Vacation rentals with a pool in Healdsburg

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.

Wine Country Retreat- Privacy-Spa/Pool/Games

Take it easy at this unique & tranquil getaway in the middle of wine country! Feel worlds away but just minutes to world-class wineries, restaurants & shopping. Enjoy your own private pool, spa & game room. The large private property is perfect for your family getaway, couples retreat, or those looking for their own slice of heaven with thoughtful amenities. You'll want to come back year after year! Separate 1/1 guest house not included in price but available upon request at time of booking.

Best View Wine Country Oasis: Pool-Hot tub-Sauna

Welcome to Quail Roost by KEVALA TERRA. Immerse yourself in the panoramic views of the Sonoma Mountains, Open floor-plan great room with high ceilings, splash in the pool, or pamper yourself in the hot tub or cedar sauna. This wine country estate is the perfect place to celebrate life’s finer moments with friends/family. 56 miles from San Francisco, the house is centrally located, just minutes from Santa Rosa's downtown area & a short drive to local wineries, regional parks, outdoor activities.

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.

Spectacular Stone Pool/Spa with Views; Near Plaza

A spectacular stone pool and spa with bubbling stream compliments the warm and welcoming Summers House. (Please see notes below regarding pool and spa fees.) The house exudes charm. Sweeping views reach to the San Francisco Bay. Art, antiques and books create an embracing ambiance. Nestled into three, private wooded acres, Summers House is near wineries, and just 10 minutes from Sonoma Plaza restaurants, shops, and events. Well equipped kitchen, great dining spaces, large deck, comfy beds.

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

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

Wine Country Gem: Heated Pool, Spa, Barn, Orchard

- Luxurious staycation - Private home for families with tons of space, apple orchard, outdoor kitchen, spacious wood deck and 6-person hot tub - Large Heated Pool (Solar Heated From April to November) - Newly remodeled farmhouse kitchen - Epic Entertainment Barn: Air Hockey, 100" TV Projector, Darts & More - Spacious Outdoor Kitchen: Grill, Neopolitan Pizza Oven - Expansive Apple Orchard with Heirloom Gravenstein Trees - Pick Seasonal Vegetables from Garden Beds - Pet Friendly Home, Fenced

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. SVR25-100

Wine Country Retreat w/ Pool, Hot Tub & Games

Happy House – Year-Round Sonoma County Getaway with Pool & Hot Tub 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

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

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.