Vacation rentals with a pool in Healdsburg

4.97 out of 5 average rating, 103 reviews

Pool - Hot Tub - Sauna | Wine Country Oasis Views

Imagine waking up to 180° panoramic views of the Sonoma Mountains, stepping onto a sun-warmed deck with coffee in hand, then spending the afternoon drifting between a solar-heated pool, a 5-person hot tub, and a cedar sauna — all without leaving the property. That's the everyday rhythm at this hillside wine-country retreat in Santa Rosa. The house was fully renovated top-to-bottom with the kind of high-end detail that makes you forget the outside world: radiant-heat concrete floors that warm yo

4.91 out of 5 average rating, 196 reviews

The villa is set against a colorful sunset, highlighting its two-story structure. A large pool reflects the warm hues of the sky, while well-maintained landscaping surrounds the outdoor area. Soft lighting from the home creates an inviting ambiance.

Villa in Santa Rosa

Villa Annadel - Stunning 5 Bedroom with a Pool

Escape to your own private sanctuary at Villa Annadel. Savor the unparalleled privacy and modern sophistication of this one-of-a-kind wine country retreat. The expansive 3,200 square foot villa sits on just under 1.5 acres of privacy with a large sparkling pool, hot tub and outdoor dining gazebo. Game lovers will rejoice, from cornhole, to darts, ping pong and vintage arcade games. It’s easy to forget you are minutes from some of Santa Rosa’s finest restaurants and wine tasting destinations!

4.95 out of 5 average rating, 549 reviews

A modern home is showcased with large sliding glass doors that open to a spacious wooden deck. The inviting heated pool features a gentle curve, with sun loungers placed nearby. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.

Home in Sonoma

Designer Sonoma Getaway with Pool, Hot Tub & Bocce

Thornsberry House is a luxe Wine Country home nestled between the two oldest wineries in California while just 5 minutes from the Sonoma Square. Renovated to accommodate the most discerning traveler, it consists of two separate buildings connected by a breezeway and large deck. Situated on the east side of town, it offers a true escape where one can walk or bike down to Gundlach Bundschu at the end of our street, or soak up the afternoon light from the heated pool, hot tub or a game of bocce.

4.97 out of 5 average rating, 159 reviews

Villa in Santa Rosa

Private 1+ acre, Bocce, Waterfall, Free Pool Heat

With over 1 acre of flat wooded land, this private gated country estate is still just a few minutes from conveniences like Whole Foods and Safeway. And with a full-size bocce court, pool table, and dining pavilion, you might not want to leave. Our new saltwater pool and spa are gas-heated to be comfortable all year, at no extra charge. A rock river and pool waterfall add to the sound of rushing water. The house is a few minutes from downtown, and within 20 minutes of the highlights of Sonoma.

Guest suite in Healdsburg

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.

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

4.93 out of 5 average rating, 481 reviews

4.87 out of 5 average rating, 126 reviews

The image displays a sunny outdoor pool area surrounded by comfortable lounge chairs. Two shaded cabanas offer shelter, while vibrant orange and red canopies provide additional shade. Lush green hills are visible in the background, contributing to a serene atmosphere.

Home in Cloverdale

Woodhawk Manor of Alexander Valley

Welcome to Woodhawk Manor! We have completed our remodel. Previous guests will now find en suite bathrooms for the four main bedrooms, plus a new tub in the master bath. Brand new hardwood floors adorn the home with freshly painted walls and ceilings to add to the charm. As of May 2024, an outdoor kitchen is available for you at the swimming pool. The property is now gated and fenced, giving you additional exclusivity on your special getaway. We invite you to come and stay at Woodhawk Manor

The exterior of a beautifully designed house is presented, showcasing a light-colored facade with decorative shutters and a newly paved pathway. A stone fountain serves as a focal point amidst landscaped greenery, highlighting the inviting entrance and two stories of windows.

