
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

Luxury home, hot tub/spa pool, walk to restaurants

House on Broadway at the Plaza!

Vineyard House Pool Hot Tub by Inspired in Sonoma

PrivateWarm&Cozy+Spa+Pool+FirePit+Wifi!

Heated Pool+Hot Tub+Ping Pong, Close to Wineries

Casa Pavone, by Vinifera Homes

Sonoma 14Acres, 2BR 2BA, Pool HotTub, Plaza 3 mi.

The Sonoma Green House*Pool
Condo rentals with a pool

Silverado Resort Dual Suite golf course villa

Silverado! Luxe 1BR King Suite This View! Balcony

Wine Country Living at it's best at Silverado CC

Casa Vina at Silverado Resort and Spa | Fireplace

Chic Retreat in Napa: Pool Access, Kitchen, Patio

Fairways Silverado Golf and Country

1 bed | 1 bath | Silverado Resort Experience

Elegant Napa Escape
Quick stats about vacation rentals with a pool in Healdsburg
Total rentals
40 properties
Nightly prices starting at
$137 CAD before taxes and fees
Total number of reviews
650 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Lake Berryessa
- Jenner Beach
- Bolinas Beach
- Brazil Beach
- Clam Beach
- Six Flags Discovery Kingdom
- Limantour Beach
- Schoolhouse Beach
- Point Reyes National Seashore
- Drakes Beach
- Santa Maria Beach
- Doran Beach
- Safari West
- Dominus Estate
- Caymus Vineyards
- Bowling Ball Beach
- Gleason Beach
- Point Reyes Beach
- Trione-Annadel State Park
- Mayacama Golf Club
- Sonoma Coast State Park
- North Salmon Creek Beach
- Johnson's Beach
- Cooks Beach