Villa holiday rentals in Healdsburg

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

3-BR/2-BA Main house + 1BR Pool House 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.

Private 1+ acre, Bocce, Waterfall, Free Pool Heat

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.

Mountain Villa 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.

Boutique Compound on Vineyard, with Guest House

Mille Vigne is a designer boutique compound on a vineyard tucked in the St. Helena mountains. Wrap-around terraces offer panoramic vineyard views. Primary villa features two bedrooms with private baths, cook's kitchen, living room, dining room, and loft with day bed. Private guest house has large terrace with vineyard views, dining room, fireplace, kitchenet and large bathroom. Grounds include manicured gardens complete with paths, romantic nighttime lighting and a hot tub on the vineyard.

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!

Exclusive Forest Retreat, 8 private acres +Hot Tub

Welcome to Foresta Retreat! -Between Russian River and the Sonoma Wine Country -A steaming hot tub beneath surreal starry skies at night -Expansive panoramic treetop deck for lounging, yoga, sipping wine and stargazing -Sunbathing beds to soak in the sun -full privacy with no neighbors, surrounded by untouched forest -Luxurious European linen bedding -BBQ and outdoor dining space overlooking forest mountains -120" cinematic TV projector for slow dreamy evenings

Farmhouse Villa w/ Captivating Views & Hot Tub

Experience the ultimate Wine Country escape. The property sits on 11 private acres, offering complete privacy, peaceful surroundings, and stunning 360-degree views, including the iconic Mount Helena. Ideally located near Calistoga (15 minutes) and Healdsburg (20 minutes) and surrounded by top-rated wineries. Whether you’re here for wine tasting, relaxation, or a scenic getaway, this property delivers space, comfort, and unforgettable views.

Luxury 3BR Retreat | Designer Home in Glen Ellen

Escape to Sonoma Valley in this stunning 3-bedroom luxury retreat in Glen Ellen. Thoughtfully designed with high-end finishes and refined wine country style, this private home offers the perfect setting for elevated getaways, wine weekends, and relaxing escapes. Whether you're here for world-class wineries, weddings, or a restorative retreat, this beautifully curated space delivers comfort, style, and privacy.

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

★ PROPERTY HIGHLIGHTS ★ ✔ Swiming Pool: Enjoy swimming or relaxing on the chaise lounges at the private pool. ✔ Hot Tub: Marvel at the night sky while relaxing in the sunken hot tub. ✔ Games: Challenge other guests to a game of Pool, Foosball, or Basketball. ✔ BBQ: Dine al fresco while eating a delicious BBQ lunch. ✔ Views: Enjoy spectacular views of vineyards and the surrounding mountains.

When in Glen | Views | Pool & Hot Tub

Welcome to your peaceful dream retreat in Glen Ellen! This hidden gem features breathtaking views and stunning sunsets. Located in the heart of wine country, just minutes away from world-class vineyards, charming boutiques, and top-rated restaurants. Relax by the pool or in the hot tub with a view. This thoughtfully designed home offers brand-new appliances and quality furnishings. No pets.

Upstairs Oasis • Check our Midweek Specials !

Russian River Retreat w/ Deck, Fire Pit & BBQ Beautiful upstairs unit with a spacious private deck—perfect for wine, BBQ, and relaxing by the fire pit. Walk to the river, beaches, restaurants, shops & grocery (under 1 mile). Near wineries, kayaking & canoe rentals at Burke’s Canoes & Johnson’s Beach. 4 parking spaces near stairs. No guest canoe use. Quiet hours 10pm–7am. TOT #4081N

Charming Home in Penngrove

Whether you plan on touring wine country, or hosting a gathering, this enchanting home will make your stay truly memorable. Nestled in a serene garden, within miles of your favorite wineries, featuring vaulted ceilings, Marvin windows, energy efficient fireplaces, chefs kitchen with Wolf Range and private entrances to each bedroom.