
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

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

Wine Country Getaway • Pool • Hot Tub • Sleeps 8

Leo’s Lodge - Lux Retreat with Pool and Hot Tub

SoLEIL *Pool OPEN thru 10/13. Hot Tub Epic View

Gorgeous Sonoma retreat (with pickleball!)

Luxurious home and pool

"La Masia" -Stunning! Heated Pool, Spa

The Estate at Sycamore- Sonoma Wine County Retreat
Condo rentals with a pool

Silverado Resort Dual Suite golf course villa

Wine Country Living at it's best at Silverado CC

Casa Vina at Silverado Resort and Spa | Fireplace

Fairways Silverado Golf and Country

1 bed | 1 bath | Silverado Resort Experience

Elegant Napa Escape

Coastal Retreat: King Bed, Balcony, Kitchen

Beautiful Premium Jr Suite, Silverado Resort & Spa
Other vacation rentals with a pool

Pool + 4 Hot Tubs! Gym, Luxury 2 bedroom villa.

Modern Wine Country Escape - 10min to Healdsburg

4BD/4BA Heated Pool & Spa: 11min Healdsburg Plaza

Sebastopol Retreat w/ Pool, Hot Tub, BBQ & Orchard

Modern Barn Nestled in the Countryside

Casa Pavone, by Vinifera Homes

Wine Country Gem | Pool | Hot tub | BBQ

The Dragonfly | A Wine Country Escape
Quick stats about vacation rentals with a pool in Healdsburg
Total rentals
40 properties
Nightly prices starting at
€ 86 before taxes and fees
Total number of reviews
630 reviews
Family-friendly rentals
20 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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- Rentals with a hot tub Healdsburg
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- Rentals with pools Sonoma County
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- Lake Berryessa
- Bolinas Beach
- Jenner Beach
- Six Flags Discovery Kingdom
- Brazil Beach
- Clam Beach
- Santa Maria Beach
- Schoolhouse Beach
- Point Reyes Beach
- Safari West
- Doran Beach
- Drakes Beach
- Caymus Vineyards
- Goat Rock Beach
- Bowling Ball Beach
- Johnson's Beach
- Sonoma Coast State Park
- Limantour Beach
- Mayacama Golf Club
- Cooks Beach
- Trione-Annadel State Park
- North Salmon Creek Beach
- Portuguese Beach
- Ceja Vineyards