Holiday rentals in Diablo Grande

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.

Peaceful Treehouse with Ocean View

Featured by Sunset Magazine as a “chic escape,” this Peaceful Treehouse-style retreat blends mid-century design with natural materials like wood and stone for a calming, sanctuary feel. Light pours through floor-to-ceiling windows beneath soaring wooden beams, and Japanese-inspired sliding doors add to the architectural charm. Set high in the trees with ocean views, the home offers three elevated decks including one with a hammock - perfect for relaxing and enjoying the surrounding canopy.

Beautiful Orchard House on the Farm- Jacuzzi/Pool

A very magical place we call home. Nestled in the middle of 20 acres of established walnut trees, lies your new favorite getaway! You can simply sit back and chill in the beautiful Orchard House or come outside and enjoy the patio/pool/barbecue/ fire pit and spa. One of the bedrooms listed is upstairs in a gaming tower, filled with entertainment options!! Also if you love animals as much as we do, you can help feed our furry and feathered friends .Either way....Prepare to fall in love!

Clean freaks, germiphobes welcome! No smoking.

Welcome! This is a newly remodeled 2 bedroom, one bath duplex home. We’re a block from Motel 6, a couple of blocks from restaurants, shopping and other hotels. We’re just a few blocks from Oak Valley Community Hospital. (Great for visiting nurses). We’re 1.5 hours from Yosemite and Bay Area. All furniture and furnishings are new with comfy pillow top mattresses. While most hotels only wash linens between guests, we launder all linens and comforters and completely sanitize after each stay.

3bd/2ba Home | Foosball Table | BBQ & Fire Pit

Beautiful and comfortable home on a corner lot waiting for you to call it your second home. The home is very spacious with a lot of natural light. The high ceilings and open floor plan make it the perfect place to enjoy your time with friends and family. The home is centrally located in Modesto in a quiet and developed area. Walking distance to a shopping mall on Coffee Rd with a Walmart Neighborhood market. Close to Sutter Health Memorial Medical Center and Doctors Medical Center.

Serene and Sunny Home, Sleeps 6, with Yard

This cheerful and sunny home is located in a quiet and safe older neighborhood close to downtown and conveniently not too far from Hwy 99. This home is the perfect cozy place to rest and relax. Our little area of Modesto is unique in that we have a wonderful walking and biking trail only a block away. You can walk to our small neighborhood shopping area that has a grocery store with a Starbucks, a very popular frozen yogurt shop, restaurants, an independent bookstore and cute shops.

Coastal Redwood Cabin | Hot tub | Private Creek

Welcome to our cozy cabin nestled in the serene beauty of the Santa Cruz Mountains! Escape the hustle and bustle of everyday life and immerse yourself in the tranquility of towering redwoods surrounding our charming studio-style cabin. Whether you're seeking a peaceful getaway or craving an adventure-filled retreat, our cabin offers the perfect balance of relaxation and excitement. Follow us @thecoastalredwoodcabin We welcome one small pet (dogs only) to join in on the fun!

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.

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.

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.