
Vacation rentals with a pool in St. Helena
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in St. Helena
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Silverado! Luxe 1BR King Suite This View! Balcony
Apartment with views! Top floor Silverado Resort true 1 bedroom (not studio), 1ba 676 sq. ft. w/ rare mountain views from balcony, living and dining rooms. Wood burning fireplace. *Price incl tax. Walk to pool, market, dining, lounge at mansion. Modern appliances, ready for your relaxation. Luxurious fine Italian linens from Frette on King bed. Just like a 5-star hotel. Roku streaming,Directv Hang out or walk in relaxing grounds! La-Z-Boy queen sofabed, Aug 2025. Free L2 EV chargers nearby.

Chic 1 BR Condo Par Excellence at Silverado Resort
Distinctly modern and exquisitely curated, this newly-remodeled 2nd floor condo at Silverado Resort is sleek, subdued, and moody. It’s perfect for a couple's retreat, a girls' getaway, 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.

Sherrie's Vineyard View Retreat-Pool, Spa, N.Napa
Enjoy our vineyard view and a glass of wine by the firepit! Relax in our ONE BEDROOM SUITE, ON THE LOWER LEVEL OF OUR TRI-LEVEL HOME. Conveniently located in N. Napa, we're near Alston Park for hiking, wineries, places to eat & shop. Enjoy a fresh-baked BREAKFAST, a dip in the pool (heated mid-June to Sept), spa (year-round) & many places for relaxing. Our suite is well appointed with a comfortable bed, fine linens, duvet, robes & slippers. DRIVING SERVICES may be added to enhance your tours.

Luxe WineCountry getaway with Pool, hottub & Bocce
Thornsberry House is a luxe Wine Country home nestled between the two oldest wineries in California while just 5 minutes from the Sonoma Square. Renovated to accommodate the most discerning traveler, it consists of two separate buildings connected by a breezeway and large deck. Situated on the east side of town, it offers a true escape where one can walk or bike down to Gundlach Bundschu at the end of our street, or soak up the afternoon light from the heated pool, hot tub or a game of bocce.

Casa Vina at Silverado Resort and Spa | Fireplace
Welcome to Casa Vina! Located in one of the best locations at Silverado, close to the HOA pool, Grill and baked goods from the Market, this end unit cottage has golf course and mountain views, a wood burning fireplace and no one upstairs. Updated with mid-century West Elm furniture, 55" TV, enlarged shower, Casper Mattress, stainless steel kitchenette and Keurig coffee maker, this is one of the nicest junior suites at Silverado. Discounted spa day passes available for purchase, when available.

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!

Eco Luxury Private Sanctuary / The Farmhouse Oasis
**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols

2 bed I Silverado Resort & Spa in Napa - Wine Town
Stay in the center of Napa Valley at this first class resort in a beautiful fully upgraded 2 bed (1 bed is a queen bed out of a sleeper sofa) 1 bath condo at Silverado Resort & Spa. Minutes from world class wineries and five star restaurants. Amenities include association pool, cocktail lounge, restaurants, pizza lounge, coffee lounge & market all on the grounds for your use! Unwind at the end of each day on your own private balcony with views of the grounds and mountains.

2bdr/2ba Silverado Resort : Gated + Golf Views
Escape to a newly renovated Silverado Resort condo tucked beneath oak trees, offering serene golf course views and a true Napa Valley retreat. Bright, spacious, and thoughtfully updated, it’s perfect for relaxing after wine tasting, exploring local wineries, or enjoying scenic mornings with coffee overlooking the greens. Guests may enjoy a complimentary wine tasting at Amizetta Winery (based on availability). Contact host after booking.

Wine Country Gem - Sonoma Cottage with Pool Oasis
Charming Sonoma cottage perfect for a romantic getaway, girls’ trip, or family stay. Explore Sonoma, Glen Ellen & Napa with ease. The private unit has gourmet appliances, a minimalist-country style, and its own deck with dining + lounge seating. The peaceful 1-acre property features vineyards, a large saltwater pool, a veggie + herb garden, and fruit trees. Relax, recharge, and enjoy the best of wine country living. TOT #3140N

Getaway in Napa! Bowling, Spa and More all Open!
Many of the area's most awarded wineries are just a short drive away. Only 10 minutes from downtown, home to Oxbow Public Market and the Napa Valley Wine Train, shopping & world-class dining. • Guest checking in must be 21+ with valid ID & card for $250/night refundable security deposit (credit card only) • Resort fee of $6.32+tax/night paid at check-in • Name on reservation must match photo ID at check-in
Popular amenities for St. Helena rentals with a pool
House rentals with a pool

Luxury home, heated spa tub, walk to restaurants

Vineyard Vista, Modern Farmhouse Cottage with Pool

Heated pool & Hot tub! Close to Sonoma & Calistoga

Sonoma Country Club Wine Country w/ pool

Wine Country Retreat- Privacy-Spa/Pool/Games

Sonoma 14Acres, 2BR 2BA, Pool HotTub, Plaza 3 mi.

Pacific Gardens Retreat

Naidu Vineyards - Views/Pool/Spa/Bocce/9 Acres
Condo rentals with a pool

*Silverado Condo Retreat near Wineries

Fairway Getaway

Wine Country Living at it's best at Silverado CC

*Fairway Retreat at Silverado

One Bedroom Cottage Along the Napa River

Your wine and wellness retreat at Silverado Resort

Mansion Condo at Silverado 2b/2b

Holiday Haven in Wine Country
Other vacation rentals with a pool

NO Cleaning Fee Vino bello Resort Napa - Studio

Cozy Silverado | Gtwy to Wine Country | Sleeps 4

Hidden Apartment at UpValley Inn & Hot Springs

Wine County Opulent Villa Pool/Hot Tub-Upper Level

*Relaxing Condo at Silverado

[Egg Farm Ranch] Heated Pool-Water Slide-Hot Tub

Art of Napa - Charming, Resort-Like w/ Pool!

Calistoga Vista-Pool, Hot Tub - Tastings Included
Quick stats about vacation rentals with a pool in St. Helena

Total vacation rentals
Explore 10 vacation rentals in St. Helena

Nightly prices starting at
St. Helena vacation rentals start at € 152 per night before taxes and fees

Verified guest reviews
Over 150 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of St. Helena vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across St. Helena rentals

5 Average rating
St. Helena stays are highly rated by guests—averaging 5 out of 5!
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