House vacation rentals in Kenwood

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Top-rated house rentals in Kenwood

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
A comfortable living room is presented, featuring a dark leather sofa, two armchairs, and a coffee table. Natural light enters through window coverings, and a decorative fireplace adds warmth. A simple artwork adorns the wall, complemented by a small welcome sign on a shelf.
Home in Santa Rosa
4.96 out of 5 average rating, 219 reviews

Cozy, Convenient, Central Wine Country Home

Quaint home located in a convenient location less than 20 minutes from Kenwood. Enjoy the fire pit in the backyard, the ping pong table, and the fireplace in the cozy living room. This home is less than a mile and a half to Howarth Park and Spring Lake, featuring renowned hiking and biking trails, tennis courts and a park. Just a short drive to both Montgomery Village and downtown Santa Rosa, where you will find shopping and superb restaurants, including the famous Russian River Brewing Company!

Top guest favorite
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.
Home in Glen Ellen
4.99 out of 5 average rating, 276 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

Top guest favorite
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.
Home in Glen Ellen
4.99 out of 5 average rating, 156 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.

Top guest favorite
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.
Home in Sonoma
4.97 out of 5 average rating, 109 reviews

Modern wine country stunner with pool & pickleball

Enjoy the best of Sonoma from this recently remodeled home. On over 1 acre with mature beautiful landscaping. Just added pickle ball/sport court! New kitchen and baths. Designer finishes. Comfy beds. Spacious and private outside seating and dining. Gorgeous pool. Hot tub and bar area in converted container. Close to the finest wineries in Sonoma. 2 minutes from Sonoma Golf Club. 10 minutes to Sonoma Square, 20 on bike. 7 minutes to Glen Ellen. 10 minutes to Kenwood. Sonoma County TOT #4481N

Top guest favorite
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
4.97 out of 5 average rating, 140 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

Guest favorite
A spacious deck offers sweeping views of the Carquinez Bridge and surrounding waterfront. Several round tables are accompanied by tall chairs with red umbrellas providing shade. A relaxing hammock is visible, inviting guests to unwind in the natural setting.
Home in Glen Cove
4.88 out of 5 average rating, 162 reviews

Summer breeze San Francisco Bay work travel ready

Newly remodeled bath and kitchen all rooms have new floors, pix coming soon Our focus is on your comfort, convenience and cleanliness. Entire house 3 comfy bedrooms 2 full baths shower - tub with bath supplies, stocked kitchen. Great Neiborhood for walks. CBenicia a great place to dine Napa Valley less then 30 minutes away. San Francisco ferry is a few minutes away. views of the waterfront. Free parking and laundry, fireplace, pit, BBQ, relaxing hammock in an outdoor tropical environment

Top guest favorite
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.
Home in Glen Ellen
4.89 out of 5 average rating, 532 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

Top guest favorite
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.
Home in Kenwood
4.94 out of 5 average rating, 113 reviews

Modern Luxury in Sonoma's Valley of the Moon

Come for an amazing visit 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. Enjoy dinner on the 650 square foot deck. Take a stroll through the Zinfandel & Petite Syrah vineyard and end the evening lounging by the warmth of the firepit.

Top guest favorite
Home in Glen Ellen
4.96 out of 5 average rating, 197 reviews

Vineyard Retreat • Walk to Wineries • Press Pick

WHY YOU'LL LOVE IT - Stroll your own private Sonoma vineyard - Resort-style outdoor living: pool, hot tub & bocce court with vineyard views - Prime location: minutes to top wineries, dining, spas & shops - Exclusive perk: complimentary tasting at the estate winery next door - Chef-ready, fully stocked kitchen - Stylish interior with thoughtful amenities - Ultra-fast, reliable WiFi - Seasoned Superhost—responsive, reliable, and thoughtful

Superhost
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.
Home in Santa Rosa
4.89 out of 5 average rating, 139 reviews

Rincon Valley Wine Country Vacation Home

Welcome to the Rincon Valley Wine Country Vacation Home located in the heart of the Sonoma Valley's Wine Country! Home features 3 bedrooms with 2 master suites, 3 bathrooms, a Game Room with a pool table, Hot Tub, Fire Pit and BBQ! An entertaining dream house. Conveniently located 5 mins from Kenwood Wineries , 25 mins from Sonoma and Calistoga in the Napa Valley, and 30 mins from the Russian River wine areas. Permit number: SVR22-070

Top guest favorite
A spacious bedroom features a comfortable bed dressed in crisp white linens with a decorative blanket. Natural light streams in through sliding glass doors leading to an outdoor area. Two nightstands with lamps flank the bed, and a wooden dresser completes the room's decor.
Home in Glen Ellen
4.94 out of 5 average rating, 181 reviews

Glen Ellen Retreat #2 King Beds

Private Wine Country home in the heart of Glen Ellen. Walking distance to restaurants, tasting rooms, and markets. We also have beautiful state parks, Jack London State Park is 5 minutes away and lovely to hike. You will definitely fall in love with this small quaint town hidden away in Sonoma Valley. Included is wi-fi, TV, coffee, and tea. Looking forward to your stay.

Guest favorite
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.
Home in Glen Ellen
4.93 out of 5 average rating, 160 reviews

Creekside Sonoma Cottage • Patio, Hot Tub & BBQ

Wake up beside the creek in our bright 2-bedroom Sonoma cottage just minutes from world-class wineries. Unwind in the private hot tub, grill local produce on the patio BBQ, or sip coffee while oaks sway overhead. Fast Wi-Fi, full kitchen, king & queen bed, and self-check-in keep stays hassle-free. Book your relaxing wine-country escape today! Permit# ZPE15-0779

Popular amenities for Kenwood house rentals

When is the best time to visit Kenwood?

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Avg. priceﺩ.ﺇ1,142ﺩ.ﺇ1,285ﺩ.ﺇ1,289ﺩ.ﺇ1,616ﺩ.ﺇ1,924ﺩ.ﺇ2,101ﺩ.ﺇ2,159ﺩ.ﺇ2,009ﺩ.ﺇ1,990ﺩ.ﺇ2,042ﺩ.ﺇ1,789ﺩ.ﺇ1,763
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Quick stats about house rentals in Kenwood

  • Total vacation rentals

    Explore 40 vacation rentals in Kenwood

  • Nightly prices starting at

    Kenwood vacation rentals start at ﺩ.ﺇ441 per night before taxes and fees

  • Verified guest reviews

    Over 2,480 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Kenwood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Kenwood rentals

  • 4.9 Average rating

    Kenwood stays are highly rated by guests—averaging 4.9 out of 5!

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