Luxury rentals in Santa Rosa

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Top-rated luxury holiday rentals in Santa Rosa

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Luxe
A modern villa is featured with gull-gray siding and an expansive pool area. Loungers are arranged around the pool, shaded by umbrellas. The surrounding patio showcases natural stones and offers scenic mountain views, enhancing the outdoor relaxation space.
Villa in Healdsburg
5 out of 5 average rating, 32 reviews

Luxury Villa, 7 minutes from Healdsburg Plaza.

Hang your (straw) hat next to the others on hooks by the pool terrace at this casual modern villa perched in the hills above Healdsburg. Gull-gray siding gives the home a Cape Cod vibe, while vaulted ceilings, mid-century-inspired furniture, mountain views, and an EV charger bring in California cool. Find a handmade decanter to remember your stay at a boutique in Healdsburg Plaza, 8 minutes away. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Dual vanity, Walk-in closet, Television, Ceiling Fan, Private balcony • Bedroom 2: Queen size bed, Ensuite bathroom with shower/bathtub combo, Walk-in closet, Private balcony • Bedroom 3: Queen size bed, Shared access to hall bathroom with shower/bathtub combo, Private balcony with furniture Additional Bedding • Games Room: Queen size murphy bed, Queen size sofa bed, Shared access to hallway bathroom, Stand-alone shower FEATURES & AMENITIES • Billiard table • Peloton Exercise Bike • More under “What this place offers” below STAFF & SERVICES Extra cost (advance notice may be required): • Activities and excursions • Housekeeping - Midstay ($295) • More under “Add-on services” below

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 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

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
Large glass sliding doors create a seamless connection to the outdoors, showcasing expansive views of the rolling hills. A cozy living area features a plush sofa, wooden side table, and decorative items, providing a warm atmosphere for relaxation and socializing.
Home in Calistoga
4.91 out of 5 average rating, 22 reviews

Modular Luxury Casita w/Pool

A Modern Modular Casita, or 'Modsita' as we call it, sits on a 17-acre property with (but separated from) our Wine Country Ranch, it's a truly amazing oasis with spectacular views! Modsita sits 1,200 ft. above the quaint Napa County town of Calistoga. Built in 2018 by Connect-Homes, a luxury modular home builder, and decorated by acclaimed designer, McMullen and Co. in a Danish style design, this showplace is a stunner! Seasonal pool heating fee (150$) can be requested at booking.

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
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
The exterior of a stylish retreat is shown, showcasing a well-maintained landscape with various plants and trees. The two-story home features a spacious deck, with the surrounding rolling hills captured in the background, enhanced by the warm glow of the setting sun.
Home in Santa Rosa
4.75 out of 5 average rating, 4 reviews

Modern Sonoma Stay w/ Deck & Views Near Wineries

- Stylish three-bedroom, two-bathroom retreat in the rolling hills of Sonoma - Bright, chic interior with modern décor, plush seating, and a cozy fireplace - Fully equipped kitchen with a dining table and bar seating for shared meals - Spacious deck with stunning wine-country views, perfect for al fresco dining - Close to top wineries, downtown Santa Rosa, and Sonoma Plaza - Ideal for wine weekends, family getaways, and relaxing retreats

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 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.

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