Holiday 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, 477 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.

A spacious living area is presented with a large leather sofa adorned with decorative pillows. A round coffee table sits in front, and light is provided by stylish wall sconces. Natural elements are highlighted with a nearby plant and neutral-colored rug.

4.99 out of 5 average rating, 208 reviews

Coastal Condo by Pool: 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!

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.

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.

4.95 out of 5 average rating, 117 reviews

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.

4.96 out of 5 average rating, 190 reviews

Home in Glen Ellen

Vineyard Home • Steps to Tastings • Press Pick

WHY YOU'LL LOVE IT -Stroll through your own private vineyard -Pool, hot tub & bocce in a stunning serene setting -Minutes to top wineries, restaurants spas & towns -Complimentary tastings at the Estate Winery next door -Stylish interior with thoughtful touches -Chef-ready fully stocked kitchen -Helpful host—quick responsive communication AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

Superhost

A serene infinity pool reflects vibrant sunset colors, with lounge chairs and umbrellas positioned nearby. The horizon displays a gradient of pinks and purples, creating a tranquil atmosphere against the backdrop of distant hills and valleys.

Home in Glen Ellen

4.89 out of 5 average rating, 140 reviews

Spectacular Sonoma: Views! Stars! Cielo.

Cielo is a modern, private 10 acre estate with 180 degree views of Sonoma Valley and miles of vineyards. See Sunsets and stars from the house, deck, hot tub and pool! Cielo is the perfect wine country retreat comfortably accommodating 8. Note: offering this beautiful property at nearly 50% off normal price, only 2 night min instead of 3, because Cavedale road suffered a mudslide. House accessible but adds 15 mins to drive. Arrive at this magical place, settle in and enjoy the bliss!

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.

5 out of 5 average rating, 120 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, 101 reviews

The image showcases a spacious swimming pool surrounded by a manicured lawn and lounge chairs. Two stylish cabanas are positioned beside the pool. Lush trees are visible in the background, complementing the modern design of the home with solar panels on the roof.

Home in Sonoma

Modern wine country stunner!

Enjoy the best of Sonoma from this recently remodeled home. On over 1 acre with mature beautiful landscaping. Just added pickle ball/sport court! New kitchen and baths. Designer finishes. Comfy beds. Spacious and private outside seating and dining. Gorgeous pool. Hot tub and bar area in converted container. Close to the finest wineries in Sonoma. 2 minutes from Sonoma Golf Club. 10 minutes to Sonoma Square, 20 on bike. 7 minutes to Glen Ellen. 10 minutes to Kenwood. Sonoma County TOT #4481N

4.96 out of 5 average rating, 179 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, 678 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

5 out of 5 average rating, 119 reviews

A Mediterranean-inspired house is set amidst lush gardens and rolling hills. The round swimming pool is surrounded by colorful landscaping and lounge chairs, inviting relaxation. The exterior features warm stucco walls and a tiled roof, showcasing a harmonious blend with the natural surroundings.

Home in Santa Rosa

Wine Country Luxury Retreat - Pool Sauna Spa Views

Welcome to Sonoma Valley Retreat! The Luxury Mediterranean-inspired resort style house in the middle of a world-class wine country. 3600 Square feet House is located in the world-famous Sonoma Valley and is perfect for all your vacation needs. It's where style and sophistication meets entertainment and fun. Enjoy stunning outdoor amenities; one of a kind round soaking pool private pool with spa, pine wood sauna and breathtaking garden, mountain views

4.95 out of 5 average rating, 269 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.

Guest house 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

Popular amenities for St. Helena rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

4.84 out of 5 average rating, 103 reviews

A spacious outdoor area features a sparkling heated pool surrounded by a well-maintained garden. Comfortable lounge chairs are positioned nearby, and a fire pit with seating is highlighted, creating an inviting space for relaxation. Vibrant trees provide a serene backdrop to the setting.

Home in Sonoma

Sonoma Country Club Wine Country w/ pool

4.93 out of 5 average rating, 141 reviews

The outdoor space features a gazebo with a fire pit, surrounded by comfortable seating. Lounge chairs are positioned near an unheated pool, and a dining table with seating is visible in the background, creating a welcoming atmosphere for relaxation and gatherings.

Home in Santa Rosa

PrivateWarm&Cozy+Spa+Pool+FirePit+Wifi!

4.95 out of 5 average rating, 101 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

4.88 out of 5 average rating, 111 reviews

The serene pool area is surrounded by lush greenery, featuring modern lounge chairs and large umbrellas for shade. The sparkling water invites relaxation, while a covered outdoor space extends from the home, providing a seamless transition to the tranquil outdoor retreat.

Home in Sebastopol

Serene Wine Country Retreat with Pool & Hot Tub

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

4.97 out of 5 average rating, 210 reviews

Home in Santa Rosa

Happy House Getaway - Pool, Hot Tub & Wine Country

4.91 out of 5 average rating, 135 reviews

A serene pool area is illuminated by soft landscape lighting, surrounded by lush greenery. A hot tub is positioned nearby, and a stylish lounge chair complements the outdoor setting. The sky displays vibrant hues of orange and pink, signaling a tranquil sunset.

Home in Sebastopol

The Deer Retreat – Privacy and Comfort

Apartment 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, 35 reviews

Fairway Getaway

4.95 out of 5 average rating, 162 reviews

Silverado Resort Dual Suite golf course villa

An open concept living and dining area showcases wooden flooring and a spacious dining table surrounded by woven chairs. A comfortable seating space features a large rug and a bright blue accent chair. Large glass doors offer views of the outdoor area with greenery.

4.95 out of 5 average rating, 110 reviews

Wine Country Living at it's best at Silverado CC

Superhost

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, 2,556 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.

4.89 out of 5 average rating, 92 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

Other holiday 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, 27 reviews

Luxurious Healdsburg Home Walk to Wineries

Superhost

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.

Flat in Calistoga

4.86 out of 5 average rating, 57 reviews

Hidden Apartment at UpValley Inn & Hot Springs

4.99 out of 5 average rating, 247 reviews

Guest house in Sonoma

707 BARREL LOUNGE Cottage

5 out of 5 average rating, 49 reviews

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.

Flat in Napa

*Relaxing Condo at Silverado

4.8 out of 5 average rating, 207 reviews

A corner of the property features a well-maintained exterior, showcasing a pathway leading to the entrance. Lush greenery surrounds the area, including a small tree and neatly trimmed bushes. A brick chimney is visible on the side, adding a rustic touch.

Townhouse in Napa

Discounted, Quiet Single Story,Corner,Private

4.95 out of 5 average rating, 41 reviews

A modern living area features a cozy sofa paired with two armchairs and a glass coffee table. A textured area rug adds warmth beneath the seating. The open-plan layout connects to a sleek kitchen, where natural light floods the space through large windows.

Home in Glen Ellen

Glen Ellen Gem-2 Bed/2 Bath Oasis + Stunning Pool

5 out of 5 average rating, 34 reviews

An outdoor dining area features a large wooden table set with plates and glasses, overlooking lush vineyards and distant mountains. A stone outdoor kitchen with a pizza oven and grill accompanies the space, while a pool and sun loungers are visible in the background.

Home in Calistoga

Calistoga Vista | A Wine Country Escape