Holiday rentals in Kenwood

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Top-rated holiday rentals in Kenwood

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Guest favourite
An outdoor fire pit surrounded by four wooden chairs offers a welcoming gathering space. The stone patio extends outward, framed by lush greenery and the vibrant hues of sunset. A vineyard is visible in the background, enhancing the natural setting.
Cottage in Sebastopol
4.91 out of 5 average rating, 386 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

Welcome to our private, renovated, personal spa in the woods. Including a large wood-burning Finnish sauna, it features a picturesque deck with hot/cold plunge over breathtaking untouched forest with fire pit vineyard-side. This all-cedar cottage is nested below Halleck Vineyard, one of Sonoma County’s prestigious wineries. A perfect retreat, you are centrally located for the best Sonoma has to offer Sonoma County Wine Tastings (0-20 mins) Bodega Bay (20 mins) Armstrong Giant Redwoods (30 mins)

Guest favourite
Two turquoise chairs are positioned near a serene creek, surrounded by lush greenery. The water reflects the surrounding trees, creating a calm and tranquil atmosphere. A wooden deck of a nearby cabin is visible above, adding to the natural setting.
Cottage in Glen Ellen
4.9 out of 5 average rating, 114 reviews

Cozy Sonoma Creekside Escape: Couples Retreat

Peaceful retreat in Glen Ellen, right on Sonoma Creek. Sleep to the sound of bubbling water! 1BR/1BA with a full kitchen, smart TV, washer/dryer, big office, and fast Wi-Fi. Relax on the deck with creek views, BBQ, and loungers. Pet-friendly, self check-in and great restaurants. Close to wineries and hiking. Perfect for couples, digital nomads, and nature lovers. You're just minutes from wineries, scenic hikes, and the charm of Glen Ellen — but you might find it hard to leave this peaceful spot.

Top guest favourite
A pathway of wooden planks meanders through lush greenery, leading towards a studio cottage nestled among trees. The exterior of the cottage features warm earth tones, blending with the natural surroundings. Sunlight filters through the foliage, casting dappled light on the ground.
Cabin in Sebastopol
4.94 out of 5 average rating, 223 reviews

Country Studio Cottage Sanctuary

Cozy, quiet studio cottage nestled on 1/3 acre of trees and surrounded by seasonal creeks. Indoor gas fireplace and full kitchen & large spacious deck. In Sonoma Wine Country, 12 minutes to downtown gourmet restaurants, and organic coffee houses. Take gorgeous backroads to Bodega Bay and Sonoma Coast. Nestle into the warm glow of a gas fireplace or watch for deer and wildlife from the deck or living room. This is a perfect retreat space for one or two people; it is not appropriate for parties.

Top guest favourite
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, 260 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 favourite
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.
Guest house in Kenwood
4.95 out of 5 average rating, 276 reviews

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

Top guest favourite
Home in Glen Ellen
4.96 out of 5 average rating, 191 reviews

Vineyard Home • Steps to Tastings • Press Pick

WHY YOU'LL LOVE IT -Stroll through your own private vineyard -Pool, hot tub & bocce in a stunning serene setting -Minutes to top wineries, restaurants spas & towns -Complimentary tastings at the Estate Winery next door -Stylish interior with thoughtful touches -Chef-ready fully stocked kitchen -Helpful host—quick responsive communication AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

Top guest favourite
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.
Flat in Santa Rosa
4.92 out of 5 average rating, 289 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.

Top guest favourite
Cottage in Kenwood
4.99 out of 5 average rating, 267 reviews

Enjoy autumn and beyond in beautiful 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

Top guest favourite
A round table with two chairs is positioned on lush green grass, overlooking a misty landscape at sunrise. The fog blankets the valley, enhancing views of rolling hills and distant trees. A potted plant adorns the table, creating a serene outdoor dining space.
Flat in Penngrove
4.97 out of 5 average rating, 474 reviews

Valley View-Sonoma Mountain Terrace

Take your wine country tour to a new level with a visit to Sonoma Mountain Terrace, a unique agri-tourism stay on a luxurious, non-traditional dairy farm. Nestled in the foothills of wine country, Sonoma Mountain provides a farm experience like none other, with the opportunity to feed a baby calf, observe milking our elite show cows, or just enjoy "being unplugged." Take a stroll through our extensive gardens, or enjoy million-dollar sunsets each night overlooking Petaluma & Rohnert Park.

Guest favourite
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, 516 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 favourite
A bright living area features a cozy twin size daybed with patterned pillows. Two upholstered chairs with a cow print design sit across from each other on a colorful area rug. Natural light streams through the windows adorned with shutters, creating a welcoming atmosphere.
Flat in Santa Rosa
4.99 out of 5 average rating, 305 reviews

Robin's Nest

Your second home is above our 2-car garage, a 1 bedroom, 1 bath, living room, full kitchen and dining area. A twin size daybed is in the living room. Local grocery stores are within a mile, a 10-minute drive to downtown Santa Rosa, 45-minute drive to the coast and little over an hour to San Francisco. We are centrally located to explore Sonoma and Napa County wineries, breweries and hiking trails. Permit #SVR23-170

Guest favourite
A spacious studio apartment features a queen bed with neutral bedding, complemented by a small wooden table and two chairs positioned nearby. Natural light enters through a window adorned with a floral wall hanging, providing a cozy atmosphere.
Guest suite in Petaluma
4.87 out of 5 average rating, 165 reviews

Family Friendly Central Petaluma Studio

Our studio is only a few blocks from the heart of Petaluma. The Theatre District, Petaluma Market, and a myriad of local restaurants are all a 10 to 15 minute walk from your doorstep. We have two kids of our own (3 and 4) and we've set up the space to be comfortable for families traveling. There is ample space for everyone to spread out with a queen bed, 2 full size futons, and a crib included in the space.

Popular amenities for Kenwood holiday rentals

When is the best time to visit Kenwood?

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Avg. price$569 SGD$569 SGD$561 SGD$596 SGD$634 SGD$675 SGD$668 SGD$654 SGD$626 SGD$718 SGD$639 SGD$467 SGD
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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Kenwood?

    Experience the best of Kenwood with our house rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do hotel rentals in Kenwood have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Kenwood. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Kenwood?

    Four-legged friends are welcome in Kenwood. Choose from more than 10 house rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Kenwood?

    Yes! Work meets play with ease at over 30 house rentals in Kenwood featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Kenwood have free parking?

    Absolutely! We offer over 40 house rentals with free parking in Kenwood. Enjoy a tailored experience with all the comforts you desire.

  • Are there Kenwood hotel rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 hotel rentals with pools in Kenwood, available on Airbnb. Make a splash and soak up the sun in style!

  • Do hotel rentals in Kenwood have wifi?

    Absolutely! We offer over 10 hotel rentals with wifi in Kenwood. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Hotel Rentals in Kenwood?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly house rentals in Kenwood?

    Kenwood has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Kenwood have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Kenwood. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Kenwood

  • Total holiday rentals

    Explore 60 holiday rentals in Kenwood

  • Nightly prices starting at

    Kenwood holiday rentals start at $78 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,330 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Kenwood holiday rentals include wifi 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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