Vacation rentals in Kenwood

4.95 out of 5 average rating, 257 reviews

A spacious sleeping area features a comfortable bed with a gray blanket and decorative pillows. Art pieces adorn the walls, while soft lighting is provided by two bedside lamps. A large glass door offers access to a garden patio, filling the room with natural light.

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 queen size bed. TOT (Transient Occupancy Tax) included. TOT #3720N

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.

4.94 out of 5 average rating, 109 reviews

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, 237 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

Superhost

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.

Apartment in Santa Rosa

4.91 out of 5 average rating, 277 reviews

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.

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, 136 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.

4.99 out of 5 average rating, 256 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

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.

4.97 out of 5 average rating, 135 reviews

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.

4.88 out of 5 average rating, 500 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

4.99 out of 5 average rating, 194 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!

4.97 out of 5 average rating, 425 reviews

An inviting outdoor space is surrounded by lush greenery and blooming lavender. Two wooden chairs are positioned to overlook sweeping views of the valley and vineyards below. A stone fire pit adds to the serene atmosphere of this natural setting.

Cottage in Penngrove

Sonoma Mountain Artist's Retreat

Enjoy the perched feeling of Sonoma Mountain's setting with sweeping views and nature. The slightly tamed wilderness with an olive orchard and gardens sets the tone as you chill on the redwood deck. This is a studio cottage with expansive views to the western valley and Marin. Mount Tam appears through the windows from your super comfy bed. This is a beautiful and unique space adjacent to a mellow artist's studio. NOTE: Well behaved and Pre-Approved dogs available for a nightly fee.

4.92 out of 5 average rating, 554 reviews

A spacious bedroom features a king bed adorned with a floral-patterned duvet. Natural light fills the room through multiple windows, with a cozy seating area visible. A flat-screen TV hangs on the wall, and a mini kitchen is positioned nearby, complemented by a small dining table.

Guesthouse in Glen Ellen

Glen Ellen Hideaway

One block to downtown Glen Ellen, with dining, shopping, & wine tasting. Hideaway is a charming, private guest house, suite-style behind our home. Spa-like bath, mini kitchen, comfy king bed! There is a large private patio for your enjoyment, great place to relax. Glen Ellen Hideaway is peaceful & private & has a separate entrance for your accommodations. Residents are Constance & Greig, and Franny, the dog, and Charm, the cat!-TOT#2398

4.92 out of 5 average rating, 296 reviews

A living area features a blue velvet sofa adorned with decorative pillows. A glass coffee table sits on a patterned area rug, and a cozy chair is positioned nearby. Natural light filters through the window, with a pet-themed photo displayed on the wall.

Cottage in Glen Ellen

Cozy Creekside Retreat in Sonoma Wine Country

Perched on the bank of the Sonoma Creek this cottage strikes a balance between small town charm, a bit of nature, and accessibility to incredible wineries. Sitting on the back porch while popping open a bottle of wine as the sun sets, your main squeeze in your arms, and maybe see some otters paddling by makes this place special. We offer a clean, cute accommodation and simple bliss.

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Popular amenities for Kenwood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Kenwood's top sights

St. Francis Winery and Vineyard15 locals recommend

Sugarloaf Ridge State Park15 locals recommend

Landmark Vineyards3 locals recommend

Other great vacation rentals in Kenwood

5 out of 5 average rating, 13 reviews

The exterior of a mid-century modern home is displayed, featuring a spacious deck adorned with umbrellas and lounge chairs. A heated pool lies in the foreground, surrounded by low landscaping, with the home’s wood and glass structure set against a clear blue sky.

Home in Santa Rosa

4BR Mid-Century Home | Pool & Views | Santa Rosa

A spacious kitchen features a large island constructed from wood barrels, complemented by modern pendant lighting. Natural light floods through a skylight, illuminating the open layout that connects to the living area, where a comfortable seating arrangement is visible.

4.92 out of 5 average rating, 64 reviews

Wine Country Creekside Retreat With Hot Tub

An outdoor dining area is presented by a white table set with dishes and glassware, shaded by a large umbrella. The pool glistens nearby, accompanied by a spacious lawn and surrounding trees. In the background, rustic buildings and a picnic table are visible.

5 out of 5 average rating, 9 reviews

Wine Country Farmhouse with pool & spa

5 out of 5 average rating, 14 reviews

The outdoor space features a well-maintained lawn leading down to a private pool, surrounded by lush greenery and vibrant gardens. Stone steps guide the way down from a wooden deck area, enhancing the natural beauty of the serene landscape and unobstructed views of the hillside.

Home in Sonoma County

Exquisite Kenwood Retreat with Pool

A serene outdoor space features a swimming pool surrounded by lounge chairs and umbrellas. Lush greenery and trees provide privacy and shade, enhancing the natural setting. A spacious meadow extends beyond the pool area, showcasing the beauty of the organic orchard and nearby forest.

5 out of 5 average rating, 11 reviews

Kenwood Ranch Retreat w/ Pool (Family Friendly!)

A welcoming exterior of a vibrant home showcases a blue door framed by greenery and flower boxes. Red seating is arranged around a wooden deck, providing a comfortable area for relaxation beneath clear skies.

5 out of 5 average rating, 14 reviews

Sol Y Luna Wine Country Home

A modern living area features a cozy sofa paired with two armchairs and a glass coffee table. A textured area rug adds warmth beneath the seating. The open-plan layout connects to a sleek kitchen, where natural light floods the space through large windows.

4.85 out of 5 average rating, 13 reviews

Glen Ellen Gem-2 Bed/2 Bath Oasis + Stunning Pool

Superhost

A spacious living area features a large sectional sofa positioned on a light area rug, with expansive windows allowing natural light and views of the outdoor greenery. A modern light fixture hangs above, and minimalistic furniture complements the open layout.