
House holiday rentals in Healdsburg
Find and book unique houses on Airbnb
Top-rated house rentals in Healdsburg
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Healdsburg house rentals
House rentals with a pool

Tuscan Wine Country Villa with Pool sleeps 6
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!

Island Vacation House w/ Pool Minutes to Downtown
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!

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

Stunning Estate home near Healdsburg/Wineries
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!

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

Happy House Getaway - Pool, Hot Tub & Wine Country
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🙌🏽😄

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views
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.

Pacific Gardens Retreat
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

Cuvée House
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.
Wine/Apple Country Cottage, Centrally Located
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.

Ocean View Spa House
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.

Vineyard Oasis: Luxury Home in the Heart of Sonoma
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!

Spectacular views from hot tub
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!

Luxe Healdsburg Home ~ Sauna, Hot Tub, EV Charger
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.

The Explorer’s Wine Country Getaway
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

Zen House on 15 acres
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

Pixel Place - A Private Arcade + Outdoor Sanctuary
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.

Luxurious Healdsburg Home Walk to Wineries
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!

Vineyard views, stunning house & deck
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!

Morning Dew - A Riverfront Healdsburg Home
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!

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

Russian River Luxury Escape | Private Hot Tub
The place looked brand new and was the perfect spot to hang out in wine country. And Kim was a great host!

Wine County Opulent Villa Pool/Hot Tub-Upper Level
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!

Spacious Healdsburg Home - Walk to the Square!
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
- Silicon Valley Holiday rentals
- North Coast Holiday rentals
- Wine Country Holiday rentals
- Oakland Holiday rentals
- Sacramento Holiday rentals
- Sacramento River Holiday rentals
- San Francisco Peninsula Holiday rentals
- Central California Holiday rentals
- San Francisco Holiday rentals
- San Francisco Bay Area Holiday rentals
- Gold Country Holiday rentals
- Northern California Holiday rentals
- Rentals with a washing machine and dryer Healdsburg
- Condo rentals Healdsburg
- Rentals with pools Healdsburg
- Rentals with a hot tub Healdsburg
- Pet-friendly rentals Healdsburg
- Hotel rentals Healdsburg
- Apartment rentals Healdsburg
- Cottage rentals Healdsburg
- Rentals with an EV charger Healdsburg
- Rentals with a fire pit Healdsburg
- Luxury rentals Healdsburg
- Fitness-friendly rentals Healdsburg
- Kid-friendly rentals Healdsburg
- Cabin rentals Healdsburg
- Family-friendly rentals Healdsburg
- Rentals with outdoor seating Healdsburg
- Rentals with a patio Healdsburg
- Rentals with a fireplace Healdsburg
- Villa rentals Healdsburg
- House rentals Sonoma County
- House rentals California
- House rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Santa Maria Beach
- Doran Beach
- Bowling Ball Beach
- Safari West
- Cooks Beach
- Caymus Vineyards
- Sonoma Coast State Park
- Mayacama Golf Club
- Pebble Beach
- Gleason Beach
- Point Reyes Beach
- South Beach
- Portuguese Beach