Luxury rentals in St. Helena

LUX Private Modern Villa | Pool, Spa, & Dogs OK

Welcome to your private Wine Country retreat in the hills above Calistoga! This newly remodeled luxury mountain-style home is where rustic charm meets upscale comfort. With panoramic views of Mt St. Helena, a sparkling heated pool with built-in spa, it’s the perfect escape for families or groups looking to relax, recharge, and create unforgettable memories. - 10-min drive to downtown Calistoga - 15-min drive to Castello di Amorosa - 10-min drive to Old Faithful Geyser - 10-min drive to Calistog

Mayacama Manor - Sonoma Retreat

Mayacama Manor is a luxury retreat at the entrance to the Sonoma Valley. This newly built estate is nestled on 6 acres with downtown Sonoma and Healdsburg within 20 minutes in either direction. The 4000sf ranch style home has a beautiful open layout with a fully equipped chef’s kitchen, spacious pantry, entertainment/TV room, and 4 bedrooms. With a large swimming pool, hot tub, fire pit, outdoor dining and fireplace, this retreat is the perfect place for gathering, entertaining and wine tasting.

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.

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.

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!

Private Sonoma Estate: Tennis, Pickleball, Pool

Massive wine country private estate will delight you and multiple guests. Enjoy a tennis court, two pickle ball nets, traditional rose gardens, pool and acres of land to roam as well as multiple TV/entertainment rooms, a formal dining room and gym. The main home is very large with 5 en-suite bedrooms plus the option to book a guest house with 2 en-suite bedrooms for an additional nightly fee. All rooms are air conditioned, sound proofed and equipped with the fastest Starlink internet.

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.

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.

Silverado Sunset: Designer home with sunset views

Welcome to Silverado Sunset, a luxurious retreat in the heart of Napa Valley. Watch beautiful sunsets from your private wraparound deck while enjoying wine and lounging on your circular sofa. Silverado Sunset is a quick ride to downtown Napa and famous Silverado Wine Trail. This airy, upscale home features 2 suites with king size beds, en suite baths, wide screen TV’s, & desks with USB ports. Third Bedroom has 2 XL full beds, an ensuite tub/ shower bath, wide screen TV & USB ports.

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.

Private Villa on 4.3 Acre Estate Pool + Hot Tub +

Just five minutes from Sonoma Square, this beautifully newly renovated, 4-½ acre privately gated family-friendly compound is your perfect base for wine tasting adventures, weekend getaways, or relaxing retreats. Whether you're sipping wine under the stars by the firepit or cooking family meals in the spacious kitchen, this home blends comfort, style, and convenience - perfect for families, wine lovers, corporate retreats and group getaways.