Holiday rentals with a pool in Calistoga

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Top-rated rentals with a pool in Calistoga

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
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
4.96 out of 5 average rating, 198 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.

Top guest favourite
Home in Glen Ellen
4.96 out of 5 average rating, 191 reviews

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

Top guest favourite
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.
Apartment in Napa
5 out of 5 average rating, 120 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.

Top guest favourite
Cottage in Kenwood
4.99 out of 5 average rating, 267 reviews

Enjoy autumn and beyond in beautiful Sonoma Valley

Escape to your home-away-from-home on a private residential compound: the perfect getaway spot in the heart of beautiful Sonoma Valley! 🏡 Why You’ll Love It: ✔️ Minutes to 25+ wineries & great restaurants ✔️ Easy drives to Sonoma, Calistoga, Healdsburg, Napa & the Coast ✔️ Great hiking in nearby parks ✔️ Birdwatching in the garden ✔️ Saltwater pool & bocce court ✔️ Stunning Mountain views ✔️ Private patio with gas grill & outdoor dining ✔️ Full kitchen, separate bedroom with ensuite bath

Top guest favourite
The image showcases a spacious swimming pool surrounded by a manicured lawn and lounge chairs. Two stylish cabanas are positioned beside the pool. Lush trees are visible in the background, complementing the modern design of the home with solar panels on the roof.
Home in Sonoma
4.97 out of 5 average rating, 102 reviews

Modern wine country stunner!

Enjoy the best of Sonoma from this recently remodeled home. On over 1 acre with mature beautiful landscaping. Just added pickle ball/sport court! New kitchen and baths. Designer finishes. Comfy beds. Spacious and private outside seating and dining. Gorgeous pool. Hot tub and bar area in converted container. Close to the finest wineries in Sonoma. 2 minutes from Sonoma Golf Club. 10 minutes to Sonoma Square, 20 on bike. 7 minutes to Glen Ellen. 10 minutes to Kenwood. Sonoma County TOT #4481N

Top guest favourite
A spacious guest house is set within a picturesque vineyard estate, featuring a distinct architectural style with multiple gabled rooftops. The driveway leads to a well-maintained entrance, surrounded by lush landscaping and mature trees, providing a serene and welcoming arrival experience.
Guest suite in Healdsburg
4.93 out of 5 average rating, 462 reviews

Pony Ranch Vineyard Estate with Pool

Guest House with private entrance on gorgeous gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keurig coffee maker, queen bed. Seasonal private pool with fabulous views, occasionally shared with owners. Toilet and sink separate from shower. 8 minutes to the Healdsburg Plaza. Less than a mile from 3 wineries, very close to dozens more. Agricultural Education Programs available. Sonoma County TOT Certificate 1362N

Top guest favourite
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.
Apartment in Napa
4.98 out of 5 average rating, 180 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.

Top guest favourite
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
4.96 out of 5 average rating, 180 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!

Top guest favourite
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
5 out of 5 average rating, 679 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 cleaning protocols

Guest favourite
A tranquil pool reflects the vibrant hues of a sunset, bordered by lush greenery and palm trees. Comfortable seating areas are visible under shaded structures, enhancing an inviting outdoor space surrounded by colorful landscaping.
Guest house in Sonoma
4.91 out of 5 average rating, 322 reviews

Romantic Tropical Garden Casita

As you step through the entrance and under the arch, you are transformed into another time and place. We have been told by guests they feel it reminds them of Italy, France, and Spain. The Hacienda is very private, behind the walls of the early California style home. The gardens are lush and filled with birds of all kinds. There are several vignettes to relax and watch nature. Nights are cool so there is no need for A/C if you leave window open at night.

Top guest favourite
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.
Guest house in Sonoma
4.95 out of 5 average rating, 269 reviews

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

Top guest favourite
The outdoor pool area is surrounded by well-maintained gardens featuring a variety of flowers. Comfortable lounge chairs and tables are positioned around the pool, offering relaxation options. Towering trees and greenery provide a serene backdrop under a clear blue sky.
Apartment in Napa
4.95 out of 5 average rating, 191 reviews

Silverado Resort Condo with Pool

Beautiful and spacious 1bd/1ba resort condo with a pool, ideal for relaxation! Explore everything Silverado has to offer, while staying in this bright and renovated condo, which features an open plan living room and dining area, a kitchen and a large bedroom suite with a king size bed, and is equipped with all the amenities you may need.

Popular amenities for Calistoga rentals with a pool

When is the best time to visit Calistoga?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$405 SGD$422 SGD$418 SGD$463 SGD$555 SGD$535 SGD$569 SGD$561 SGD$521 SGD$379 SGD$506 SGD$411 SGD
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Quick stats about holiday rentals with a pool in Calistoga

  • Total holiday rentals

    Explore 40 holiday rentals in Calistoga

  • Nightly prices starting at

    Calistoga holiday rentals start at $130 SGD per night before taxes and fees

  • Verified guest reviews

    Over 500 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Calistoga holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Calistoga rentals

  • 4.7 Average rating

    Calistoga stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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