Holiday rentals in Diablo Grande

Airstream With Gorgeous Views of Silicon Valley

Stay in a Vintage Airstream with Scenic Views Near San Jose, CA Escape to our beautifully restored vintage Airstream, perfectly located in the peaceful San Jose foothills. Just minutes from the heart of Silicon Valley, our hillside retreat offers stunning panoramic views, cozy charm, and easy access to top Bay Area attractions. Only 12 minutes from Highway 680, you're ideally situated to explore San Francisco, Santa Cruz, Napa Valley, and beyond — all while enjoying a quiet, nature-filled stay.

Private Guest-House in the Redwoods

Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

Adorable 2-bedroom country guesthouse

Our little guesthouse is located in the Central valley. It is nestled in an almond orchard on our family farm. Only a 1/2 mile from Highway 99 it has easy access to many of California’s beautiful sights. This home includes a cozy living room, two bedrooms (with a queen bed and a full bed) and a minimally stocked kitchen. It does include a Keurig. Only five minutes away are plenty of choices of fast food restaurants and grocery stores. There is also laundry soap available for washing clothes.

Beautiful Farmhouse in Walnut Orchard

Welcome to our charming farmhouse nestled in a picturesque 4 acre walnut orchard. Our home is located in the peaceful countryside, offering the perfect getaway for those seeking a break from the hustle and bustle of city life. Our farmhouse is pet-friendly, with beautiful sunrise over the orchard. Whether you're looking for a peaceful retreat or an adventure in the countryside, our farmhouse is the perfect home for your next vacation. Stay and experience the beauty and serenity of farm life.

Damon's Hideaway

Named after our first grandson, Damon's Hideaway is brand new construction (2023) that's designed to be unique and with a style all its own. We are former antique dealers and have tried to incorporate that interest in the whimsical decor. Whether desiring to kick back and relax or prepare a meal for a group, or both, this living space can easily accommodate. It's our wish that you thoroughly enjoy your experience, so please don't hesitate to contact us with any thoughts or concerns.

The Nest

Located just across the street from Lincoln Park, a family friendly park with walking paths. Upstairs is a Cozy Rustic Farmhouse studio with a 1940's charm. Exceptionally clean! Comfy queen size bed, hardwood floors with cowhide rug. Recliner chair for downtime and a desk for work time. Full kitchen to cook if desired or microwave to warm up takeout. For our guest who stay awhile and need to do Laundry, no problem. You have your own laundry room! We hope you enjoy your stay!

The Oasis

Welcome to your luxury retreat in Downtown Modesto! This fully remodeled 2BR/1.5BA Midcentury Modern home offers: • 1,150 sq ft of stylish double story home with spacious living space with new kitchen and baths • Large yard with paver-lined grass, Edison lights, and fire pit • 65” Smart TV, 1200mbps WiFi, 4K security system, and smart garage • Queen bed with desk, plus two twin beds, all with premium linens • Walking distance to fine dining, nightlife, and attractions

The Cottage at The A Bar

Kick back and relax in this calm, stylish cottage nestled in the middle of an almond orchard on a private road. Collect fresh eggs from the chickens for breakfast paired with fresh fruits and vegetables from the garden! Spend a peaceful evening sipping a beverage on the porch or take a relaxing walk along the river. Geographically speaking, we like to say we are in between The Golden Gate Bridge, San Francisco and Half Dome in Yosemite National Park.

Mountain Top Yurt in the Redwoods

Peaceful, clean, spacious, beautifully decorated and quiet 24' Yurt completely surrounded by Redwoods on top of the Santa Cruz Mountains. Spend a couple days meditating, reading or writing the next chapter of your memoir. Walking distance to Mount Madonna Retreat Center (open now through reservation only). County Park hiking and horseback riding trails located within 3 miles. Ideal place for photography and mountain/road biking.

La Loma Casita “B” - Entire House

This special place is close to everything, making it easy to plan your visit. Located in La Loma neighborhood. This Casita offers a fully stocked kitchen, laundry room (washer & dryer), queen size bed & 1 full bathroom. AC & Heather (via mini split system) Driveway fits two cars. Overall, a beautiful little house with lots of renovations. Self check-in with electronic keypad door lock. No smoking, no parties.

Casa Orozco 2

We put all our heart and Love into our Newly renovated Casa Orozco #2. We take great pride in staying that we believe that you will love your stay. The place truly feels like a home away from home. The place is a modern style open concept design. You will have a driveway, front yard with grass, back yard, and the whole place to yourself. The place is well decorated and has little touches we hope you'll enjoy.

Creekside Log Cabin

Get away from it all and find peace and privacy at this storybook cabin in the Santa Cruz Mountains. Nestled at the edge of a babbling creek, this cabin is a place for basking in the scenery of a lush woodland grove, observing passing wildlife, and unwinding each evening in a private hot tub. Permit number 211400