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House holiday rentals in Healdsburg

Find and book unique houses on Airbnb

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Popular amenities for Healdsburg house rentals

House rentals with a pool

Guest favourite
Home in Glen Ellen
5 out of 5 average rating, 145 reviews

Tuscan Wine Country Villa with Pool sleeps 6

DonicaRating, 5 stars1 month ago
We would like to extend a HUGE thank you to Maurine and the hosts of this AirBNB! This house is truly a gem and exceeded our expectations! We loved everything about this property- from the comfortable, homey setting to the beautiful landscaping and outdoor spaces. Directions and communication were clear and guest friendly. On behalf of the 5 of us, on our girls' getaway, we thank you all wholeheartedly and are already planning on returning next April! Thank you for sharing this truly special home with us. It was a perfect 5 star get-away from beginning to end!
Guest favourite
Home in Windsor
4.96 out of 5 average rating, 136 reviews

Island Vacation House w/ Pool Minutes to Downtown

AmandaRating, 5 stars3 weeks ago
Great place to stay! Ted and Michelle were great hosts. The house was perfect for our group - big rooms, spacious living area and kitchen, and the pool, hot tub, pool table and ping pong table were so fun. The neighborhood is also very walkable and close to some great little shops. Wish we could have stayed longer!
Guest favourite
Home in Santa Rosa
4.92 out of 5 average rating, 118 reviews

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

AlexisRating, 5 stars2 weeks 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
4.9 out of 5 average rating, 158 reviews

Stunning Estate home near Healdsburg/Wineries

BriaRating, 5 stars2 weeks ago
This Airbnb was AMAZING!!! My friends and i absolutely loved staying here. The location was great for the wineries we went to which were sterling vineyard and Caymus. The only downfall was the pool rules and hours, also no microwave in the home. Either way i would definitely book this airbnb again!
Superhost
Home in Sebastopol
4.92 out of 5 average rating, 106 reviews

Luxury home (+ pool house) with views, pool & spa

ErikaRating, 5 stars1 month ago
Andrew’s house is spectacular. We had such a great time and there was so much space for everyone. The kids loved the pool and we watched the Warriors games in the pool house. The property landscaping was beautiful also. Andrew was a great communicator. I would highly recommend his place for a great getaway.
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 stars2 weeks 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🙌🏽😄
Top Guest favourite
Home in Sebastopol
4.98 out of 5 average rating, 177 reviews

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

TessRating, 5 stars2 weeks ago
I loved this place. It was beautifully decorated and had amazing views. The pool was an added benefit on hot days! It’s somewhat small for a group because it only has one bedroom but still worth the experience.
Top Guest favourite
Home in Junior College
4.98 out of 5 average rating, 146 reviews

Pacific Gardens Retreat

KaitlinRating, 5 stars5 months ago
Matthew’s home exceeded expectations and was incredibly cozy, private, spacious, clean, and spa-like. It was luxurious! It was very pet-friendly, I brought my Labrador with me and he loved lounging on the deck. The weather subsided (though I love the rain) all day Friday to allow for an entire day outdoors! The hot tub was clean and instructions were easy to follow. I loved that Matthew included local recommended spots to check out— I went to Russian River Brewing and Pacific Markets— both great spots with ample walking areas. The home decor is unique and has such character and charm without feeling like you’re stepping into “Magnolia Farms”— so far from it! There are beautiful works of art, antiques, classic and contemporary books; it’s lovely. Matthew is a responsive and kind, generous host. I found my stay tranquil and will be staying again as well as recommending to others! Matthew, thank you for providing a wonderful space for others to enjoy! All my best! Kaitlin & Buddy.

