Villa vacation rentals in Healdsburg

Find and book unique villas on Airbnb

Top-rated villa rentals in Healdsburg

Guests agree: these villas are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

Villa in Novato

4.91 out of 5 average rating, 232 reviews

The Blue Heron

Amazing creekside listing in vacation-ready Bel Marin Keys! Completely remodeled villa featuring stunning open space views! Come experience our beautiful sunrises and sunsets in a private and comfortable location for your family/group! Spacious Mediterranean interior with beautiful bamboo floors and stainless steel appliances! Kayak off your own private dock and explore the Novato Creek to the San Pablo Bay! Bird watch and spot a blue heron! Enjoy your hot tub on the deck! Coffee pods included!

Sep 8 – 15

$356 per night

Guest favorite

Villa in Sonoma

4.98 out of 5 average rating, 182 reviews

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

3-BR/2-BA Main house + Private Cottage with Bathroom Spanish style home located on a quiet lane surrounded by rolling hills of vines. The inside features an open floor plan with gourmet and fully equipped kitchen, living room, TV Room, spacious bedrooms, hardwood floors and designer furniture. The outside area has a covered terrace ideal for dining and lounging. Expansive garden with many trees and a pool under majestic oaks. Minutes (by car) from Sonoma, Glen Ellen, Restaurants and vineyards.

Mar 6 – 13

$767 per night

Guest favorite

Villa in Santa Rosa

5.0 out of 5 average rating, 33 reviews

Modern Farmhouse Villa with Captivating Views

Newly renovated modern farmhouse villa on 11 acres of private property. With expansive decks surrounding the house, you can view both sunsets and sunrises while enjoying serene unobstructed views of Mount Helena. Perfectly situated between cities of Calistoga (15 mins away), Healdsburg (20 mins away), and surrounded by wineries, this is the perfect place for you and your friends/families to decompress. Brimming with natural light and 360 degree views, this cheerful home will leave you in awe!

Jun 9 – 16

$711 per night

Guest favorite

Villa in Santa Rosa

4.95 out of 5 average rating, 64 reviews

Private 1+ acre, Bocce, New Heated Pool & Hot Tub

With over 1 acre of flat wooded land, this private gated country estate is still just a few minutes from conveniences like Whole Foods and Safeway. And with a full-size bocce court, pool table, and dining pavilion, you might not want to leave. Our new saltwater pool and spa are gas-heated to be comfortable all year, at no extra charge. A rock river and pool waterfall add to the sound of rushing water. The house is a few minutes from downtown, and within 20 minutes of the highlights of Sonoma.

Oct 31 – Nov 7

$816 per night

Guest favorite

Villa in Santa Rosa

4.91 out of 5 average rating, 11 reviews

Mountain Villa near Calistoga

This unique spot in the mountains between Napa & Sonoma Valleys is 10 minutes from Calistoga & 13 minutes from highway 12 through Sonoma Valley. You’ll have fantastic views of the mountain forest and constellations in the night sky, while sharing the property with deer & other wildlife. You will immediately notice the quiet nature & the smell of trees. There are many attractions nearby, including Russian River, Safari West, Petrified Forest, various hot springs, & wineries galore to explore.

Jun 30 – Jul 7

$275 per night

Guest favorite

Villa in Napa

4.96 out of 5 average rating, 102 reviews

An Italian Villa in the heart of Napa Valley!

Villa RayEl was inspired by the farmhouses and small villas of Italy. Located midway between downtown Napa and Yountville, this property sits on 2 acres providing great privacy. It sits next to a year-round creek with a view of a vineyard and nightly sunsets. It has a pool and an attached hot tub. Located 5 minutes off Highway 29, 8 minutes to Downtown Napa and 8 minutes to Yountville. It is convenient to great wineries, restaurants. Its the perfect getaway for families and friends!

Apr 14 – 21

$770 per night

Guest favorite

Villa in Jenner

4.97 out of 5 average rating, 135 reviews

Villa Vista, The Absolute Jewel of Jenner

A tri-level apartment with stunning water views from each floor. A private deck off the master bedroom overlooking the Russian River and the Pacific OceanBreathtaking views of the Russian River & the Pacific from this private suite. A short stroll down the hill brings you to kayak rentals & Cafe Aquatica for best coffee, sandwiches, pastries, & live music on the weekends. A short stroll uphill brings you to the Jenner Headlands gate which you can enter with our proprietary code.

Apr 2 – 9

$350 per night

Guest favorite

Villa in Cazadero

4.95 out of 5 average rating, 210 reviews

Luxury in Redwoods w/ Hot Tub and Fire Pit

Elements is a sophisticated estate compound set on landscaped acres, hidden amongst redwood groves. Your friends & family will find privacy and seclusion while being close to all that wine country has to offer. A variety of unique amenities will make your stay unforgettable: a jetted hot tub in a circle of redwoods, several decks & lounge areas, a yoga/exercise studio, an outdoor shower, a board game collection, fast internet and 150+ channels of sports/movies

Jan 27 – Feb 3

$777 per night

Superhost

Villa in Sonoma

4.68 out of 5 average rating, 22 reviews

The Cline Winery Vineyard Estate

Discover Wine Country luxury at its best! Experience the Cline Vineyard Estate, nestled within the scenic Cline Family Cellars winery in Sonoma Valley's Carneros Region. This private retreat boasts 4 king en suite bedrooms, each offering unique features such as balconies, French doors, and tranquil garden views. Outdoor amenities include a pool, hot tub, fire pit, BBQ, and alfresco dining. Plus, enjoy a complimentary tasting for up to 10 guests with every stay.

Feb 28 – Mar 7

$879 per night

Superhost

Villa in Healdsburg

4.94 out of 5 average rating, 114 reviews

Hilltop Vista Villa

Set on an Acre by Fitch Mountain Park and Open Space Preserve, Hilltop Vista Villa offers a quiet private setting, spectacular views of world class vineyards, private access to hiking trails and proximity to the Russian River beach. This inviting single level retreat has an open floor plan with lots of sunshine. The open kitchen features stainless steel appliances, custom cabinetry, and a granite topped island. The Master Suite includes a custom soaking tub.

Mar 9 – 16

$395 per night

Superhost

Villa in Sebastopol

4.95 out of 5 average rating, 66 reviews

Green Valley Retreat - Luxury Home in Wine Country

Green Valley Retreat is a wine county gem near renowned restaurants and wineries. You can pick fresh produce from the massive guest garden and orchard and then enjoy it inside or out. The large back deck has an in-line gas BBQ and guests love cooking outside. The backyard contains a meadow of native bunch grasses along with a stand of redwood trees, oodles of flowers and one of our favorite built-in propane fire pits. BYOM (Bring Your Own Marshmallows).

Oct 30 – Nov 6

$780 per night

Guest favorite

Villa in Santa Rosa

4.9 out of 5 average rating, 71 reviews

Spacious wine country villa with pool

Relax with your whole family in this spacious Sonoma wine country villa, with beautiful greenery all around, scenic vistas, and easy short drives from great family-friendly wineries, hiking trails and conveniences. No matter your preference - either a relaxed stay far away from civilization, or a roomy place for family get-togethers, this place has it all. Pool is heated from June - September only. TOT #3719N

Jan 5 – 12

$585 per night