Vacation rentals with a pool in St. Helena

The image showcases a scenic view of the Silverado Resort grounds, featuring well-maintained grassy areas and a sparkling pool surrounded by trees. The backdrop includes distant mountains and a clear blue sky, providing a tranquil outdoor setting.

4.99 out of 5 average rating, 485 reviews

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.

4.96 out of 5 average rating, 198 reviews

A serene courtyard features a circular firepit surrounded by four wicker chairs, inviting relaxation. Sunlight filters through the trees, creating a warm ambiance. Lush greenery and a vineyard view extend beyond the enclosure, enhancing the tranquil outdoor space.

Guest suite in Napa

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.

4.95 out of 5 average rating, 513 reviews

A modern home is showcased with large sliding glass doors that open to a spacious wooden deck. The inviting heated pool features a gentle curve, with sun loungers placed nearby. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.

Home in Sonoma

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.

A modern living space is displayed with a sectional sofa adorned with decorative pillows. A rectangular coffee table is centered on a subtle area rug, while a round mirror adds depth to the room. The open layout connects to a kitchen area featuring sleek cabinetry and bar seating.

4.99 out of 5 average rating, 123 reviews

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.

4.97 out of 5 average rating, 130 reviews

Villa in Santa Rosa

Private 1+ acre, Bocce, Waterfall, Free Pool Heat

With over 1 acre of flat wooded land, this private gated country estate is still just a few minutes from conveniences like Whole Foods and Safeway. And with a full-size bocce court, pool table, and dining pavilion, you might not want to leave. Our new saltwater pool and spa are gas-heated to be comfortable all year, at no extra charge. A rock river and pool waterfall add to the sound of rushing water. The house is a few minutes from downtown, and within 20 minutes of the highlights of Sonoma.

The open-concept kitchen features modern appliances, including a microwave and oven, complemented by a large island with seating. Natural light floods the space, which seamlessly connects to the living area, revealing views of the outdoor patio through oversized windows.

4.93 out of 5 average rating, 136 reviews

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~

4.96 out of 5 average rating, 181 reviews

The exterior of the villa is adorned with lush greenery and shrubs, creating a serene atmosphere. The warm-toned facade features a tiled roof and wooden shutters. A gravel driveway leads to the entrance, framed by neatly arranged garden spaces and decorative pots.

Villa in Napa

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!

5 out of 5 average rating, 682 reviews

A private backyard features a solar heated swimming pool surrounded by lounge seating and potted plants. A tiki bar is visible in the background, with palm trees providing shade in the sunlight. The space combines relaxation and outdoor living for a serene atmosphere.

Home in Graton

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

A comfortable living area features a light-colored sofa adjacent to a modern coffee table. Large glass doors lead to an outdoor space with views of the golf course, allowing natural light to fill the room. A fireplace adds a cozy touch.

4.89 out of 5 average rating, 157 reviews

Napa relaxation at its finest at Silverado Resort

Relax in our remodeled 1 bedroom king bed, 1 queen sleeper sofa & 1 bath condo at Silverado Resort & Spa on the 1st & 18th Fairway on the PGA North Golf Course. Plan a meeting or just get away from it all in the beauty of Napa Valley's wine country, only 10 min by car to downtown Napa, world class wineries & 5 star restaurants. Amenities include access to association pool, cocktail lounge, restaurants, pizza lounge, coffee lounge & market. Carport parking for one car included

4.95 out of 5 average rating, 271 reviews

A modern cottage is set against a backdrop of vibrant landscaping, showcasing a large, clear salt-water pool. Various outdoor seating areas are visible, complemented by lush trees and greenery that enhance the serene environment.

Guesthouse in Sonoma

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

A serene view of a golf course is framed by large oak trees, showcasing lush green grass and a clear blue sky. The landscape features rolling hills and scattered trees, offering a tranquil outdoor space in the Napa Valley area.

4.89 out of 5 average rating, 294 reviews

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.

