Holiday rentals with a pool in St. Helena

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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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Guest favourite

Condo in Napa

4.99 out of 5 average rating, 380 reviews

Silverado! Large 1BR Suite Mountain Views 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

Condo in Napa

4.99 out of 5 average rating, 187 reviews

Chic 1 BR Condo Par Excellence at Silverado Resort

Distinctly modern and exquisitely curated, this newly-remodeled 2nd floor condo at Silverado Resort is sleek, subdued, and moody. It’s perfect for a couple's retreat, a girls' getaway, 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.

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

Condo in Napa

4.99 out of 5 average rating, 163 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 Glen Ellen

5 out of 5 average rating, 136 reviews

Tuscan Wine Country Villa 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!

Superhost

Guest suite in Sonoma

4.91 out of 5 average rating, 379 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, 161 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.

Guest favourite

Home in Sonoma

4.95 out of 5 average rating, 444 reviews

Thornsberry House, A Luxe Country Getaway

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 and bocce court. 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.

Guest favourite

Condo in Napa

4.98 out of 5 average rating, 170 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 Napa

4.95 out of 5 average rating, 133 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, 604 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

Superhost

Condo in Napa

4.84 out of 5 average rating, 110 reviews

Beautiful Premium Jr Suite, Silverado Resort & Spa

Nested in in the heart of Napa Valley, located at the beautiful exclusive Silverado Resort and Country Club you will find this privately owned comfortable studio, one bath suite. Perfect for a romantic getaway, a Napa Valley wedding, a trip to the Wine Country, a business convention, or just looking to relax, this cozy one bedroom suite will not disappoint. If you're here for business or pleasure, this centrally located condo in Mansion Estates will work perfect for one or two people.