Villa vacation rentals in Healdsburg

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Top-rated villa rentals in Healdsburg

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Guest favorite

Villa in Novato

4.9 out of 5 average rating, 254 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!

Superhost

Villa in Geyserville

4.94 out of 5 average rating, 31 reviews

Adventure Alexander Valley Lodge w/ Pool & Hot tub

Your group will be comfortable in this spacious, unique pool villa on top of the hill overlooking Alexander Valley only 10 min to downtown Healdsburg. Lodge sits on 53 private acres with hiking trails, pool ( fee to heat), hot tub, tiki bar and pool table. There is plenty to do at this 4100 sq ft home both inside and out. Lawn games, fire pit, and BBQ are all there for you to enjoy. Set up a private wine tasting or chef services or wine tour. Just ask how we can help you plan your stay. 683N

Guest favorite

Villa in Santa Rosa

5 out of 5 average rating, 59 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!

Guest favorite

Villa in Santa Rosa

4.94 out of 5 average rating, 16 reviews

Mountain Villa near Calistoga with Hot Tub

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.

Guest favorite

Villa in Napa

4.95 out of 5 average rating, 133 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!

Superhost

Villa in Sonoma

4.8 out of 5 average rating, 10 reviews

Vineyard Villa: Pool | Spa | Games Room | EV Char.

Chardonnay View is a spectacular 3BR/3BA 1,805 Ft2 home located on a 5-acre lot with incredible views of the large swimming pool, hot tub, manicured garden, and vineyard. The home has a chef's kitchen, dining room with seating for 8 guests, designer living room with fireplace, family room, game room with a pool table, and al-fresco dining on the outdoor patio. There is also a basketball court on the driveway, which can also accommodate 4 cars. Book now for a vacation to remember!

Villa in Healdsburg

4.93 out of 5 average rating, 43 reviews

Healdsburg Wine Country

Situated on 3 acres in prime Sonoma wine country, the Chatthaveli home is a bucolic delight, located within minutes of downtown Healdsburg and award winning wineries like Aperture Cellars, J Vineyards and Rodney Strong. Sway on the porch swing with your morning cup of coffee, or enjoy the in-ground swimming pool and adjacent spa. Gather your friends and family around two large farm-style tables for al-fresco dining, or stay indoors at a custom live edge table for 8 in the dining room.

Guest favorite

Villa in Cazadero

4.95 out of 5 average rating, 219 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

Superhost

Villa in Healdsburg

4.95 out of 5 average rating, 148 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.

Superhost

Villa in Sebastopol

4.96 out of 5 average rating, 72 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).

Guest favorite

Villa in Santa Rosa

4.89 out of 5 average rating, 93 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

Guest favorite

Villa in Cazadero

5 out of 5 average rating, 39 reviews

A Grand Family Retreat Among the Redwoods

This beautiful private two acre family vacation retreat that has been passed down through generations and nestled among the towering California Redwoods along the banks of the Austin Creek in historic Cazadero. It is the perfect setting for a memorable vacation with family and friends or a romantic couple's getaway. It's the ideal spot to relax, unwind, and balance your life with nature.