Weekly house rentals

Top Guest favourite
Home in Healdsburg
5 out of 5 average rating, 25 reviews

Cuvée House

EmilyRating, 5 stars1 month ago
We had a great stay at the Cuvee house. Sarah was extremely responsive and helpful throughout the trip which made this stay even better. The place was super cute and comfortable and it's located right behind a bubble bar which was fun to go to before dinner. The location can't be beat as it's right around the corner from the square and lots of shops and restaurants. Thanks for a great stay, we'd definitely come again.
Guest favourite
Home in Sebastopol
4.9 out of 5 average rating, 823 reviews

Wine/Apple Country Cottage, Centrally Located

DongjinRating, 5 stars1 week ago
This accommodation is clearly the work of someone with incredibly refined taste and a great sense of style. From the moment I stepped inside, I could feel the beauty in every part of the space. I truly appreciated the attention to detail—even the smallest things were thoughtful and delightful. The neighborhood is peaceful, with many beautiful and charming areas nearby, along with plenty of great restaurants. Overall, the entire experience was truly a happy one.
Guest favourite
Home in Bodega Bay
4.94 out of 5 average rating, 557 reviews

Ocean View Spa House

EllieRating, 5 stars2 weeks ago
This property is amazing in every way. There’s a view from the ocean from almost every room, beautiful tile work and gorgeous, well appointed bathrooms. A sauna and extra hot hot tub. The kitchen had everything we could possibly need. The house itself is beautiful with private spaces, but also a large living room where everyone can gather around a beautiful tiled potbelly fireplace. It’s a short walk to the beach through a charming neighborhood. The host Rebekah was very communicative and generous, allowed us flexible, check-in and check out. I will 100% be staying here again.
Top Guest favourite
Home in Healdsburg
5 out of 5 average rating, 34 reviews

Vineyard Oasis: Luxury Home in the Heart of Sonoma

DarcyRating, 5 stars3 days ago
Super great location near Windsor and 12 minutes from Healdsburg. Easy check in, lovely view, and comfortable beds. Fenced in yard as well. Would definitely go back!
Top Guest favourite
Home in Geyserville
5 out of 5 average rating, 60 reviews

Spectacular views from hot tub

ChristopherRating, 5 stars1 week ago
Had a wonderful experience on the top of the hill. Views were spectacular and the hot tub was placed perfectly for sunsets and star gazing. Wish I had booked more nights!
Top Guest favourite
Home in Healdsburg
4.99 out of 5 average rating, 97 reviews

Luxe Healdsburg Home ~ Sauna, Hot Tub, EV Charger

StephenRating, 5 stars2 weeks ago
Sarah’s home was the perfect spot for our trip to wine country. It is a beautiful home, centrally located and a great spot to jump off exploring in wine country. The amenities in her home were top-notch and inclusive of everything we needed and more…the grounds were beautifully landscaped also. We actually changed our plans one nite just to stay in and enjoy the home. Sarah was very responsive prior to our arrival and also once we were there. I highly recommend her home for a wine country adventure and we will certainly be returning on future trips to Sonoma.
Guest favourite
Home in Santa Rosa
4.92 out of 5 average rating, 230 reviews

The Explorer’s Wine Country Getaway

DeniseRating, 5 stars1 month ago
We enjoyed our stay very much. This sweet cozy apartment had everything my husband and I needed while visiting our family in the Santa Rosa area. The kitchen had all the essentials and the bed was super comfy! We hope to be back soon. ~Denise
Top Guest favourite
Home in Sonoma
4.95 out of 5 average rating, 463 reviews

Zen House on 15 acres

IsaacRating, 5 stars2 weeks ago
This was one of the best stays we’ve experienced! The house was spacious and very comfortable and the garden outside was gorgeous. It was very secluded, quiet, and peaceful—we hope to come back!

