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Healdsburg, California, United States of America

Healdsburg vacation rentals

We found 754 vacation rentals — enter your dates for availability

Discover a selection of 1,000 vacation rentals in Healdsburg, CA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $129 per night, and houses and cottages are popular options for a stay in Healdsburg. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Healdsburg
Stayed Nov 2021

Secret Gem

This is our second stay at this charming property. The hosts are just as great! Location is absolutely perfect and the place has everything you would need! We took daily morning walks and super easy walk home from town. This place a secret gem for a ...

Corine M.
Corine M.

Las Vegas Nevada

Stayed Nov 2021

Wonderful stay

Beautiful place and ideal location. Linda and Bill are a treasure. So helpful, warm and friendly. Linda helped set up wine tastings and had great recommendations on local restaurants. The property is beautiful. One morning we just walked the property...

Christine W.
Christine W.

Lino Lakes

Stayed Nov 2021

Great choose!

I nothing but great things to say about the property, and the owners. The house was great, and it had everything we needed for our home base for day trips to various wine tastings in the area. It was in a great location, and had an awesome farmhouse...

Joy B.
Joy B.
Stayed Nov 2021

The Best Place I've Ever Stayed

Where do I start? Just book this. It's private - so private! it's modern and fabulous! The pool and hot tub are Beyonce-worthy. Each guest en-suite is perfection. The doors that open and open and open to the patio are magical! And then the giant scre...

Sarah B.
Sarah B.
Stayed Nov 2021

Loved this property.

The property is well maintained, spacious, and comfortable. Ron and Susan are terrific hosts, very communicative and attentive to any needs or recommendations. We particularly loved the rural location surrounded by vineyards yet close enough to ameni...

Dennis H.
Dennis H.
Stayed Nov 2021

Great View!

House was perfect for 3 of us and would be for more people also. It is roomy, clean and comfortable. The view was outstanding. Very nice kitchen. The drive to the house is a little scary the first time as it is just a one lane road. The only reason f...

Tracy T.
Tracy T.

Fair Oaks, CA, USA

Stayed Nov 2021

Walkable Convenience in Healdsburg

This detached cottage is clean, spacious, charming and incredibly convenient to downtown Healdsburg. It has a dedicated bedroom, natural lighting with great views into two lush gardens. The location is perfect for someone without a car. It has it's o...

Lorenzo P.
Lorenzo P.
Stayed Oct 2021

Perfect spot for a wine weekend

We had such a wonderful time staying at Cynthia’s. The house was spacious and super clean, kitchen stocked with all the tools we needed for home cooked dinners after long days of wine tasting close by. We had one amazing sunny day where we biked tour...

Kristin L.
Kristin L.

Find the best place to stay — Healdsburg

Elegant - Peaceful - Romantic - Private

Sleeps 2 · 1 Bedroom · 1 Bathroom
$185 avg/night
(190)

Downtown Healdsburg Luxury Apartment Just 1 block to the Square

Sleeps 2 · 1 Bedroom
$129 avg/night

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

Sleeps 2 · 1 Bedroom · 1 Bathroom
$250 avg/night
(188)

Coop is our Fully Renovated, Beautiful Vineyard Cottage 1.5 miles from downtown

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$606 avg/night
(137)

Dry Creek Cottage - Healdsburg

Sleeps 4 · 1 Bedroom · 1 Bathroom
$295 avg/night
(80)

Healdsburg - Chalk Hill Wine Country Cottage

Sleeps 4 · 1 Bedroom · 1 Bathroom
$149 avg/night
(163)

Search 754 vacation rentals

How many vacation rentals are available around Healdsburg, CA?

Our 2021 property listings offer a large selection of 754 vacation rentals around Healdsburg. From 574 house rentals to 88 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Healdsburg?

Yes, of course. Vrbo has 574 Houses in Healdsburg. Our other popular types of vacation rentals in Healdsburg include:

  • Cottages: 88 rentals available
  • Cabins: 88 rentals available
  • Villas: 12 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Healdsburg?

Yes, you can select your preferred vacation rental with pool among our 272 vacation rentals with pool available in Healdsburg. Please use our search bar to access the selection of vacation rentals available.

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