Villa vacation rentals in Kenwood

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Top-rated villa rentals in Kenwood

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Guest favorite

Aerial view of a modern farmhouse villa surrounded by lush, rolling hills. Vibrant flowering trees line the property, alongside a grassy landscape that slopes gently upward. The natural setting offers a sense of seclusion, with trees creating a backdrop against clear blue skies.

Villa in Santa Rosa

4.99 out of 5 average rating, 86 reviews

Farmhouse Villa w/ Captivating Views & Hot Tub

Welcome to your perfect retreat in the heart of wine country! This newly renovated modern farmhouse villa offers 11 acres of private serenity, surrounded by nature and breathtaking 360-degree views, including the majestic Mount Helena. Perfectly situated between the cities of Calistoga (15 mins away), Healdsburg (20 mins away), and surrounded by amazing wineries, this is the perfect place for you and your friends/families to decompress. Book your stay today and experience the magic for yourself!

Superhost

The exterior of the lodge is surrounded by lush greenery and mature palms, highlighting a mix of natural stone and wood finishes. A stone pathway leads to an inviting entrance flanked by steps, enhancing the connection to the serene outdoor space.

Villa in Geyserville

4.93 out of 5 average rating, 44 reviews

Adventure Alexander Valley Lodge w/ Pool & Hot tub

Your group will be comfortable in this spacious, unique pool villa on top of the hill overlooking Alexander Valley only 10 min to downtown Healdsburg. Lodge sits on 53 private acres with hiking trails, pool ( fee to heat), hot tub, tiki bar and pool table. There is plenty to do at this 4100 sq ft home both inside and out. Lawn games, fire pit, and BBQ are all there for you to enjoy. Set up a private wine tasting or chef services or wine tour. Just ask how we can help you plan your stay. 683N

Superhost

A hot tub is positioned on a stone patio, surrounded by a forest of pine trees. Views of the lush greenery create a serene atmosphere. A wooden bench sits nearby, enhancing the outdoor space for relaxation and gathering.

Villa in Occidental

4.84 out of 5 average rating, 82 reviews

Dreamy Artist Cabin w/ Jacuzzi in a Private Forest

Nurtured by the Russian River, Surrounded by the Sonoma Valley vineyards, a few miles from the Pacific Ocean, and created by a painter and an architect, KORSI is an earthly paradise nested in a forest of pine trees, volcanic crystals and abundance of birds and wildlife. If you love nature, art, disconnecting from the outside world, soaking in the hot tub, watching the stars, gathering around the fireplace and making core memories with your loved ones, this is for you! Certificate No: 4684N

Guest favorite

The exterior of the house is presented at twilight, showcasing its elevated design supported by red stilts. Lush greenery lines the driveway, with pine trees in the background. A colorful sunset creates a serene backdrop that enhances the peaceful rural setting.

Villa in Santa Rosa

4.96 out of 5 average rating, 26 reviews

Mountain Villa near Calistoga with Hot Tub

This unique spot in the mountains between Napa & Sonoma Valleys is 10 minutes from Calistoga & 13 minutes from highway 12 through Sonoma Valley. You’ll have fantastic views of the mountain forest and constellations in the night sky, while sharing the property with deer & other wildlife. You will immediately notice the quiet nature & the smell of trees. There are many attractions nearby, including Russian River, Safari West, Petrified Forest, various hot springs, & wineries galore to explore.

Guest favorite

A solar-heated pool glistens under sunlight, surrounded by a grassy lawn and majestic oak trees providing shade. Lounge chairs are positioned neatly along the pool's edge, while a covered terrace is visible in the background, enhancing the outdoor relaxation space.

Villa in Sonoma

4.98 out of 5 average rating, 204 reviews

Twin Oaks • Pool, Garden, Terrace, Bocce & Hot tub

3-BR/2-BA Main house + Pool House with Bathroom. Spanish style home located on a quiet lane surrounded by rolling hills of vines. The inside features an open floor plan with gourmet and fully equipped kitchen, living room, TV Room, spacious bedrooms, hardwood floors and designer furniture. The outside area has a covered terrace ideal for dining and lounging. Expansive garden with many trees and a pool under majestic oaks. Minutes (by car) from Sonoma, Glen Ellen, Restaurants and vineyards.

Guest favorite

A serene outdoor area features a crystal-clear pool and an attached hot tub, surrounded by lounge chairs. Shade is provided by umbrellas over the seating area. Lush greenery and decorative plants enhance the tranquil environment, with a charming villa visible in the background.

Villa in Napa

4.96 out of 5 average rating, 158 reviews

An Italian Villa in the heart of Napa Valley!

