Luxury rentals in Healdsburg

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

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 land to roam as well as huge rooms for enjoyment. The home is large with 5 bedrooms (and the option to book two additional King or Double Twin Bedrooms) all with en-suite bathrooms. All are air conditioned, sound proofed and equipped with the fastest Starlink internet. Please note the pool is not heated. NO WEDDINGS INQUIRIES PLEASE.

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.

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.

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!

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.

3 BR | Saltwater Pool | Spa | Walk to Wineries

Escape to this luxurious 3-bedroom home in Healdsburg, perfect for exploring wine country. - Stylish interiors with premium furnishings - Spacious layout with indoor/outdoor flow - Modern amenities including high-speed Wi-Fi and flat-screen TVs - Outdoor oasis with a saltwater pool and spa - New construction completed in 2024 - Universal electric vehicle charger available for your use - charging from 12am-5am complimentary - Must be 25 years of age to rent this property

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

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.

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.

Mid-Century Secluded Oasis

Situated on over 85 acres of breathtaking views, this property, along with an adjacent home, offers ample space to host large groups, perfect for birthdays, bachelor/bachelorette parties, or wedding-related events. You can choose to rent both homes together or just one, depending on your needs. For details on the sleeping capacity and amenities of each home, feel free to reach out anytime. We’d be happy to assist!

Mill Creek - AvantStay | Patio, Hot Tub, A+ Design

Welcome to Mill Creek, your charming retreat located just 6 minutes from downtown Healdsburg and 1.5 hours from San Francisco. This stunning 2BR home boasts modern architecture and a cozy design that pairs perfectly with its lush, private, tree-surrounded setting.