Villa holiday rentals in Kenwood

Serene Retreat! Amazing Views! Minutes to Plaza!

New to Airbnb but highly rated with over 145 5 star reviews on other platforms! Villa Serena is located on 1/2 acre in the prestigious Mission Highlands, just a 6 minute drive from the historic Sonoma Plaza. This luxurious home is beautifully appointed, with impeccable attention to detail. Surrounded by majestic oaks, olive trees, and maples, Villa Serena offers secluded privacy, a lush garden setting and pool area, and an expansive deck with sweeping views of the Sonoma Valley and Mount Tam.

Location · View · Bathroom

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

Location · Value · Heating

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 · Amenities

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.

Location · Family · Indoor spaces

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 · Location · Quiet

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 · Parking

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 · Location · Amenities

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.

Location · Family · Checkout

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.

Location · Family · Condition

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

Family · Location · Heating

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 · Family · Air conditioning

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 · Condition