Luxury rentals in Healdsburg

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Top-rated luxury vacation rentals in Healdsburg

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Luxe

Villa in Napa

5 out of 5 average rating, 10 reviews

Wine Country Vista

With a lofty vantage point on a 55-acre private vineyard, this villa gazes out on panoramic vistas of wine-rich Napa Valley. Dip into the outdoor hot tub and plunge into the pool, or sip a local vintage in the cavernous great room by the fire. Tours and tastings abound in every direction, while the world-class restaurants of Napa Town and Oakville are less than 10 miles away. Built of natural wood and stone, the contemporary house and its tiered terraces harmonize with the surrounding pine forests and lush landscape. Enjoy playful afternoons on the pool terrace or explore the estate’s vineyard and pond below. Crawl into the hot tub for a sunset soak, and grill up your spoils from Oxbow Public Market for an alfresco feast. Indoors, the great room forms the villa’s luminous heart, with cathedral ceilings and windows that infuse the space with the valley’s expansive grandeur. The open kitchen with large bar creates an ideal setting for family time and socializing, while the kids will love the playroom with bunk and trundle beds. This region is, of course, an oenophile’s dream, with myriad boutique wineries, wine tours, and tasting rooms within easy reach. World-class and local-favorite dining options include The Restaurant at Meadowood, Goose & Gander, Redd Wood, and Ciccio (where the Valley’s Italian immigrant traditions can be savored). Get deeper into the natural beauty of California Wine Country at the Bouverie Wildflower Preserve or Sonoma Overlook Trail, and drive about 20 miles to Sonoma Square. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Dual Vanity, View of vineyard • Bedroom 2: Queen size bed, Shared access to hall bathroom with bedroom 3, Stand-alone shower, Dual Vanity, View of vineyard • Bedroom 3: Queen size bed, Shared access to hall bathroom with bedroom 2, Stand-alone shower, Dual Vanity, View of vineyard • Bedroom 4: Queen size bed, Shared access to hall bathroom with bedroom 5, Stand-alone rain shower & bathtub, Direct access to outside • Bedroom 5: Queen size bed, Shared access to hall bathroom with bedroom 4, Stand-alone rain shower & bathtub, Direct access to outside Additional Bedding • Playroom: 3 twin size beds, 2 twin size trundle beds, Shared access to hall bathroom OUTDOOR FEATURES • Swimming Pool - heating at extra cost from November 1st to March 31st • More under “What this place offers” below

Luxe

A serene swimming pool is featured, surrounded by a spacious terrace with lounge chairs. Soft evening light reflects off the water while nearby trees provide shade. The modern villa is visible in the background, integrating harmoniously with the natural environment.

Villa in Healdsburg

5 out of 5 average rating, 28 reviews

Decanter Healdsburg

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

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, 12 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 lounge area is presented with a built-in fire pit surrounded by comfortable seating. Bright blue cushions add a pop of color against the neutral concrete, with a backdrop of lush greenery and clear skies, perfect for enjoying warm evenings.

Home in Santa Rosa

5 out of 5 average rating, 31 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

An outdoor dining area showcases a round stone table surrounded by four black woven chairs. A BBQ grill is positioned nearby. Large glass doors provide an unobstructed view of the surrounding landscape, enhancing the open space feel and inviting outdoor dining.

Villa in Santa Rosa

5 out of 5 average rating, 5 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

Place to stay in St. Helena

5 out of 5 average rating, 25 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

An aerial view reveals a beautifully shaped pool surrounded by manicured greenery, accented by two lounge chairs positioned near the water. The rustic home blends harmoniously with the natural landscape, enhancing the serene ambiance of the property.

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 Napa

5 out of 5 average rating, 10 reviews

Luxury Napa Vineyard Estate – Long Term Stays

This luxurious gated estate is the pinnacle of wine country, set on 7 acres of pristine Napa Valley vineyards, 75 olive trees, vegetable gardens, redwood groves, fruit orchards, a pickleball court. Your own warm lake to paddleboard, swim, and play on. Interior brings new meaning to the term "open-concept" with soaring vaulted barn-style ceilings. Separate 2k/sqft guest house, separate building with a gym, and Peloton cycling on-the-water.

Luxe

A stone pathway leads to the villa, illuminated by soft lighting amidst lush greenery. A decorative fountain sits at the forefront, surrounded by vibrant plants and flowers, enhancing the serene ambiance of the entrance.

Villa in Sonoma

5 out of 5 average rating, 9 reviews

Villa Casterno by BeautifulPlaces

With contemporary styling, this luxurious gated vineyard estate offers secluded privacy and sweeping views of the Sonoma Valley. (4 bedrooms and 4.5 bathrooms, plus office, and pool house). The exterior architecture is modeled after a modern Italian villa and the landscaping is designed to capture the stunning views and highlight the swimming pool and spa.

Luxe

A spacious pool area is bordered by well-maintained landscaping, including palm trees and cypress. Several lounge chairs surround the pool, providing relaxation options. A large deck features seating and umbrellas, offering shaded areas for leisure and socialization.

Villa in St. Helena

5 out of 5 average rating, 4 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

The modern villa features a sleek design with flat roofs and expansive glass windows, showcasing unobstructed views of the ocean. A spacious terrace is visible, surrounded by golden grasses, overlooking the coastline and gently rolling hills.

Villa in Dillon Beach

5 out of 5 average rating, 23 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.