Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Healdsburg Vacation Rentals with Pool(53)

53 Results
$880 - $1,080
per night
2 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 - 3 night minimum stay
(55)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 5 night minimum stay
(32)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(34)
$1,000 - $1,200
per night
2 - 3 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 - 3 night minimum stay
(7)
$600 - $850
per night
2 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(42)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 night minimum stay
(23)
$1,395 - $1,595
per night
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
2 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
2 night minimum stay
2 Reviews
$650 - $975
per night
2 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 night minimum stay
(19)
  • 5 BR,
  • 4 BA,
  • Sleeps 17
2 - 3 night minimum stay
(12)
$800
per night
4 - 6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 6 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night minimum stay
(4)
$999 - $1,250
per night
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 night minimum stay
(3)
  • 4 BR,
  • 4 BA,
  • Sleeps 12
2 night minimum stay
2 Reviews
  • 3 BR,
  • 3 BA,
  • Sleeps 6
(47)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 - 3 night minimum stay
(25)
$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
$2,000 - $2,300
per night
3 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
3 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 night minimum stay
(13)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(71)
$1,400 - $1,500
per night
2 night minimum stay
  • 6 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
2 night minimum stay
(12)
$1,250 - $1,450
per night
2 night minimum stay
  • 6 BR,
  • 4 BA,
  • Sleeps 12
2 night minimum stay
(13)
$675 - $875
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(5)
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 Reviews
$1,000 - $1,400
per night
2 - 3 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 - 3 night minimum stay
1 Review
$395
per night
2 night minimum stay
  • 4 BR,
  • 1 BA,
  • Sleeps 7
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(13)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
(9)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 night minimum stay
(5)
Advertisement
 

Recent Healdsburg Reviews

Wedding Weekend Bliss!!!

5 of 5
We stayed here for 4 nights while attending a wedding in Healdsburg. We were two couples and a 5th person and we had a few couples over for dinner/drinks. We sincerely did spend time discussing the fact that we could not find one aspect of the home that was not done perfectly. The property itself is spectacular. You cannot do it justice with pictures. Describing the property is a simple game of one item being better than the next. The pool with retractable cover to keep it nice and warm, Smith & Hawken outdoor furniture throughout, the 4' candelabra made of horse shoes, the bar with beer fridge, wine fridge and ice make, the fireplace with a spectacular coffee table, the kitchen with dual sinks, dual dishwashers and dining table to seat plenty, the deck off the kitchen - Smith & Hawken again, soon to be firepit sitting area, hammock... it goes on and on, I'm sure I'm missing so much. Truly one of the most beautiful places any of us had ever stayed. Everyone who visited with us remarked that is was, hands down, the best house they'd seen. Thank you for sharing your property with us. We realized half way back to SFO that we forgot to sign your guest book. I trust you'll read how much we enjoyed the home here and we're can't wait to go back (thinking next fall for a 50th)!
  • Submitted: Oct 15, 2014
  • Stayed: Oct 2014

Private Retreat

5 of 5
Our family had an absolutely wonderful time staying in Ed's beautiful home. It was fun seeing the animals on the surrounding properties. The landscaping/gardens were terrific. There was plenty of activities to do at the home (i.e. pool/spa, basketball, table tennis, horseshoes) when you got home from visiting vineyards. No doubt we will be back in the future! Ed, your home was everything we could have asked for. Thanks.
  • Submitted: Oct 14, 2014
  • Stayed: Oct 2014

Prefect Location. Perfect House.

5 of 5
The house and property was even nicer than the pictures. Beautiful remodel and great location with sweeping view of the vineyards. Great for a weekend getaway or longer stay. Owner was extremely helpful and accommodating. We'll definitely be back.
  • Submitted: Aug 26, 2014
  • Stayed: Aug 2014