4.97 out of 5 average rating, 110 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

Welcome to Brush Creek, 20-minutes from Sonoma, Napa, Russian River, Alexander, and Knight's Valleys. Our cozy villa offers 2 unique bedrooms, including a regal King Master suite and a second King bedroom. Complimentary EV charging. Healdsburg, Calistoga, and the trendy Barlow are easily accessible. Brush Creek: where comfort, luxury, and character converge for an unforgettable wine country retreat. Heated Pool (fees may apply). No one else in the property during your stay. SVR26-101

4.94 out of 5 average rating, 267 reviews

A Tuscan-inspired villa is set among rolling hills and vineyards. The property features a well-maintained front yard with a gravel drive, surrounded by lush grapevines. Elegant seating options are visible near the entrance, framed by vibrant trees and a scenic backdrop of the mountainous landscape.

Guesthouse in Cloverdale

Wing in Tuscan Villa with Vineyard and two bedrms

Beautiful Tuscan-inspired villa perched at the northern most corner of Alexander Valley and Sonoma County. Perfect abode to escape the city and experience the beautiful outdoors with luxurious amenities. Cloverdale, Healdsburg & Anderson Valley Wineries all within short drive on Highway 128 wine trail - 1 hour’s drive to coast and town of Mendocino. Modern private space with full kitchen and private bathroom with access to pool, jacuzzi, outdoor kitchen/grill, and fire pit. TOT# 2713N

A heated swimming pool reflects the early evening sky, surrounded by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a shaded umbrella. The vineyard is visible in the background, enhancing the peaceful atmosphere of this outdoor space.

4.92 out of 5 average rating, 133 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.

5.0 out of 5 average rating, 720 reviews

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

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

4.97 out of 5 average rating, 234 reviews

Wine Country Retreat | Pool, Hot Tub + Vibes

Summer-ready backyard + hot tub | Close to wineries Welcome to Happy House, a comfortable, clean, and welcoming home—perfect for a Sonoma County getaway any time of year. Ideal for wine tasting, visiting local breweries, hiking, mountain biking, plus weekend escapes, or remote work. 🌿 Private Backyard Large yard with pool, hot tub, and easy parking. 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal note: Outdoor cushions/umbrellas stored late Oct–mid May. Permit # SVR25-160

A Mediterranean-inspired house is set amidst lush gardens and rolling hills. The round swimming pool is surrounded by colorful landscaping and lounge chairs, inviting relaxation. The exterior features warm stucco walls and a tiled roof, showcasing a harmonious blend with the natural surroundings.

4.99 out of 5 average rating, 140 reviews

Wine Country Luxury Retreat - Pool Sauna Spa Views

Welcome to Sonoma Valley Retreat! The Luxury Mediterranean-inspired resort style house in the middle of a world-class wine country. 3600 Square feet House is located in the world-famous Sonoma Valley and is perfect for all your vacation needs. It's where style and sophistication meets entertainment and fun. Enjoy stunning outdoor amenities; one of a kind round soaking pool private pool with spa, pine wood sauna and breathtaking garden, mountain views

Popular amenities for Healdsburg rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 214 reviews

A private outdoor pool area features a sleek, blue pool surrounded by smooth stone tiles. Chaise lounges are positioned nearby, inviting relaxation. The setting is complemented by a rustic wooden structure and a charming home with a brick chimney, set against a colorful sunset sky.

Home in Sonoma

Vineyard-House Escape in Sonoma Wine Country

4.99 out of 5 average rating, 191 reviews

Home in Guerneville

Modern farmhouse (pool can be heated year round)

4.98 out of 5 average rating, 124 reviews

Spacious 5 BR 3BA Pool EV Charger Group Getaway

4.95 out of 5 average rating, 128 reviews

A modern kitchen features a spacious island with three woven bar stools. Hexagon-tiled walls in a soothing grey tone complement open shelving displaying dishware. Large windows allow natural light to fill the space, with greenery visible outside.

Home in Sonoma

Modern wine country stunner with pool & pickleball

4.97 out of 5 average rating, 389 reviews

The exterior features a bright green front door framed by contrasting black trim. Two large windows with decorative wooden accents are present beside the door. A wooden deck extends in front, providing accessibility and a welcoming entryway.

