Vacation rentals with a pool in Healdsburg

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Healdsburg

  • Total vacation rentals

    Explore 40 vacation rentals in Healdsburg

  • Nightly prices starting at

    Healdsburg vacation rentals start at R 1,625 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 1,030 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Healdsburg vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Healdsburg rentals

  • 4.8 Average rating

    Healdsburg stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Healdsburg

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

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Guest favorite
A serene infinity pool extends towards the horizon, bordered by lush greenery. Eight lounge chairs, with two umbrellas, face the pool, inviting relaxation. A wooden structure sits in the background, along with a staircase leading to the home, all under a soft, pastel sky.
Home in Santa Rosa

Farpoint: Heated Infinity Pool, Mountain Views

Nestled in the Mayacamas mountains, this elevated home offers a peaceful and luxurious retreat in the center of Sonoma wine country. The large infinity pool - gas-heated all year - perches over the magnificent view. Inside, the living room and dining room are furnished to comfortably seat 12 adults. A pool table, ping pong, three dining tables, 75" 4K TV, and large hot tub provide endless options. Hiking trails surround the house. Grocery stores and farmer’s markets are less than 8 minutes away.

4.93 out of 5 average rating, 149 reviews
Guest favorite
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!

4.91 out of 5 average rating, 198 reviews
Guest favorite
An expansive backyard is shown, featuring a sparkling pool surrounded by a stone patio. A gazebo offers shaded seating, while a cozy fire pit creates an inviting gathering space. Lush greenery and trees frame the scene, enhancing the tranquil setting of the home.
Home in Santa Rosa

5-Bedroom Creekside Wine Country Retreat

Welcome to our spacious and luxurious 5-bedroom, 3-bathroom home in the heart of Sonoma County's Wine Country! With a sparkling pool, relaxing spa, cozy fire pit, and stunning backyard, this impeccably designed home is the perfect vacation home for families or groups of friends looking to experience Wine Country in style. Our Creekside Retreat is located in one of Santa Rosa's most desirable neighborhoods - close to nature and just minutes away from the area's top destinations and attractions.

4.96 out of 5 average rating, 102 reviews
Top guest favorite
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.

4.95 out of 5 average rating, 553 reviews
Guest favorite
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.

4.97 out of 5 average rating, 161 reviews
Top guest favorite
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

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
Guest favorite
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

4.87 out of 5 average rating, 126 reviews
Top guest favorite
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.
Home in Santa Rosa

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

4.97 out of 5 average rating, 112 reviews
Guest favorite
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.

4.93 out of 5 average rating, 134 reviews
Top guest favorite
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

5.0 out of 5 average rating, 727 reviews
Top guest favorite
Home in Sebastopol

Pool, Hot Tub, Ent Barn, Fire Pit, Apple Orchard

Welcome to Green Hill Retreat. Swim in the solar-heated pool, soak in the 6-person hot tub, or lounge poolside on the spacious wood deck with stunning views of the outdoor space. Stargaze at the dark sky among the apple trees or by the wood fire pit. Head to the entertainment barn for a wet bar, air hockey, big-screen TV projector, darts, and cornhole. The main house features TVs in every room and a new open-concept kitchen. Pet- and family-friendly, EV charging, and fast WiFi.

4.98 out of 5 average rating, 127 reviews
Top guest favorite
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.
Home in Santa Rosa

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

4.99 out of 5 average rating, 141 reviews

Popular amenities for Healdsburg rentals with a pool

When is the best time to visit Healdsburg?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 9,752 ZARR 8,533 ZARR 9,752 ZARR 9,053 ZARR 11,329 ZARR 10,955 ZARR 8,354 ZARR 8,371 ZARR 8,127 ZARR 8,354 ZARR 9,671 ZARR 10,809 ZAR
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