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.

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

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!

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.

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.

Elephant Master Suite | Private Vineyard Retreat

Contemporary farmhouse chic - the Elephant Suite is a large, airy, and bright getaway. Enjoy your own private master bedroom suite with a private entryway and parking, a private patio, as well as a peaceful sitting room and stunning bathroom. Self-check-in. We maintain clean, sterile environments using current industry standards for sterilizing hard surfaces, appliances, and guest areas. We are a licensed short-term rental. Ask about our other Napa listings if the dates here are booked.

An Italian Villa in the heart of Napa Valley!

Villa RayEl was inspired by the farmhouses and small villas of Italy. This rustic 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 and several outdoor living spaces. 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 -EV Charger -BBQ and outdoor dining space overlooking forest mountains -120" cinematic TV projector for slow dreamy evenings

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.

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.

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.

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.