Holiday rentals with a pool in St. Helena

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Top-rated rentals with a pool in St. Helena

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Guest favourite

Apartment in Napa

4.99 out of 5 average rating, 366 reviews

Silverado Resort! Large 1BR Mountain View, Balcony

Apartment with views! Top floor Silverado Resort true 1 bedroom (not studio), 1ba 676 sq. ft. w/ rare mountain views from the balcony, living and dining rooms. Wood burning fireplace. *Price includes tax. Walk to pool, market, dining, lounge at mansion. Newly remodeled, modern appliances, ready for your relaxation. Luxurious fine Italian linens from Frette. Just like a 5-star hotel. Roku streaming,Directv Hike or hang out in relaxing grounds! Solid surfaces, knobs sanitized during cleaning.

Guest favourite

Home in Glen Ellen

4.96 out of 5 average rating, 173 reviews

Stay on a Vineyard. Great Views & Location

Immerse yourself in a Wine Country experience that has captured the attention of prestigious publications - Condé Nast Traveler - Esquire - House Beautiful - House & Garden - Refinery 29 - The Bold Italic - The Wine Daily - Bon Traveler - Sunset Magazine WHY YOU'LL LOVE IT - Vineyard setting and views - Minutes to award-winning wineries, restaurants & spas - Pool, hot tub, bocce ball court - Fully-stocked kitchen - Ultra high-speed Internet - Complimentary tasting at the Estate Winery next door

Guest favourite

Home in Glen Ellen

5 out of 5 average rating, 133 reviews

Tuscan Wine Country Villa with Pool sleeps 6

Picturesque and beautifully appointed villa on acreage with heated (seasonally) pool. Hot tub spa open year 'round. Gourmet kitchen, fireplace, stone work, patio and vistas. Ideal location for luxuriating in the beautiful Sonoma Valley; near wineries and quaint village of Glen Ellen. Discount for 7+nights not blocking both weekends. When requesting a reservation, please tell us about yourselves and confirm you understand our house rules: no additional visitors or parties of any kind. Thank you!

Guest favourite

Guest suite in Sonoma

4.91 out of 5 average rating, 371 reviews

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.

Guest favourite

Guest suite in Napa

4.95 out of 5 average rating, 156 reviews

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.

Superhost

Home in Napa

4.86 out of 5 average rating, 111 reviews

Silverado Napa Breath Taking Remodel 3 bed 2 bath

Brand New breath taking 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. 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.

Guest favourite

Apartment in Napa

4.98 out of 5 average rating, 167 reviews

Elegant Napa Escape

A designer gem for your next vacation to the wine country! A warm and inviting Napa escape is situated on a lovely serene golf course. Has one bedroom /one bath, kitchen, dining area and living room. High ceilings add to the spacious open feel, along with large sliding glass doors from both the living room and bedroom, opening to a patio and picturesque views of the fairway. Beautifully furnished and handsomely appointed, all details for your comfort and relaxation have been attended to.

Guest favourite

Villa in Sonoma

4.98 out of 5 average rating, 196 reviews

Twin Oaks • Pool, Garden, Terrace, Bocce & Hot tub

3-BR/2-BA Main house + Pool House with Bathroom. Spanish style home located on a quiet lane surrounded by rolling hills of vines. The inside features an open floor plan with gourmet and fully equipped kitchen, living room, TV Room, spacious bedrooms, hardwood floors and designer furniture. The outside area has a covered terrace ideal for dining and lounging. Expansive garden with many trees and a pool under majestic oaks. Minutes (by car) from Sonoma, Glen Ellen, Restaurants and vineyards.

Guest favourite

Apartment in Napa

4.98 out of 5 average rating, 152 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.

Guest favourite

Villa in Napa

4.95 out of 5 average rating, 127 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 Graton

5 out of 5 average rating, 595 reviews

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 covid cleaning protocols

Guest favourite

Apartment in Napa

4.98 out of 5 average rating, 163 reviews

Luxe 1BR Condo Par Excellence at Silverado Resort

Experience the allure of Napa Valley in this sleek condo at Silverado Resort. Enjoy modern comforts and amenities in a stunning setting perfect for a romantic escape, a fun getaway with friends, or a peaceful retreat after wine tasting. Just 10 mins from downtown Napa, with wineries nearby and many more within a 15-min drive. Luxuriate in the modern design, a plush King bed with bamboo linens, and two electronic fireplaces for a cozy ambiance.

