
Holiday rentals with a pool in Healdsburg
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Top-rated rentals with a pool in Healdsburg
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Healdsburg rentals with a pool
House rentals with a pool

Luxury home, hot tub/spa pool, walk to restaurants
Linda’s home in Glen Ellen was perfect! We were minutes from some great wineries and walking distance into town (restaurants, grocery store, bar, etc). The house is so inviting, we spent time reading, relaxing, and enjoying the backyard. We’ll definitely stay here again!

Heated Pool+Hot Tub+Ping Pong, Close to Wineries
Jenny's place was perfect for our girls trip! The large living space, pool and hot tub were a definite plus for our purpose. The beds were amazing and the house was fully stocked with all necessary items. Jenny was very responsive to any questions we had. We would definitely stay here again for a nice weekend getaway from the Bay Area.

Heated Pool / Hot Tub. Walk to Shops, Wine, Food.
Absolutely loved our stay! The place was spotless, beautifully decorated, and exactly as described. Stewart was friendly and responsive, making everything super easy. Would definitely stay again!

Stay on a Vineyard. Walk to Wineries.
My wife and I were meeting long time friends and their adult daughter, everyone was delighted with this house. Not only is it in a great setting but everything is just right. From communication with Bill to his helpful guidebook to the very nice pots and pans we used to cook each day. The house is beautiful and is spotless throughout. The windows and doors are new and keep the space peaceful. There are (to my count) 10 separate seating areas outside, we used 9! Bocce ball was fun and we had dinner outside. The spa was the right temperature and simple to use. The furniture and linens were great. And the views perfectly framed…. Beautiful landscaping with water features and abundant olive trees and large mature trees. Gorgeous The only downside was that we had to leave. It wasn’t inexpensive but we certainly were happy with the experience for what we paid, I’d be more than happy to visit again.

Sonoma Green House *Pool*Close to Wine Country
Conveniently located, lovely decorated home. Quiet neighborhood with access to downtown Santa Rosa, wine country, Russian River, Healdsburg, and more. Comfortable accommodations with everything you need. We spent afternoons floating in the pool after wine tasting. The property owner communicated well and responded quickly when messaged.

4BD House with Pool, Close to Sonoma Plaza
Great find in Sonoma! Well located with easy walks but in a peaceful neighborhood. Plenty of space for our four women on a girls’ trip!

Naidu Vineyards - Views/Pool/Spa/Bocce/9 Acres
Had a great time, beautiful views, great wine!

The Deer Retreat – Privacy and Comfort
We were in town for a family wedding. Dave's house was just beautiful! Very private with beautiful grounds! We were fortunate enough to have great weather and were able to take advantage of the pool, which was lovely. The bathrooms were all beautifully redone. The beds were HEAVENLY! We were unable to take advantage of the many recommendations because we had family obligations, but they were plentiful! The location of the house is just perfect... less than 2 miles into the center of Sebastopol and less than 30 mins to some great excursions! Would absolutely stay here again!
Condo rentals with a pool

Silverado Resort Dual Suite golf course villa
We loved our time here. The condo is a great location at the start of Silverado Trail, an easy drive to many wineries. It is also a short drive to downtown Napa. We visited for a wedding and Matt was very helpful and accommodating with all our questions. We hope to stay here again next time we visit Napa!

Silverado! Luxe 1BR King Suite This View! Balcony
We really enjoyed our stay. Place was spotless & exactly as described. Comfortable bed. Wonderful swimming pool. Dave was fantastic and communicated extremely well with very fast response. Thanks to Dave & his wonderful property, this was a special trip.

Charming Condo: King Bed, Pool Access, 2 Patios
"We had a wonderful stay at this charming Airbnb! The space was quaint and impeccably clean, nestled in a cozy and quiet area that made for a relaxing getaway. The bed was incredibly comfortable, ensuring we got plenty of restful sleep. We appreciated the soft, fluffy towels available, even though we didn’t get a chance to use the kitchen. The grounds of the property are beautiful, and having a Starbucks within sight was a lovely bonus for that morning caffeine boost. However, the coffee provided in the condo was perfect for our needs, and we took full advantage of it. Getting around Napa was a breeze with quick Uber services available whenever we needed them. Overall, we had no issues at all and can't wait to come back!

