishings, stone counters and much more. Ideally suited for the sophisticated traveler who desires high quality modern accommodations. Relax in the private backyard overlooking a vineyard and seasonal creek. Relax and enjoy dinner on the 650 SQ. foot deck. Take a stroll through the Zinfandel & Petite Syrah vineyard and end the evening lounging by the warmth of the firepit.

KitchenFamilyCleanliness

4.97 out of 5 average rating, 146 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. Sonoma County TOT #373

FamilyIndoor spacesNearby

Popular amenities for Kenwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5 out of 5 average rating, 123 reviews

Home in Sebastopol

Pixel Place - A Private Arcade + Outdoor Sanctuary

Indoor spacesKitchenCheck-in

4.91 out of 5 average rating, 193 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 spacesKitchenLayout

4.98 out of 5 average rating, 122 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-Pool, Spa, Barn, OD Fire & Kitchen

Indoor spacesFamilyBeach

4.97 out of 5 average rating, 158 reviews

Villa in Santa Rosa

Private 1+ acre, Bocce, Waterfall, Free Pool Heat

KitchenIndoor spacesValue

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, 108 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

KitchenFamilyComfort

4.96 out of 5 average rating, 125 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

Indoor spacesKitchenAir conditioning

5 out of 5 average rating, 264 reviews

A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.

Home in Healdsburg

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

FamilyIndoor spacesBiking

4.97 out of 5 average rating, 159 reviews

Home in Sonoma

Stunning Sonoma | HOT TUB | Game Room | Sleeps 6

Indoor spacesKitchenHot tub

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 469 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

KitchenFamilyAir conditioning

4.96 out of 5 average rating, 518 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

Indoor spacesFamilyWifi

4.99 out of 5 average rating, 572 reviews

The exterior of a modern, wooden cottage is showcased with a welcoming front porch. Steps lead up to double French doors, surrounded by vibrant landscaping and trees. Large windows and a triangular peak create an inviting entrance, while plants line the walkway.

Cabin in Sonoma

Sonoma Berry Blossom Farm

FamilyIndoor spacesGrill

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, 210 reviews

Quiet Glen Ellen Home with a View

Indoor spacesFamilyGetting around

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, 1,022 reviews

Casa Relaxo: Mt top getaway with beautiful views

KitchenIndoor spacesCleanliness

4.97 out of 5 average rating, 122 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

FamilyIndoor spacesHeating

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, 209 reviews

Pacific Gardens Retreat

Indoor spacesFamilyAmenities

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, 160 reviews

Valley of the Moon Vintage Guest Cottage

FamilyKitchenAccuracy

Family-friendly home rentals with a pool

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.

4.91 out of 5 average rating, 217 reviews

Luxury home, heated spa tub, walk to restaurants

Indoor spacesKitchenOutdoor spaces

The outdoor area features a large swimming pool surrounded by lounge chairs and umbrellas. A spacious barn-like structure is visible in the background, nestled among trees, while a hot tub is situated adjacent to the pool, creating a serene and functional outdoor retreat.

4.98 out of 5 average rating, 122 reviews

Luxury Wine Country Barn Retreat on 25 Acres

Indoor spacesKitchenView

4.93 out of 5 average rating, 130 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

Indoor spacesKitchenCleanliness

4.99 out of 5 average rating, 257 reviews

Guesthouse in Sonoma

707 BARREL LOUNGE Cottage

KitchenFamilyBathroom

4.95 out of 5 average rating, 293 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

KitchenIndoor spacesAmenities

The outdoor space features a gazebo with a fire pit, surrounded by comfortable seating. Lounge chairs are positioned near an unheated pool, and a dining table with seating is visible in the background, creating a welcoming atmosphere for relaxation and gatherings.

4.93 out of 5 average rating, 187 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

FamilyKitchenWifi

4.98 out of 5 average rating, 122 reviews

Spacious 5 BR 3BA Pool EV Charger Group Getaway

FamilyIndoor spacesBackyard