Vacation rentals in Healdsburg

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Healdsburg vacation rentals

Stay near Healdsburg's top sights

Healdsburg Wine Tours160 locals recommend
Willi's | Seafood & Raw Bar76 locals recommend
Bravas Bar de Tapas68 locals recommend
Barndiva62 locals recommend
Campo Fina59 locals recommend
Valette43 locals recommend

Dog friendly vacation rentals in Healdsburg

Guest favorite
Home in Santa Rosa
4.94 out of 5 average rating, 243 reviews

Russian River Valley Brew-cation Home

MariannRating, 5 stars2 weeks ago
Excellent stay. Everything in place, even coffee beans for us. Beautiful view and nice terrace. Spacious living room and bedrooms. Very well equipped kitchen with everything you need. Mariann and Jan
Top guest favorite
Home in Sonoma
4.98 out of 5 average rating, 199 reviews

Vineyard Retreat | 3BR Home Near Sonoma & Napa

KatieRating, 5 stars2 weeks ago
Julie is an excellent host! We had a fantastic time at the cottage and casita. The pictures and description matched the Airbnb posting and we couldn’t have been more pleased about the picturesque vineyard surroundings. Julie also added the best tiny details like robes in every room, shampoo and conditioner, and additional home supplies. Her guidebook to the surrounding area was also an excellent touch. I would definitely recommend this home for your next getaway!
Superhost
Home in Inverness
4.85 out of 5 average rating, 136 reviews

Sunny Classic Inverness Home

StacyRating, 5 stars2 months ago
we loved this spot! we were visiting family who live in town and this house was ideal for entertaining a small group, it was fun to have them over for dinner and to lounge in the living room. the outdoor spaces are great. this house is so well equipped, everything we needed we found easily. It has a wonderful family vacation home feel to it, very lived-in and cozy. we felt lucky to be there and hope to stay again.
Superhost
Home in Guerneville
4.83 out of 5 average rating, 115 reviews

The Wright Cottage-Walk to town-Hot Tub

MarthaRating, 5 stars6 months ago
Great spot in a cute location! Tom's instructions were clear and easy-to-follow and the place was clean and very comfortable. Would definitely recommend this spot to others - it was perfect for our weekend getaway!
Guest favorite
Cottage in Dillon Beach
4.97 out of 5 average rating, 144 reviews

Sundog - EV - Walk to Beach & Food - Yard for Dog

MollieRating, 5 stars1 month ago
Sundog cottage is lovely! We were so happy to find that it was even more beautiful in person than the pictures. Super clean, great kitchen, deck and backyard were perfect for our dogs and just relaxing and listening to the ocean. The linens are amazing and the beds comfy! Valerie went above and beyond as a host, even left us local eggs, butter and crackers. She was friendly and easy to communicate with. Sundog is a gem and we can’t wait to come back!
Guest favorite
Bungalow in Santa Rosa
4.92 out of 5 average rating, 497 reviews

Downtown Retro Bungalow Dog Friendly

KarenRating, 5 stars1 month ago
My stay at Allen's place was great. It was an easy walk to the dog park, a small grocery and lots of restaurants. What really stood out was how much he really meant "dog friendly". There were toys, a dog bed, blankets to cover the furniture, towels for muddy paws and more. And the fenced in backyard was just perfect. Also, he was super responsive to the one small hiccup I ran into. Overall, I would definitely stay again.
Superhost
Guesthouse in Inverness
4.83 out of 5 average rating, 254 reviews

Inverness Writer's Den

LindsayRating, 5 stars3 days ago
Camille was accommodating! Super friendly and non intrusive. The space was exactly what we expected! We were so happy to have our dog with us as we explored the area. Would definitely come back again!
Guest favorite
Home in Calistoga
4.92 out of 5 average rating, 261 reviews

Cozy Craftsman Cottage

LisaRating, 5 stars2 months ago
Our second stay at this sweet little cottage. All the amenities we needed. Super cozy and quiet except for nature sounds. Just what we needed. Bonus points for the really nice shower with the tankless on-demand heating. Hot water all the time.