Wine Country Living at it's best at Silverado CC
Daniel was extremely proactive, helpful and responsive. We had a great time at his place, and would definitely return! Highly recommend

Casa Vina at Silverado Resort and Spa | Fireplace
I just had an amazing experience staying in Craig’s beautiful place (Unit 240). After a long ride over, I was happily greeted by a super clean, beautifully decorated place with high end towels and linens. Oh! and a nice array of sweets. I loved that the sun shined on both sides of the Unit and it has a little patio with chairs and table to sit and watch the world go by. Craig over communicated with me which I appreciated, even checking in with me during my stay to make sure everything was going well and to see if there was anything I needed. Silverado is a large property and this Unit is near everything. A 3-5 minute walk to: the Mansion where there’s a bar that has a mountainous view and overlooks one of the golf courses, The Grill restaurant where they serve all day, a Pro Shop, a little market with coffee, pastries, sandwiches, sundries and the swimming pool. Full service spa, gym tennis courts, bocce, pickleball are just across the street. I will definitely be back!

Fairways Silverado Golf and Country
I’m so glad to have found this airbnb! It was in a quiet, beautiful neighborhood. The place was cozy, clean and had everything we needed for a comfortable stay. We did have issues with wifi connections and would get bad signal on/off, also had trouble with opening the door (several tries with the code and being able to push open the door), but other than that, everything was perfect! Highly recommend this place and Kristina was awesome! I definitely would book here again if the need arises!

Elegant Napa Escape
The absolute perfect choice for our stay in Napa! The condo was clean, quiet and so comfortable. Debbie went above and beyond with her suggestions, communication throughout and even stocked the fridge with many breakfast goodies for us - an unexpected surprise!

Silverado Resort Condo with Pool
This is a great spot at Silverado Resort. It’s very peaceful and the grounds are beautiful. The condo is quiet, clean and tasteful! Would definitely stay again.
Home rentals with a private pool

Riverside Lodge House in Guerneville
this was the perfect space for a weekend getaway with good friends. we really enjoyed the design details and the functionality of the spaces!

Eclectic Hideaway with Backyard Pool & Hot Tub
Our group of six friends had such a blast staying at Dave and Donna’s place. It was centrally located, clean, and had plenty of space for the group to spread out. He provided great food and wine recs in the area and was very responsive via messaging. We’d definitely stay at this home again if ever visiting the Sonoma area!

Lovely and Spacious Ranch-Style Home With a Poolside Oasis
Griselda was a wonderful host. Our stay was super last minute and she was very accommodating, responsive and flexible. The location was perfect. We came to hike in Armstrong Redwood Park and her place was only about a 3 min drive there. It was also a three minute drive from the downtown so great location. Beautiful house with lots of space and a huge yard. I'd love to come back in the summer when we could use the outdoor space more, but the hot tub was perfect for the winter.

Family Home - Heated Pool, Hot Tub, bikes, + more!
Lawrence’s house was perfect for my group of 6. Plenty of space and it was nice all of the bedrooms did not share a wall as there was two couples. The instructions and guide that was provided was perfect and gave all of the details plus recommendations. The hot tub and pool were a great addition as this allowed our group to skip restaurants and going places and just stay at the house to cook or grill. One additional thing we noticed was the bedrooms did not include tvs, but we absolutely loved this for our group! I think we only turned on the living room tv once, otherwise we enjoyed each others company for this trip. Absolutely enjoyed staying at this home.
Quick stats about holiday rentals with a pool in Healdsburg
Total rentals
40 properties
Nightly prices starting at
$154 AUD 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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- Lake Berryessa
- Jenner Beach
- Bolinas Beach
- Clam Beach
- Drakes Beach
- Limantour Beach
- Six Flags Discovery Kingdom
- Point Reyes National Seashore
- Schoolhouse Beach
- Chandon
- Dominus Estate
- Doran Beach
- Santa Maria Beach
- Bowling Ball Beach
- Safari West
- Cooks Beach
- Caymus Vineyards
- Sonoma Coast State Park
- Mayacama Golf Club
- Pebble Beach
- Point Reyes Beach
- Gleason Beach
- Johnson's Beach
- South Beach