Villa RayEl was inspired by the farmhouses and small villas of Italy. Located midway between downtown Napa and Yountville, this property sits on 2 acres providing great privacy. It sits next to a year-round creek with a view of a vineyard and nightly sunsets. It has a pool and an attached hot tub. Located 5 minutes off Highway 29, 8 minutes to Downtown Napa and 8 minutes to Yountville. It is convenient to great wineries, restaurants. Its the perfect getaway for families and friends!

Guest favorite

A sunny living area is highlighted by a curved, plush sectional sofa adorned with decorative pillows. Large windows offer views of the surrounding hills, and a modern chandelier hangs overhead. A potted plant and a floral arrangement add touches of nature to the space.

Villa in Novato

4.83 out of 5 average rating, 6 reviews

Luxury 2-Acre Oak Retreat Serene Outdoor Hot Tub

Welcome to The Oak Estate — a luxurious 3238 Sq. Ft. Spanish Colonial villa tucked away on two private acres in Novato, just minutes from downtown Novato, Sonoma wineries, and San Francisco. With 4 bedrooms and 3 bathrooms, this peaceful retreat is perfect for anyone looking for serenity and to explore the best of Northern California. Relax in sun-drenched living spaces, relax under the oaks, and experience the perfect blend of wine country charm and upscale comfort in every detail.

Guest favorite

Villa in Sebastopol

5 out of 5 average rating, 16 reviews

5 Acre Villa Retreat w/ Vineyard, Pool, & Spa

Nestled on over 5 acres in Sebastopol, Burnside Villa is a luxury 4-bedroom, 4.5-bathroom Wine Country retreat with expansive vineyard views, spacious rooms, and exceptional outdoor amenities. Ideal for families or groups, this estate offers the ultimate Wine Country experience—whether you’re here for tasting tours, coastal adventures, or simply to unwind in a beautiful setting. 10 mins to Downtown Sebastopol 20 mins to Bodega Bay 30 mins to the Russian River 1 hour to San Francisco

Guest favorite

A spacious living area features large windows allowing natural light to illuminate the room, showcasing wood accents on the walls and ceiling. Comfortable seating includes a leather sofa and sturdy armchairs, while a wooden coffee table adds a rustic touch. A decorative chandelier hangs above.

Villa in Cazadero

4.95 out of 5 average rating, 222 reviews

Luxury in Redwoods w/ Hot Tub and Fire Pit

Elements is a sophisticated estate compound set on landscaped acres, hidden amongst redwood groves. Your friends & family will find privacy and seclusion while being close to all that wine country has to offer. A variety of unique amenities will make your stay unforgettable: a jetted hot tub in a circle of redwoods, several decks & lounge areas, a yoga/exercise studio, an outdoor shower, a board game collection, fast internet and 150+ channels of sports/movies

Guest favorite

The exterior of the villa is framed by tall, slender cypress trees, creating a serene entrance. The structure features a flat roof and large windows, with a backdrop of rolling vineyards and soft, distant hills illuminated by the warm light of sunset.

Villa in Healdsburg

4.93 out of 5 average rating, 168 reviews

Hilltop Vista Villa

Set on an Acre by Fitch Mountain Park and Open Space Preserve, Hilltop Vista Villa offers a quiet private setting, spectacular views of world class vineyards, private access to hiking trails and proximity to the Russian River beach. This inviting single level retreat has an open floor plan with lots of sunshine. The open kitchen features stainless steel appliances, custom cabinetry, and a granite topped island. The Master Suite includes a custom soaking tub.

Superhost

A wooden deck features two lounge chairs beneath large white umbrellas, offering shade. The in-ground pool reflects the clear blue sky and is surrounded by native grass and landscaping. A pathway extends along the deck, connecting to nearby rooms.

Villa in Sebastopol

4.94 out of 5 average rating, 78 reviews

Green Valley Retreat ~ Wine Country, Pool & Hot

Green Valley Retreat is a wine county gem near renowned restaurants and wineries. You can pick fresh produce from the massive guest garden and orchard and then enjoy it inside or out. The large back deck has an in-line gas BBQ and guests love cooking outside. The backyard contains a meadow of native bunch grasses along with a stand of redwood trees, oodles of flowers and one of our favorite built-in propane fire pits. BYOM (Bring Your Own Marshmallows).

Guest favorite

An aerial view of a spacious villa surrounded by lush greenery, featuring a curved swimming pool in the backyard. The property's layout includes outdoor seating near the pool, with multiple areas of lawn visible. Scenic vistas of rolling hills are seen in the distance.

Villa in Santa Rosa

4.9 out of 5 average rating, 98 reviews

Spacious wine country villa with pool

Relax with your whole family in this spacious Sonoma wine country villa, with beautiful greenery all around, scenic vistas, and easy short drives from great family-friendly wineries, hiking trails and conveniences. No matter your preference - either a relaxed stay far away from civilization, or a roomy place for family get-togethers, this place has it all. Pool is heated from June - September only. TOT #3719N