Villa vacation rentals in Kenwood

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.

4.98 out of 5 average rating, 99 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!

The villa is set against a colorful sunset, highlighting its two-story structure. A large pool reflects the warm hues of the sky, while well-maintained landscaping surrounds the outdoor area. Soft lighting from the home creates an inviting ambiance.

4.92 out of 5 average rating, 161 reviews

Villa Annadel - Stunning 5 Bedroom with a Pool

Escape to your own private sanctuary at Villa Annadel. Savor the unparalleled privacy and modern sophistication of this one-of-a-kind wine country retreat. The expansive 3,200 square foot villa sits on just under 1.5 acres of privacy with a large sparkling pool, hot tub and outdoor dining gazebo. Game lovers will rejoice, from cornhole, to darts, ping pong and vintage arcade games. It’s easy to forget you are minutes from some of Santa Rosa’s finest restaurants and wine tasting destinations!

The exterior scene captures a serene backyard featuring a newly remodeled saltwater pool surrounded by a stone waterfall and lush landscaping. Lounge chairs are positioned near the pool, and the home is partially nestled among tall trees, creating a peaceful ambiance during sunset.

4.97 out of 5 average rating, 122 reviews

Private 1+ acre, Bocce, New Heated Pool & Hot Tub

With over 1 acre of flat wooded land, this private gated country estate is still just a few minutes from conveniences like Whole Foods and Safeway. And with a full-size bocce court, pool table, and dining pavilion, you might not want to leave. Our new saltwater pool and spa are gas-heated to be comfortable all year, at no extra charge. A rock river and pool waterfall add to the sound of rushing water. The house is a few minutes from downtown, and within 20 minutes of the highlights of Sonoma.

4.97 out of 5 average rating, 32 reviews

Villa in Calistoga

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.

4.96 out of 5 average rating, 25 reviews

An expansive outdoor pool area is framed by a landscaped backyard, with comfortable lounge chairs positioned around the water. Beyond the pool, rolling vineyards stretch across the horizon, highlighted by the soft glow of a setting sun.

Villa in Sebastopol

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

4.96 out of 5 average rating, 174 reviews

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

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!

4.8 out of 5 average rating, 92 reviews

Villa in Occidental

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

4.76 out of 5 average rating, 34 reviews

Villa in Monte Rio

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!

4.93 out of 5 average rating, 15 reviews

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

Luxury 2-Acre Napa Inspired Serene Retreat Hot Tub

Welcome to The Oak Estate, a luxurious 4-bedroom Spanish Colonial villa nestled on two private acres in Novato wine country, minutes from Sonoma wineries, downtown Novato, and San Francisco. This 3238-sq-ft designer retreat offers sunlit living areas, curated décor, and effortless indoor-outdoor flow. Unwind beneath heritage oaks, soak in the hot tub under the stars, and experience peaceful, refined California living.

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.

4.91 out of 5 average rating, 115 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

4.94 out of 5 average rating, 177 reviews

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

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.