Home in Calistoga

Vineyard Farmhouse w/ Pool & Mt. Helena Views

4.93 out of 5 average rating, 190 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

4.91 out of 5 average rating, 127 reviews

A spacious property sits atop a knoll, surrounded by lush greenery and vineyards. A private pool glistens in the sunlight, while lounge chairs are arranged nearby. The outdoor seating area features a cozy fire-pit, inviting relaxation amidst scenic views of rolling hills.

Home in Sebastopol

Naidu Vineyards - Views/Pool/Spa/Bocce/9 Acres

A hot tub bubbles gently, positioned next to a large swimming pool. Lush greenery surrounds the area, complemented by a vibrant sky with hues of orange and pink. A lounge chair and a sun umbrella are visible in the background, enhancing the outdoor relaxation space.

4.86 out of 5 average rating, 270 reviews

Charming Home w Pool+Hot Tub. Walk to Shops & Wine

Condo rentals with a pool

A cozy dining area featuring a rustic wooden table set for six, complemented by soft white upholstered chairs. A stone fireplace provides warmth, while a modern television is mounted on the wall. Natural light flows in through large sliding doors, leading to an outdoor space.

4.99 out of 5 average rating, 102 reviews

Fairway Escape | BBQ | Firepit | Golf Course View

4.99 out of 5 average rating, 549 reviews

Silverado! Luxe King Suite Mountain View Balcony

The open-concept kitchen features modern appliances, including a microwave and oven, complemented by a large island with seating. Natural light floods the space, which seamlessly connects to the living area, revealing views of the outdoor patio through oversized windows.

4.94 out of 5 average rating, 153 reviews

Fairways Silverado Golf and Country

4.99 out of 5 average rating, 159 reviews

Modern Napa Escape | 2BR Golf Course View | Pool

4.89 out of 5 average rating, 211 reviews

2 bed I Silverado Resort & Spa in Napa - Wine Town

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.

4.99 out of 5 average rating, 142 reviews

Serene 1 BR Condo at Silverado Resort

Superhost

A comfortable sofa sits against a light blue wall, adorned with decorative cushions featuring intricate patterns. A small lamp stands beside it, providing ambient lighting. In the background, a well-equipped kitchen is visible, featuring wooden cabinetry and modern appliances.

Condo in Windsor

Resort Living w/ Pools - 2 Bdm Condo Slps 6

4.92 out of 5 average rating, 106 reviews

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.

4.95 out of 5 average rating, 215 reviews

Silverado Resort Condo with Pool

Other vacation rentals with a pool

4.99 out of 5 average rating, 274 reviews

A serene outdoor space features a sparkling saltwater pool surrounded by lush greenery and colorful landscaping. A cozy cottage is positioned in the background, with a gray roof and welcoming entrance. Comfortable lounge chairs are arranged neatly beside the pool, inviting relaxation.

Cottage in Kenwood

Pool & garden getaway in beautiful Sonoma Valley!

4.89 out of 5 average rating, 246 reviews

A spacious outdoor space features a shimmering pool surrounded by wooden decking. A covered seating area with comfortable furniture is visible nearby, alongside a barbeque setup. Lush greenery encompasses the area, creating a tranquil retreat. A water slide adjoins the pool for added fun.

Guesthouse in Santa Rosa

2 Wine Country Gem 2 Bedroom Upstairs

5.0 out of 5 average rating, 6 reviews

The Grove on Alexander Valley

4.97 out of 5 average rating, 29 reviews

ALBA | A modern luxury retreat in Healdsburg

4.98 out of 5 average rating, 90 reviews

Wine Country Estate: Pool, Spa & Vineyard Views

4.83 out of 5 average rating, 29 reviews

Haven at Healdsburg, by Vinifera Homes

5.0 out of 5 average rating, 20 reviews

Villa in Forestville

La Cachette Florale Estate + Pool + Hot Tub

Superhost

The exterior of the modern home showcases a spacious deck with lounge seating and an umbrella, adjacent to a well-maintained lawn and a private lap pool. Large glass doors provide a view into the inviting indoors, emphasizing the open design.