Vacation rentals in Kenwood

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, 112 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, 247 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, 265 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

4.91 out of 5 average rating, 280 reviews

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

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.

4.99 out of 5 average rating, 261 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, 137 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 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, 100 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.

4.97 out of 5 average rating, 438 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.

Guest suite in Glen Ellen

A private room features a spacious queen bed with a white comforter. Adjacent, there is a small refrigerator and a television. Natural light enters through a large window and glass doors, leading to a cozy sitting area. Light wood flooring enhances the inviting atmosphere.

4.94 out of 5 average rating, 211 reviews

Wine Country Harvest Hideaway-Private entry/space

Welcome to our Harvest Hideaway! We’re centrally located in the heart of Sonoma Valley, right in downtown Glen Ellen. We are walking distance to restaurants, tasting rooms, and the great Glen Ellen Village Market. With dozens of wineries nearby, we are a 10 minute drive to Kenwood, and 15 minutes to the Sonoma Square. Within an hour, you can be on the coast in Bodega Bay or on the Golden Gate Bridge entering San Francisco. We are sure you'll have a fantastic stay!

4.92 out of 5 average rating, 306 reviews

A cozy living area is filled with natural light, featuring a blue sectional sofa and a round coffee table topped with a neutral-colored book. Sheer curtains frame the window, and a plant adds a touch of greenery. A framed image is displayed on the wall.

Cottage in Glen Ellen

Charming Cozy Creekside Cottage in Wine Country

Escape to our secluded cute 800‑sq‑ft creekside cottage (half of a duplex) in Glen Ellen. Sip wine on the deck while the sun sets over Sonoma Creek—maybe spot an otter (they really do hold hands while they float)! Perfect for two with a queen bed, private office, full kitchen, smart TV, board games, fast Wi‑Fi and awesome dedicated workspace. Dog‑friendly with backyard and creek access. Enjoy cozy country charm, all minutes from wineries and trails.

4.92 out of 5 average rating, 563 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

4.97 out of 5 average rating, 721 reviews

A rustic cabin interior features wooden walls and ceiling, showcasing a spacious bed with red and black plaid bedding. A cozy seating area includes a leather couch and a patterned throw pillow. A small dining table rests nearby, complemented by large windows allowing natural light.

Cabin in Glen Ellen

Wine Country Cabin in the Woods

Enjoy our family owned historic cabin and the beautiful area. Our gas fireplace, hot spa, fine bedding, and high speed wi-fi await. We're 5-10 min from wineries/dining in Kenwood and Glen Ellen in the heart of Sonoma Valley, adjacent to Napa Valley, with fantastic wineries, restaurants, breweries and 4 state parks with a free pass! We welcome friendly people of all backgrounds!

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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 Vineyard207 locals recommend

Sugarloaf Ridge State Park113 locals recommend

Landmark Vineyards43 locals recommend

Other great vacation rentals in Kenwood

Superhost

A bright living area features a blue tufted sofa positioned opposite a wooden coffee table. A brick accent wall provides texture, while a large window allows natural light to illuminate the space. A small plant adds a touch of greenery.

4.76 out of 5 average rating, 116 reviews

2 Queen Beds • Dog Friendly • Just 3 mins to town

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, 13 reviews

Wine Country Farmhouse with pool & spa

The home is set amidst lush greenery beside a tranquil creek, with a spacious deck inviting relaxation. Sunset rays stream through trees, creating a warm ambiance. The gentle flow of water enhances the serene environment, offering a picturesque backdrop for outdoor gatherings.

5 out of 5 average rating, 7 reviews

Sonoma Creek Haven – Creekside Near 20+ Wineries

5 out of 5 average rating, 9 reviews

A seating area is furnished with two sofas and a glass-topped coffee table. Large windows offer views of trees and natural scenery, while a door opens to a private balcony area. Natural light fills the space, emphasizing the inviting atmosphere.

Chalet in Kenwood

Amazing views in heart of wine country- Spacious!

4.89 out of 5 average rating, 37 reviews

A cozy living space features a gray sofa and a light coffee table, positioned on a textured rug. The space is illuminated by warm lighting, showcasing a mirror against a dark wall. A soft curtain separates the living area from the bedroom in the background.

Apartment in Glen Ellen

Spacious Studio Apt. Glen Ellen

4.98 out of 5 average rating, 47 reviews

A bright sleeping area features a spacious bed with white bedding, complemented by two bedside tables and lamps. Two pieces of wall art showcase natural patterns, while a comfortable seating area is provided by a red chair and a small lamp on a side table.

Apartment in Santa Rosa

Suite Retreat

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, 14 reviews

Kenwood Ranch Retreat w/ Pool (Family Friendly!)

Superhost

A spacious outdoor area features a blue swimming pool surrounded by landscaped gardens. A hot tub is positioned nearby, with mountain views in the background. The sun loungers and patio areas invite relaxation amidst the lush greenery.