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Holiday 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.

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Home in Guerneville

4.83 out of 5 average rating, 177 reviews

Lovely and Spacious Ranch-Style Home With a Poolside Oasis

Savor outdoor suppers under a forest skyline in this wine country ranch. A lush, treelined perimeter encloses a shaded patio area featuring furnished terraces, a fire pit, and a central pool. Warm up in the hot tub after an evening swim. The layout of the house is unique. Each section of the house provides its own artistic and cozy energy. You can access the entire house except for the garage. I'm available 24/7 for any questions and needs. Guerneville is a small, rustic community nestled in the Russian River Valley. Sample local varietals at some of the world's finest vineyards or hike into the towering Redwood Forest. The town of Guerneville offers an array of fine local eateries. Please call me when you arrive and I'll walk you through the details of the home and the town!

Guest favourite

Apartment in Napa

4.99 out of 5 average rating, 177 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!

Guest favourite

Home in Kenwood

4.99 out of 5 average rating, 297 reviews

4/3 Vineyard Home With Pool & Views (Sleeps 8)

1 King bedroom; 2 Queen bedrooms; 1 sleeping den with two twin beds; 3 full baths. One of the loveliest spots in Sonoma Valley. Stunning views of vineyards and mountains. Swimming pool and hot tub. Bocce Ball court through olive trees. Interior designer furnishings. Gourmet kitchen overlooking pool and vineyard. Wineries nearby. Beautiful lawn surrounding pool. Two acres. Fire pit overlooking vineyards. Perfect for friends & families in town for lazy weekends or Wine Country weddings.

Guest favourite

Home in Windsor

4.97 out of 5 average rating, 191 reviews

Luxury Wine Country Estate with pool & hot tub

Welcome to our amazing Wine Country oasis, perfect for your relaxing getaway! This home features a large chef’s kitchen, four spacious bedrooms, and two living rooms. Enjoy the outdoor amenities, including large pool, hot tub, outdoor kitchen, bathroom, and dining area. You can also play a game of pool or pingpong in the finished garage! This home is located close to the Sonoma County Airport, wineries, and world-class dining, making it the perfect choice for enjoying all wine country offers

Home in Santa Rosa

4.86 out of 5 average rating, 207 reviews

Hot Tub/Pool ~ Walk To Wine, Shops & Restaurants

Escape to our Mid Century Modern home in beautiful Sonoma Wine Country, a 10 min drive to some of the best wineries in the world! Relax in the large pool & hot tub, by the Traeger grill for BBQ dinners - where pets are welcome! Walking distance to Howarth Park, Spring Lake, in the neighborhood of Annadel State Park for hiking & biking. One block from Montgomery Village, full of boutique shops & Wine-Country restaurants. A 20 minute drive to Sonoma, & near Healdsburg, Kenwood + Bodega Bay.

Apartment in Napa

4.86 out of 5 average rating, 109 reviews

Silverado Mansion Junior Suite | Pool | 1Bd | 1Ba

Enjoy tranquility in the ground floor Silverado Mansion junior studio suite; elegant finishes and no neighboring units. Recently remodeled, it’s near top wineries and restaurants. Amenities include a kitchenette, comfy bed, and cozy patio. Many Silverado Resort amenities are available, though golf and the fitness center are not included (spa/fitness passes may be available for a fee). A short walk takes you to a pool, Silverado Market, and the dining and cocktail lounge at “The Mansion.”

Guest favourite

Villa in Napa

4.95 out of 5 average rating, 142 reviews

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!

Guest favourite

Home in Healdsburg

4.91 out of 5 average rating, 107 reviews

Vineyard Vista, Modern Farmhouse Cottage with Pool

Our architect remodeled (2021), five star, elegant Farmhouse with great room and fireplace, is simply perfect throughout. This unique wine country two-acre property, with heated swimming pool (for a fee), looks out to the beautiful Russian River vineyards and the never-ending Western panorama. Only minutes from award winning food and shopping in downtown Healdsburg, it’s within easy walking or bicycling distance of tasting rooms at J, Rodney Strong and other acclaimed Sonoma wineries.

Guest favourite

Guest house in Santa Rosa

4.88 out of 5 average rating, 165 reviews

2 Wine Country Gem 2 Bedroom Upstairs

Looking for a place to stay in Santa Rosa that offers comfort, convenience, and charm? Look no further than our cozy guest house, located in a private gated property. You’ll have your own entrance and access to a shared laundry room with supplies. Enjoy the use of our pool, barbeque, and outdoor kitchen and seating area, where you can relax and soak up the sun. And as a special treat, you’ll get to savor our private tiffin service that delivers delicious home-cooked meals too.