4.96 out of 5 average rating, 192 reviews

Home in Glen Ellen

Vineyard Home • Press Pick • Walk to Wineries

WHY YOU'LL LOVE IT - Stroll your own private Sonoma vineyard - Resort-style outdoors: pool, hot tub & bocce with vineyard views - Prime location: minutes to top wineries, dining, spas & shops - Exclusive perk: complimentary tasting at the estate winery next door - Stylish, modern interior with thoughtful amenities - Chef-ready, fully stocked kitchen - Attentive, responsive host

Popular amenities for St. Helena rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 197 reviews

A beautifully landscaped garden features a pathway bordered by gravel and decorative plants. White wicker chairs surround a small table, inviting relaxation. The wooden deck and spa pool are visible in the background, complementing the modern home adorned with solar panels.

Home in Glen Ellen

Luxury home, hot tub/spa pool, walk to restaurants

4.92 out of 5 average rating, 119 reviews

A heated swimming pool reflects the early evening sky, surrounded by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a shaded umbrella. The vineyard is visible in the background, enhancing the peaceful atmosphere of this outdoor space.

Home in Healdsburg

Vineyard Vista, Modern Farmhouse Cottage with Pool

4.95 out of 5 average rating, 165 reviews

An outdoor space features a plunge pool surrounded by a sun deck with lounge chairs and a sun umbrella. The home, with its wood accents, is set against a backdrop of tall redwood trees, contributing to a serene, natural setting.

Home in Occidental

Modern mid-century-inspired, Deer Ranch

4.99 out of 5 average rating, 181 reviews

A private outdoor pool area features a sleek, blue pool surrounded by smooth stone tiles. Chaise lounges are positioned nearby, inviting relaxation. The setting is complemented by a rustic wooden structure and a charming home with a brick chimney, set against a colorful sunset sky.

Home in Sonoma

Vineyard-House Escape in Sonoma Wine Country

4.88 out of 5 average rating, 240 reviews

A well-maintained backyard features a trimmed green lawn, surrounded by mature trees and shrubs. A seating area with lounge chairs and a barbecue grill is visible on a paved patio, providing a comfortable outdoor space for relaxation. The home is situated in a serene environment.

Home in Santa Rosa

Spacious home w/heated pool/hot tub, lovely yard

4.95 out of 5 average rating, 103 reviews

A spacious living room features a comfortable arrangement of seating, including a plush sofa, and a large television. Large windows provide views of the surrounding landscape, while the decor is finished with subtle, modern accents.

Home in Healdsburg

Pool•Spa•6 Bikes•1mi to Town•Fire Pit•ShuffleBoard

4.91 out of 5 average rating, 120 reviews

A spacious outdoor area features a large pool surrounded by natural stone walls. Comfortable lounge chairs are positioned for relaxation, and green umbrellas provide shade. Lush landscaping enhances the serene environment, with trees and plants framing the scene.

Home in Sebastopol

Luxury home (+ pool house) with views, pool & spa

4.86 out of 5 average rating, 118 reviews

A modern hillside lodge is surrounded by lush greenery, featuring a wrap-around deck adorned with string lights. Steps lead up to the entrance, with multiple levels of wooden decking providing serene outdoor spaces.

Home in Guerneville

Leo’s Lodge - Lux Retreat with Pool and Hot Tub

Condo rentals with a pool

An open kitchen and dining area feature a round table with four soft chairs. A modern kitchen includes stainless steel appliances and a decorative wall clock. Natural light enters through a nearby window, illuminating the neutral tones and wood-like flooring.

5 out of 5 average rating, 45 reviews

*Silverado Condo Retreat near Wineries

A modern living space features a stylish fireplace with a lit fire, beside a coffee table displaying a bottle of wine and two glasses. A large television screen showcases a golf scene, while sliding glass doors provide access to a private balcony with green views.

4.97 out of 5 average rating, 36 reviews

Fairway Getaway

The exterior of a private cottage is displayed, featuring a inviting entrance framed by shrubs and trees. Sunlight filters through the branches, casting a warm glow on the cottage dimensions. A pathway leads to the door, complementing the landscaped surroundings.

