House vacation rentals in Healdsburg
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Top-rated house rentals in Healdsburg
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Healdsburg house rentals
House rentals with a pool
Home in Santa Rosa
4.92 out of 5 average rating, 114 reviewsStunning Estate home near Healdsburg/Wineries
Feb. 17 – 24
Home in Cloverdale
4.86 out of 5 average rating, 110 reviewsWoodhawk Manor of Alexander Valley
Jan. 26 – Feb. 2
Home in Windsor
4.93 out of 5 average rating, 147 reviewsLuxurious home and pool
Oct. 10 – 17
Home in Occidental
4.96 out of 5 average rating, 114 reviewsModern mid-century-inspired, Deer Ranch
Jan. 19 – 26
Home in Sonoma
5.0 out of 5 average rating, 116 reviewsSonoma Vineyard House with Pool close to Plaza
Aug. 15 – 22
Home in Santa Rosa
4.98 out of 5 average rating, 101 reviewsPacific Gardens Retreat
Mar. 22 – 29
Home in Sebastopol
4.98 out of 5 average rating, 150 reviewsSebastopol Gem, The Birdhouse. Hottub. Pool. Views
May 5 – 12
Home in Sonoma
4.99 out of 5 average rating, 215 reviewsQuiet Mid Century Sonoma with Pool/Spa
Jan. 1 – 8
Weekly house rentals
Home in Santa Rosa
4.88 out of 5 average rating, 234 reviewsSunshine cottage
Jun. 29 – Jul. 6
Home in Healdsburg
4.81 out of 5 average rating, 105 reviewsRedwood River House
Oct. 19 – 26
Home in Santa Rosa
5.0 out of 5 average rating, 106 reviewsVINEYARD VIEW - Beautiful 3 bed/2 bath, Santa Rosa
Nov. 11 – 18
Home in Forestville
4.96 out of 5 average rating, 242 reviewsForest Cozy Home
Jan. 11 – 18
Home in Marshall
4.99 out of 5 average rating, 177 reviewsTomales Bay: Tranquility, Bay Views, Kayaks &
Nov. 7 – 14
Home in Sonoma
4.97 out of 5 average rating, 453 reviewsThe Loft at Palmer-Close to it all!
Sep. 4 – 11
Home in Guerneville
4.95 out of 5 average rating, 240 reviewsRedwood Treehouse with HotTub
May 19 – 24
Home in Healdsburg
4.81 out of 5 average rating, 124 reviewsSpectacular Vineyard View!! SPA, Close to Plaza!
Apr. 22 – 29
Private house rentals
Home in Sonoma
4.98 out of 5 average rating, 119 reviewsEasy elegance in this wine country home
Oct. 23 – 30
Home in Healdsburg
4.98 out of 5 average rating, 53 reviewsHidden Oasis ~ a Private Luxury Home in Healdsburg
Jan. 30 – Feb. 6
Home in Healdsburg
5.0 out of 5 average rating, 38 reviewsVineyard views, stunning house & deck
Sep. 23 – 30
Home in Healdsburg
5.0 out of 5 average rating, 20 reviewsCreekside Cottage
Dec. 30 – Jan. 6
Home in Geyserville
4.97 out of 5 average rating, 31 reviewsHealdsburg Wine Country Oasis, Hot Tub & Bocce
Aug. 19 – 26
Home in Healdsburg
5.0 out of 5 average rating, 39 reviewsHealdsburg House - Chiquita Road
Mar. 18 – 25
Home in Geyserville
5.0 out of 5 average rating, 24 reviewsSpectacular vineyard views
Nov. 5 – 12
Home in Healdsburg
5.0 out of 5 average rating, 45 reviewsIvy House Healdsburg @Ivyhousehealdsburg
Mar. 31 – Apr. 7
Quick stats about house rentals in Healdsburg
Total rentals
50 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
2.4K reviews
Nightly prices starting at
$137 CAD before taxes and fees
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