Vacation rentals in Kenwood

4.94 out of 5 average rating, 253 reviews

A serene outdoor patio is presented, featuring two colorful umbrellas providing shade over a small round table and chairs. Surrounding greenery and well-maintained landscaping enhance the inviting atmosphere. The space is easily accessible from the private entrance of the studio.

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

A spacious backyard is showcased, featuring a heated swimming pool bordered by lush lawns and vibrant green umbrellas. The area is surrounded by trees and vineyard views, creating a peaceful outdoor retreat perfect for relaxation and enjoyment.

4.99 out of 5 average rating, 301 reviews

4/3 Vineyard Home With Pool & Views (Sleeps 8)

1 King bedroom; 2 Queen bedrooms; 1 sleeping den with two twin beds; 3 full baths. One of the loveliest spots in Sonoma Valley. Stunning views of vineyards and mountains. Swimming pool and hot tub. Bocce Ball court through olive trees. Interior designer furnishings. Gourmet kitchen overlooking pool and vineyard. Wineries nearby. Beautiful lawn surrounding pool. Two acres. Fire pit overlooking vineyards. Perfect for friends & families in town for lazy weekends or Wine Country weddings.

The exterior of the house is visible, featuring a white wooden façade and a covered front porch supported by beams. A white picket fence encloses the garden, which includes neatly arranged low shrubs and seasonal plants. The sky is partially cloudy, enhancing the property's inviting appearance.

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.

4.92 out of 5 average rating, 273 reviews

An outdoor seating area features four cushioned chairs arranged around a circular fire pit, set on stone pavers. Surrounding vegetation includes olive trees and palm trees, providing a natural backdrop. Umbrella-shaded tables can be seen in the distance, enhancing the outdoor space.

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, 255 reviews

A well-appointed bathroom features a neutral-toned countertop and a round sink. White towels are neatly hung on a towel rack, accompanied by a decorative mirror above. A small painting of a landscape adds a touch of visual interest, alongside various toiletry items organized neatly nearby.

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 charming craftsman cottage is framed by lush greenery and blooming flowers. The entrance features a covered porch with inviting seating and a decorative lantern, leading to a bright door. The warm yellow exterior is complemented by the surrounding nature.

4.97 out of 5 average rating, 132 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

4.93 out of 5 average rating, 175 reviews

The spacious studio features a large king size bed centered in the room, flanked by two bedside lamps. Comfortable seating is provided by a leather armchair and a modern chair. A small wooden table is set up with a coffee station, and large windows allow natural light to enter.

Guesthouse in Sonoma

Cozy Sonoma Studio Nearby Wineries and Restaurants

Our super cozy Sonoma studio nestled on a twelve acre parcel has a welcoming living area, a comfortable king size bed, kitchen, and a recently refreshed bathroom. Self check in for privacy and social distancing. Home is cleaned and disinfected for 24 hours between guests, including all surfaces, sheets, towels, bedspreads, etc. This studio is a perfect wine country retreat, located about 4.4 miles from Sonoma Square, 3.7 miles to Glen Ellen, and surrounded by a multitude of wineries.

4.97 out of 5 average rating, 417 reviews

A bright living area features unique angled windows that frame the scenic views outside. A stylish desk with wooden accents is complemented by two comfortable chairs. A cozy couch, decorated with plush cushions, sits next to a vibrant rug, contributing to the inviting ambiance of the studio.

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.

4.85 out of 5 average rating, 216 reviews

Bungalow in Kenwood

Heiter House- sip | soak | savor + a Kenwood gem

Discover our charming 2-bedroom, 2-bath gem—perfectly designed for 4 to 6 guests—nestled in the heart of Kenwood just minutes from downtown. Every detail has been thoughtfully considered to ensure a flawless stay: a fully stocked kitchen, reliable Wi-Fi, a smart TV with cable, and even a ping pong table tucked away in the garage. Additional conveniences include two garages, a sun-kissed deck offering breathtaking sunrise views, and air-conditioned bedrooms for ultimate comfort.

Guest suite in Glen Ellen

A deer is seen standing among lush green foliage, with plants and shrubs framing the scene. The natural landscape provides a serene backdrop, with the deer appearing calm and curious in its environment.

4.95 out of 5 average rating, 261 reviews

Hummingbird Hideaway, Glen Ellen in Sonoma Valley

Hummingbird Hideaway is the perfect location to enjoy everything wine country has to offer. Located in the heart of Glen Ellen in the Sonoma Valley, you can stroll to wine tasting, restaurants, French Bakery, gourmet market and historic saloon for a night cap. Hiking the trails at the Jack London State Park is just minutes up the road. When you're ready to venture further, Sonoma is a short 15 minute drive, Kenwood is 10 minutes and just an hour to Bodega Bay on the Coast.

4.92 out of 5 average rating, 550 reviews

A historic brick building features large windows and a covered entrance. A second-floor balcony extends over the porch area, providing a charming outdoor space. Lush greenery surrounds the property, enhancing its character. The clear blue sky and sunlight create a bright ambiance.

