Family-friendly holiday rentals in Gilroy

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.

Treehouse , San Jose

250 sq ft treehouse with stairs leading to 2 lofts with beds overlooking the most gorgeous view of the Silicon Valley. The treehouse opens to a deck 14 foot high nestled in between 3 sycamore trees.Custom made stained glass window and spiral staircase leads up into the tree. Includes full functioning bathroom , kitchenette w sink , cooking stove, mini fridge . Sleeps 4 people. ( 1 queen bed in each open loft) You are living with a live tree in nature so think glamping - an amazing experience .

Remodeled spacious 2Bdr/2Bath King beds w/backyard

This is the main house of this 2-unit property. It is located in historic Willow Glen. Private backyard, designated parking, private entrance. Mid century modern inspired architecture and decoration. Oversized bedrooms, open living space, functioning kitchen. High ceiling throughout. Easy access to Caltrain, LightRail, bus. Close to downtown San Jose developing technology centers, restaurants and shops. 12 minutes to SJ airport. Very safe and high end neighborhood. Hosts are fully vaccinated.

Private Studio Guesthouse with A/C in Willow Glen

Updated private 400 sq ft studio guesthouse (with A/C) with separate fenced yard and entrance. Steps away from Lincoln Ave and downtown Willow Glen restaurants and shops. Convenient to freeways, SAP Center, and downtown San Jose. One queen bed; sleeps up to 4 adults with optional queen size high quality inflatable bed. Full kitchen with all cookware, dishes, spices, coffee, etc. Access to main house laundry room available on request. Basic shower essentials and hair dryer provided.

Comfortable Whole Home on two house lot

This home has lots of light, new appliances and furniture. You are renting the entire home in the rear of the property. This is in an older, diverse neighborhood, with friendly Hispanic, Portuguese, Viet, Black and White neighbors, and a low crime rate. The pets in the listing are actually in the front house. The back house is pet friendly, but cleaned after each visit. There are neighborhood cats outside. Easy access to bus lines, and two major highways (101 and 280).

Kinderwood Farms Suite

>>Now is the perfect time to visit!<< 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. Activities may include farm to table meals, goat milking, cuddling baby goats, cheesemaking, sourdough, soap making & more. Join us for a visit you will remember for a lifetime

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

Cozy,Quiet”Home Away from Home”.attached cottage

Very large 1 bedroom. Heat/AC, Private entry, Loaded with Amenities. Private Patio, Garden View, parking in front. Nice, Quiet neighborhood; near trails, Pond, Freeways, Light Rail(VTA). 10 min walk to Westfield Oakridge Mall, Restaurants/Movies, Bowling, Mini golf, Walmart, Costco, Bass Pro, and much more. 1 HR to SFO/Monterey 30 Min to Santa Cruz Beach/Gilroy Outlets 20 Min Dwntwn SJ/SJSU

Back-to-Eden Guest House on a Farm

Peaceful, comfortable guest house with 3 bedrooms and 2 baths plus spacious living room. Fresh country air, quiet surroundings, beautiful sunrise and sunset. 8-10 people max. Any larger group will need prior arrangement with the host. Super fun animal interaction tour may be available during your stay . Please inquire upon booking regarding joining a tour.