Owner Direct Vacation
Rentals in Healdsburg
The Best Owner Direct Vacation Rentals in Healdsburg. Explore thousands of vacation home rentals, large cabins, and villas near Healdsburg
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Explore the Best Healdsburg Vacation Homes
Looking for the perfect place to stay in Healdsburg? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Healdsburg character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Healdsburg Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Healdsburg
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Popular Neighborhoods for Healdsburg Vacation Rentals
What are the best areas to stay in Healdsburg
Discover the top neighborhoods in Healdsburg and choose a place that suits your stay.
Tuesday Feb 10
Healdsburg, California
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Healdsburg vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Healdsburg
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How to Reserve Your Healdsburg Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Healdsburg Vacation Rental FAQs
1. What are the top vacation rentals in Healdsburg?
There are a lot of options in Healdsburg. If you plan on staying in the Healdsburg area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Healdsburg:
- Wooded Restful Retreat, with broad scenic views, outdoor dining
- ✨Rustic Cabin in Dry Creek Valley with beautiful views/5 miles to Plaza ✨
- Wine Country Retreat with Panoramic Views-5 min from downtown Healdsburg
- Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
- "Dry Creek Villa" at Lavender Hill Vineyards
- 5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
- Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
- Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
- Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views
- TandaTula, Wine Country Sanctuary with Pool, Hot Tub, Bocce, Fire Pits and More!
2. How many vacation rentals have private pools in Healdsburg?
There are 64 vacation rentals with private pools near Healdsburg. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Healdsburg are best for families?
If you are looking for a family-friendly vacation home in Healdsburg, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Healdsburg:
4. How many vacation rentals are available in Healdsburg?
Currently, the total number of properties listed in 2026 is over 339 in the Healdsburg area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Healdsburg.