House holiday 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, 113 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.

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, 284 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

4.96 out of 5 average rating, 99 reviews

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.

A comfortable living room is displayed, featuring a leather sectional couch complemented by decorative cushions. A television is positioned nearby, with a stylish wooden coffee table in front. Warm light filters through a large window, illuminating the open kitchen area with modern appliances.

4.97 out of 5 average rating, 104 reviews

Fireside Sips & Oak Dreams in Sonoma Valley

Ultimate wine country escape! Stylish 3-bedroom, 1-bathroom oasis nestled in serene Sonoma Valley. Charming getaway features an equipped kitchen, inviting outdoor patios, BBQ grill, outdoor games, and cozy fire pit, perfect for enjoying stunning wooded backdrop. Unwind on the Peloton bike or indulge in board games. Ideal destination! Downtown Glen Ellen and Kenwood wineries are just a five-minute drive away. A perfect balance of seclusion and convenience await you. Pets are allowed, with fee.

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, 159 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.

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, 141 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

4.96 out of 5 average rating, 114 reviews

A modern living area features a large dark green sofa complemented by a cozy white chair and a stylish coffee table. Natural light streams through multiple windows, illuminating a patterned area rug. A dining area and kitchen are visible in the background.

Home in Calistoga

Calistoga Tejas Trails

Welcome to Tejas Trails, your country getaway nestled in Calistoga's mountain vistas, just 10 minutes from downtown. This new home (2023) is easy to share with friends or family. Enjoy refreshing mountain sunrises, dinners on the huge deck, watch sunsets sipping wine by the firepit, swing under a large oak tree, and take tranquil walks on the country road. This is the perfect place to leave the hustle and bustle behind, while still minutes from Napa Valley’s finest restaurants and wineries!

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, 535 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

An open living space is presented with vaulted ceilings and skylights that allow natural light to fill the room. A cozy dining table is surrounded by chairs, while a white sofa and dark seating option create a welcoming area. Shelves display dishware and decorative items.

4.96 out of 5 average rating, 531 reviews

A sophisticated Wine Country Cottage with Hot tub

Escape to Thornsberry Cottage, a luxe wine country retreat 5 mins from Sonoma Square. This unique property features two separate cottages, each with a private bed/bath, perfect for guests seeking privacy and togetherness. Enjoy vaulted ceilings, a large deck, a private hot tub, and a fire pit under ancient oaks. 5 minutes from the Sonoma Square, 3 minutes to the oldest wineries in California, or walk or bike to Gundlach Bundschu at the end of our road. Your serene getaway awaits!

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.

4.93 out of 5 average rating, 116 reviews

Modern Luxury in Sonoma's Valley of the Moon

Experience 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. 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.

5 out of 5 average rating, 232 reviews

A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.

Home in Healdsburg

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

4.97 out of 5 average rating, 202 reviews

Private Vineyard • 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

Popular amenities for house rentals in Kenwood

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The spacious farmhouse is set amidst lush greenery, showcasing a serene pool surrounded by a patio. The exterior glows softly in the evening light, accentuating the property's inviting architecture and tranquil atmosphere.

4.9 out of 5 average rating, 130 reviews

Farmhouse at Sonoma Oaks: Hot Tub · Pool · Bocce!

4.98 out of 5 average rating, 107 reviews

Home in Sebastopol

Sebastopol Retreat w/ Pool, Spa, BBQ, Dog Friendly

4.95 out of 5 average rating, 169 reviews

An outdoor space features a plunge pool surrounded by a sun deck with lounge chairs and a sun umbrella. The home, with its wood accents, is set against a backdrop of tall redwood trees, contributing to a serene, natural setting.

Home in Occidental

Modern mid-century-inspired, Deer Ranch

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, 102 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

The outdoor space features a gazebo with a fire pit, surrounded by comfortable seating. Lounge chairs are positioned near an unheated pool, and a dining table with seating is visible in the background, creating a welcoming atmosphere for relaxation and gatherings.

