57 Results
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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Healdsburg Vacation Rentals with pool(57)

57 Results
$1,695
per night
2 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
2 night min stay
(3)
  • 5 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 6 night min stay
(5)
$1,250
per night
3 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 night min stay
(3)
  • 4 BR,
  • 5 BA,
  • Sleeps 10
2 - 4 night min stay
(31)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night min stay
(42)
$800 - $1,200
per night
3 - 7 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night min stay
(9)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 5 night min stay
(6)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 night min stay
(24)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 4 night min stay
(33)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night min stay
(4)
$1,080 - $1,180
per night
2 - 3 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 - 3 night min stay
(55)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 - 4 night min stay
(38)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 night min stay
1 Review
$800 - $1,000
per night
2 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 night min stay
(19)
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
3 night min stay
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 night min stay
(20)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
$675 - $875
per night
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night min stay
(6)
$1,400 - $1,500
per night
2 night min stay
  • 6 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
2 night min stay
(15)
$1,300
per night
3 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
3 night min stay
2 Reviews
$1,250 - $1,450
per night
2 night min stay
  • 6 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
(15)
$1,495
per night
2 night min stay
  • 3 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 night min stay
2 Reviews
  • 4 BR,
  • 1 BA,
  • Sleeps 7
2 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night min stay
$1,300 - $1,500
per night
2 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
2 night min stay
(5)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night min stay
(11)
  • 6 BR,
  • 6 BA,
  • Sleeps 12
3 night min stay
(29)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(3)
 View map Map
Advertisement
 

Recent Healdsburg Reviews

Good as it gets!

5 of 5
We just returned from a four day adult weekend at Villa Terra Bella. The weekend was fantastic. Great property, great location, endless amenities. This property and location speaks for itself, so I must emphasize what a pleasure it was working with Darlene to plan our weekend. She is very professional, accommodating and reliable. She is also readily available at all times, and was prompt to respond to any and all of our needs. Let me also note that I worked off of her list of recommendations available on her website. We arranged for Robert Negoesco of Eli Grace Catering to prepare a private dinner in the Villa one evening. He much like Darlene was great to work with, prompt, efficient, precise and reliable. He designed and executed the perfect family style dinner party for eight people that we enjoyed from beginning to end. May I also point out that the fresh flowers and bottle of wine on the dining room table was a very nice touch to welcome us to the property. I highly recommend Villa Terra Bella, Darlene and her associates. Thank you for everything, I hope to return soon!
  • Submitted: Mar 25, 2015
  • Stayed: Mar 2015

Amazing Stay in Wine Country

5 of 5
Spent three wonderful days in this fantastic home and couldn't have been happier with the experience! The house itself is just as beautiful as the pictures on the site show. Everything from the state of the art kitchen (well stocked with cooking utensils), cozy fire place area, heated pool, deck with great outdoor table, family/media room and bedrooms were perfectly designed for enjoying wine country to its fullest. The location of the house was ideal, with many great wineries/tasting rooms near by (including a few in walking distance - Medlock Ames which turns into the Alexander Valley Bar at night is a must visit and a 5 minute walk from the house), the Jimtown Store next door (had a great lunch there) and downtown Healdsburg are a short drive or Uber away (which has tons of great eats and drinks off the square). The few days we spent here went by too fast, will definitely look to rent this place again in the future. The combination of such an amazing house in such a great location is tough to beat.
  • Submitted: Mar 8, 2015
  • Stayed: Mar 2015

Absolutely loved it.

5 of 5
Thank you to the owners for opening their home to people and allowing them to enjoy it. It is absolutely incredible property. Totally secluded and private. We fell in love with it instantly and it was heart breaking to leave but we had to pass button to others. Strongly recommend to anyone.
  • Submitted: Mar 4, 2015
  • Stayed: Feb 2015