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 7 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Healdsburg

Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths

•

~$260 less than other sites

Luxury

Dry Creek Wonderland, Private Farm Estate in Wine Country

4 bedrooms•4 baths

•

~$305 less than other sites

Luxury

Sonoma Glass House

3 bedrooms•3.5 baths

•

New

~$340 less than other sites

Luxury

Ross Ranch and Vineyards

7 bedrooms•5 baths

•

New

~$540 less than other sites

Pool and Hot Tub Retreat near Healdsburg Wineries

4 bedrooms•3.5 baths

•

New

~$170 less than other sites

Boho Betty

4 bedrooms•2.5 baths

•

New

~$1,095 less than other sites

Luxury

Sunset Ridge, Luxury Wine Country Retreat

4 bedrooms•4 baths

•

~$365 less than other sites

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.

Available soon in Healdsburg

Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths

•

~$260 less than other sites

Luxury

Dry Creek Wonderland, Private Farm Estate in Wine Country

4 bedrooms•4 baths

•

~$305 less than other sites

Luxury

Sonoma Glass House

3 bedrooms•3.5 baths

•

New

~$340 less than other sites

Luxury

Ross Ranch and Vineyards

7 bedrooms•5 baths

•

New

~$540 less than other sites

Pool and Hot Tub Retreat near Healdsburg Wineries

4 bedrooms•3.5 baths

•

New

~$170 less than other sites

Luxury

Sunset Ridge, Luxury Wine Country Retreat

4 bedrooms•4 baths

•

~$365 less than other sites

Featured private pool vacation rentals in Healdsburg

Luxury

Dry Creek Wonderland, Private Farm Estate in Wine Country

4 bedrooms•4 baths

•

~$305 less than other sites

Luxury

Sonoma Glass House

3 bedrooms•3.5 baths

•

New

~$340 less than other sites

Luxury

Ross Ranch and Vineyards

7 bedrooms•5 baths

•

New

~$540 less than other sites

Luxury

Sunset Ridge, Luxury Wine Country Retreat

4 bedrooms•4 baths

•

~$365 less than other sites

Highlights in Healdsburg

Discover world-class wineries, farm-to-table dining, and scenic river adventures in the heart of California's Sonoma Wine Country.

Healdsburg Plaza

Jordan Vineyard & Winery

Ferrari-Carano Vineyards and Winery

Armstrong Redwoods State Natural Reserve

Seghesio Family Vineyards

Russian River

Dry Creek Vineyard

Healdsburg Farmers' Market

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Healdsburg

Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths

•

~$260 less than other sites

Luxury

Dry Creek Wonderland, Private Farm Estate in Wine Country

4 bedrooms•4 baths

•

~$305 less than other sites

Luxury

Sonoma Glass House

3 bedrooms•3.5 baths

•

New

~$340 less than other sites

Luxury

Ross Ranch and Vineyards

7 bedrooms•5 baths

•

New

~$540 less than other sites

Pool and Hot Tub Retreat near Healdsburg Wineries

4 bedrooms•3.5 baths

•

New

~$170 less than other sites

Boho Betty

4 bedrooms•2.5 baths

•

New

~$1,095 less than other sites

Luxury

Sunset Ridge, Luxury Wine Country Retreat

4 bedrooms•4 baths

•

~$365 less than other sites

View all homes

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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.

FAQs: Vacation Rentals in Healdsburg

Why should I book a Wander in Healdsburg over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.

Every home in Healdsburg delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Healdsburg?

Some of our most popular private pool vacation rentals in Healdsburg include Healdsburg Haven - 3 BD plus Den, Pool, Spa & Wine Tasting, Dry Creek Wonderland | Private Farm Estate in Wine Country, and Sonoma Glass House. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Healdsburg?

Wander offers 7 private pool vacation rentals in Healdsburg, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Healdsburg?

You can check-in to Wander private pool vacation rentals in Healdsburg after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Healdsburg have WiFi access?

Yes. Every Wander home in Healdsburg has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.