Vacation rentals with a pool in Healdsburg

4.97 out of 5 average rating, 120 reviews

The home is framed by lush greenery and vibrant plants, with a patio featuring outdoor furniture. Warm light spills from the windows, hinting at a cozy interior. A barbecue grill is positioned nearby, providing an inviting space for outdoor gatherings.

Home in Kenwood

Vineyard Haven: Pool, Hot Tub & Wine Country Charm

Property is managed by Inspired in Sonoma. Welcome to your private wine-country vineyard haven, nestled on an acre of quiet woodland in the heart of Kenwood, California—a serene pocket of Sonoma Valley where golden light filters through oak trees, and every day feels like a celebration of good living. This spacious elegantly appointed 3-bedroom house, swimming pool and Hot Tub invites up to eight guests to unwind, reconnect, and savor the beauty of Kenwood’s vineyards, tasting rooms, and parks.

4.95 out of 5 average rating, 553 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.

4.98 out of 5 average rating, 243 reviews

A solar-heated pool glistens under sunlight, surrounded by a grassy lawn and majestic oak trees providing shade. Lounge chairs are positioned neatly along the pool's edge, while a covered terrace is visible in the background, enhancing the outdoor relaxation space.

Villa in Sonoma

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

3-BR/2-BA Main house + 1BR 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 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, 484 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

4.94 out of 5 average rating, 270 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

4.93 out of 5 average rating, 134 reviews

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.

Home in Healdsburg

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, 729 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

4.93 out of 5 average rating, 193 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

Escape to our stylish Santa Rosa home, your perfect base for wine country! Comfortably sleeps 8 with 4 bedrooms. Relax in the private backyard oasis featuring a pool, soaking hot tub, and a cozy gas fire pit under a gazebo. Centrally located near world-class wineries, breweries, and dining. Ideal for families and friends seeking a memorable getaway in a quiet, convenient neighborhood. We are happy to help plan your trip or arrange a private wine tasting at the house. Just ask!

A spacious outdoor area features a large pool surrounded by natural stone walls. Comfortable lounge chairs are positioned for relaxation, and green umbrellas provide shade. Lush landscaping enhances the serene environment, with trees and plants framing the scene.

4.92 out of 5 average rating, 136 reviews

Private Resort with Pool, Pool House, View and Spa

This wine country luxury retreat is a perfect venue for a family or small group escape. Includes a 2 level main house with 3 bedrooms, a large pool, hot tub and separate pool house. Plus wine cellar/game room, work area, family room, gourmet kitchen, five gorgeous stone fireplaces, and a patio kitchen with a gas range & dining area. This beautiful property feels like your own private resort, set on nearly 4 acres including gardens and spectacular views of Mt St Helena.

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, 142 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

4.98 out of 5 average rating, 122 reviews

A serene outdoor space is showcased, featuring a sparkling pool surrounded by neatly arranged white lounge chairs. Lush greenery and blooming shrubs create a natural border, enhancing the tranquil atmosphere.

Home in Geyserville

Historic Home; Walk to Cyrus, Diavola, Catelli's

This remodeled historic home is a Sonoma County Historic Landmark, called "The Bosworth, 1904," after the family who built it at the turn of the century. Beautifully restored, this 4 bed/4 bath home is two blocks from Geyserville's restaurants and wineries and a 10 minute drive from downtown Healdsburg and all the wineries the Anderson Valley and Dry Creek have to offer. TOT# 2463N

Popular amenities for Healdsburg rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 131 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, 236 reviews

Wine Country Retreat | Pool, Hot Tub + Vibes

4.98 out of 5 average rating, 137 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

4.99 out of 5 average rating, 116 reviews

Home in Glen Ellen

Camp Sonoma - Private, Sunset Views, Pool, Hot Tub

A modern outdoor area is highlighted by a sparkling pool surrounded by a stone deck. Sun loungers and a large umbrella provide shaded seating, while lush greenery adds a natural backdrop. The home's exterior features clean lines and expansive windows, inviting relaxation.

4.89 out of 5 average rating, 103 reviews

Serene Wine Country Haven with Pool & Hot Tub

A private outdoor area showcases a heated pool surrounded by a spacious deck. Lounge chairs are positioned for relaxation, and white umbrellas offer shade. Lush greenery and trees create a serene backdrop, enhancing the inviting and open atmosphere.

4.94 out of 5 average rating, 214 reviews

Gorgeous Sonoma retreat (with pickleball!)

Superhost

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.

4.9 out of 5 average rating, 129 reviews

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

A private outdoor area features a hot tub adjacent to a wooden deck. A white dining table is positioned for meals, surrounded by lush greenery. Soft lighting hangs above, adding to the relaxed setting. A window on the house offers natural light to the space.

4.98 out of 5 average rating, 219 reviews

Pacific Gardens Retreat

Condo rentals with a pool

4.99 out of 5 average rating, 553 reviews

Silverado! Luxe King Suite Mountain View Balcony

4.98 out of 5 average rating, 196 reviews

Designer Napa Valley Retreat • Patio •10Min to DT

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, 143 reviews

Serene 1 BR Condo at Silverado Resort

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, 218 reviews

Silverado Resort Condo with Pool

4.89 out of 5 average rating, 213 reviews

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

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, 104 reviews

Fairway Escape | BBQ | Firepit | Golf Course View

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

4.91 out of 5 average rating, 107 reviews

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, 154 reviews

Fairways Silverado Golf and Country

Other vacation rentals with a pool

4.99 out of 5 average rating, 275 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, 248 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

4.95 out of 5 average rating, 207 reviews

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

An Italian Villa in the heart of Napa Valley!

4.97 out of 5 average rating, 31 reviews

Home in Healdsburg

ALBA | A modern luxury retreat in Healdsburg

4.83 out of 5 average rating, 30 reviews

Home in Healdsburg

Haven at Healdsburg, by Vinifera Homes

5.0 out of 5 average rating, 13 reviews

Alta Mayacama | Views, Hot Tub, Plunge Pool

5.0 out of 5 average rating, 22 reviews

Villa in Forestville

La Cachette Florale Estate + Pool+Hot Tub

Luxe

An outdoor pool area features a heated swimming pool surrounded by sleek lounge chairs. Two large umbrellas provide shade, while a built-in hot tub with a fire pit is situated nearby. Lush greenery and trees create a serene backdrop.