We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Pet Friendly Holiday Rentals in Healdsburg

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
loading...
Sort by
From
$638
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
19 photos Details
Reviews (4) Make Enquiry
From
$346
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
Reviews (2) Make Enquiry
From
$303
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
5 photos Details
Reviews (1) Make Enquiry
From
$160
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
6 photos Details
Reviews (6) Make Enquiry
From
$372
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (1) Make Enquiry
From
$691
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
30 photos Details
Reviews (8) Make Enquiry
From
$314
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
8 photos Details
Reviews (4) Make Enquiry
From
$154
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
17 photos Details
Reviews (1) Make Enquiry
From
$420
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
24 photos Details
Reviews (1) Make Enquiry
From
$633
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
20 photos Details
Reviews (5) Make Enquiry
Get the List
From
$1,542
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
22 photos Details
Reviews (4) Make Enquiry
From
$633
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Reviews (2) Make Enquiry
From
$846
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Reviews (3) Make Enquiry
From
$420
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
Reviews (2) Make Enquiry
From
$420
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
17 photos Details
Reviews (1) Make Enquiry
From
$665
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Reviews (3) Make Enquiry
From
$420
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
22 photos Details
Reviews (4) Make Enquiry
From
$527
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 10
20 photos Details
Reviews (2) Make Enquiry
From
$207
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
25 photos Details
Reviews (11) Make Enquiry
From
$303
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
8 photos Details
Make Enquiry
From
$207
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
Make Enquiry
From
$372
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
Make Enquiry
From
$638
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
16 photos Details
Make Enquiry
From
$372
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
20 photos Details
Make Enquiry
From
$1,276
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
30 photos Details
Make Enquiry
Go to map view
Book Online(10)
Use filters to find the best results!

Suitability

  • Wheelchair access (4)
  • Elder access (12)
  • Suitable for children (15)
  • Pet friendly (25)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (18)
  • Internet (16)
  • Washer/Dryer (16)
  • Air Conditioning (14)
  • Hot Tub (14)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities
Healdsburg Vacation Rentals

Beautiful Northern California has many fabulous destinations, and the town of Healdsburg in Sonoma County is at the top of the list. And if you are looking for a vacation rental in this slice of world famous wine country, we’ve got you covered. We have a huge variety of Healdsburg vacation rental listings. You might be looking for a large house for the whole family, or a quaint cottage for a special romantic getaway. Whatever your needs and budget, we can help you find the perfect vacation rental that will make your stay in Healdsburg even more amazing. We can also provide you with helpful user reviews of vacation rentals in Healdsburg and the surrounding area, so you’ll be sure to get good value for your money.

Healdsburg a Slice of Paradise

Small town charm, beautiful landscapes and outstanding weather are just a few of the trademark qualities that make Healdsburg so popular. Healdsburg combines five-star cuisine, rolling hills and world-acclaimed wine growing appellations for an experience you will never forget. When it’s time to relax at the end of the day, why stay in a cramped hotel when you can enjoy the comforts of home in one of our rental cottages, houses or cabins?

Lots of Activities

If you love the vibrant outdoors and colorful festivals, you will love Healdsburg. In April, you can help harvest roses and distill them into fragrant rose oil and rosewater as part of the Classic Perfume Rose Harvest & Distillation Tours. An annual sea food dinner at the Healdsburg Fire Department is also in April. From February to June, enjoy the "Russian River Good Old Days" exhibit at the Healdsburg Museum. And on the first Friday of the month, Williamson Wines sponsors an Epicurean Dinner at the Dry Creek Kitchen at Hotel Healdsburg.

Food, Wine and Fun

Speaking of eating, you won’t want to miss the chance to dine at Healdsburg’s amazing restaurants, including Affronti, Agave Mexican Restaurant &Tequila Bar, Thai Orchid Cuisine, Willi's Seafood & Raw Bar and Zin Restaurant & Wine Bar. And don’t forget to visit the beautiful wine country all around you, featuring names like Alexander Valley, Chalk Hill, Dry Creek Valley, and Russian River Valley. We’re here to help you make the most of your visit to Healdsburg. Let us help you find the perfect cozy cottage, cabin or house to make your stay in Healdsburg one you will always remember.