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

4.91 out of 5 average rating, 291 reviews

The serene creek reflects the surrounding trees and sunlight. Two blue lounge chairs are positioned along the bank, offering a peaceful spot to relax. The gentle slope leads up to the cottage, which is partially visible through the foliage.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Hotels

Stylish accommodations and amenities

Popular amenities for Kenwood vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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, 6 reviews

A modern single-story cottage is surrounded by lush greenery and features large windows for natural light. A small staircase leads to the front entrance, which is framed by a grassy area and ornamental plants. The exterior showcases a mix of gray siding and white accents.

Cottage in Glen Ellen

Modern Cottage on Sonoma Creek

KathleenRating, 5 stars2 days ago

Jena is a great host. Accommodations great for a weekend, would return for a longer trip. she answered all my questions and the place had everything I needed and more.

A covered deck features rustic wooden tables and benches, with a vase of plants on the table. Expansive views of the vineyard and hills are visible through large openings, providing a scenic backdrop of greenery and distant mountains.

Apartment in Kenwood

5 out of 5 average rating, 3 reviews

Beautiful Private Apartment on Vineyard Estate

KatherineRating, 5 stars8 months ago

We had a lovely stay at the property. The photos on the app are nice, but simply cannot do it justice until you see it for yourself. Did I mention the delightful aroma of wood as it is an actual restored barn (wish for that to last forever). The owner did not miss a thing when it came to providing a welcoming space to stay away from home. The property is vast and you can enjoy a bit of nature and beautiful landscapes. It is near enough to drive to dozens of wonderful restaurants, hiking spots, spas, and wineries. I only had one concern prior to booking that my partner who is 6’3 may bump his head on the low part of the ceilings. Turns out, he was the first to say how cozy and happy he was with the unit. Adding, “Im cautious everywhere and bump my head often” 😹.. We live in the Bay Area and have stayed many places, and this one is a standout. Book your stay! You will be pleased and have lovely photos of sunsets and scenic backgrounds.

Place to stay in Sebastopol

An outdoor soaking tub is featured on a wooden deck with panoramic views of the surrounding landscape. A minimalistic side table accompanies the tub, and large glass doors provide a seamless connection to the interior space, inviting natural light into the area.

5 out of 5 average rating, 92 reviews

The Sonoma Spyglass | Incredible Views + Sauna

RustyRating, 5 stars1 week ago

We loved our stay at Jade’s Spayglass! Such a lovely place and absolutely beautiful surrounding Sonoma County rural/farm country. Everything was as expected and better. We will be coming back!

4.99 out of 5 average rating, 89 reviews

Home in Santa Rosa

Wine Country Retreat- Privacy-Spa/Pool/Games

NickRating, 5 stars2 weeks ago

Amanda's place is absolutely the place you want to stay in. My girlfriend and I stayed here for her birthday trip to Napa and it definitely worth the money and time spent here. Location is perfect for both privacy and closeness to numerous surround long towns with tons to do and just a short drive to both Napa and Sonoma county The house itself is beautiful, extremely clean and organized, fantastic views from any location inside the house. Bedrooms were super comfortable with luscious space Multiple bathrooms made it great for getting ready to go out and about Kitchen has everything you need The property was great private but doesn't feel desolate The pool was great the hot tub was so relaxing The detached game room made for some great fun at the end of the nights All in all amanads place was amazing and I would absolutely recommend to someone staying in the area If I return I will definitely be rebooking this listing Thank you again for the great hosting!

5 out of 5 average rating, 28 reviews

[Egg Farm Ranch] Heated Pool-Water Slide-Hot Tub

JenniferRating, 5 stars4 weeks ago

We loved staying here! So nice that its walkable to so many things. The house was well stocked and really felt like a home.

A spacious wooden deck features a hot tub surrounded by bubbles. Comfortable outdoor seating for four is provided under a large umbrella, while a sliding glass door leads into the house. The exterior of the home showcases a simple white façade with multiple windows.

4.81 out of 5 average rating, 108 reviews

Romantic Wine Country Cottage

DarrenRating, 5 stars2 weeks ago

We truly enjoyed the home and our stay. The rate for its location and amenities was inline with what I would expect. Rob was extremely communicative and responsive. Although we were there more for wine tours, there are many other activities that Rob's handbook points out. Would I stay there again - yes. Thanks Rob for the hospitality and providing us a great place to stay for our 10 year anniversary.

5 out of 5 average rating, 36 reviews

A tranquil outdoor area is showcased, featuring a wooden deck with comfortable seating arrangements. Surrounding trees display vibrant autumn leaves, enhancing the serene atmosphere. A pathway leads further into the natural landscape, offering access to the peaceful wooded surroundings.

Home in Glen Ellen

Fireside Sips & Oak Dreams in Sonoma Valley

ShayneRating, 5 stars1 day ago

I cannot rave enough about Tara's charming, secluded, peaceful home. we felt right at home. Everything was considered. clean house, comfortable beds, great amenities, including a fantastically appointed coffee bar. even the TP was top shelf! :-). Her communication was also first class. For the area, her price is beyond reasonable. If we make it back this way again, we will absolutely stay again.