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.

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

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

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.

Quiet guesthouse near SJ airport with EV charger

Kick back and relax in this calm, stylish space. Brand new guesthouse build and landscape completed in 2023. Our guesthouse offers a full kitchen, WiFi, self check-in, FREE parking and washer and dryer. Tesla Universal EV charger Level 2 60 amp avilable for guest use. Centrally located in Downtown San Jose. A quick drive to the SJ airport, SAP Center, San Pedro Square, Levi’s Stadium, San Jose State University and Santa Clara University.

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.

Modern Turlock Studio

The Studio is a warm, more modern styled cottage, safely nestled in the backyard of a home, as a detached structure with a private entrance, front porch & plant life. Located in a quiet, tree lined residential neighborhood. It’s fully furnished, loaded with amenities...from appliances, kitchenware and condiments to personal care items. Comfortably hosts 1-2 adults, featuring a queen size bed with memory foam mattress.

Amazing Country Setting at Cottage Creek Vineyards

Lovely 1000 Sq. ft. Cottage in the heart of wine country. A 400 sq. ft. delightful back patio with fire pit, full kitchen and bathroom makes this the perfect home away from home. Amenities include queen bed, wifi, TV's, fire place, & parking. We are a live winery and have wine tasting two weekends and two Friday evenings a month. We usually have live music, wine tasting is in the same vicinity as the Cottage.

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.