Villa vacation rentals in Healdsburg

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Popular amenities for Healdsburg villa rentals

Private villa rentals

Guest favorite
A serene outdoor area features a crystal-clear pool and an attached hot tub, surrounded by lounge chairs. Shade is provided by umbrellas over the seating area. Lush greenery and decorative plants enhance the tranquil environment, with a charming villa visible in the background.
Villa in Napa
4.95 out of 5 average rating, 146 reviews

An Italian Villa in the heart of Napa Valley!

CarliRating, 5 stars1 month ago
Could not have been a more perfect place for a girls weekend in Napa! House was extremely clean. Easy to communicate with the host. Would definitely stay again!
Guest favorite
A serene outdoor space showcases a sparkling swimming pool surrounded by lush greenery. A deck with seating options can be seen adjacent to the pool, providing a relaxing area for guests. The expansive landscape offers a beautiful view under a clear blue sky.
Villa in Santa Rosa
4.92 out of 5 average rating, 142 reviews

Villa Annadel - Stunning 5 Bedroom with a Pool

JeanneRating, 5 stars3 weeks ago
Great place for a multi-generational gathering. There were many spaces to gather and the home is large enough to peel off for some quiet time. The outdoor spaces are lovely and private and the pool makes for a beautiful setting. The kitchen has plenty of glassware, dinnerware and flatware which makes feeding a crowd for several meals a day very do-able. Spring lake park is accessible by a path just up the road and the trail around the lake makes for a lovely walk/run. Folks enjoyed "practicing" their fishing techniques but didn't get a nibble. Proximity to Rossmoor community made this a very pleasant getaway with very little travel for our older parents.
Superhost
The exterior of the lodge is surrounded by lush greenery and mature palms, highlighting a mix of natural stone and wood finishes. A stone pathway leads to an inviting entrance flanked by steps, enhancing the connection to the serene outdoor space.
Villa in Geyserville
4.95 out of 5 average rating, 39 reviews

Adventure Alexander Valley Lodge w/ Pool & Hot tub

EvanRating, 5 stars1 month ago
Absolutely perfect place for our family and kiddos! It was above and beyond expectations. And Scott was a super host. Thank you so much for helping us build magical memories with friends and family.
Superhost
A wooden balcony offers a view of the surrounding landscape at sunset. The space features a built-in bench along the railing, with tiled flooring and a stone chimney visible in the background.
Villa in Penngrove
4.92 out of 5 average rating, 104 reviews

Charming Home in Penngrove

MoyraRating, 5 stars3 months ago
Frank was very easy to work with and was extremely responsive. Penngrove is such a quaint town. Franks place feels like a treehouse! So beautiful inside and out.
Superhost
A backyard area features a modern swimming pool surrounded by a wooden deck. Lounge chairs are positioned under umbrellas on one side, while a spacious main house with multiple entries is visible in the background among lush greenery.
Villa in Sebastopol
4.95 out of 5 average rating, 75 reviews

Green Valley Retreat ~ Wine Country, Pool & Hot

JamesRating, 5 stars3 months ago
Truly perfect house in the perfect setting. Great for our family but would come back as a couples retreat to. The landscaping, amenities and quality of everything is top notch.
Top guest favorite
The exterior of the house is presented at twilight, showcasing its elevated design supported by red stilts. Lush greenery lines the driveway, with pine trees in the background. A colorful sunset creates a serene backdrop that enhances the peaceful rural setting.
Villa in Santa Rosa
4.95 out of 5 average rating, 22 reviews

Mountain Villa near Calistoga with Hot Tub

MilanRating, 5 stars1 week ago
what an amazing place and such great hosts. everything was smooth and easy, the place was great.
Guest favorite
A heated pool is framed by a spacious patio featuring outdoor seating and an umbrella. The villa's exterior is characterized by earthy tones with large windows providing views of the surrounding greenery. The sky is bright with scattered clouds above.
Villa in Santa Rosa
4.89 out of 5 average rating, 94 reviews

Spacious wine country villa with pool

KatyRating, 5 stars4 months ago
We really enjoyed our Thanksgiving stay at this beautiful property. Our kids loved the swing set, the yard, watching deer and listening to frogs, and all the toys and games inside. The adults in our party enjoyed the gorgeous scenery and spacious clean property.
Guest favorite
A solar-heated pool glistens under sunlight, surrounded by a grassy lawn and majestic oak trees providing shade. Lounge chairs are positioned neatly along the pool's edge, while a covered terrace is visible in the background, enhancing the outdoor relaxation space.
Villa in Sonoma
4.98 out of 5 average rating, 203 reviews

Twin Oaks • Pool, Garden, Terrace, Bocce & Hot tub

KarenRating, 5 stars3 days ago
The location for a multi family long weekend was perfect! We all had our own indoor space and the outdoor living area was amazing! The home was very inviting and worked well for our group of 8 adults.

