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.

4.97 out of 5 average rating, 120 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.

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

4.95 out of 5 average rating, 315 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

4.99 out of 5 average rating, 275 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

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, 553 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

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

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.

4.95 out of 5 average rating, 240 reviews

4.99 out of 5 average rating, 258 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 two-story play structure features a slide, swings, multiple climbing areas, and a spacious platform. The wooden design blends with the natural surroundings, with a soft ground of wood chips enhancing safety for children at play.

4.97 out of 5 average rating, 289 reviews

Kid Friendly with Breathtaking Views on 10 Acres

Escape to your own slice of paradise in this exclusive gated WINE COUNTRY retreat boasting breathtaking 360° vistas. With a spacious 2,700 sqft layout and lofty ceilings. Let the little ones' imaginations run wild on our two-story play structure. With a trampoline, horseshoe pit, and shelves stocked with books and an abundance of toys, we've thought of everything to make your stay stress-free. Indulge in the ultimate family getaway. Book now and embark on an unforgettable adventure!

4.93 out of 5 average rating, 123 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.

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

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

Experience the ultimate Wine Country escape. The property sits on 11 private acres, offering complete privacy, peaceful surroundings, and stunning 360-degree views, including the iconic Mount Helena. Ideally located near Calistoga (15 minutes) and Healdsburg (20 minutes) and surrounded by top-rated wineries. Whether you’re here for wine tasting, relaxation, or a scenic getaway, this property delivers space, comfort, and unforgettable views.

Popular amenities for Kenwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The exterior showcases a landscaped garden featuring diverse greenery, decorative rocks, and a serene stone pathway. A gazebo is positioned in the garden, complementing the house’s two stories, which are framed by trees and plants. The scene is illuminated by soft natural light.

4.97 out of 5 average rating, 244 reviews

Elegant & Spacious Luxury Wine Country Estate

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, 141 reviews

Wine Country Luxury Retreat - Pool Sauna Spa Views

Superhost

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, 194 reviews

Creekside Sonoma Cottage • Patio, Hot Tub & BBQ

A bright and open living area is presented, featuring large windows that offer views of the exterior greenery. Soft, modern furniture is arranged around a central rug, creating a cozy atmosphere. Natural light streams in, accentuating the neutral color palette and elegant decor.

4.99 out of 5 average rating, 134 reviews

Stylish Sonoma Oasis + Hot Tub - Near Wineries

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, 112 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

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, 171 reviews

GlenEllenHaven/HotTub/YogaYurt/EvCHGR/Pet Friendly

4.97 out of 5 average rating, 236 reviews

Wine Country Retreat | Pool, Hot Tub + Vibes

4.92 out of 5 average rating, 113 reviews

Family Fun in Glen Ellen: Pool, Hot Tub & Views!

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, 212 reviews

Quiet Glen Ellen Home with a View

4.98 out of 5 average rating, 167 reviews

Sunset Sonoma | VIEWS | HOT TUB | | Sleeps 6

An outdoor seating area features two cushioned chairs and a wooden coffee table set atop a textured area rug. A vase with lemon branches and a wine bottle accompany glasses, inviting guests to enjoy leisurely moments in a peaceful garden setting.

4.98 out of 5 average rating, 112 reviews

Luxury wine country home 5 bedroom

4.97 out of 5 average rating, 266 reviews

Cottage in Santa Rosa

Wine Country Farmhouse with Hot Tub

4.95 out of 5 average rating, 207 reviews

The exterior of the villa is adorned with lush greenery and shrubs, creating a serene atmosphere. The warm-toned facade features a tiled roof and wooden shutters. A gravel driveway leads to the entrance, framed by neatly arranged garden spaces and decorative pots.

Villa in Napa

An Italian Villa in the heart of Napa Valley!

4.94 out of 5 average rating, 238 reviews

Apartment in Santa Rosa

Downtown Santa Rosa Walk to Russian River Brewery

4.92 out of 5 average rating, 267 reviews

A private hot tub is positioned on the deck, overlooking Tomales Bay. Clear blue water sparkles in the sunlight, with green hills visible in the background. Wooden decking surrounds the hot tub, providing space for relaxation while enjoying the scenic views.

Home in Marshall

Family Beach Cottage

4.9 out of 5 average rating, 153 reviews

Modern Panoramic Hillside Escape

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 298 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

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, 271 reviews

Sonoma Valley Vacation Home with Seasonal Pool

4.92 out of 5 average rating, 135 reviews

A spacious outdoor area features a large pool surrounded by natural stone walls. Comfortable lounge chairs are positioned for relaxation, and green umbrellas provide shade. Lush landscaping enhances the serene environment, with trees and plants framing the scene.

Home in Sebastopol

Private Resort with Pool, Pool House, View and Spa

4.96 out of 5 average rating, 395 reviews

The exterior features a bright green front door framed by contrasting black trim. Two large windows with decorative wooden accents are present beside the door. A wooden deck extends in front, providing accessibility and a welcoming entryway.

Home in Calistoga

Vineyard Farmhouse w/ Pool & Mt. Helena Views

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

4.95 out of 5 average rating, 188 reviews

A private pool area features a clear blue pool surrounded by lounging chairs and large umbrellas for shade. Lush greenery and palm trees provide a tropical feel, while the neighboring buildings blend harmoniously into the serene landscape.

Guesthouse in Santa Rosa

Sonoma Mountain Retreat

4.98 out of 5 average rating, 137 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

A serene outdoor area features a clear swimming pool surrounded by well-maintained grass. Two chaise lounges with neutral cushions are positioned under large umbrellas, providing shade. The backdrop includes a dining table set for six and a cozy cottage, complemented by a vibrant sunset sky.