
Vacation rentals with a pool in Healdsburg
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Top-rated rentals with a pool in Healdsburg
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Popular amenities for Healdsburg rentals with a pool
House rentals with a pool

Pet Friendly with Hot Tub. Pool Heat Avail!
We spent a long weekend in this charming, spacious, and peaceful place in Sonoma County. The house is fully stocked with everything you need, and the outdoor garden and pool space were absolutely gorgeous! Fruit trees and beautiful flowers surround the backyard. Windsor was just a 15-minute bike ride/5 min drive, and Healdsburg was only a 10-minute drive. The bedrooms were very spacious, and the primary bedroom had the most beautiful sunset views overlooking the vineyard. We loved it and would book this home again!

Charming 4 bd/2 ba w/ Pool
This was a lovely four-bedroom old farmhouse tastefully updated and very convenient. It was very quiet at night, and felt like it was out in the country even though there was a neighborhood on one side of it. The pool was lovely, and the the house had everything we needed. Jessica was communicative, helpful and accommodating. It was my first AirBnB experience and it was great!

Sonoma Ranch, private pool on 7 acres!
My friends and I had a fantastic stay at Tina's home! Tina was so welcoming and offered flexible check-in/out times. She also left a bottle of wine for us in the fridge. The home is in a beautiful, rural part of Sonoma. It's such a peaceful and private location, but close to everything! We enjoyed watching the hot air balloons above the backyard in the morning and going on walks/runs from the house. The house is clean, comfortable, and had everything we needed! The weather was warm, so we were able to enjoy the pool and hot tub. I can't wait to come back with my family!

[Egg Farm Ranch] Heated Pool-Water Slide-Hot Tub
My family booked a long weekend at Adrian's home. The house was well furnished and supplied. The kids loved the pool & hot tub. Adrian was very responsive and attentive. We had a wonderful stay!

STAY AWHiLE G'ville Hot Tub Yard Real Fireplace
Had a wonderful stay at this adorable cottage. Extremely peaceful and as others have mentioned, much larger than the photos depict. Our dogs loved exploring the spacious yard and we felt so cozy and at home playing games around the fireplace. We stayed on a mostly rainy weekend, but there was still so much to do. Would love to enjoy this home in the warmer months. Thanks again to Russian River Getaways for another great stay.

Happy House Getaway - Pool, Hot Tub & Wine Country
Not only was the house super cute with big pool and hot tub, but a well stocked kitchen with quality pots and pans, snacks, and wonderful gas range. We had a great time staying at happy house and Brook was super friendly and gracious. She rushed over when there was a question and was so helpful.

Sonoma Green House *Pool*Close to Wine Country
This was a perfect location for my friends and I on a wine country weekend. Would definitely stay there again. The hosts were absolutely wonderful throughout.

The Deer Retreat – Privacy and Comfort
Great place! My only disappointment was that we couldn't use the pool because it had flooded a few weeks prior and it hadn't been cleaned out. The pool was one of the reasons I booked this home. It would've been nice to have been told we couldn't use it.
Condo rentals with a pool

2/2 Iconic Napa Silverado Resort
This was a great home base to explore Napa Valley. Very convenient access to the market for coffee each morning, although you don’t need it as the kitchen is very well stocked. Appreciated the sparkling water and snacks as nice touches! We were not bothered by the minimal noise from the upstairs neighbors. It was hardly noticeable and we were working remotely from the space all day. Live music on Friday nights as the resort was fun!

Silverado Resort Dual Suite golf course villa
Us and another couple decided to take a few days off and head out to Napa for a midweek getaway. It was our 23rd year anniversary and both of our friend’s birthdays and 34th year anniversary! Matt’s rental was awesome. He was very responsive and within a couple hrs we rented the house. This beautiful condo is located in a gated community within 15-20 min walking distance to Silverado Resort. Checking in was easy and straight up. One of the rooms has a beautiful local view of the hills and houses around. Matt’s vacation rental is clean and neighbors are very quiet. The kitchen is loaded with all the necessary bowls, pans, utensils etc. Bathrooms were clean and plenty towels were provided. If you plan to have a nice stay in Napa i’ld definitely give them a try! 5 stars all around

Spacious 2 BDRM Condo in Sonoma Wine County
Loved the rental! The area and location is perfect for surrounding wineries and restaurants. Great views and feels just like home away from home!

Wine Country 2 Bdrm Condo w/ Pools & Hot Tubs
This location was perfect for my employees, who are working on a new home construction project in the area. They felt right at home and couldn't believe how accommodating everything & everyone was.

Silverado Resort - Private 3 Bedroom, 2 Bath Condo
Dan’s place was very clean, located on a golf course, close to the pool, it has two patios perfect for our girls weekend.

Gorgeous Napa Getaway
Great bungalow type place. Perfect back porch that overlooks beautiful golf course. Good value for this place.

Fairways Silverado Golf and Country
Peaceful location with beautiful patio overlooking the golf course. Kitchen was fully stocked, beds were comfortable, and you can’t beat the location. I appreciate Kristina’s quick responses and flexibility on check-in time.

*Fairway Retreat at Silverado
As an Airbnb member for over 8-10 years with many stays between me and my wife’s account from all over the world. This is one of our most favorite homes in the world. The tranquility, cleanliness, and comfort felt here is one if a kind. Everything was as described. Host was not a bother at all. The check in was smooth. Parking is a breeze. Neighbors are extremely friendly. The home is definitely made for a luxury experience and with the guests peace of mind put forward. Bathroom is spacious, the kitchen is beautiful and the living areas are very comfortable with stunning views of the golf course. 100 out of 10 rating. Book this aribnb without a second question. Keep in mind it’s 1 spacious bedroom and 1 master-like bathroom! Thank you Jeanne for everything! ⭐️⭐️⭐️⭐️⭐️⭐️⭐️
Quick stats about vacation rentals with a pool in Healdsburg
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
640 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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- Clam Beach
- Sonoma Coast State Park
- Point Reyes National Seashore
- Chandon
- Dominus Estate
- Six Flags Discovery Kingdom
- Caymus Vineyards
- Pebble Beach
- Safari West
- Bowling Ball Beach
- Schoolhouse Beach
- Portuguese Beach
- Gleason Beach
- North Salmon Creek Beach
- Doran Beach
- Santa Maria Beach
- Chateau St. Jean
- Kelham Beach
- Black Point Beach
- Shell Beach
- South Beach
- Kistler Vineyards-Trenton Roadhouse Tastings by Appointment
- Driftwood Beach
- Point Reyes Beach