Luxury rentals in St. Helena

Pool, Hot Tub, Pool Table & Views—Near Plaza

With hilltop views of Sonoma Valley, this impeccably designed private estate offers a refined wine country stay just 6 mins from historical Sonoma Plaza. Enjoy a new heated pool & spa, rooftop deck, game room with pool table, and fireplaces throughout. Pet-friendly and ideal for weekends that blend relaxation, connection, and indulgence. It’s the perfect location to disappear from it all or take in all the adventures that Sonoma and Napa Valley wine country offer. TVR25-0142/LIC25-0595/TOT 2294N

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

Private Sonoma-Napa 2-Acre Retreat + Hot Tub

Rated in the top 5% Guest Favorites, this modern country home offers luxury and classic California indoor-outdoor living. Set on an expansive sun-filled lot with lawns, fruit trees and a garden, it is framed by peaceful low hills on three sides. Explore over 250 Sonoma and Napa wineries, hot springs, beaches, rivers, and redwood forests all within 30 miles. While private, Santa Rosa city amenities are just 10 minutes away. Ideal for wine country getaway, wedding trip, remote work or staycation.

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

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!

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 and there is NO hot tub.

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 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.