
Luxury rentals in Wine Country
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Top-rated luxury holiday rentals in Wine Country
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Magical Wine Country Compound – Epic Views & Pool
Escape to a Magical Wine Country Retreat Perched atop a hill with sweeping views of 47 private acres, this newly renovated and impeccably styled compound offers the ultimate blend of seclusion and sophistication. Soak in sunsets from the heated pool or unwind in the hot tub under the stars. Justminutes from the charming towns of Geyserville and Healdsburg, enjoy a balance of quiet countryside and vibrant wine country food, drinks and culture. Relax, connect, and create unforgettable memories!

Calistoga Mansion - 38 Acres | Heated Pool | Views
Escape to your own private 38-acre luxury retreat in pristine Calistoga wine country, with sweeping vineyard views and resort-style amenities. Designed for up to 16 guests, the estate features a main house over 5,000 sq ft, private guest house, 75-ft lap pool with optional heating, outdoor kitchen and bar, game rooms, serene pond, and so much more. Enjoy exceptional privacy just 20 minutes north of downtown Calistoga—perfect for upscale getaways to Napa Valley, Sonoma Valley, or even Healdsburg!

Luxury Villa, Pool, Spa, BBQ, By Healdsburg
Welcome to Villa Montage - Brand new, luxury 4br/3.5ba Villa in the heart of Sonoma. Close to Wineries & Healdsburg. An award-winning architecture firm in SF designed the house. ★★★★★ "From the moment you drive into the driveway, there is an immediate “Wow!" ☞ New & modern home ☞ Pool & Spa (Pool heated April-Oct) ☞ Outdoor & Indoor fireplaces ☞ Pool table ☞ BBQ with covered patio and dining table ☞ Chef's kitchen ☞ Baby-friendly (crib, toys, monitor) ☞ Tesla Charger ☞ IG @Villamontage.sonoma

Sonoma-Napa Private Retreat by the Hills + Hot tub
Rated in the top 5% Guest Favorites, this modern country home offers luxury and classic California indoor-outdoor living. Set on an expansive lot with lawns, fruit trees and a garden, it is surrounded by peaceful hills on three sides. Explore over 250 Sonoma and Napa wineries, hot springs, beaches, rivers, and redwood forests all within 30 miles. While completely private, Santa Rosa city amenities are just 10 minutes away. Ideal for wine country getaway, wedding trip, remote work or staycation.

Stunning California Home & Pool
Imagine lounging by a shimmering pool with a captivating book, the sun dancing on the water's surface. As twilight falls, laughter fills the air around a barbecue, stars twinkling overhead. This serene retreat in San Rafael blends comfort and elegance, where luxury whispers in every detail. Step inside to a spacious interior where floor-to-ceiling windows invite natural light in. Each thoughtfully designed space features modern furnishings and artistic accents, creating an inviting atmosphere.

10 Acre Estate with Views, Teahouse, and Picklebal
Discover a private paradise at this 10-acre estate. Surrounded by a hobby vineyard, oak woodlands, and seasonal creeks, this property is a destination in itself. Unwind in the Japanese teahouse, play on the private tennis and pickleball courts, or take in the views from the outdoor patio. The beautifully appointed home features fireplaces, a gourmet kitchen, and a deck overlooking the landscape. It's an unparalleled retreat for relaxation, recreation, and exploring the best of Sonoma County.

Boho Mod Farmhouse Estate Sonoma Pool Spa Bocce Cl
Nestled on 2.1 acres in the heart of Sonoma, this stunning modern farmhouse—recently remodeled and soon to be featured on Staycation—blends elegance with wine country charm. Lounge by the 50-ft pool, soak in the hot tub, or enjoy the bocce court, redwood grove, and sunset swing. With 4 bedrooms (3 king, 1 queen), 3 baths, a sunroom, and open-concept living, every detail invites relaxation and luxury. Book your stay today! The farmhouse is centrally located btwn Sonoma & Napa Valleys.

Luxury Organic Ranch Fabulous for Groups with Farm
We built your dream! The Estate Villa at NewTree Ranch is perfect for intimate weddings, celebrations, corporate retreats, board meetings & family & friends vacations! We're here to assist you with all your weekend celebration plans, from curated dining experiences to unforgettable activities. Our luxury villa sleeps 8 and offers access to unique ranch experiences. Add another villa with 2 bedrooms to accommodate a total of 12 people.

Luxurious 3-Bedroom Home in Healdsburg
Escape to this luxurious 3-bedroom home in Healdsburg, perfect for exploring wine country. - Stylish interiors with premium furnishings - Spacious layout with indoor/outdoor feel - Modern amenities including high-speed Wi-Fi and flat-screen TVs - Outdoor oasis with a saltwater pool and spa - New construction completed in 2024 - Universal electric vehicle charger available Must be 25 years of age to rent this property.

The Overlook by Sonoma Stays – Modern Luxe Retreat
Set on nearly eight acres in the quiet hills of Santa Rosa, this spacious and modern 5-bedroom, 4-bath home offers comfort, privacy, and stunning scenery. Perfect for families or groups, it features a pool and spa, private yoga studio, bocce court, and beautifully landscaped grounds. With open living spaces, natural light, and contemporary design, there’s plenty of room to relax and enjoy moments with friends and family.

Sonoma Mountain Nest w/ Pool, Hot Tub, Pickleball!
Escape to Sonoma Nest, a luxurious family retreat in Santa Rosa, California. This stunning 4-bedroom house boasts a private pool, hot tub, and breathtaking mountain views. Enjoy a fully-equipped kitchen, outdoor seating, and easy access to Wine Country's finest wineries and family attractions. Perfect for creating unforgettable memories.

Sky House • Luxury Villa with Spa, Theater & Gym
"It’s magical and unique, thoughtfully designed and exquisite...this may be one of the most beautiful places you’d ever stay in." - Ben, Malibu Perched above the untouched Dillon Beach coastline, Sky House is a designer retreat that invites you to experience the rhythm of the coast in effortless, elevated style.
Popular amenities for Wine Country luxury holiday rentals
Other great luxury holiday rentals in Wine Country

The Francis House Estate

Calistoga Wine Ranch Estate

Calistoga Wine Ranch

Casa Rosa

Expansive Ocean-View Retreat with Home Theatre & S

Villa Nel Bosco

Modern Sonoma Stay w/ Deck & Views Near Wineries

Twilight Ridge by BeautifulPlaces
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- Jenner Beach
- Doran Beach
- Safari West
- Goat Rock Beach
- Johnson's Beach
- Sonoma Coast State Park
- Trione-Annadel State Park
- Chateau St. Jean
- V. Sattui Winery
- Charles M. Schulz Museum
- Armstrong Redwoods State Natural Reserve
- Sugarloaf Ridge State Park
- Iron Horse Vineyards
- Harbin Hot Springs
- Salt Point State Park
- St. Francis Winery and Vineyard
- VJB Vineyard & Cellars
- Mendocino National Forest
- Healdsburg Plaza
- Sonoma State University
- Bodega Head
- Francis Ford Coppola Winery
- Ledson Winery & Vineyards
- Clear Lake State Park
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