Luxury rentals in St. Helena

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Top-rated luxury holiday rentals in St. Helena

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Luxe
A villa is depicted with a tranquil pool in the foreground and a spacious outdoor living area behind it. The rear of the structure features multiple glass doors that create a seamless connection to the landscape, surrounded by well-maintained grass and flowering shrubs.
Villa in Sonoma
5 out of 5 average rating, 4 reviews

The Attune Estate

This beautiful Sonoma villa is nestled in the heart of wine country and sits amongst the Attune Estate’s Pinot Noir vineyards. When you’re not out exploring the valley, visiting World-class tasting rooms, or dining at Sonoma’s best restaurants, grab a poolside lounger and soak up the warm Californian sun. After sunset, pour another glass of wine and curl up by the fireplace with someone special. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Television, Fireplace, Terrace • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Television, Terrace • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower, Television, Terrace • Bedroom 4: Queen size bed, Ensuite bathroom with stand-alone shower and bathtub, Television • Bedroom 5: Queen size bed, Ensuite bathroom with stand-alone shower and bathtub, Television OUTDOOR FEATURES • Outdoor living area • Garage - 4 spaces STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions

Luxe
An infinity-edge pool is showcased, reflecting the colorful twilight sky. Lush greenery surrounds the pool area, providing a natural backdrop. The horizon reveals rolling hills under a soft blend of warm sunset hues.
Home in Geyserville
5 out of 5 average rating, 24 reviews

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!

Luxe
An outdoor pool area features a heated swimming pool surrounded by sleek lounge chairs. Two large umbrellas provide shade, while a built-in hot tub with a fire pit is situated nearby. Lush greenery and trees create a serene backdrop.
Home in Fountaingrove
4.98 out of 5 average rating, 51 reviews

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

Luxe
The modern home is set against a picturesque landscape, featuring a shimmering saltwater pool surrounded by a spacious deck. Lush greenery and a well-maintained garden frame the property, while outdoor seating invites relaxation. Expansive windows offer views of the surrounding hills.
Villa in Santa Rosa
5 out of 5 average rating, 16 reviews

Sunset Ridge | Luxury Wine Country Retreat

Perched on a private one-acre estate with breathtaking views, Sunset Ridge is a luxurious wine country retreat designed for relaxation, adventure, and special occasions. This newly built ~3,000 sq. ft. home seamlessly blends indoor and outdoor living, featuring resort-style amenities—including a saltwater pool, spa, world-class sauna, and gym—plus 4 elegant bedrooms and 5 plush beds. With easy access to top wineries, fine dining, and outdoor adventures, your unforgettable getaway begins here.

Luxe
Home in Sebastopol
5 out of 5 average rating, 3 reviews

10 Acre Estate w/ Views | Teahouse | Pickleball

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.

Luxe
Home in Healdsburg
5 out of 5 average rating, 10 reviews

Chalk Hill 360°

Perched atop a hill in the Chalk Hill region of Healdsburg, we designed our house to be the kind of place where you immediately feel at home and never want to leave. The 4 bedroom main house features expansive views, a bright open floor plan and ample spaces for gathering indoors and out including an oversized poolside lounge bed and outdoor dining area. Note that we are only renting to guests (8 max) who want a quiet, relaxing getaway and agree to our rental rules. TOT618N | LIC24-0442

Luxe
An aerial view showcases a sprawling estate surrounded by lush greenery and rolling hills. A sparkling pool is visible in the foreground, with a patio and seating area. The property is bordered by neat rows of grapevines, creating a picturesque and tranquil setting.
Villa in Calistoga
5 out of 5 average rating, 5 reviews

Luxury Napa Mansion - 40 Acres, Pool, Views

Escape to a private 38-acre Calistoga estate with vineyard views, pool, fire pit, and luxury interiors. Sleeps 16+. Enjoy Stunning Mountain Views, Chef’s kitchen, Pool, Guest House, Game room, Open Concept Living/Dining, Outdoor dining for 20, Outdoor Kitchen, Pond, Bocce ball, Fire Pits, Fruit trees, and more. Just minutes from town, yet completely serene & private. Perfect for group getaways, family gatherings, elopements, and wine country retreats!

Luxe
A charming home is framed by lush greenery and vibrant flowers, featuring a welcoming front entrance with a staircase leading to a spacious porch. A fountain adds a tranquil touch to the landscaped yard, complemented by a sunny blue sky and scattered clouds.
Home in St. Helena
5 out of 5 average rating, 38 reviews

Casa Rosa

This sprawling home is located in California’s coveted Napa Valley. The sun-drenched backyard is the perfect spot to savor a meal al fresco before plunging into the pool. In the evenings, a plump sofa entices you to curl up with a favorite flick. Local attractions on Main Street are just a couple of blocks away. Peruse shops, head out for a gourmet lunch, and of course, indulge in delicious wine. Copyright © Luxury Retreats. All rights reserved.

Luxe
The exterior of a spacious villa is showcased, set against lush green hills and a partly cloudy sky. Diverse landscaping features ornamental shrubs and trees, while a pool reflects the surrounding nature. Outdoor seating areas provide inviting spaces for relaxation.
Villa in Healdsburg
5 out of 5 average rating, 11 reviews

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.

Luxe
Home in Santa Rosa
5 out of 5 average rating, 8 reviews

The Nest w/ Pool, Hot Tub, Pickleball!

Escape to Sonoma Nest, a luxurious Wine Country retreat perfect for families. This stunning 4-bedroom, 4.5-bathroom home boasts a private pool, hot tub, and breathtaking views, ensuring a memorable stay. Enjoy the fully-equipped kitchen, outdoor seating, and proximity to world-class wineries and attractions. Create lasting memories at this exceptional Santa Rosa estate.

Luxe
A shaded outdoor terrace features a circular dining table with four chairs, positioned beside a tranquil pool. Lush vineyards stretch into the distance, framed by graceful palm trees under a clear blue sky, creating a serene environment for relaxation.
Villa in St. Helena
5 out of 5 average rating, 5 reviews

Spring Mountain Retreat

Property is in the town of St. Helena, center of the Napa Valley wine region. Beautiful farmhouse home that is nicely decorated. Walk into town to enjoy the great restaurants and shopping. Private, beautiful property setting, adjacent to active vineyard, pool, bocce court, lots of outdoor and indoor space. City of St. Helena permitted short term rental.

Luxe
A spacious living area is highlighted by floor-to-ceiling windows offering 270-degree ocean views. A centrally located Malm fireplace provides warmth, while modern furnishings include a grey sofa and contemporary dining table. Soft natural light fills the room, creating a bright and open atmosphere.
Villa in Dillon Beach
5 out of 5 average rating, 26 reviews

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 St. Helena luxury holiday rentals

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