Stay in the Beautiful Santa Ynez Valley

Explore Our Properties
We'll find you the perfect place to call home!

Who We Are

When I first relocated to the Santa Ynez Valley in 2016, I was captivated by the rolling hills, open pastures, and roads leading to picturesque fields adorned with oak trees, deer, horses, and cows. The sight of vast landscapes with solitary oak trees evoked a sense of tranquility and allure. The idea of reading a book or enjoying a picnic under those old oak trees sparked a sense of curiosity and calmness within me.

After several years of managing an estate vineyard in the Santa Rita Hills and historical bungalows in Los Olivos, I aspired to collaborate with homeowners who shared my vision for the valley. Together, we aimed to offer their personal homes to guests so they could experience the unique climate, natural beauty, and diverse wildlife of the central coast, even if just for a few days, weeks, or months.

My goal is to ensure that staying at one of our properties is a positive, personal, and memorable experience for our guests, homeowners, and local communities. We prioritize using high-quality linens, eco-friendly soaps, and encourage recycling to minimize our environmental footprint and impact on the homes. We strive to ensure that each stay is a suitable fit for both our guests and the surrounding community.

We invite you to be our guests, whether for a weekend, a week, or longer, so you can find inspiration under a random oak tree during your vacation and return home revitalized and refreshed.

Jordan Dorian
Random Oak Vacation Rentals

We offer Personal and Elevated Experiences

Random Oak Vacation Rentals boast unique characteristics that reflect the local culture and architecture of the Santa Ynez Valley. From charming cottages and homes to luxurious privately gated estates and modern apartments, the variety of options ensures that you will find a property that perfectly suits your preferences and enhances the overall experience of your vacation.

Reviews
Pearson's 1886 is absolutely stunning! Our group took over the entire property and each unit was beautifully appointed, super comfortable and our host Jordan couldn't have been more accommodating. We still can't stop talking about our stay.

If you're looking for a perfect getaway in the Santa Ynez Valley, you must check out Pearson's 1886!
Kenneth William
I cannot say enough about how much we loved staying at Jordan’s place! It exceeded our expectations from the moment we pulled into the driveway. The property and landscaping is beautiful. It has all sorts of nooks and crannies to discover - a little guest house, a jacuzzi, a veranda overlooking Los Olivos and multiple fire pits.

The inside of the house was just as great. It was clean and so aesthetically pleasing. It has all the amenities you could ever need. We adored this property and can’t wait to stay there again next time we are in the area.
Shannon
Perfect stay to walk everywhere in Los Olivos! We walked to all the great tasting rooms and restaurants. So convenient! The property itself is so relaxing and the beds were so comfortable! Every amenity you could ask for was there! Thank you for the fantastic stay!
Sarah
Enjoying The Santa Ynez Valley
Things to do
Restaurants & Tasting Rooms