House holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Healdsburg
House rentals with a pool
Home in Santa Rosa
4.92 out of 5 average rating, 114 reviewsStunning Estate home near Healdsburg/Wineries
17–24 Feb
Home in Cloverdale
4.86 out of 5 average rating, 110 reviewsWoodhawk Manor of Alexander Valley
26 Jan – 2 Feb
Home in Windsor
4.93 out of 5 average rating, 147 reviewsLuxurious home and pool
10–17 Oct
Home in Occidental
4.96 out of 5 average rating, 114 reviewsModern mid-century-inspired, Deer Ranch
19–26 Jan
Home in Sonoma
5.0 out of 5 average rating, 116 reviewsSonoma Vineyard House with Pool close to Plaza
15–22 Aug
Home in Santa Rosa
4.98 out of 5 average rating, 101 reviewsPacific Gardens Retreat
22–29 Mar
Home in Sebastopol
4.98 out of 5 average rating, 150 reviewsSebastopol Gem, The Birdhouse. Hottub. Pool. Views
5–12 May
Home in Sonoma
4.99 out of 5 average rating, 215 reviewsQuiet Mid Century Sonoma with Pool/Spa
1–8 Jan
Weekly house rentals
Home in Santa Rosa
4.88 out of 5 average rating, 234 reviewsSunshine cottage
29 Jun – 6 Jul
Home in Healdsburg
4.81 out of 5 average rating, 105 reviewsRedwood River House
19–26 Oct
Home in Santa Rosa
5.0 out of 5 average rating, 106 reviewsVINEYARD VIEW - Beautiful 3 bed/2 bath, Santa Rosa
11–18 Nov
Home in Forestville
4.96 out of 5 average rating, 242 reviewsForest Cozy Home
11–18 Jan
Home in Marshall
4.99 out of 5 average rating, 177 reviewsTomales Bay: Tranquility, Bay Views, Kayaks &
7–14 Nov
Home in Sonoma
4.97 out of 5 average rating, 453 reviewsThe Loft at Palmer-Close to it all!
4–11 Sep
Home in Guerneville
4.95 out of 5 average rating, 240 reviewsRedwood Treehouse with HotTub
19–24 May
Home in Healdsburg
4.81 out of 5 average rating, 124 reviewsSpectacular Vineyard View!! SPA, Close to Plaza!
22–29 Apr
Private house rentals
Home in Sonoma
4.98 out of 5 average rating, 119 reviewsEasy elegance in this wine country home
23–30 Oct
Home in Healdsburg
4.98 out of 5 average rating, 53 reviewsHidden Oasis ~ a Private Luxury Home in Healdsburg
30 Jan – 6 Feb
Home in Healdsburg
5.0 out of 5 average rating, 38 reviewsVineyard views, stunning house & deck
23–30 Sep
Home in Healdsburg
5.0 out of 5 average rating, 20 reviewsCreekside Cottage
30 Dec – 6 Jan
Home in Geyserville
4.97 out of 5 average rating, 31 reviewsHealdsburg Wine Country Oasis, Hot Tub & Bocce
19–26 Aug
Home in Healdsburg
5.0 out of 5 average rating, 39 reviewsHealdsburg House - Chiquita Road
18–25 Mar
Home in Geyserville
5.0 out of 5 average rating, 24 reviewsSpectacular vineyard views
5–12 Nov
Home in Healdsburg
5.0 out of 5 average rating, 45 reviewsIvy House Healdsburg @Ivyhousehealdsburg
31 Mar – 7 Apr
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
€ 93 before taxes and fees
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