Guest favourite

Home in El Sobrante

4.99 out of 5 average rating, 203 reviews

Zen Meets Pool Retreat!

Welcome to your peaceful get-away! Just minutes off both hwy 80 and hwy 24 and BART, you will find this quiet nook waiting for you to enjoy private outdoor living, complete with pool and hot tub, pool side seating with umbrellas and fire pit, patio with grill and of course, all the modern amenities inside to ensure a quiet and decompressing time away from it all! Have a fun sneak preview on youtube by entering the following search: Airbnb 100 Reviews Zen Meets Pool Retreat

Guest favourite

Home in Glen Ellen

4.91 out of 5 average rating, 172 reviews

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

Luna Lodge, a 3 bedroom 2 bath Glen Ellen village luxury home in the heart of Sonoma wine country. The home has a beautiful garden with spa pool by a peaceful creek. Everything you need for a great vacation is at your fingertips. Situated on a quiet lane, 5 min walk to wine tasting rooms, top restaurants, food markets. Enjoy a gourmet private chef dinner while at the home. Let us know if you are interested and we will help you arrange a very special dining experience.

Guest favourite

Apartment in Napa

4.88 out of 5 average rating, 144 reviews

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.

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Popular amenities for St. Helena rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Sonoma

5 out of 5 average rating, 8 reviews

Upscale Private Sonoma Wine Country Retreat

Guest favourite

Home in Concord

4.92 out of 5 average rating, 199 reviews

Pool, Hot tub, Napa, SFO Clean

Guest favourite

Home in Fairfield

4.92 out of 5 average rating, 118 reviews

Near Napa + Sauna/Hot Tub/Pool/Arcade/Game Room!

Guest favourite

Home in Kenwood

5 out of 5 average rating, 19 reviews

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

Home in Guerneville

4.83 out of 5 average rating, 163 reviews

STAY AWHiLE: Hot Tub Real Wood-burning Fireplace!

Guest favourite

Home in Santa Rosa

4.96 out of 5 average rating, 176 reviews

Happy House w/large pool, hot tub & chefs kitchen

Guest favourite

Home in Sonoma

4.94 out of 5 average rating, 238 reviews

4BD House with Pool, Close to Sonoma Plaza

Guest favourite

Home in Sebastopol

4.92 out of 5 average rating, 118 reviews

The Deer Retreat – Privacy and Comfort

Apartment rentals with a pool

Guest favourite

Apartment in Napa

4.95 out of 5 average rating, 59 reviews

ICONIC NAPA VALLEY SILVERADO CONDO

Guest favourite

Apartment in Napa

4.95 out of 5 average rating, 143 reviews

Silverado Resort Dual Suite golf course villa

Apartment in Windsor

4.84 out of 5 average rating, 32 reviews

Wine Country 2 Bdrm Condo w/ Pools & Hot Tubs

Guest favourite

Apartment in Napa

4.91 out of 5 average rating, 76 reviews

Silverado Resort - Private 3 Bedroom, 2 Bath Condo

Guest favourite

Apartment in Napa

4.98 out of 5 average rating, 219 reviews

Gorgeous Napa Getaway

Guest favourite

Apartment in Napa

4.94 out of 5 average rating, 110 reviews

Fairways Silverado Golf and Country

Guest favourite

Apartment in Napa

4.95 out of 5 average rating, 19 reviews

*Silverado Mansion Estates Condo LL

Apartment in Napa

4.77 out of 5 average rating, 235 reviews

1 bed | 1 bath | Silverado Resort Experience

Home rentals with a private pool

Guest favourite

Home in Guerneville

4.92 out of 5 average rating, 181 reviews

Riverside Lodge House in Guerneville

Guest favourite

Home in Sonoma

4.93 out of 5 average rating, 255 reviews

Eclectic Hideaway with Backyard Pool & Hot Tub

Home in Guerneville

4.83 out of 5 average rating, 177 reviews

Lovely and Spacious Ranch-Style Home With a Poolside Oasis

Guest favourite

Home in Sonoma

4.82 out of 5 average rating, 371 reviews

Family Home - Heated Pool, Hot Tub, 2 fire places

Quick stats about holiday rentals with a pool in St. Helena

Total rentals
10 properties
Total number of reviews
120 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Meadowood Napa Valley, Farmstead at Long Meadow Ranch and The Culinary Institute of America at Greystone

Destinations to explore