4.94 out of 5 average rating, 168 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

4.98 out of 5 average rating, 125 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

A natural stone pool is surrounded by vibrant foliage, showcasing a mix of green and fiery red leaves. Two wooden lounge chairs face the pool, complemented by a bright red umbrella. Scenic views of the rolling landscape extend into the distance.

4.92 out of 5 average rating, 128 reviews

Spectacular Stone Pool/Spa with Views; Near Plaza

The image showcases the Quail Roost property, featuring a spacious outdoor deck with a fire pit and pool. The interior highlights a cozy seating area with artful touches, large windows providing natural light, and elegant furnishings. The exterior view captures the pool and surrounding scenic landscape.

4.97 out of 5 average rating, 100 reviews

Best View Wine Country Oasis: Pool-Hot tub-Sauna

Weekly house rentals

4.94 out of 5 average rating, 294 reviews

Russian River Brewcation · Wine Retreat

A spacious multi-level deck is furnished with comfortable seating and a table. A patio heater stands beside a cozy seating area, surrounded by trees and ambient lighting. The home is visible in the background, enhancing the serene outdoor environment.

4.94 out of 5 average rating, 168 reviews

Charming Sonoma Escape: Near the Historic Square

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, 43 reviews

Sonoma Creek Haven | Creekside Hot Tub Retreat

4.97 out of 5 average rating, 196 reviews

Buena Vista Sonoma Style House

An outdoor living space features comfortable gray couches with soft cushions, styled with a low wooden coffee table. Stone walls and olive trees create a natural backdrop, while string lights provide gentle illumination overhead. A landscaped area with gravel completes the serene atmosphere.

5 out of 5 average rating, 53 reviews

Luxury Retreat & Zen Garden w/ Fireplace & Hot Tub

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.

4.94 out of 5 average rating, 185 reviews

Glen Ellen Retreats Coastal Cottage

4.95 out of 5 average rating, 278 reviews

A spacious living area features high wooden ceilings and large windows filling the space with natural light. Comfortable seating arrangements include upholstered chairs and a plush sofa. Artwork adorns the walls, and a wood stove adds warmth and character to the room.

Home in Inverness

Artist Retreat by Point Reyes with Level 2 charger

A bright dining room features a large wooden table surrounded by six chairs. A wood-burning stove is positioned in the corner, with greenery from potted plants enhancing the space. Skylights above allow natural light to flood the room, creating an inviting atmosphere.

4.97 out of 5 average rating, 557 reviews

Wine Country Nest • Hot Tub Retreat • Sonoma

Private house rentals

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, 19 reviews

Wine Country Farmhouse with pool & spa

4.89 out of 5 average rating, 47 reviews

Himmel House ~ Private Kenwood Wine Country

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, 17 reviews

Kenwood Ranch Retreat w/ Pool (Family Friendly!)

The outdoor area features a circular brick patio surrounded by lush greenery and a large tree. A pathway leads to the home, which has a mix of wood and metal siding. A covered seating area is visible in the background, providing additional outdoor space.

5 out of 5 average rating, 46 reviews

Oak Den - Secluded Charm in the Heart of Sonoma

4.9 out of 5 average rating, 10 reviews

Elegant Cobb House w/ Spa | Pond | Chef Kitchen

The outdoor pool area features a spacious swimming pool surrounded by lounge chairs and umbrellas. Views of rolling vineyards and lush greenery are visible in the background, enhancing the tranquil setting under a clear blue sky.

5 out of 5 average rating, 27 reviews

Kenwood Vista by AvantStay | 7acres, Vineyard View

5 out of 5 average rating, 6 reviews

New! Completely Brand New Home| Wineries & Dining

A bright living area features a comfortable sofa and armchair, complemented by a round coffee table. Sunlight is shown streaming through the windows, illuminating plants and a dining table set for gatherings. A ceiling fan enhances airflow in the inviting space.