Vacation rentals in Kenwood

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Top-rated vacation rentals in Kenwood

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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
4.91 out of 5 average rating, 111 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 favorite
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, 216 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.

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

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.

Top guest favorite
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
4.95 out of 5 average rating, 274 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 favorite
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
4.99 out of 5 average rating, 265 reviews

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

Top guest favorite
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.
Apartment in Penngrove
4.97 out of 5 average rating, 469 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.

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, 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

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
4.88 out of 5 average rating, 514 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
Home in Glen Ellen
4.96 out of 5 average rating, 189 reviews

Vineyard Retreat • 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 and quick communication AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | The Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

Guest favorite
A cozy guest suite features a queen-size bed with a textured blanket and decorative pillows. A small desk with a chair and a mini fridge are positioned nearby. Soft lighting and wall art enhance the ambiance, while a ceiling fan provides comfort.
Guest suite in Junior College
4.94 out of 5 average rating, 226 reviews

Cozy Private Guest Suite Centrally Located

This recently remodeled guest suite in Santa Rosa’s Junior College neighborhood offers a cozy retreat for 1-2 guests. It features a queen-size bed with a natural latex mattress, Smart TV, WiFi, mini fridge, microwave, Keurig coffee maker, and electric kettle. Relax in the shared garden courtyard with Adirondack chairs, a bistro table, and a propane grill. On-street parking is plentiful, and with a Walk Score of 85, you’re close to shops, dining, and the college.

Guest favorite
A private patio area is depicted, featuring wooden decking and surrounding foliage. A small metal chair is positioned on the patio, providing a peaceful spot to enjoy the outdoor scenery. In the background, a green landscape with distant hills is visible under a cloudy sky.
Guest suite in Santa Rosa
4.9 out of 5 average rating, 743 reviews

Wine Country guest house

This large private studio apartment is modern and cozy. You are next to beautiful country side while you are in the city. There is a large patio for you to relax and enjoy the beautiful wine country view. You can drive or ride your bike to Sonoma Wine Country at HWY 12 or to Russian River Brewery. The Listing excludes Tax. The unit has short term permit form Santa Rosa SVR24-056.

Top guest favorite
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
4.97 out of 5 average rating, 733 reviews

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!

Popular amenities for Kenwood vacation rentals

When is the best time to visit Kenwood?

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Avg. priceG$91,306 GYDG$91,306 GYDG$90,049 GYDG$95,704 GYDG$101,777 GYDG$108,269 GYDG$80,207 GYDG$79,369 GYDG$79,579 GYDG$115,179 GYDG$102,614 GYDG$74,971 GYD
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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 vacation rentals in Kenwood?

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

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

    Yes! Work meets play with ease at over 20 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 house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 house 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 40 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 vacation rentals in Kenwood

  • Total vacation rentals

    Explore 60 vacation rentals in Kenwood

  • Nightly prices starting at

    Kenwood vacation rentals start at G$12,565 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,330 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 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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