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Vacation 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 favorite
Home in Sonoma
4.93 out of 5 average rating, 107 reviews

Sonoma Ranch, private pool on 7 acres!

KristinRating, 5 stars7 months ago
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!
Guest favorite
Home in Kenwood
5 out of 5 average rating, 25 reviews

[Egg Farm Ranch] Heated Pool-Water Slide-Hot Tub

SidhantRating, 5 stars1 week ago
Fantastic home in a great location! Very family friendly, so we had plenty of ways to keep the kids busy at home and at nearby attractions. At the same time, we were also very close to wineries and great restaurants. Adrian was very responsive and accommodating and made this a great stay!
Superhost
Home in Guerneville
4.83 out of 5 average rating, 164 reviews

STAY AWHiLE *Pool is OPEN Hot Tub Yard in G'ville

KarlynneRating, 5 stars4 months ago
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.
Guest favorite
Home in Santa Rosa
4.96 out of 5 average rating, 179 reviews

Happy House Getaway - Pool, Hot Tub & Wine Country

IrinaRating, 5 stars1 month ago
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.
Guest favorite
Home in Santa Rosa
4.98 out of 5 average rating, 119 reviews

Sonoma Green House *Pool*Close to Wine Country

StacyRating, 5 stars1 week ago
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.
Superhost
Home in Sebastopol
4.91 out of 5 average rating, 121 reviews

The Deer Retreat – Privacy and Comfort

LynneRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Timber Cove, Jenner
5 out of 5 average rating, 106 reviews

Ocean Front with Pool on Wild Sonoma Coast

CatrinaRating, 5 stars1 month ago
This home is the most incredible place I’ve ever stayed! It’s right on the bluff, crashing waves, privacy and everything you could need in a home. It’s worth every ounce of the cost and is as unique as a home can be. The owners are helpful, available and have everything you could need in the kitchen and home. Hope I get to go back!
Guest favorite
Home in Guerneville
4.92 out of 5 average rating, 186 reviews

Riverside Lodge House in Guerneville

DavidRating, 5 stars1 week ago
Fantastic! Hot tub, pool, river access - what more do you need? The house was well equipped for bigger groups. Kitchen was decent for cooking group meals. Great grill too. River access is a 1 min walk across the road. We saw turtles and a mink on the river

Condo rentals with a pool

Superhost
Condo in Napa
4.95 out of 5 average rating, 59 reviews

2/2 Iconic Napa Silverado Resort

JuliaRating, 5 stars6 months ago
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!
Guest favorite
Condo in Napa
4.95 out of 5 average rating, 152 reviews

Silverado Resort Dual Suite golf course villa

EmanuelRating, 5 stars2 weeks ago
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
Superhost
Condo in Windsor
5 out of 5 average rating, 3 reviews

Spacious 2 BDRM Condo in Sonoma Wine County

MosesRating, 5 stars12 months ago
Loved the rental! The area and location is perfect for surrounding wineries and restaurants. Great views and feels just like home away from home!
Superhost
Condo in Windsor
4.84 out of 5 average rating, 32 reviews

Wine Country 2 Bdrm Condo w/ Pools & Hot Tubs

AmandaRating, 5 stars30 months ago
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.
Guest favorite
Condo in Napa
4.9 out of 5 average rating, 81 reviews

Silverado Resort - Private 3 Bedroom, 2 Bath Condo

MelanieRating, 5 stars2 days ago
Great price, location and host! Would definitely stay here again.
Guest favorite
Condo in Napa
4.98 out of 5 average rating, 221 reviews

Gorgeous Napa Getaway

RobRating, 5 stars2 weeks ago
Great bungalow type place. Perfect back porch that overlooks beautiful golf course. Good value for this place.
Guest favorite
Condo in Napa
4.94 out of 5 average rating, 120 reviews

Fairways Silverado Golf and Country

HeatherRating, 5 stars2 weeks ago
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.
Top guest favorite
Condo in Napa
5 out of 5 average rating, 65 reviews

*Fairway Retreat at Silverado

AndieRating, 5 stars5 months ago
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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