Vacation rentals with a pool in St. Helena

Coastal Retreat: King Bed, Balcony, Kitchen

Come experience a comfortable and relaxing retreat in the amenity-rich Silverado resort community and convenient to Napa Valley attractions. Everything you need is here – from a well-equipped kitchen to cozy bedroom, 2 king beds, fireplace, and balcony overlooking the condominium pool. You’ll enjoy access to resort amenities – restaurants, pool, Tesla charging station, laundry, and more. Guests rave about cleanliness, coastal decor, and responsive host. Launch your wine-country exploration here!

Luxe WineCountry getaway with Pool, hottub & Bocce

Thornsberry House is a luxe Wine Country home nestled between the 2 oldest wineries in California and just minutes from the Sonoma Square. It is renovated with a boutique hotel feel to accommodate the most discerning traveler. It consists of 2 separate buildings with 3 bedrooms, connected by a breezeway and large deck with a heated pool, hot tub and bocce. Situated on the east side of town, it is in short equal distance to Buena Vista and Gundlach Bundschu, the 2 oldest wineries in California.

Serene 1 BR Condo at Silverado Resort

Calming, relaxing, and stylish, this newly-remodeled 2nd floor condo at Silverado Resort is modern, serene, and peaceful. It’s perfect for a couple's celebration, a special birthday, or a quiet place to stay after enjoying one of the many events hosted at this famed property! Blending urban sophistication with Wine Country charm, this exquisite condo features upscale amenities, 100% bamboo linens, a posh sleeper sofa, two fireplaces, and a premium King size mattress for next level sleep bliss.

Luxury Container Home w Infinity Pool + 360 Views

This property will be moving to a new Airbnb listing under the same owner and host, Olivia. For reservations starting October 31, 2025 and beyond, please book through the new listing: airbnb.com/rooms/1474914649755099444 Enjoy the sounds of nature from your own private 12 acre oasis in this unique container home. Set on a private road, and built on a ridge with incredible 360-degree panoramic views from sunrise to sunset, this modern dwelling was crafted with indoor-outdoor living in mind.

Fairways Silverado Golf and Country

Our condo is located in the heart of world-renowned wine country. Featuring stunning views of the Silverado golf course, it is the perfect place for anyone looking to relax in luxury. The spacious living area and fully-equipped kitchen has everything you need to cook up delicious meals. The beds are cozy & comfortable. Whether you're a golf enthusiast or a wine lover, this condo is the perfect place to stay for adults or families. ~I host another condo that sleeps 6 in this same complex~

An Italian Villa in the heart of Napa Valley!

Villa RayEl was inspired by the farmhouses and small villas of Italy. Located midway between downtown Napa and Yountville, this property sits on 2 acres providing great privacy. It sits next to a year-round creek with a view of a vineyard and nightly sunsets. It has a pool and an attached hot tub. Located 5 minutes off Highway 29, 8 minutes to Downtown Napa and 8 minutes to Yountville. It is convenient to great wineries, restaurants. Its the perfect getaway for families and friends!

Farmhouse at Sonoma Oaks: Hot Tub · Pool · Bocce!

Spread over 5 gorgeous, oak treed acres, this spacious + peaceful family estate welcomes groups to wine country with a Bocce court, pool, hot tub, and a seasonal creek. The stylishly appointed home features 4 King bedrooms, formal dining, expansive game room with Foosball table and 2 fireplaces. Bonus King bedded guest cottage included for 9+ guests. Wild turkeys and deer roam the property. Close to wineries. 10-15 min to Kenwood + Glen Ellen. 30 to Sonoma Square + Healdsburg.

Sustainable Luxury Barn - Secluded Sonoma Retreat!

Relax in the most beautiful, secluded setting Sonoma County has to offer. Hilltop views, walking trails right next to the property, and wineries so close, there is one just across the access road to the property. Constructed from trees that once stood where the Barn now stands, makes this property blend in with the natural surroundings. The trees were milled and dried on site. All siding, beams, flooring, basically anything made of wood is sourced from the property.

Immaculate 2 bd 2 bath at Silverado Country Club

Nestled among oak trees of the Silverado Resort, this secluded gated community boasts sweeping golf course views and spacious accommodations. Set among the rolling hills of Napa Valley’s wine country, our condo is newly renovated. As our guest(s), based on availability, enjoy a complimentary wine tasting at the Amizetta Winery and 10% off ER Sawyer Jewlers! Contact host immediately after booking your reservations.