Private house rentals

Top Guest favourite
Home in Sebastopol
5 out of 5 average rating, 47 reviews

Pixel Place - A Private Arcade + Outdoor Sanctuary

HowardRating, 5 stars2 weeks ago
Had a great stay. Michael and Edna have been great at communication and everything about the home and instructions to usages were well thought out. Tastefully decorated. Details like having all types of usb charging cables and small things like that tell you the hosts care very much about your experience. Sparkling clean. Highly recommend.
Luxe
Home in Healdsburg
5 out of 5 average rating, 18 reviews

Luxurious Healdsburg Home Walk to Wineries

ReginaRating, 5 stars3 weeks ago
An indoor/outdoor living dream! The pool/hot tub/pool house/covered patio area was perfect and was where we spent most of our time during the day. Loved how private and peaceful the surrounding area was, while also being walking distance to wineries and a short drive to Healdsburg square. Home was spacious and everyone slept comfortably. Our family loved this Airbnb so much that we’ve already booked our next stay!
Guest favourite
Home in Healdsburg
4.96 out of 5 average rating, 84 reviews

Vineyard views, stunning house & deck

AlexaRating, 5 stars2 weeks ago
This was one of my favorite Airbnb's of all time !! The location is perfect - serene, private, and quiet all while being just around the corner from tons of wineries and Healdsburg square. The space is so clean, spacious, and has amazing natural light. We spent lots of time on the deck overlooking the wineries and beautiful trees. The house was stocked with everything you might need along with a beautiful wine bar with glasses, decanter, and more :) This was a family trip with me and my husband and my parents. Both couples had our own bedroom and bathroom - and lots of space to gather. Will fore sure be recommending and coming back when in the area!
Superhost
Home in Healdsburg
4.9 out of 5 average rating, 80 reviews

Morning Dew - A Riverfront Healdsburg Home

MargaretRating, 5 stars4 weeks ago
This place was so quiet, private and beautiful. We got to see a huge deer right next to the house! Great back deck where we spent a ton of time play games ans drinking wine...nice big kitchen, really comfy beds! It is a ways outside of town so a car is necessary and the road there is pretty curvy and dark at night. Cell service is limited out there, but the wifi worked well. Over all our stay was great and our host was very responsive. Would definitely stay here again!
Top Guest favourite
Home in Sebastopol
4.98 out of 5 average rating, 80 reviews

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

AlfredoRating, 5 stars3 weeks ago
This won’t be my last time staying at this house! The house is cozy and has all the amenities you need for a relaxing getaway in Sonoma. We especially made use of all the outdoor lounging and dining space, enjoying all of our home-cooked meals al fresco. And the location is super central in West Sonoma, which made it easy to explore local wineries and nearby towns like Bodega Bay, Guerneville and Forestville. The best part? After an exhausting day of eating and drinking, you get to come home to a gorgeous pool to wind down the day.
Guest favourite
Home in Forestville
4.95 out of 5 average rating, 61 reviews

Russian River Luxury Escape | Private Hot Tub

RileyRating, 5 stars1 week ago
The place looked brand new and was the perfect spot to hang out in wine country. And Kim was a great host!
Guest favourite
Home in Santa Rosa
4.99 out of 5 average rating, 79 reviews

Wine County Opulent Villa Pool/Hot Tub-Upper Level

AnashaRating, 5 stars2 weeks ago
We had the most amazing time at Carl’s stunning home. The house was even more beautiful than the pictures—spacious, perfectly designed, and filled with thoughtful details. The views were absolutely breathtaking, and the layout of the home made it easy to relax and enjoy every moment. The amenities were incredible—from the sparkling pool and relaxing hot tub to the Nespresso machine that made our mornings extra special. Carl was a fantastic host. We communicated by email before the trip, and he provided us with wonderful vineyard recommendations that turned out to be highlights of our stay. On our way out, we had the pleasure of meeting Carl in person, and he was just as kind and welcoming as we expected. This was truly a special experience in a truly exceptional home. We can’t recommend it enough and are already dreaming about coming back!
Guest favourite
Home in Healdsburg
5 out of 5 average rating, 48 reviews

Spacious Healdsburg Home - Walk to the Square!

JulioRating, 5 stars1 month ago
Ashwin was very inviting and made staying at the home seamless. I have another event coming up in the next few months and will absolutely rebook with him.

Quick stats about house rentals in Healdsburg

  • Total rentals

    80 properties

  • Nightly prices starting at

    $166 NZD before taxes and fees

  • Total number of reviews

    3.8K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Healdsburg
  6. House rentals