Family friendly vacation rentals in Healdsburg

Guest favorite
Cabin in Guerneville
4.92 out of 5 average rating, 285 reviews

Family Friendly Cabin on the River-Stunning View!

JessicaRating, 5 stars3 weeks ago
Great relaxing home. The beds are comfortable and the interior is well appointed. Location is right on the river and has a great view of the redwoods and the river. Home is a bit older and kitchen supplies (knives and such) are a bit run down but nothing major to complain about. All in all a great stay and nice property.
Top guest favorite
Bungalow in Sonoma
4.98 out of 5 average rating, 247 reviews

Vineyard Villa Cottage

NizaRating, 5 stars4 days ago
Went on a girls trip to Napa and stayed at Arlene’s place. We had an amazing time. The cottage was lovely and just as described. Plenty of outdoor space to take a walk and just chill and enjoy the views. It’s close to restaurants and grocery store. The beds were very comfortable. Arlene was very friendly and responsive. We got to meet their dog Syrah and fell in love with her. She is a very lovey and friendly dog. The hospitality was just amazing and the stay was worth the price.
Guest favorite
Home in Bodega Bay
4.92 out of 5 average rating, 175 reviews

Bodega Bay-Magical Ocean Front and Coastal View!

GillianRating, 5 stars6 days ago
We thoroughly enjoyed our stay at Deja Blu. The location is perfection! Private, with beautiful gardens, only a hop, skip and a jump from the ocean. Falling asleep to the sound of crashing waves at night was divine. The home was clean and comfortable, and Barr was a lovely, helpful host. If you are looking to unwind in serenity, I highly recommend this home.
Guest favorite
Apartment in Sonoma
4.89 out of 5 average rating, 393 reviews

Modern Family Farm

MattRating, 5 stars1 week ago
Eileen sent my wife and I, tons of recommendations before our trip ensuring we had a good inside scoop on local recommendations. The farm was exactly as described and perfectly located for Sonoma and Napa trips. It was nice and private with lots of restaurants and wineries within 10 minutes so we did not have to travel far. Will try and stay here for all our Sonoma and Napa trips going forward.
Top guest favorite
Home in Healdsburg
4.93 out of 5 average rating, 581 reviews

Healdsburg Garden House

SarahRating, 5 stars2 weeks ago
Very responsive and friendly host. The property was perfect for us with our one mid-size and one very little dog, i.e., fully fenced, large yard, safe, and clean. It was a comfortable home with multiple bedrooms and nice size kitchen and amenities for prepping home cooked meals. We'd absolutely stay there again.
Guest favorite
Home in St. Helena
4.86 out of 5 average rating, 237 reviews

The Dollhouse in Saint Helena

JanineRating, 5 stars3 days ago
Location, location, location! We enjoyed walking to restaurants for dinner and breakfast. The shops in St. Helena are also darling. Would recommend and stay again.
Guest favorite
Home in Napa
4.93 out of 5 average rating, 111 reviews

Harvest Lane Vacation Villa

ClaraRating, 5 stars3 weeks ago
This house on harvest lane is grrat place to stay with your family. You feel right at home. It has a big kitchen where you can hang out with your family. It has a big deck in the back facing a vineyard. Its a beautiful sit in the morning. Its also has a hotube. Overall it was a great place to stay with the family. It also has nearby supermarket and places to eat. The pictures on the website is what you get. My family and i loved it.
Guest favorite
Guesthouse in Santa Rosa
4.88 out of 5 average rating, 172 reviews

2 Wine Country Gem 2 Bedroom Upstairs

BetsyRating, 5 stars4 days ago
Our host was kind and responsive. The airBB is an upstairs unit with 2 nice bedrooms, remodeled bathroom and kitchen, living room. The location is not really walkable but within a mile of Flamingo Inn and close to Montgomery Village with all its restaurants and shops. We enjoyed the stay.

Home rentals in Healdsburg

Guest favorite
Home in Napa
4.91 out of 5 average rating, 173 reviews

3 Blocks from downtown Napa

ChaneyRating, 5 stars6 months ago
Nice home in a nice neighborhood with a beautiful yard. Linden made our stay easy which was much appreciated since we were in town for a funeral.
Superhost
Home in Healdsburg
4.81 out of 5 average rating, 145 reviews

Spectacular Vineyard View!! SPA, Close to Plaza!

