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

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.

Private Pool & Large Deck: Modern Cotati Villa!

Solarium | 3 Outdoor Dining Areas w/ Umbrellas | Mountain Views A truly high-end escape awaits at this stunning 4-bedroom, 3-bath Cotati vacation rental in the California Wine Country. Take a dip in the private pool, then prepare a delicious meal in the elegant kitchen and dine in the scenic solarium or out on the villa’s spacious deck. Use Greetwell's concierge services to book luxury experiences like private cooks and home massages before touring Korbel Winery or hiking in Armstrong Woods.

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.

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!

Spring Special:Resort 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.

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.

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

Upstairs Oasis • Deck, Fire Pit • Hot Tub-River

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.

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.