Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Book Faster

Property Type

Bungalows
Cottages
Estates
Homes
Villas
Apartments
Barns
Boats
Cabins
Castles
Chalets
Condos
Farmhouses
Hotels
Lodges
Studios
Townhomes
Yachts

Book Faster

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Healdsburg Vacation Rentals(47)

47 Results
  • 5 BR,
  • 3 BA,
  • Sleeps 10
2 - 3 night minimum stay
(52)
$440 - $790
per night
2 - 3 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 - 3 night minimum stay
(49)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night minimum stay
(27)
$1,395 - $1,595
per night
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
2 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 3 night minimum stay
(38)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night minimum stay
(8)
$575 - $600
per night
3 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 night minimum stay
(9)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
(16)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(10)
$1,750 - $2,150
per night
3 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
3 night minimum stay
1 Review
$1,400 - $1,500
per night
2 night minimum stay
  • 6 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
2 night minimum stay
(13)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(16)
$314 - $611
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
30 night minimum stay
(20)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 night minimum stay
(37)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
(16)
$445 - $625
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
2 Reviews
  • 2 BR,
  • 1 BA,
  • Sleeps 6
25 more choices from the HomeAway Network
$795 - $1,295
per night
1 - 3 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
1 - 3 night minimum stay
(8)
$1,665 - $1,850
per night
2 night minimum stay
  • 13 BR,
  • 8 BA,
  • Sleeps 47
2 night minimum stay
(7)
$3,000 - $4,200
per month
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
30 night minimum stay
(4)
$500 - $600
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(6)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
5 night minimum stay
(7)
$400 - $450
per night
2 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 - 3 night minimum stay
(29)
$520 - $778
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 3 night minimum stay
2 Reviews
$495
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
(4)
Advertisement
 

Recent Healdsburg Reviews

Great home in the perfect Healdsburg location

5 of 5
Stayed in this charming Healdsburg home for a long weekend last winter with my husband, sister, and brother-in-law. The home feels very private with gorgeous mountain views, but is centrally located and an easy drive to many nearby wineries. We loved the rustic/modern decor, newly renovated kitchen, and open floor plan. Great home base for a Sonoma vacation. Highly recommend.
  • Submitted: Dec 22, 2014
  • Stayed: Jan 2014

Beautiful lodge on the river.

4 of 5
Firefly was our home away from home over the Food & Wine Affair in Oct/Nov 2014. The reservation and checkin/checkout processes were very simple. The house easily accommodated our group of 9. Literally on the river, we enjoyed views and sunrises daily. Anything you need in the kitchen for staple items or supplies are plentiful. Plenty of towels and a large table everyone can fit around are available. The guys enjoyed the game room with ping pong too. This is such a convenient location and Healdsburg is definitely where you want to be! I would recommend this property for sure. There is one point worth mentioning for consideration though... The house is nestled between other homes on the street/River, and while no fault of the owners, the neighbors - who must not like that Firefly is a rental for temporary guests, were not particularly welcoming and were pretty intolerant of any noise. While we weren't particularly loud, whenever you fill a home with 9 people reuniting for a great time, there is going to understandably be lots of laughter, fun, and yes - a bit of noise. If your group won't have this issue, Firefly is the place for you. We worked through it, but after a neighbor actually said something to us within an or so after our arrival, we had to be very conscious of our laughter etc when the door to the deck was open. It's really a beautiful place and we loved our stay at Firefly.
  • Submitted: Nov 22, 2014
  • Stayed: Oct 2014

Perfect place for a large group

5 of 5
What a beautiful place and so perfectly located. A couples long weekend get away for 12 adults and we had a blast. The hot tub and grill area allowed us to prepare and eat outdoors and then enjoy the hot tub. My friends and I visited for the Wine Road tour and I have to say, having a super nice place to come back to each night was a huge plus. Everyone had a great time and so enjoyed the house and cottage. We will definitely hope to stay here again. Darlene is so accommodating and always available should you need anything. Can't wait for another trip!
  • Submitted: Nov 5, 2014
  • Stayed: Oct 2014