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Holiday rentals with a pool in Healdsburg

Find and book unique homes with a pool on Airbnb

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Popular amenities for Healdsburg rentals with a pool

House rentals with a pool

Guest favourite
Home in Glen Ellen
4.92 out of 5 average rating, 180 reviews

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

HetherRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Sonoma
4.95 out of 5 average rating, 148 reviews

Sonoma Moon House

SeanRating, 5 stars8 months ago
We cannot say enough about this place. The perfect wine-tasting weekend! Exceeded expectations all around. We will stay here again!
Guest favourite
Home in Santa Rosa
4.92 out of 5 average rating, 118 reviews

PrivateWarm&Cozy+Spa+Pool+FirePit+Wi-Fi!

AlexisRating, 5 stars1 week ago
We had a wonderful experience having a small family reunion here. We had two older adults who use walkers and a baby, so I wanted to make sure that the house could accommodate all of us. Place was perfect for this with 3 bedrooms on the first floor, and only a couple steps to manage into the front door. Robin and other hosts were really helpful in answering all of my questions prior to the booking (and after). Loved the pool, hot tub and gazebo sitting area. Used the grill for family dinners. Will treasure our memories here!
Guest favourite
Home in Santa Rosa
4.88 out of 5 average rating, 228 reviews

Heated Pool / Hot Tub. Walk to Shops, Wine, Food.

DawnRating, 5 stars2 weeks ago
What a great find! The home was so cozy. Well equipped and decorated with attention to detail. The location was great. Nice quiet neighborhood. The backyard is a perfect paradise and my family of 6 were so happy to spend time just chilling in that beautiful fruit tree lined backyard. Highly recommend!!
Guest favourite
Home in Santa Rosa
4.96 out of 5 average rating, 187 reviews

Happy House Getaway - Pool, Hot Tub & Wine Country

JoseRating, 5 stars1 week ago
10/10 I stayed here with my girlfriend and my dog and it was really peaceful and had a great time,the pool and jacuzzi was amazing and the house was really clean🙌🏽😄
Guest favourite
Home in Santa Rosa
4.98 out of 5 average rating, 124 reviews

Sonoma Green House *Pool*Close to Wine Country

DawnRating, 5 stars1 week ago
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.
Guest favourite
Home in Sonoma
4.94 out of 5 average rating, 238 reviews

4BD House with Pool, Close to Sonoma Plaza

LindaRating, 5 stars5 months ago
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!
Guest favourite
Home in Sebastopol
4.91 out of 5 average rating, 127 reviews

The Deer Retreat – Privacy and Comfort

KristenRating, 5 stars2 weeks ago
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!

Apartment rentals with a pool

Guest favourite
Apartment in Napa
4.96 out of 5 average rating, 156 reviews

Silverado Resort Dual Suite golf course villa

ChanceRating, 5 stars1 week ago
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!
Top guest favourite
Apartment in Napa
4.99 out of 5 average rating, 432 reviews

Silverado! Luxe 1BR King Suite This View! Balcony

Sylvia ARating, 5 stars1 week ago
Beautiful place. Host was very helpful and friendly. Definitely recommend .
Top guest favourite
Apartment in Napa
4.99 out of 5 average rating, 136 reviews

Charming Condo: King Bed, Pool Access, 2 Patios

CorinaRating, 5 stars2 weeks ago
"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!
Guest favourite
Apartment in Napa
4.94 out of 5 average rating, 100 reviews

Wine Country Living at it's best at Silverado CC

RebeccaRating, 5 stars4 weeks ago
Daniel was extremely proactive, helpful and responsive. We had a great time at his place, and would definitely return! Highly recommend
Top guest favourite
Apartment in Napa
4.98 out of 5 average rating, 102 reviews

Casa Vina at Silverado Resort and Spa | Fireplace

DanaRating, 5 stars2 weeks ago
We had a fantastic stay! Craig was incredibly responsive and was able to rent to us same day as we didn't want to leave Silverado Resort and beautiful Napa! The condo decor was stylish and modern with an upscale vide that fit perfectly with Silverado Resort. The unit is stand alone with no one upstairs which was a plus. Silverado Resort is a one-of-a kind complete destination resort with golf, pools, tennis, spa and restaurants. Added bonus we were less than 10 minutes to downtown Napa. Can't wait to come back!
Guest favourite
Apartment in Napa
4.94 out of 5 average rating, 123 reviews

Fairways Silverado Golf and Country

Maria LeahRating, 5 stars2 days ago
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!
Top guest favourite
Apartment in Napa
4.98 out of 5 average rating, 181 reviews

Elegant Napa Escape

AlisonRating, 5 stars2 weeks ago
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!
Guest favourite
Apartment in Napa
4.95 out of 5 average rating, 173 reviews

Silverado Resort Condo with Pool

AudreyRating, 5 stars3 weeks ago
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

Guest favourite
Home in Guerneville
4.92 out of 5 average rating, 190 reviews

Riverside Lodge House in Guerneville

TamiRating, 5 stars3 weeks ago
this was the perfect space for a weekend getaway with good friends. we really enjoyed the design details and the functionality of the spaces!
Guest favourite
Home in Sonoma
4.93 out of 5 average rating, 259 reviews

Eclectic Hideaway with Backyard Pool & Hot Tub

WilliamRating, 5 stars1 month ago
We enjoyed are stay at Dave's AirBNB. We were attending a wedding and the location was very convenient for us to attend all the wedding events. This being our first time staying at an AirBNB we had a couple questions during our stay. Dave was always quick to respond and assist with our questions.
Superhost
Home in Guerneville
4.82 out of 5 average rating, 179 reviews

Lovely and Spacious Ranch-Style Home With a Poolside Oasis

KiranRating, 5 stars3 months ago
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.
Guest favourite
Home in Sonoma
4.83 out of 5 average rating, 384 reviews

Family Home - Heated Pool, Hot Tub, bikes, + more!

ToriRating, 5 stars1 week ago
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

    ₹8,564 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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