Villa holiday rentals in Kenwood

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

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.

5 Acre Villa Retreat w/ Vineyard, Pool, & Spa

Nestled on over 5 acres in Sebastopol, Burnside Villa is a luxury 4-bedroom, 4.5-bathroom Wine Country retreat with expansive vineyard views, spacious rooms, and exceptional outdoor amenities. Ideal for families or groups, this estate offers the ultimate Wine Country experience—whether you’re here for tasting tours, coastal adventures, or simply to unwind in a beautiful setting. •10 mins to Downtown Sebastopol •20 mins to Bodega Bay •30 mins to the Russian River •1 hour to San Francisco

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

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

Resort style house w/Spa & pool between Napa/SF

Spectacular views in a safe, secure location! This resort-style hilltop home lies between Napa Valley and the San Francisco Bay Area, offering stunning sunsets, bay, and mountain views. Enjoy retreat-style living with a chef’s kitchen. Just 5–10 minutes from Starbucks, grocery stores, fine dining, entertainment, and golf. Ideal for weddings, family gatherings, business trips, vacations, concerts, or wine tasting adventures—this destination has it all.

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.

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

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

★ PROPERTY HIGHLIGHTS ★ ✔ Pool/Spa: Enjoy the vineyard setting from the pool or sunken spa. ✔ Tennis/Pickleball: One of the very few properties with both! ✔ Bocce Ball Court: Have fun with friends/family playing Bocce. ✔ BBQ: Dine al fresco while eating a delicious BBQ lunch. ✔ Fire pit: The perfect spot to relax and enjoy wine with friends.

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.

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.