Healdsburg vacation rentals

We found 582 vacation rentals — enter your dates for availability

Select from 144 homes, 24 cottages, and other vacation rentals in Healdsburg to find one that's perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.
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Artsy Healdsburg will entice you

The area's wineries and art galleries are just a few of the reasons to vacation in Healdsburg. Well known for its restaurants, riverfront and shopping, this walkable city won't disappoint. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Healdsburg

Are you searching for attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Healdsburg a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Dry Creek Vineyard (4.2 mi / 6.8 km)
  • Francis Ford Coppola Winery (4.9 mi / 7.9 km)
  • Trentadue Winery (4.9 mi / 7.9 km)
  • Windsor Golf Club (6.7 mi / 10.8 km)
  • Korbel Winery (8.8 mi / 14.1 km)
  • Kendall-Jackson Wine Estate and Gardens (9.1 mi / 14.6 km)

Exploring the natural landscape of Healdsburg

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Healdsburg is a great place to spend some time outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Russian River (4.4 mi / 7 km)
  • Armstrong Redwoods State Park (9 mi / 14.5 km)
  • Kendall-Jackson Wine Estate and Gardens (9.1 mi / 14.6 km)
  • Safari West (10.1 mi / 16.3 km)
  • Johnson's Beach (10.3 mi / 16.6 km)
  • Lake Sonoma (10.9 mi / 17.6 km)

Traveling to and around Healdsburg

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 7.7 mi (12.5 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Healdsburg?
The most desirable types of vacation rentals in Healdsburg are cottages. After something a little different? Vrbo offers a variety of options to match our guests’ unique needs, so you’ll see properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — discover yours today.
How much does it cost to rent a vacation rental in Healdsburg?
Length of stay, property type and season are among the factors that can influence the price of a vacation home. Simply enter your dates of travel to find your perfect fit. From quaint country cottages to plush villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Healdsburg?
When you travel and the style and size of the property will influence the cost of your beachside escape. Type in your Healdsburg travel dates to see all your options on Vrbo. Did someone just say “hot tub”? Use our filters to choose the amenities and features you want in your beach house.
Are there pet-friendly vacation rentals in Healdsburg?
Good news. There are. Choose from 61 stays that allow pets in Healdsburg on Vrbo. Our furry best friends need a getaway too, so simply use our search function for pet-friendly vacation rentals to find a perfect property where Fido can be near his favorite humans.
Can I rent a house with a pool in Healdsburg?
Add a whole new level of fun to your getaway by booking one of the 15 houses with a private pool in Healdsburg. Use our search filter to find properties with pools on Vrbo, then spend your days frolicking in a swimming pool that’s exclusively for you.
What are popular rental amenities in Healdsburg?
A fireplace, a water view and a barbecue grill are rated the most popular rental amenities in Healdsburg. Whether you’re traveling on your own, with your significant other or as a family group, Vrbo can help you find a vacation home that matches your style with all the options you need.
Are there large group vacation rentals in Healdsburg?
With two vacation rentals that can sleep 10 people or more in Healdsburg, there’s no need to leave anyone off your invite list. From family vacations to events like anniversary parties and weddings, Vrbo can help you find a large group rental to suit the occasion.
Are there vacation rentals in Healdsburg that welcome kids?
With 61 family-friendly vacation homes to pick from in Healdsburg, now is a superb time to introduce the kids to the joys of travel. Simply check our “Properties good for families” filter to discover stays that come with amenities ideal for vacationing families, such as living rooms, pools, entertainment units and bunk beds.
What are the top attractions for families in Healdsburg?
Keeping the kids amused during your vacation in Healdsburg is easy with these cool family-friendly attractions:

  • Healdsburg Golf Club
  • Healdsburg Plaza
  • Jordan Vineyard & Winery

Are there one-bedroom vacation rentals in Healdsburg?
There are 11 one-bedroom properties in Healdsburg to pick from. A one-bedroom vacation rental is a superb choice if it’s only you and your partner or if you’re traveling alone. Toss in more convenience, space and privacy than a hotel, and you’re sure to have an unforgettable getaway.
Can I find two-bedroom vacation rentals in Healdsburg?
You can select from 23 two-bedroom vacation homes in Healdsburg. Put your little ones in the second room or maybe fill it with a couple of your best buddies. There’s space for whoever’s fortunate enough to be joining your adventure.
Are there vacation rentals with WiFi in Healdsburg?
Healdsburg has 37 vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming Hollywood blockbusters to checking emails, these Vrbo homes make it easy to get online.
How can I find vacation rentals with air conditioning in Healdsburg?
Select your travel dates and then use the filter tool to locate vacation rentals with ac in Healdsburg on Vrbo. With 47 air-conditioned properties available, you can enjoy a comfy and cool stay.
How old do you have to be to rent a vacation rental in Healdsburg?
You should check with the Healdsburg vacation home you’d like on Vrbo as the minimum age differs. However, typically it’s 16, 18 or 21.
How long can I rent a vacation rental in Healdsburg for?
The amount of time you can stay in a Healdsburg vacation rental for is up to each property. Just put in your travel dates to see options offering extended stays. They have all you need to make your extended trip more enjoyable and comfortable, such as kitchens and backyards. Some properties might also offer weekly or monthly discounted prices, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Healdsburg?
On Vrbo, you’ll find fantastic discounts and bargains for Healdsburg. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re planning a weekend getaway or an extended stay, Vrbo has lots of options for every style and budget.

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