Olive & Oak

Forty acres of oak-studded hillside wrap around Olive & Oak, a modern retreat set high on Trinity Road where the Mayacamas foothills roll down toward the Valley of the Moon. Getting here is part of the appeal: a winding seven-minute climb up from the valley floor, curve after curve, until the road hands you over to something that feels entirely your own. Privacy is the whole point --- the nearest distraction is the view, which reaches across ridgelines and open valley in every direction, and the loudest thing you'll hear most mornings is birdsong. Walls of glass pull that landscape inside, opening the home's clean, open-concept layout to light and air from sunrise straight through to the golden-hour glow that settles over the hills each evening.

Outside is where the home really shows off. A 75-foot saltwater pool anchors the grounds, long enough for a dedicated swim lane and a real morning workout, framed by a pergola-shaded lounge and an outdoor dining setup made for long, unhurried meals under the open sky. There's a hot tub for cooler evenings, a sauna for a proper reset, an outdoor shower for rinsing off between swims, and a half bath right off the pool deck so nobody has to track water through the house. A full outdoor kitchen --- BBQ plus its own refrigerator --- means dinner never has to move indoors, and rows of olive trees and silvery olive bushes give the whole setting a Mediterranean ease that feels right at home in Sonoma.

Inside, the floor plan keeps everyone connected. The full kitchen is ready for real cooking and stocked with the everyday essentials --- coffee, tea, olive oil, and a lineup of pantry basics --- so slow mornings and group dinners come together without a supply run. A separate TV room and den give the crew a place to spread out, and a dedicated laundry room keeps longer stays easy. Every bathroom is stocked with full-size Grown Alchemist bath amenities --- proper bottles, not travel minis --- so there's no rationing shampoo on day four.

Five bedrooms sleep ten in comfort. Four are set with king beds, each a quiet corner to retreat to, and the fifth holds two twins --- an easy fit for kids or friends splitting a room. Every bedroom comes with its own desk and chair, which makes a working morning or a longer stay far simpler than it usually is in a house built for a group. Four full bathrooms and a half bath mean there's rarely a wait, whether the house is winding down after a day out or gearing up for one.

The location threads the needle beautifully. That same seven-minute descent puts you on the Sonoma Valley floor, with roughly fifteen more over the ridge toward the Napa side, and Glen Ellen's easygoing village --- plus the beloved Glen Ellen Village Market for sandwiches and provisions --- waiting just down the hill. Jack London State Historic Park sits nearby, with shaded trails, historic ruins, and a hilltop museum to explore, and Sugarloaf Ridge State Park opens up miles of hiking and big-sky stargazing a short drive north. Down valley, the historic Sonoma Plaza rounds things out with its mission, shops, and tree-lined square. It's a rare kind of home base --- remote enough to feel like your own private ridge, close enough to be in the heart of wine country whenever you want to be.

AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we're at your fingertips.

Known for its vineyards, local cuisine, and nature parks, Sonoma County (45 minutes from San Francisco) offers a wide array of activities for those looking to retreat from city life. Touring local wineries, dining at farm-to-table restaurants, and visiting world-class spas are classic ways to experience the area. While unwinding is certainly the attitude in Sonoma, activities like horseback riding, hot-air ballooning, and kayaking attract those looking for a little adventure. In the evening, watch the sunset over the vineyards and rolling hills, wine glass in hand.

Local Attractions: Sonoma Plaza, Sonoma State Historic Park, Maxwell Farms Regional Park, B.R. Cohn Winery, Kunde Family Winery, Ledson Winery & Vineyards, Matanzas Creek Winery, Roche Winery, Maxwell Farms Regional Park, Sonoma Overlook Trail, The Girl & The Fig, Dutton Estate Winery, Merry Edwards Winery, Iron Horse Vineyards, Lynmar Estate, Armstrong Redwoods State Natural Reserve, Bohemian Highway, Bodega Bay

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Parking details

All bookings over 30 days require a security deposit to be charged after booking.

STR Permit: LIC26-0067