Luxury rentals in Healdsburg
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Top-rated luxury holiday rentals in Healdsburg
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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 relaxing getaway & agree to our rental rules. No parties. TOT618N | LIC24-0442
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Private 2-Acre Sonoma & Napa Retreat + Hot Tub
Escape to a gated 2-acre private estate nestled among peaceful hills, minutes from Sonoma Valley, Napa Valley, and downtown Santa Rosa. Relax in the hot tub, enjoy expansive lawns, a children's play area, and complete privacy—a rare find in Wine Country. Explore 250+ wineries, hot springs, beaches, rivers, and redwood forests within 30 miles, with shopping, dining, and everyday conveniences just 10 minutes away. Perfect for Wine Country getaways, wedding weekends, remote work, and staycations.
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Luxury Modern Home w/ Infinity Pool - 3400 sq ft
Welcome to Chestnut Knoll, a gated luxury Sonoma residence offering approximately 3,400 sq ft with 3 bedrooms and 3.5 bathrooms, featuring sweeping valley and vineyard views and a private infinity-edge pool and hot tub. Built in 2009, the home blends modern design with high-end finishes, a chef’s kitchen, open living spaces, and seamless indoor-outdoor flow. Set on a 1.24-acre lot just minutes from Sonoma Plaza and world-class wineries, the property also features expansive entertaining areas.
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New! The Quails Crossing- Healdsburg Vineyard Home
Brand new modern luxury home designed to maximize the natural beauty & surrounding calm. Perched on a hill surrounded by 100 year old oak trees, this spectacular home was built facing beautiful rolling hills and vineyards with ultimate guest comfort in mind. Enjoy your AM coffee watching a family of quails roaming the vineyard and end your evening with a glass of wine on the deck watching the sun set behind the golden vineyard hills. Located approx 3.5 miles (6min) from the Healdsburg Plaza.
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10 Acre Estate with Views, Teahouse, and Picklebal
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.
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Calistoga Mansion - 38 Acres | Lap Pool | Views
Escape to your own private 38-acre luxury retreat in pristine Calistoga wine country, with sweeping vineyard views and resort-style amenities. Designed for up to 16 guests, the estate features a main house over 5,000 sq ft, private guest house, 75-ft lap pool with optional heating, outdoor kitchen and bar, game rooms, serene pond, and so much more. Enjoy exceptional privacy ~20 minutes north of downtown Calistoga perfect for upscale getaways to Napa Valley, Sonoma Valley, or even Healdsburg!
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Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn
Welcome to Sonoma Valley Villa, your one-of-a-kind wine country oasis in Kenwood. The newly built gated villa overlooking vineyards features all the luxury amenities of a five-star resort. → Year-round heated swimming pool with cover → Spacious hot tub → Cozy outdoor fire pit → Vineyard views for miles → Outdoor kitchen and dining → Chef's kitchen with everything for gourmet meals → Fast wifi → Dedicated office area → Lots of space for everyone Walking distance to Kenwood wineries.
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Luxury Villa, Pool, Spa, BBQ, By Healdsburg Sonoma
Top 5% of homes, Luxe badge, and guest favorite badge by Airbnb. 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. ☞ 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
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Luxury Calistoga Retreat
Kalla Calistoga is a peaceful retreat tucked away in the hills of wine country. Thoughtfully designed with high-end finishes throughout, it offers a quiet space to relax, recharge, and enjoy the natural beauty of Calistoga. Whether you’re here to share time with friends and family, take in the surrounding nature, or simply slow down from the pace of everyday life, this home was created as a place to reconnect - with yourself, with each other, and with the land around you.
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Wine Country Estate
Unique wine country massive estate will delight you and multiple guests. Enjoy a tennis court, two pickle ball nets, traditional rose gardens and acres of private land to roam as well as huge rooms for enjoyment. The home is large with 5 bedrooms all with en-suite bathrooms. Enjoy 2 king rooms, 1 queen room and 2 rooms with single beds. All rooms are air conditioned, sound proofed and equipped with the fastest Starlink internet. Please note the pool is not heated.
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Farmstay Estate | Pool, Cedar Hot Tub & Honey Farm
Welcome to our gracious home and honey farm, nestled in the rolling hills of Healdsburg. - 4 bedrooms / 4 bathrooms – sleeps up to 8 guests - Open, light-filled living space with seamless indoor-outdoor flow - Fully equipped kitchen and spacious dining area - Outdoor patios with BBQ grill and sweeping countryside views - Unique opportunity to participate in a "hive dive" - Easy access to local wineries and hiking - Farmstay
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Modern, private Healdsburg oasis
Recently constructed in 2020, our 5 BR house is located on 50 acres with vast views. Less than 15 minutes to Healdsburg Square, but a world away. You will have privacy and serenity, but not isolation. Enjoy indoor/outdoor living at its finest at our home, designed to be sustainable and integrate with the natural surroundings, including plentiful redwoods and madrone trees. 50+ 5-star reviews on a different platform.
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Popular amenities for Healdsburg luxury holiday rentals
Other great luxury holiday rentals in Healdsburg
Mayacama Manor - Sonoma Retreat
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Alexander Valley Estate
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Sonoma Pool, Hot Tub, Pool Table & Views!
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Sunset View by BeautifulPlaces
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The Overlook by Sonoma Stays – Modern Luxe Retreat
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Bella Vista
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Private Villa on 4.3 Acre Estate Pool + Hot Tub +
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Bungalow Twins
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