Luxury villa rentals

Guest favorite
A serene outdoor area features a crystal-clear pool and an attached hot tub, surrounded by lounge chairs. Shade is provided by umbrellas over the seating area. Lush greenery and decorative plants enhance the tranquil environment, with a charming villa visible in the background.
Villa in Napa
4.95 out of 5 average rating, 146 reviews

An Italian Villa in the heart of Napa Valley!

CarliRating, 5 stars1 month ago
Could not have been a more perfect place for a girls weekend in Napa! House was extremely clean. Easy to communicate with the host. Would definitely stay again!
Guest favorite
A serene outdoor space showcases a sparkling swimming pool surrounded by lush greenery. A deck with seating options can be seen adjacent to the pool, providing a relaxing area for guests. The expansive landscape offers a beautiful view under a clear blue sky.
Villa in Santa Rosa
4.92 out of 5 average rating, 142 reviews

Villa Annadel - Stunning 5 Bedroom with a Pool

JeanneRating, 5 stars3 weeks ago
Great place for a multi-generational gathering. There were many spaces to gather and the home is large enough to peel off for some quiet time. The outdoor spaces are lovely and private and the pool makes for a beautiful setting. The kitchen has plenty of glassware, dinnerware and flatware which makes feeding a crowd for several meals a day very do-able. Spring lake park is accessible by a path just up the road and the trail around the lake makes for a lovely walk/run. Folks enjoyed "practicing" their fishing techniques but didn't get a nibble. Proximity to Rossmoor community made this a very pleasant getaway with very little travel for our older parents.
Superhost
Villa in Monte Rio
4.74 out of 5 average rating, 31 reviews

Rivendell – Lovely Riverfront Home, Classic Style

AshishRating, 5 stars4 months ago
Great place as described!! Highly recommend for large families. Megan was very helpful.
Superhost
The exterior of the lodge is surrounded by lush greenery and mature palms, highlighting a mix of natural stone and wood finishes. A stone pathway leads to an inviting entrance flanked by steps, enhancing the connection to the serene outdoor space.
Villa in Geyserville
4.95 out of 5 average rating, 39 reviews

Adventure Alexander Valley Lodge w/ Pool & Hot tub

EvanRating, 5 stars1 month ago
Absolutely perfect place for our family and kiddos! It was above and beyond expectations. And Scott was a super host. Thank you so much for helping us build magical memories with friends and family.
Superhost
A backyard area features a modern swimming pool surrounded by a wooden deck. Lounge chairs are positioned under umbrellas on one side, while a spacious main house with multiple entries is visible in the background among lush greenery.
Villa in Sebastopol
4.95 out of 5 average rating, 75 reviews

Green Valley Retreat ~ Wine Country, Pool & Hot

JamesRating, 5 stars3 months ago
Truly perfect house in the perfect setting. Great for our family but would come back as a couples retreat to. The landscaping, amenities and quality of everything is top notch.
Top guest favorite
The exterior of the house is presented at twilight, showcasing its elevated design supported by red stilts. Lush greenery lines the driveway, with pine trees in the background. A colorful sunset creates a serene backdrop that enhances the peaceful rural setting.
Villa in Santa Rosa
4.95 out of 5 average rating, 22 reviews

Mountain Villa near Calistoga with Hot Tub

MilanRating, 5 stars1 week ago
what an amazing place and such great hosts. everything was smooth and easy, the place was great.
Guest favorite
A heated pool is framed by a spacious patio featuring outdoor seating and an umbrella. The villa's exterior is characterized by earthy tones with large windows providing views of the surrounding greenery. The sky is bright with scattered clouds above.
Villa in Santa Rosa
4.89 out of 5 average rating, 94 reviews

Spacious wine country villa with pool

KatyRating, 5 stars4 months ago
We really enjoyed our Thanksgiving stay at this beautiful property. Our kids loved the swing set, the yard, watching deer and listening to frogs, and all the toys and games inside. The adults in our party enjoyed the gorgeous scenery and spacious clean property.
Guest favorite
A solar-heated pool glistens under sunlight, surrounded by a grassy lawn and majestic oak trees providing shade. Lounge chairs are positioned neatly along the pool's edge, while a covered terrace is visible in the background, enhancing the outdoor relaxation space.
Villa in Sonoma
4.98 out of 5 average rating, 203 reviews

Twin Oaks • Pool, Garden, Terrace, Bocce & Hot tub

KarenRating, 5 stars3 days ago
The location for a multi family long weekend was perfect! We all had our own indoor space and the outdoor living area was amazing! The home was very inviting and worked well for our group of 8 adults.

