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
6–13 Nov
Home in Cloverdale
4.86 out of 5 average rating, 110 reviewsWoodhawk Manor of Alexander Valley
25 Jan – 1 Feb
Home in Windsor
4.93 out of 5 average rating, 147 reviewsLuxurious home and pool
13–20 Aug
Home in Occidental
4.96 out of 5 average rating, 114 reviewsModern mid-century-inspired, Deer Ranch
22–29 Mar
Home in Sebastopol
4.98 out of 5 average rating, 150 reviewsSebastopol Gem, The Birdhouse. Hottub. Pool. Views
13–20 Feb
Home in Santa Rosa
4.98 out of 5 average rating, 101 reviewsPacific Gardens Retreat
6–13 Dec
Home in Kenwood
4.99 out of 5 average rating, 270 reviewsSonoma Vineyard Home With Pool & Stunning Views
5–12 Dec
Home in Sonoma
4.92 out of 5 average rating, 182 reviewsHouse on Broadway at the Plaza!
6–13 Oct
Weekly house rentals
Home in Santa Rosa
4.92 out of 5 average rating, 205 reviewsCharming 1-Bd Boho Flat Amid Wineries
1–8 Apr
Home in Santa Rosa
4.88 out of 5 average rating, 233 reviewsSunshine cottage
26 Sep – 3 Oct
Home in Healdsburg
4.81 out of 5 average rating, 105 reviewsRedwood River House
14–21 Jan
Home in Healdsburg
4.89 out of 5 average rating, 294 reviewsPeaceful location, hot tub, fire pit, game room!
21–28 Feb
Home in Guerneville
4.95 out of 5 average rating, 240 reviewsRedwood Treehouse with HotTub
5–12 May
Home in Santa Rosa
5.0 out of 5 average rating, 106 reviewsVINEYARD VIEW - Beautiful 3 bed/2 bath, Santa Rosa
1–8 Mar
Home in Sonoma
4.97 out of 5 average rating, 453 reviewsThe Loft at Palmer-Close to it all!
4–11 Sep
Home in Windsor
4.99 out of 5 average rating, 101 reviewsGorgeous Victorian in the HEART of Windsor
26 Mar – 2 Apr
Private house rentals
Home in Sonoma
4.98 out of 5 average rating, 118 reviewsEasy elegance in this wine country home
23–30 Oct
Home in Santa Rosa
4.97 out of 5 average rating, 150 reviewsAMITABHA Wine Country Cottage
1–8 Oct
Home in Healdsburg
5.0 out of 5 average rating, 57 reviews10 Acre Vineyard Cottage w/Hot Tub + Bocce Court
20–27 Jan
Home in Healdsburg
5.0 out of 5 average rating, 20 reviewsCreekside Cottage
18–25 Nov
Home in Healdsburg
5.0 out of 5 average rating, 38 reviewsVineyard views, stunning house & deck
14–21 Apr
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 Jan
Home in Geyserville
5.0 out of 5 average rating, 24 reviewsSpectacular vineyard views
24 Jun – 1 Jul
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
2.4T reviews
Nightly prices starting at
₹8,341 before taxes and fees
Destinations to explore
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