Luxury rentals in Healdsburg

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Top-rated luxury vacation rentals in Healdsburg

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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, 30 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

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 Santa Rosa

4.98 out of 5 average rating, 49 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

Home in Healdsburg

5 out of 5 average rating, 9 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

A spacious deck features a Modpool with a sleek blue surface reflecting the surrounding landscape. Two umbrellas provide shaded seating near the pool, while wooden lounge chairs are arranged for comfort. The backdrop includes rolling hills illuminated by the evening sun, creating a serene environment.

Home in Calistoga

4.88 out of 5 average rating, 16 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 outdoor space features a luxurious pool reflecting the twilight sky. A modern home with expansive windows showcases warm lighting from within. Comfortable lounge chairs line the poolside, while nearby trees and landscaped grounds create a serene atmosphere.

Home in Healdsburg

5 out of 5 average rating, 23 reviews

Luxurious Healdsburg Home Walk to Wineries

Welcome to your luxurious getaway in Healdsburg wine country! - Stylish interiors with premium furnishings and natural light. - Enjoy a seamless indoor/outdoor experience with a covered patio and pool. - Relax with modern amenities including a fully equipped kitchen, high-speed Wi-Fi, and plush bedding. - Nearby attractions include Limerick Lane Cellars and Healdsburg Plaza. - Universal electric vehicle charger available for your use. THINGS TO KNOW:

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.

Home in Calistoga

5 out of 5 average rating, 3 reviews

Luxury Calistoga 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, weddings, and wine country retreats.

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

A serene bedroom features a large bed with soft floral bedding, complemented by a stylish sofa and minimalist decor. Expansive windows frame panoramic views of rolling hills and valleys, allowing natural light to fill the room, while a mounted TV adds convenience.

Home in Santa Rosa

5 out of 5 average rating, 7 reviews

The Nest w/ Pool, Hot Tub, Pickleball!

Indulge in the ultimate family getaway at Sonoma Nest, a luxurious Wine Country haven. This exquisite 4-bedroom, 4.5-bathroom home features a private pool, hot tub, and stunning views, promising relaxation and fun for everyone. Enjoy a fully equipped kitchen, a shared sports court, and easy access to renowned wineries and dining. Experience an unforgettable vacation at Sonoma Nest.

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, 25 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.