Luxury Vacation Rentals with a Private Pool in Healdsburg
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 4 private pool vacation rentals – enter your dates for availability.
Welcome to private poolside luxury in Healdsburg
Escape to wine country with luxury private-pool vacation rentals in Healdsburg, where every Wander feels like your own boutique resort. Our portfolio spans vineyard-view villas, contemporary farmhouses, and secluded hillside estates, all meticulously maintained and exactly as pictured. Expect pristine cleaning, inspiring views, and 24/7 concierge service.
Outdoors, your private heated pool often pairs with a spa, fire features, and shaded lounging for sun-soaked afternoons or starlit swims. Inside, enjoy chef-ready kitchens, premium linens, and work-friendly touches like ultra fast WiFi and dedicated desks. With hotel-grade amenities throughout, each home makes it effortless to relax, focus, and celebrate in style.
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
All homes in Healdsburg
Discover more beyond the pool in Healdsburg
Set among rolling vineyards and redwood-studded hills, Healdsburg is shaped by the Russian River and the famed Dry Creek and Alexander Valley appellations. Cool morning fog, golden afternoons, and clear, starry nights create a magnetic rhythm across the seasons.
Sip at intimate tasting rooms by the historic plaza, cycle quiet backroads between wineries, or kayak gentle bends of the river. Seasonal markets, design-forward boutiques, and destination dining give each day a distinct flavor. With year-round beauty and easy access from San Francisco, this corner of Sonoma is ideal for quick escapes and longer stays, which is why Wander's luxury private-pool vacation rentals in Healdsburg are the perfect choice, whether you're traveling for work or leisure.