4.94 out of 5 average rating, 121 reviews

Casa Vina at Silverado Resort and Spa | Fireplace

A row of charming cottages is lined along a walkable path, featuring varied exterior colors including blue, yellow, and red. Each unit has large windows and decorative gables, surrounded by neatly trimmed hedges and lush green trees, enhancing the inviting neighborhood atmosphere.

4.73 out of 5 average rating, 2,561 reviews

One Bedroom Cottage Along the Napa River

A modern kitchen features light cabinetry and a spacious island with seating for four. Two pendant lights hang over the counter. Stainless steel appliances are strategically placed, with natural light streaming in through a window, highlighting the sleek design.

5 out of 5 average rating, 80 reviews

*Fairway Retreat at Silverado

A light-filled living area showcases a comfortable sofa accompanied by decorative pillows. A round dining table with chairs is positioned nearby, complemented by potted plants. The kitchenette features cabinetry and appliances, while a large window offers a view to the patio.

4.88 out of 5 average rating, 93 reviews

Your wine and wellness retreat at Silverado Resort

An inviting living space features a comfortable sofa with accent pillows and a striped design. A stylish armchair with a floral pattern sits nearby. A dining area with chairs and a wooden table is visible. Natural light fills the room through the sliding glass doors.

4.96 out of 5 average rating, 82 reviews

Mansion Condo at Silverado 2b/2b

An outdoor swimming pool features a well-maintained deck lined with red lounge chairs. Umbrellas provide shade adjacent to the pool, which is surrounded by verdant landscaping and serene hills. The resort building rises in the background, showcasing its colorful facade.

5 out of 5 average rating, 3 reviews

Vino Bello Resort - Studio 4

Other vacation rentals with a pool

Luxe

An outdoor space features a luxurious pool reflecting the twilight sky. A modern home with expansive windows showcases warm lighting from within. Comfortable lounge chairs line the poolside, while nearby trees and landscaped grounds create a serene atmosphere.

Home in Healdsburg

5 out of 5 average rating, 28 reviews

Luxurious Healdsburg Home Walk to Wineries

Luxe

An outdoor pool area features a heated swimming pool surrounded by sleek lounge chairs. Two large umbrellas provide shade, while a built-in hot tub with a fire pit is situated nearby. Lush greenery and trees create a serene backdrop.

Home in Fountaingrove

4.98 out of 5 average rating, 55 reviews

Luxury Villa, Pool, Spa, BBQ, By Healdsburg

Guest suite in San Rafael

A spacious guest studio features large windows that provide natural light and panoramic views. The room includes a comfortable queen bed with premium linens, a small dining table with two chairs, and a minimalist wooden dresser. A warm color palette enhances the cabin-like feel.

4.9 out of 5 average rating, 470 reviews

Romantic Mtn Studio - Pool, Sauna, Views!

A light-filled living area features a comfortable sofa, decorative chairs, and a dining table for four. Large glass doors provide views of the outdoor space. The well-equipped kitchen is visible in the background, accented by cheerful neutral tones and inviting textures.

4.93 out of 5 average rating, 75 reviews

Cozy Silverado | Gtwy to Wine Country | Sleeps 4

4.86 out of 5 average rating, 57 reviews

A modern kitchen and living area is featured, equipped with stainless steel appliances, a stylish countertop, and a ceiling fan. A blue sectional sofa offers seating, accompanied by a wooden dining table and orange chairs. Decorative plants add a touch of greenery to the space.

Apartment in Calistoga

Hidden Apartment at UpValley Inn & Hot Springs

4.95 out of 5 average rating, 22 reviews

Home in Sonoma

Private Sonoma Vineyard Estate + pool, spa, views

5 out of 5 average rating, 4 reviews

Home in Glen Ellen

Oak & Vine: Pool | Hot Tub | Fire Table | BBQ

A well-equipped kitchen features a large central island with a light-colored countertop, two pendant lights hanging above. The space showcases stainless steel appliances, ample cabinetry, and an open layout that connects to the living area and dining space, with views of the outdoor surroundings.