ZakRating, 5 stars1 week ago
Loved our stay and would be happy to come back on our next trip
Superhost
Home in Sonoma
4.79 out of 5 average rating, 212 reviews

Casa Bonita- A Wine Country Retreat

SimonRating, 5 stars6 months ago
This was the best place we could've stayed at for our trip to Sonoma. We utilized Barry's recommendations of restaurants in the area every day and they were all spot on! Great location, and great host.
Superhost
Home in Windsor
4.87 out of 5 average rating, 133 reviews

Charming Windsor Home

JoshuaRating, 5 stars2 weeks ago
The best cozy house to visit Windsor. Our family comes every year for the Pliny celebration, it was just the right distance to the brewery. The house is also short walking distance to a nice, clean park for the kids the let out energy. We couldn’t have asked for a better place or hosts. The attention to detail and thought that went into what a guest would need to have the perfect stay was amazing. 
Top guest favorite
Home in Guerneville
4.99 out of 5 average rating, 103 reviews

The Ranchette- luxe 1 BR w/hot tub/ & prvt. patio

MichaelRating, 5 stars1 week ago
I was honestly shocked at how nice this place was. It’s so peaceful and quiet, the back space with the hot tub is private with lots of sunshine, and the house was stocked with everything we could need. It’s not too long of a walk to town. Sean was very friendly and made sure we were taken care of. Highly recommend for a weekend couples getaway.
Guest favorite
Home in Sebastopol
4.91 out of 5 average rating, 172 reviews

Grateful Home

RobertaRating, 5 stars1 month ago
A quick but lovely stay in Sebastopol. The house is just as pictured and spotlessly clean. Beds and furniture are comfortable and the rooms are very spacious. Bonus: there are lots of closets with quality hangers! Downtown attractions are walk-able and this home is well-located for guests wanting to explore Sonoma's wine country or the coast/Russian River. There's a Keurig and electric kettle for morning beverages in the nice kitchen, but The Grateful Bagel is literally next door and delicious. Vann was excellent at communication, providing detailed information about the house and location. Easy to find and made for a terrific getaway. Would definitely stay again!
Guest favorite
Home in Napa
4.94 out of 5 average rating, 328 reviews

Casita Rosa - Luxury in Downtown Napa

KdRating, 5 stars2 weeks ago
what an incredible spot for enjoying all that Napa has to offer. perfect layout for 2 couples, and the kitchen and dining room were perfect for gathering. would definitely stay again.
Guest favorite
Home in Sonoma
4.93 out of 5 average rating, 112 reviews

Wine Country Escape with 4 King beds & hot tub!

KristinRating, 5 stars1 month ago
Really enjoyed our stay here while visiting wineries in Sonoma and Napa! The place felt like home and was very well appointed with everything we needed. We brought our 1 year old son along and they had many baby items we were able to use and it was easy to keep the main living area pretty baby safe for a kiddo on the move. Location was great, quiet neighborhood but still close to many wineries and downtown Sonoma. Just be aware of strict noise policy at nighttime so don’t plan to use the hot tub/fire pit super late at night. Overall was a great stay and would stay again if we come back!

Quick stats about vacation rentals in Healdsburg

  • Total rentals

    140 properties

  • Nightly prices starting at

    ﺩ.ﺇ367 before taxes and fees

  • Total number of reviews

    6.5K reviews

  • Family-friendly rentals

    90 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Healdsburg?

    Yes! Work meets play with ease at over 70 vacation rentals in Healdsburg featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Healdsburg?

    Four-legged friends are welcome in Healdsburg. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there Healdsburg vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Healdsburg, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in hotel rentals in Healdsburg?

    Experience the best of Healdsburg with our hotel rentals, starting at about $400 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Healdsburg have a bbq area?

    Absolutely! We offer over 40 house rentals with a bbq area in Healdsburg. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Healdsburg have self check-in?

    Absolutely! We offer over 30 house rentals with self check-in in Healdsburg. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Healdsburg have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Healdsburg. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Healdsburg?

    Healdsburg has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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