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, 123 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.

KitchenIndoor spacesCheck-in

4.97 out of 5 average rating, 118 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.

KitchenFamilyOutdoor spaces

4.95 out of 5 average rating, 312 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

Indoor spacesKitchenWalkability

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, 307 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

FamilyKitchenOutdoor spaces

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, 131 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.

KitchenFamilyHospitality

4.91 out of 5 average rating, 197 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

Escape to your own private sanctuary at Villa Annadel. Savor the unparalleled privacy and modern sophistication of this one-of-a-kind wine country retreat. The expansive 3,200 square foot villa sits on just under 1.5 acres of privacy with a large sparkling pool, hot tub and outdoor dining gazebo. Game lovers will rejoice, from cornhole, to darts, ping pong and vintage arcade games. It’s easy to forget you are minutes from some of Santa Rosa’s finest restaurants and wine tasting destinations!

KitchenIndoor spacesNearby

4.99 out of 5 average rating, 274 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

KitchenFamilyGetting around

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, 552 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

Indoor spacesFamilyRiver

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

4.95 out of 5 average rating, 238 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.

Indoor spacesKitchenComfort

4.99 out of 5 average rating, 256 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 spacesFamilyPool

4.93 out of 5 average rating, 122 reviews

Home in Kenwood

Modern Luxury in Sonoma's Valley of the Moon

Experience an amazing stay 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.

Indoor spacesFamilyGrill

4.97 out of 5 average rating, 147 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. An Oasis

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

KitchenIndoor spacesAmenities

Popular amenities for Kenwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 131 reviews

Aerial view of a modern farmhouse villa surrounded by lush, rolling hills. Vibrant flowering trees line the property, alongside a grassy landscape that slopes gently upward. The natural setting offers a sense of seclusion, with trees creating a backdrop against clear blue skies.

Villa in Santa Rosa

Farmhouse Villa w/ Captivating Views & Hot Tub

Indoor spacesKitchenGrill

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, 170 reviews

GlenEllenHaven/HotTub/YogaYurt/EvCHGR/Pet Friendly

Indoor spacesFamilyValue

A Mediterranean-inspired house is set amidst lush gardens and rolling hills. The round swimming pool is surrounded by colorful landscaping and lounge chairs, inviting relaxation. The exterior features warm stucco walls and a tiled roof, showcasing a harmonious blend with the natural surroundings.

4.99 out of 5 average rating, 140 reviews

Wine Country Luxury Retreat - Pool Sauna Spa Views

Indoor spacesKitchenCondition

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.

4.92 out of 5 average rating, 133 reviews

Wine Country Villa | Heated Pool | Hot Tub

Indoor spacesFamilyCheckout

4.97 out of 5 average rating, 160 reviews

Villa in Santa Rosa

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

Indoor spacesFamilyOutdoor spaces

4.97 out of 5 average rating, 235 reviews

Wine Country Retreat | Pool, Hot Tub + Vibes

KitchenIndoor spacesBackyard

A wooden deck extends from the cottage, featuring a comfortable seating area with cushions. String lights are hung overhead, offering a warm glow as the sun sets. Surrounding trees provide a natural backdrop, creating a peaceful outdoor space.

4.93 out of 5 average rating, 192 reviews

Creekside Sonoma Cottage • Patio, Hot Tub & BBQ

FamilyIndoor spacesBackyard

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.

4.95 out of 5 average rating, 129 reviews

Modern wine country stunner with pool & pickleball

Indoor spacesKitchenHospitality

Family- and pet-friendly home rentals

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, 211 reviews

Quiet Glen Ellen Home with a View

FamilyKitchenAir conditioning

4.98 out of 5 average rating, 124 reviews

Spacious 5 BR 3BA Pool EV Charger Group Getaway

FamilyKitchenWalkability

4.96 out of 5 average rating, 521 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

KitchenIndoor spacesCleanliness

An inviting backyard space is adorned with string lights overhead, creating a cozy ambiance. Two Adirondack chairs and an outdoor sofa provide comfortable seating on the lush green lawn. A small table is situated between the chairs, enhancing the setting for relaxation.

4.96 out of 5 average rating, 169 reviews

2 BD/1 BA Home- Wine Country Getaway

KitchenIndoor spacesBathroom

4.97 out of 5 average rating, 266 reviews

Cottage in Santa Rosa

Wine Country Farmhouse with Hot Tub

FamilyKitchenGetting around

A hot tub bubbles gently, positioned next to a large swimming pool. Lush greenery surrounds the area, complemented by a vibrant sky with hues of orange and pink. A lounge chair and a sun umbrella are visible in the background, enhancing the outdoor relaxation space.

4.86 out of 5 average rating, 270 reviews

Charming Home w Pool+Hot Tub. Walk to Shops & Wine

FamilyIndoor spacesAccuracy

4.98 out of 5 average rating, 165 reviews

Stunning Sonoma | HOT TUB | Game Room | Sleeps 6

FamilyKitchenDecor

An inviting game room features a pool table centrally placed on a smooth floor. Silver 'GAME ON' letters are displayed on the wall, complemented by a small table and two high chairs. Ample storage cabinets line one side, with large garage doors allowing natural light.

4.89 out of 5 average rating, 152 reviews

Rincon Valley Wine Country Vacation Home

KitchenIndoor spacesCleanliness

Family-friendly home rentals with a pool

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.

4.95 out of 5 average rating, 550 reviews

Designer Sonoma Getaway with Pool, Hot Tub & Bocce

FamilyKitchenSleep quality

4.95 out of 5 average rating, 297 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

Indoor spacesFamilyHeating

4.98 out of 5 average rating, 134 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

Indoor spacesKitchenView

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, 213 reviews

Pacific Gardens Retreat

Indoor spacesFamilySleep quality

4.98 out of 5 average rating, 125 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

Heated Pool, Hot Tub, Ent Barn, Orchard, Fire Pit

KitchenFamilyNearby

A spacious backyard features a seasonal pool, surrounded by a tiled deck. Comfortable seating arrangements include several adirondack chairs around a fire table. A dining table is set nearby, offering an inviting space for outdoor meals. Lush greenery adds a touch of privacy.

4.99 out of 5 average rating, 270 reviews

Sonoma Valley Vacation Home with Seasonal Pool

Indoor spacesKitchenOutdoor spaces

A serene infinity pool extends towards the horizon, bordered by lush greenery. Eight lounge chairs, with two umbrellas, face the pool, inviting relaxation. A wooden structure sits in the background, along with a staircase leading to the home, all under a soft, pastel sky.

4.93 out of 5 average rating, 149 reviews

Farpoint: Heated Infinity Pool, Mountain Views

KitchenIndoor spacesWifi