Holiday rentals for every style

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Popular amenities for St. Helena rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Glen Ellen

4.92 out of 5 average rating, 161 reviews

Luxury home, heated spa pool, walk to restaurants

Guest favourite

Home in Sonoma

4.93 out of 5 average rating, 196 reviews

House on Broadway at the Plaza!

Guest favourite

Home in Healdsburg

4.9 out of 5 average rating, 101 reviews

Vineyard Vista, Modern Farmhouse Cottage with Pool

Guest favourite

Home in Occidental

4.95 out of 5 average rating, 133 reviews

Modern mid-century-inspired, Deer Ranch

Guest favourite

Home in Santa Rosa

4.9 out of 5 average rating, 131 reviews

Stunning Estate home near Healdsburg/Wineries

Guest favourite

Home in Windsor

4.98 out of 5 average rating, 171 reviews

Luxury Wine Country Estate with pool & hot tub

Guest favourite

Home in Sonoma

4.88 out of 5 average rating, 288 reviews

*Heated* Swimming Pool Retreat Near Sonoma Square

Guest favourite

Home in Santa Rosa

4.96 out of 5 average rating, 175 reviews

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

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Apartment rentals with a pool

Guest favourite

Apartment in Napa

4.95 out of 5 average rating, 57 reviews

ICONIC NAPA VALLEY SILVERADO CONDO

Superhost

Apartment in Napa

4.84 out of 5 average rating, 87 reviews

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

Guest favourite

Apartment in Napa

4.95 out of 5 average rating, 80 reviews

Wine Country Living at it's best at Silverado CC

Guest favourite

Apartment in Napa

4.99 out of 5 average rating, 75 reviews

Silverado Resort - Napa | Fireplace | EV Charger

Superhost

Apartment in Napa

4.75 out of 5 average rating, 20 reviews

Big 1 Bedroom Suite in Napa - Fully equipped!

Guest favourite

Apartment in Napa

5 out of 5 average rating, 6 reviews

Perfect Golf course view at Silverado resort

Guest favourite

Apartment in Napa

5 out of 5 average rating, 60 reviews

*Fairway Retreat at Silverado

Superhost

Apartment in Napa

4.72 out of 5 average rating, 2,338 reviews

One Bedroom Cottage Along the Napa River

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Home rentals with a private pool

Guest favourite

Home in Guerneville

4.91 out of 5 average rating, 176 reviews

Riverside Lodge House in Guerneville

Guest favourite

Home in Sonoma

4.93 out of 5 average rating, 251 reviews

Eclectic Hideaway with Backyard Pool & Hot Tub

Home in Guerneville

4.83 out of 5 average rating, 171 reviews

Lovely and Spacious Ranch-Style Home With a Poolside Oasis

Guest favourite

Home in Sonoma

4.82 out of 5 average rating, 362 reviews

Family Home - Heated Pool, Hot Tub, bikes, firepit

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

Total rentals
10 properties
Total number of reviews
110 reviews
Pet-friendly rentals
10 properties allow pets
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Farmstead at Long Meadow Ranch, Meadowood Napa Valley and The Culinary Institute of America at Greystone

Holiday rentals with a pool in St. Helena

Top-rated rentals with a pool in St. Helena

Holiday rentals for every style

Flats

Villas

Houses

Popular amenities for St. Helena rentals with a pool

House rentals with a pool

Home in Glen Ellen

Home in Sonoma

Home in Healdsburg

Home in Occidental

Home in Santa Rosa

Home in Windsor

Home in Sonoma

Home in Santa Rosa

Apartment rentals with a pool

Apartment in Napa

Apartment in Napa

Apartment in Napa

Apartment in Napa

Apartment in Napa

Apartment in Napa

Apartment in Napa

Apartment in Napa

Home rentals with a private pool

Home in Guerneville

Home in Sonoma

Home in Guerneville

Home in Sonoma

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

Total rentals

Total number of reviews

Pet-friendly rentals

Wifi availability

Popular amenities

Local attractions

Destinations to explore