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

4.98 out of 5 average rating, 97 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

4.91 out of 5 average rating, 46 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

Guest favorite

Villa in Calistoga

4.97 out of 5 average rating, 30 reviews

Mountain Villa 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.

Top 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, 214 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

Villa in Sebastopol

4.95 out of 5 average rating, 22 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

Top guest favorite

The exterior of the villa is adorned with lush greenery and shrubs, creating a serene atmosphere. The warm-toned facade features a tiled roof and wooden shutters. A gravel driveway leads to the entrance, framed by neatly arranged garden spaces and decorative pots.

Villa in Napa

4.96 out of 5 average rating, 171 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!

Superhost

Villa in Occidental

4.81 out of 5 average rating, 89 reviews

Russian River Artist Cabin, Private Forest+Jacuzzi

Nestled in 8 private acres of forest near the Russian River and Sonoma wine country, KORSI is a hidden paradise where art, nature, and magic collide. A boutique retreat crafted for intimate luxury, it features a hot tub under the stars, handcrafted interiors, and panoramic forest views. Every corner designed to inspire awe and connection. If you crave nature, beauty, magic and want to create unforgettable memories with your loved ones, KORSI is where you belong. Certificate No: 4684N

Guest favorite

A serene outdoor patio is highlighted, featuring a dark wooden dining table surrounded by chairs. The villa's exterior is visible, showcasing a tile roof and large windows. Lush green plants and trees provide a natural backdrop, with hills and a cloudy sky in the distance.

Villa in Novato

4.93 out of 5 average rating, 15 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.

Superhost

The charming exterior of the house showcases wood paneling and a stone hearth, framed by lush greenery and towering redwood trees. A winding pathway leads to the entrance, bordered by flowering plants and landscaping that evokes a serene country setting.

Villa in Monte Rio

4.76 out of 5 average rating, 34 reviews

Rivendell – Lovely Riverfront Home, Classic Style

Rivendell embodies the charm of a bygone era. Built in the 1930s as a country manor for a well-to-do family from San Francisco, the interior is updated with modern comforts, but retains elements of a fine country home. A stone hearth, beautiful wood paneling, wood floors and a formal dining room add to the charm. French doors open to a series of terraces leading to the river. The outdoor spaces are unmatched with stone and brick work throughout four separate outdoor living spaces!

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

4.91 out of 5 average rating, 112 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

Superhost

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

4.94 out of 5 average rating, 177 reviews

Hilltop Vista Villa

Nestled on a serene acre beside the scenic Fitch Mountain Park & Open Space Preserve, Hilltop Vista Villa offers a private sanctuary with sweeping views of world-class vineyards. Enjoy direct access to tranquil hiking trails and close proximity to the Russian River’s inviting beaches. This bright and welcoming single-level retreat features an open-concept floor plan filled with natural light.

Superhost

Aerial view of a spacious villa featuring a private swimming pool, surrounded by well-maintained gardens. Chaise lounges and umbrellas provide comfort around the pool area. Scenic views of vineyards and hills create a serene backdrop, highlighting the inviting outdoor living space.

Villa in Sonoma

4.89 out of 5 average rating, 37 reviews

Vineyard Villa: Pool | Spa | Games Room | EV Char.

★ PROPERTY HIGHLIGHTS ★ ✔ Swiming Pool: Enjoy swimming or relaxing on the chaise lounges at the private pool. ✔ Hot Tub: Marvel at the night sky while relaxing in the sunken hot tub. ✔ Games: Challenge other guests to a game of Pool, Foosball, or Basketball. ✔ BBQ: Dine al fresco while eating a delicious BBQ lunch. ✔ Views: Enjoy spectacular views of vineyards and the surrounding mountains.