Luxury rentals in Healdsburg

Find and book unique accommodations on Airbnb

Top-rated luxury vacation rentals in Healdsburg

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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

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

A scenic view of a welcoming estate is presented, featuring a sparkling swimming pool and comfortable loungers. The outdoor area is highlighted by stone accents and landscaped greenery, while the main structure showcases a charming mix of wood and stone elements under a clear sky.

Villa in Healdsburg

Lytton Springs

Bask in the California sun on a poolside lounger at this inviting estate on the edge of Healdsburg. A hot tub, fire pit, bocce court, alfresco dining, and climbing playground provide diversions before and after the tasting trail, and a whitewashed vaulted ceiling stretches over French country furnishings and a sleek grand piano. A 4-minute walk to the nearest winery, Lytton Springs puts you in the heart of wine territory. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: Primary - Queen size bed, Shared access to hall bathroom with bedroom 2, Stand-alone shower, Dual Vanity • Bedroom 2: 2 Twin size beds, Shared access to hall bathroom with bedroom 1, Stand-alone shower, Dual Vanity • Bedroom 3 - Master: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Dual Vanity, Adjoining nursery, Television, Direct access to balcony • Bedroom 4: Queen size bed, Ensuite bathroom with shower/bathtub combo, Direct access to terrace FEATURES & AMENITIES • Wine fridge OUTDOOR FEATURES • Swimming Pool (heated at extra cost with advance notice) • Playground

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, 20 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

4.97 out of 5 average rating, 39 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

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

4.82 out of 5 average rating, 11 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, 19 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

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

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, 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

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, 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.