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Vacation rentals with a pool in Healdsburg
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Healdsburg
Guests agree: these homes with a pool 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 rentals with a pool
House rentals with a pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-52918029/original/8e8c8f3a-f79b-4d6f-bc8e-7c65b2401c9b.jpeg?im_w=720)
Home in Santa Rosa
4.93 out of 5 average rating, 123 reviewsStunning Estate home near Healdsburg/Wineries
![](https://a0.muscache.com/im/pictures/b05cfbf6-6995-4dc1-8003-b35c5d120b0a.jpg?im_w=720)
Home in Sebastopol
4.91 out of 5 average rating, 102 reviewsThe Deer Retreat – Privacy and Comfort
![](https://a0.muscache.com/im/pictures/b7c7e1c7-6523-4220-bf36-eaca3bc63586.jpg?im_w=720)
Home in Windsor
4.93 out of 5 average rating, 151 reviewsLuxurious home and pool
![](https://a0.muscache.com/im/pictures/9280c198-a5cc-4e8c-89c8-983ce71007d3.jpg?im_w=720)
Home in Kenwood
4.99 out of 5 average rating, 279 reviewsSonoma Vineyard Home With Pool & Stunning Views
![](https://a0.muscache.com/im/pictures/miso/Hosting-12114985/original/b3ee5f42-2254-4fd2-ab83-4947311b1e59.jpeg?im_w=720)
Home in Santa Rosa
4.98 out of 5 average rating, 168 reviewsHappy House w/large pool, hot tub & chefs kitchen
![](https://a0.muscache.com/im/pictures/cf10a47c-c408-4d9e-8073-926f803e1457.jpg?im_w=720)
Home in Santa Rosa
4.98 out of 5 average rating, 109 reviewsPacific Gardens Retreat
![](https://a0.muscache.com/im/pictures/732d8962-b11b-4322-8c93-cbd7d824f55a.jpg?im_w=720)
Home in Sebastopol
4.92 out of 5 average rating, 154 reviewsGorgeous West County Sonoma retreat
![](https://a0.muscache.com/im/pictures/miso/Hosting-3606115/original/414e68ad-2371-431e-9ef0-7397f24e428e.jpeg?im_w=720)
Home in Sonoma
4.95 out of 5 average rating, 146 reviewsCasa Sonoma-Pool, Spa, Bocce
Condo rentals with a pool
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Condo in Napa
4.98 out of 5 average rating, 138 reviewsChic Retreat at Silverado: Pool Access, Kitchen
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Condo in Napa
4.98 out of 5 average rating, 162 reviewsElegant Napa Escape
![](https://a0.muscache.com/im/pictures/miso/Hosting-47797528/original/81e25675-ff78-45a9-a71c-5631d51f9e88.jpeg?im_w=720)
Condo in Napa
4.99 out of 5 average rating, 346 reviewsSilverado Resort! Large 1BR Mountain View, Balcony
![](https://a0.muscache.com/im/pictures/de766ac3-6ad8-402a-83c3-7874b2232f3c.jpg?im_w=720)
Condo in Napa
4.95 out of 5 average rating, 145 reviewsSilverado Resort Condo with Pool
![](https://a0.muscache.com/im/pictures/102331101/50f28475_original.jpg?im_w=720)
Condo in Napa
4.87 out of 5 average rating, 225 reviews♥Luxe 2BR, 2 patios, pool, 10 Min To Dwtn/wineries
![](https://a0.muscache.com/im/pictures/miso/Hosting-545676370764563585/original/fd13413b-596f-4874-9a86-a74955a21e7a.jpeg?im_w=720)
Condo in Napa
4.99 out of 5 average rating, 162 reviewsChic 1 BR Condo Par Excellence at Silverado Resort
![](https://a0.muscache.com/im/pictures/miso/Hosting-38380520/original/55d128ed-8d62-4e9f-ad4c-740acfd2f9b8.jpeg?im_w=720)
Condo in Napa
4.98 out of 5 average rating, 119 reviewsSilverado Resort Dual Suite golf course villa
![](https://a0.muscache.com/im/pictures/miso/Hosting-713899406650140625/original/80bcc602-510a-4a3a-8fc7-2f3f34067499.jpeg?im_w=720)
Condo in Napa
4.84 out of 5 average rating, 116 reviews2 bed I Silverado Resort & Spa in Napa - Wine Town
Home rentals with a private pool
![](https://a0.muscache.com/im/pictures/24ad7197-1210-42c5-a050-3d5cdd5c1729.jpg?im_w=720)
Home in Sonoma
4.93 out of 5 average rating, 246 reviewsEclectic Hideaway with Backyard Pool & Hot Tub
![](https://a0.muscache.com/im/pictures/4d358138-e831-46e8-9b4d-4625c86f9f77.jpg?im_w=720)
Home in Sonoma
4.82 out of 5 average rating, 351 reviewsFamily Home - Heated Pool, Hot Tub, bikes, firepit
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Home in Guerneville
4.91 out of 5 average rating, 169 reviewsRiverside Lodge House in Guerneville
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Home in Guerneville
4.83 out of 5 average rating, 161 reviewsLovely and Spacious Ranch-Style Home With a Poolside Oasis
Quick stats about vacation rentals with a pool in Healdsburg
Total rentals
20 properties
Nightly prices starting at
$170 before taxes and fees
Total number of reviews
250 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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