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, 472 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.

4.95 out of 5 average rating, 503 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 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.

4.91 out of 5 average rating, 415 reviews

A spacious studio apartment features a king size bed with a colorful patterned quilt. Nightstands with lamps are positioned on either side. A kitchenette area is visible with open shelving and a small dining cart. Light wood flooring complements the bright, neutral walls.

Guest suite in Sonoma

Wildwood Retreat and Pool

The Wildwood Retreat is located on a wooded 2 acre country property in the hills above Sonoma just minutes from the Historic Downtown Sonoma Plaza. The newly remodeled studio apt is very private on a separate level below the main house conveniently close to the pool. Amenities include a king size bed, kitchenette, private bath,sunny deck,pool access and convenient parking. Great walks are just outside your door. This tranquil retreat is ideally located for enjoying all the Wine Country offers.

4.96 out of 5 average rating, 196 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, 116 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.

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, 115 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.

4.96 out of 5 average rating, 189 reviews

Home in Glen Ellen

Vineyard Retreat • 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 and quick communication AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | The Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

4.87 out of 5 average rating, 175 reviews

A light-filled living area features a cozy fireplace and large windows, offering views of the surroundings. The open floor plan connects the living space to a dining area and a fully equipped kitchen. Modern amenities such as Wi-Fi and cable TV are indicated in the foreground.

Home in Napa

Silverado Napa Breath Taking Remodel 3 bed 2 bath

Beautiful Silverado Resort & Spa luxury remodeled home with 2 bedrooms, 3 beds (one is pullout sofa in living room), 2 bath, and luxury accommodations with gated entry. One bathroom is ensuite. Home sleeps 6 guests. One of the pools is next to the unit (open seasonally). Remodeled kitchen, dining room and laundry in property. Tennis courts access and extensive walking trails. Located on the grounds of Silverado Resort and Country Club. Just minutes to downtown Napa and numerous wineries.

A bright living area features a spacious sofa and armchair, complemented by warm lighting and natural decor. Artwork adorns the walls, while a large TV is mounted opposite the seating. Sliders provide access to the outside, enhancing the airy ambiance.

4.98 out of 5 average rating, 179 reviews

Chic Retreat in Napa: Pool Access, Kitchen, Patio

Imagine vacationing a stone’s throw from Napa Valley wineries while staying in a resort so entertaining that the fun and relaxation is multiplied exponentially. You’ll have every comfort and convenience in this stylish condo with king bed, 2 patios and access to resort amenities, such as restaurants, pool, Tesla charging station, and laundry. Guests rave about cleanliness, décor, and responsive host. Make this condo your headquarters for wine tasting or exploring downtown Napa/Yountville

4.96 out of 5 average rating, 177 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, 676 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

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.

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

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

4.95 out of 5 average rating, 164 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, 176 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 Pool Hot Tub by Inspired in Sonoma

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.

4.93 out of 5 average rating, 138 reviews

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

4.98 out of 5 average rating, 108 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

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

4.98 out of 5 average rating, 186 reviews

A lively pool area is featured, showcasing a clear blue swimming pool surrounded by lounge chairs and vibrant inflatable floats. A shaded cabana provides a relaxing spot, while a nearby umbrella offers additional shade. The surrounding landscape includes lush greenery and a stone wall.

Home in Sebastopol

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

4.97 out of 5 average rating, 208 reviews

Happy House Getaway - Pool, Hot Tub & Wine Country

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, 42 reviews

*Silverado Condo Retreat near Wineries

4.95 out of 5 average rating, 162 reviews

Silverado Resort Dual Suite golf course villa

4.87 out of 5 average rating, 15 reviews

A spacious living area features a comfortable sofa with decorative pillows, a wooden coffee table in front, and a cozy gas fireplace. Natural light enters through a nearby window, illuminating the patterned accent chair and vibrant wall art.

Condo in Windsor

LAST MINUTE PRICE - 2 Bdrm Slp 6 - No Cleaning Fee

A spacious room is presented, featuring a king bed with soft linens and two bedside lamps. A jetted tub is positioned next to a granite counter, providing a relaxing feature. Natural light filters through the window, which is adorned with elegant drapes.

4.96 out of 5 average rating, 25 reviews

2br 2ba Full kitchen, jacuzzi bathtub, fireplace

A spacious outdoor pool area is framed by well-maintained stone tiles. Red lounge chairs with elegant patterns are arranged around the pool, and umbrellas provide shade from the sun. In the background, a multi-story building blends into the landscape, with rolling hills visible beyond.

4.86 out of 5 average rating, 22 reviews

Vino Bello Resort - Studio 1

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, 2,546 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, 78 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, 89 reviews

Your wine and wellness retreat at Silverado Resort

Other vacation rentals with a pool

The exterior of a mid-century modern home is displayed, featuring a spacious deck adorned with umbrellas and lounge chairs. A heated pool lies in the foreground, surrounded by low landscaping, with the home’s wood and glass structure set against a clear blue sky.

4.96 out of 5 average rating, 23 reviews

Cozy Santa Rosa Home with Scenic Views

A clear view of the shimmering saltwater pool is presented, surrounded by eight loungers and two blue umbrellas. The pool's edge offers an expansive outlook over the rolling vineyards and countryside, providing a serene backdrop for relaxation.

5 out of 5 average rating, 40 reviews

Sky View: Heated Pool & Hot Tub, 5 Acres

4.86 out of 5 average rating, 56 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

4.93 out of 5 average rating, 14 reviews

Home in Sonoma

Private Sonoma Vineyard Estate + pool, spa, views

5 out of 5 average rating, 25 reviews

The outdoor pool area features a spacious swimming pool surrounded by lounge chairs and umbrellas. Views of rolling vineyards and lush greenery are visible in the background, enhancing the tranquil setting under a clear blue sky.

Home in Kenwood

Kenwood Vista by AvantStay | 7acres, Vineyard View

4.95 out of 5 average rating, 19 reviews

A covered patio is furnished with comfortable seating arrangements, featuring woven lounge chairs and a round coffee table. Natural light filters in through large openings, showcasing views of lush greenery and mature trees beyond.

Home in Napa

Silverado Napa Retreat, by Vinifera Homes

4.98 out of 5 average rating, 47 reviews

An outdoor seating area features a stone fire pit surrounded by comfortable chairs. Soft lighting casts a warm glow on the wooden deck and nearby trees, enhancing the inviting ambiance during the evening hours. Large glass doors are visible, leading to the interior space.

Home in Healdsburg

The Dragonfly | A Wine Country Escape