A Private wine country vacation rental
The Oak Villa
Six bedrooms. 25-mile views. One of wine country’s best-kept secrets.
The kind of place your guests talk about long after they leave.
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Our Family’s retreat. Now yours.
Welcome Home
This is where our family escapes the noise of everyday life. We don’t share it with everyone — just a discerning few who will love it the way we do.
You won’t find the Oak Villa on Airbnb or VRBO. No third-party platforms. No algorithms. No double-bookings. When you book with us, you book directly — and the entire villa is yours, guaranteed.
We keep it this way on purpose. To protect the property. To know who’s coming. And to make sure every guest feels the difference.
Photo Gallery
Built for Gathering
That spirit is still here
The Oak Villa was designed by Ken Kragen and architect Woody Woodruff as a personal residence — not a rental property.
8,200 square feet of Mediterranean architecture. Six bedrooms with views from every window. A chef’s kitchen made for long mornings. A fourth-floor observatory with a retractable roof and professional telescope.
This is where Kragen hosted Kenny Rogers, Lionel Richie, and friends. Where astronomers from Berkeley came to stargaze. Where family gathered for weeks at a time
See Yourself Here
Wake up and walk to the window. Rolling hills stretch toward the horizon. Your people are already downstairs — coffee brewing, no rush, nowhere to be.
Spend the afternoon by the pool. Play pickleball on the Oak Court. Watch the sunset from the terrace with a glass of something good.
No schedule. No shared walls. No compromise. Just you, your people, and the hills.
Kind Words
Two Ways to Enjoy the Oak Villa
The Oak Villa is included with every wedding & specialty event package — along with exclusive access to all event spaces across the estate.
Your bridal party gets ready upstairs. The groomsmen gather below. Your ceremony happens steps away. And at the end of the night, you walk to bed — no shuttles, no goodbyes. Everything in one place.
This is what makes Eagle Oak Ranch one of the most sought-after central California wedding venues. The place you stay and the place you celebrate are one and the same.
Escape to the rolling hills of Paso Robles wine country. The Oak Villa is your private retreat — six bedrooms, an infinity pool, a chef’s kitchen, and views that don’t quit.
Spend your days wine tasting, relaxing poolside, or doing absolutely nothing. While you’re here, ask about a private tasting of our California extra virgin olive oil — pressed from the grove just beyond the terrace.
Perfect for: Family reunions. Milestone birthdays. Friendsgivings. Corporate retreats. Or a quiet week with someone you love. You decide how you spend your time — we just make sure you have everything you need.
Details
We handle the details. You enjoy the moment.
Curated Experiences
At the Table
A private chef preparing dinner in your kitchen. A tasting of our estate-grown California extra virgin olive oil on the terrace. A sommelier-led wine tasting featuring Paso Robles favorites from our family’s cellar. Breakfast delivered so you can sleep in.
Across the Estate
Explore 751 acres on horseback with a guided equestrian tour. Take the UTVs out to the Lookout Point where Dolly and Kenny once sang. Pack a picnic and find your own quiet spot in the hills. Or head up to the fourth-floor observatory after dark — the skies here are extraordinary.
Beyond the Gates
Paso Robles wine country is minutes away. We’ll arrange private tastings at our favorite local wineries, reserve the best tables, and coordinate drivers so no one has to navigate unfamiliar roads. Just tell us what you like — we know who to call.