Family-friendly holiday rentals in Santa Clara County

Santa Cruz A-Frame

This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame

Peaceful Treehouse with Ocean View

Permit 171035 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 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.

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.

Santana Row Luxury Executive 2 Story Loft

Beautiful, luxury and clean 2 story open plan loft on the top floor at Margo building right on Santana Row. 2 bedroom 1,5 bath. Panoramic view of the mountains, downtown San Jose and the planes landing at SJC. Your favorite restaurants and shops downstairs. Valley Fair Mall is across the street. Brand new king size bed in the Master Bedroom, walk-in closet, kitchen, Nespresso coffee, teas. Underground parking with EV/Tesla hookup. Security on site 24/7. Ideal for business travelers and families.

Cozy Coastal Redwood Cabin

Rest and connect in this warm, cozy, and private cabin that is nestled in the redwoods. Only minutes away from Henry Cowell State Park, where you can enjoy world class mountain biking trails, hiking, or swimming in the river. Or, enjoy the beach 15 minutes away. This is a perfect place to refresh in the magic of the Coastal Redwoods. Music fills most nights either from the Felton Music Hall or from the chorus of frogs. And wake up in the mornings to the mist in the trees when the fog rolls in.

Dreamy Redwoods A-Frame+fireplace+tub for 2+dogs

Featured in Condé Nast’s “30 Cozy A-Frame Cabins for Cold-Weather Getaways,” Whiskey Hollow is the quintessential romantic retreat! Wake to majestic Redwood views from the loft bed, soak by candlelight in the oversized tub, cozy up by the wood fireplace, or cook a meal in the fully appointed kitchen. Nestled in the Redwoods yet just 2 miles to downtown Felton, 1.5 miles to Henry Cowell State Park, 15 minutes to downtown Santa Cruz, and 20 minutes to the beach (Permit #191282).

Kinderwood Farm Stay • Animal & Culinary Adventure

*UPDATE Baby goats born May 19th 2026* Nestled in an enchanting forest of redwood trees & ferns, lies a treasured, sustainability-focused homestead, waiting for you to enjoy its bounty. This is a one of a kind, immersive culinary & farm adventure with cozy accommodations & unique experiences. Subject to availability, Add-On Activities may include goat milking & feeding baby goats, cheesemaking, sourdough, and soapmaking. Join us for a visit you will remember for a lifetime.

Private Pool Villa for family getaways

Looking for a comfy space to spend time with friends and family? Beach or great outdoors more your thing? 10 minutes from Seacliff State Beach and 12 minutes to Nisene Marks, this sunny locale is your comfortable home base for your next adventure. Why not just hang out by the pool? The water typically stays comfortable for swimming from April-September. Enjoy dining for 8 inside or on the patio. So close to the sea, but above the foggier lower elevations. Family friendly!

Peaceful Coastal Mountain Cabin

Redwood Skye, our classic A-frame home, is nestled among the towering trees in the Santa Cruz mountains. Escape, unwind, and enjoy nearby hiking, biking, beaches, parks and more — all of which got us featured on the Emmy award-winning TV series, “Staycation.” Conveniently located: 5 mins to Henry Cowell State Park, Roaring Camp Railroad & Felton Music Hall; 15 mins to Santa Cruz with its famous boardwalk and spectacular beaches; 45 mins to San Jose; ~1 hr to SFO.

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!

Sherwood Cottage @ Royal-T Ranch

Relax at this unique getaway. Stay in the original farmhouse built in 1900. 1 bedroom 1 bath with full kitchen.This is not just a place to stay. It is a fully hands on animal experience that you will not forget. Great for the whole family. The grounds are beautiful and park like. Enjoy meals on the patio with umbrellas, tables and bbq or picnic on the grass. Stay includes 2 hr animal experience. Check in anytime after three. Check out 10 AM.

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.