Villa holiday rentals in Santa Rosa

The Hilltop-5acre Oasis, Views, Hot Tub, Game Room

Surround yourself in serenity in this Eichler-inspired mid-century modern retreat that boasts majestic views and privacy, perched on 5 acres above the beautiful Russian River Valley. Watch birds soar over the towering redwoods through floor to ceiling windows, or unwind in the hot tub where the magnificent views create a perfect backdrop for relaxation. As the evening sets in, gather around the warm fire pit, or head to the game room that overlooks a large lawn to create memories for all ages!

Location · Family · River

Villa Annadel - Stunning 5 Bedroom with a Pool

Escape to your own private sanctuary at Villa Annadel. Savor the unparalleled privacy and modern sophistication of this one-of-a-kind wine country retreat. The expansive 3,200 square foot villa sits on just under 1.5 acres of privacy with a large sparkling pool, hot tub and outdoor dining gazebo. Game lovers will rejoice, from cornhole, to darts, ping pong and vintage arcade games. It’s easy to forget you are minutes from some of Santa Rosa’s finest restaurants and wine tasting destinations!

Location · Family · Cleanliness

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.

Family · Value · Backyard

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.

Value · Family · Hot tub

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.

Family · Value · Accuracy

Idyllic NatureEstate:Pool,Jacuzi,PuttGreen,Gardens

Mountaintop gated 1 acre nature estate, serene, private, 2300 sq' home; 2500 sq' expansive decks & patios. Solar heated swimming pool. Sun! Enormous forest views. 4BD,3 BA; (4th BD is large family room w/ exc American Leather queen sofabed, twin bed, pool table). Living room fireplace; high speed wi-fi; 65"tv; prem cable pkg. Jacuzzi ($150 min. charge), WeberBBQ & outdoor sink. Putting green. Huge garden, patios, carpeted child's play area. Parties or events not allowed during Covid.

Family · Value · Checkout

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 -EV Charger -BBQ and outdoor dining space overlooking forest mountains -120" cinematic TV projector for slow dreamy evenings

Value · Location · Amenities

Luxury in Redwoods - Hot Tub & 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

Value · Family · Beach

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.

Family · Location · View

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

Value · Family · Wi-Fi

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.

Location · Value · Kitchen

Hilltop Villa with Sweeping Views & Trail Access

Perched above Fitch Mountain, this private hilltop villa offers sweeping wine-country views, direct access to scenic hiking trails, and peaceful seclusion just minutes from downtown Healdsburg. Bright interiors, high ceilings, and a fenced yard make it ideal for couples or small groups seeking a refined, nature-forward getaway.

Location · Family · Layout