Villa rentals with a pool

Villa in Santa Rosa
4.71 out of 5 average rating, 21 reviews

Vineyard Villa: Pool/Spa | Pickleball/Tennis | Dog

Nicholas RobertRating, 5 stars1 week ago
Such a good few days - we could escape from everything by staying in what is almost a resort while so easy to get to so many great wine destinations - we have a 5, 17 and 19 year old and all three where more than well occupied and loved the space. Will definitely return when we can...
A private patio is visible through glass doors, featuring a stone floor and surrounded by lush greenery. Several outdoor tables are placed near planters, with a mix of shrubs and tall plants creating a tranquil setting.
Villa in Bodega
4.63 out of 5 average rating, 40 reviews

Grand Residence at Sonoma Coast Villa

DaphneRating, 5 stars9 months ago
The villa is even more spacious in person than photos. It is separated from the rest of the hotel so we enjoyed the privacy while still being able to access the amenities and host support. Kitchen is huge but only has basic seasoning options (salt & pepper) so you might want to bring your own seasons if you want to cook dinner there. Great foods, beaches and activities (horseback riding, fishing etc) are only within 5-20min drive. Our family had a great time!
An outdoor patio area is surrounded by palm trees, offering views of the distant hills. The space features a stone pathway, a seating arrangement with four chairs, and a small table. Colorful plants add a natural touch to this tranquil setting.
Private room in Geyserville
5 out of 5 average rating, 3 reviews

Alexander Valley Lodge - Queen Room

GalenRating, 5 stars124 months ago
The hosts were awesome and Danielle was very generous. This is a GREAT place to use a base for wine tasting. They serve wine and cheese in the afternoon, and breakfast was delicious. They also have tons of connections to the local wineries, and we were always treated wonderfully when we mentioned we were staying at the Alexander Valley Lodge. The lodge and the property are beautiful and comfortable; this would be an awesome place for parties.
A stone patio area features a set of outdoor furniture surrounded by lush greenery and palm trees. A small water feature is visible, with the backdrop of rolling hills beneath a bright sky, creating a serene environment for relaxation.
Private room in Geyserville
4.83 out of 5 average rating, 6 reviews

Alexander Valley Lodge - Jr Suite

DonaldRating, 5 stars66 months ago
Danielle heard that there would be power outages due to high winds and fire danger in Geyserville so seamlessly found us another bnb in Healdsburg. Thank goodness, as there was a fire and all Geyserville got evacuated. This is a high level of customer service and a tribute to how the inn keepers in Sonoma look out for their guests and each other. Thanks Danielle, you saved our trip. We’ll be back.
Superhost
A spacious deck is featured, surrounded by bamboo and palm trees, providing a serene atmosphere. Comfortable seating is arranged for relaxation, with sunlight filtering through the greenery and a clear sky above, creating an inviting outdoor space.
Private room in Santa Rosa
4.7 out of 5 average rating, 123 reviews

Beautiful En-suite bedroom with balcony -room3

MiriamRating, 5 stars3 weeks ago
I enjoyed staying at Ruby's. It was peaceful, clean quiet for my last night in California and easy to get to the airport from there.
A landscaped outdoor area features a stone-paved terrace surrounded by palm trees and shrubs. A dining set with four chairs and a table is visible, offering a scenic view of the rolling hills and trees in the distance under a cloudy sky.
Private room in Geyserville
4.64 out of 5 average rating, 14 reviews

Alexander Valley Lodge Valley View Grand Suite

LucasRating, 5 stars127 months ago
I could not have asked for anything more. It was the perfect setting for my girlfriends birthday. Looking out the lodge's windows are like looking into a beautiful painting. Our host Daniell was exceptional, very warm and open. All in all I could not recommend that place more. It is close to many beautiful wineries and if you dont feel like leaving the lodge there is plenty to do there. perfect place to stay.
A serene outdoor pool area is surrounded by lush greenery and tall trees. Sun loungers are positioned nearby for relaxation. Soft reflections are visible on the water's surface, creating a calm ambiance. The space is designed for enjoyment and provides a quiet retreat.
Villa in Calistoga
4.5 out of 5 average rating, 12 reviews

Villa in French Chateau Estate in Napa Valley

JamesRating, 5 stars2 months ago
Our family of three really enjoyed the stay in Calistoga. The house is great and very clean. The location is beautiful and very peaceful. The house is close to 5 min away from downtown and we drove there a few times for meals. We also visited the petrified forest which is about 15 min away. Overall was a great stay.
Villa in Geyserville
4.71 out of 5 average rating, 84 reviews

Alexander Valley Lodge Pool/Hot Tub

HeidiRating, 5 stars62 months ago
We had a fabulous time as a group of 10 girls celebrating my sister's engagement. The house has the most beautiful view and did not disappoint! The best part of our experience was that Danielle was SO helpful in planning our wine tasting day and giving recommendations. We were unfamiliar with Alexander Valley, and she was able to help us coordinate and afforable, unforgetable day visiting wineries!

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