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, 384 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, 189 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, 176 reviews

Stay on a Vineyard. Great Location. Great Views.

Immerse yourself in a Wine Country experience that has captured the attention of prestigious publications - Condé Nast Traveler - House Beautiful - House & Garden - Esquire - 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 - Fully-stocked kitchen - Pool, hot tub, bocce ball court - Ultra high-speed Internet - Complimentary tasting at the Estate Winery next door

Guest favourite

Condo in Napa

4.99 out of 5 average rating, 166 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!

Guest favourite

Guest suite in Napa

4.95 out of 5 average rating, 164 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, 446 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

4.96 out of 5 average rating, 134 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, 606 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

Rental unit in Napa

4.93 out of 5 average rating, 106 reviews

Napa relaxation at its finest at Silverado Resort

Relax in our newly remodeled 1 bedroom king bed, 1 queen sleeper sofa & 1 bath condo at Silverado Resort & Spa on the 1st & 18th Fairway on the PGA North Golf Course. Plan a meeting or just get away from it all in the beauty of Napa Valley's wine country, only 10 min by car to downtown Napa, world class wineries & 5 star restaurants. Amenities include access to association pool, cocktail lounge, restaurants, pizza lounge, coffee lounge & market. Carport parking for one car included

Guest favourite

Condo in Napa

4.96 out of 5 average rating, 136 reviews

Silverado Resort Dual Suite golf course villa

Light and bright updated 2 bedroom, 2 bathroom villa in The Fairways of Silverado Resort and Spa. Fully stocked with everything you need for a wine country or golf vacation. Back patio opens up to the 5th fairway on the Silverado North course. Villa has private pool access. Golf Reservations can be made per availability 21 days in advance at unaccompanied guest Rate. SPA reservations and services available per availability and associated rate.