Holiday rentals in Old Gilroy

Countryside Container Home

Our family’s custom container (tiny) home blends minimalist style and natural warmth with all the comforts of home. Inside, you’ll find curated design, tons of sunlight, and a peaceful energy that invites you to slow down and relax. You’ll enjoy a: Raised full sized bed with plush bedding for ultra-comfy nights Intimate lounge with seating and a Smart TV Fully stocked kitchenette Fast WiFi for work or winding down An outdoor fire pit + dining table Private, fenced-in outdoor area with parking

Cozy Spanish-Style Casita Retreat

Escape to this charming Spanish-style casita, newly renovated to provide a perfect blend of modern luxury and serene tranquility. Nestled on the outskirts of town, this retreat invites you to unwind, relax, and reconnect. The casita is equipped with state-of-the-art appliances, offering everything you need for a comfortable stay. Whether you're whipping up a meal in the modern kitchen or streaming your favorite shows on the smart TV, this space has been designed to cater to all your needs.

Downtown Hollister 1 BR 1 BA Free Parking & WiFi

If your looking for a quality centrally located place to stay. Fifth Street Retreat is your choice. RIGHT DOWNTOWN. We are also close to other cities. If you want the ocean Monterey and Carmel Valley and Santa Cruz is right next door. If you want the city, San Francisco is above us. If your interested in hiking, Pinnacle National Park is in our back yard. Hollister Hills if you are a motorcycle enthusiast. Walking and bicycling trails. So many great restaurants, bakeries and bars. #enjoyus

Alpacas and More Guest House

This is an air-conditioned 3 bedroom 2 bath house. Most of the beds are bunkbeds. It can accommodate 5 adults plus 3 children comfortably. Any larger group will only be accommodated if approved with the host. Fresh country air, queit country surrounding. We host a super fun petting zoo (family with kids) and a farm experience (adults who loves animals) that may be available during your stay. Please inquire upon booking to get a link for a discounted visit with the alpacas and more.

New Modern 1-Story Home w/ Mountain Views

Modern, comfortable 4 bedroom 2 bath home with spacious bedrooms. Comfy living room with 75 inch TV. Fully equipped kitchen. Large beautiful backyard with views of the mountains. No stairs. Don't be packed like sardines! 3 bedrooms are large and private. 4th bedroom fits 4 people. Max 10 people. No bunk beds for your safety. Eagle Ridge Golf Club - 5 mins Gilroy Gardens - 10 mins Gilroy Premium Outlets - 10 mins San Jose - 30 mins Monterey - 45 mins Santa Cruz - 50 mins

The Silverbird - vintage 1986 Airstream with views

Escape to a dreamy vintage Airstream perched above Monterey Bay with breathtaking 180° views stretching from Santa Cruz to Big Sur. Just 30 minutes to Santa Cruz, an hour to Big Sur, and minutes from the beach, this glamping gem blends retro charm with modern comfort. Enjoy an outdoor kitchen, cozy fire pit, and romantic interior—all surrounded by wildlife. Perfect for couples or solo travelers seeking stargazing, sunsets, and a peaceful, elevated retreat in nature.

Poolside Wine Country Retreat

Ideally located between downtown Morgan Hill and dozens of local wineries. Savor the quiet, sample local favorites, or explore the outdoors. Within a short drive to coastal beaches and towns, San Juan Bautista, Pinnacles National Park, and many other State and local parks. The guest house is private and peaceful, including one bedroom with a queen size bed, queen size convertible sofa, full bathroom, full kitchen, private patio, and seasonal pool.

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.