Holiday houses in Gilroy

Campervan/RV in East San Jose

4.98 out of 5 average rating, 123 reviews

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.

Guest suite in Scotts Valley

4.96 out of 5 average rating, 731 reviews

Snug and Cozy between the Skyline and the Sea

Super private, peaceful, and quiet; an excellent place for the traveler who is excited about exploring the Santa Cruz mountains and coast. Completely private In-law unit with extras needed to make it cozy. Snuggled between Scotts Valley, Felton, and Santa Cruz it's near Henry Cowell Redwoods State Park, 1440 Multiversity, and Mount Hermon Conference Center yet less than an hour from Silicon Valley. The Airbnb cleaning handbook is followed making this one of the cleanest places you’ll stay at!

Superhost

Treehouse in East San Jose

4.92 out of 5 average rating, 735 reviews

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 .

5 out of 5 average rating, 171 reviews

Farm stay in San Martin

Guesthouse Farmstay @ BarrelCreek Farm & Vineyards

Come and get away! Enjoy a country setting in our custom Lindal Cedar guesthouse nestled in a vineyard setting! Half a mile from amazing biking and hiking trails! Minutes away from lovely wineries and Gilroy Premium Outlets! Our property also houses a small farm with friendly goats, (one entered for world’s smallest goat), sheep, ducks, a goose and free range chickens of various colors! We also have a 150+ fruit orchard, and a seasonal garden. One guided morning farm tour included with booking.

4.98 out of 5 average rating, 247 reviews

Home in Livermore

The French Door

This space is a private entry 275 square foot small studio with a private bath, connected to the main house but with no access to the main house. The unit has a standard sized mini fridge, microwave and keurig coffee maker with coffees to choose from, a very mini toaster oven for one bagel or one piece of toast, lite snacks and waters for you. Also a small table and chair set, desk and a brand new queen sized bed, the location is great if you work at the lab or if visiting family in the area.

5 out of 5 average rating, 63 reviews

Peaceful Home w/Patio by Wineries & Gilroy Gardens

Private and peaceful 2 bed 1 bath single family home with fenced in front yard and patio oasis, centrally located in South Bay’s Wine Country. ▪️Perfect for couples get away or family trip! ▪️Walking Distance to Downtown (0.5 mile) ▪️Adjustable King Bed with HDTV ▪️Newly Remodeled Bathroom ▪️Large Living Room Space w/ 85” 4K TV ▪️Patio equipped w/ propane Fire Pit and Grill ▪️Ready to Cook in Kitchen ▪️Workspace w/ Monitor and Fast WIFI ▪️Nearby Restaurants, Shopping, and Wineries!

4.91 out of 5 average rating, 215 reviews

Guest suite in San Jose

Entire Guest Suite Private Entrance Kitchen & Bath

Whether you’re here for a business trip, traveling for pleasure, visiting your friends/relatives, or looking for a short term rental, our fully furnished unit can offer everything you need! What you’ll get from staying at our converted garage: * Separate entrance with self check-in (keyless entry) * Workspace with high-speed wifi * TV with Netflix * Fully stocked & equipped kitchen * Private bedroom with queen bed, wall closet, high ceiling * Private bathroom * Free parking on premise

4.96 out of 5 average rating, 71 reviews

Guesthouse in Hollister

Luna Llena

Welcome to our spacious studio nestled on the second floor of a detached unit within this picturesque estate. With an enchanting backdrop of Diablo Range mountains, while the surrounding vineyard provides a delightful ambiance to relish. You can wake up to the occasional misty mornings that add a touch of mystery and charm. prepare to be captivated by the most gorgeous sunsets that paint the sky with hues of enchanting colors. Welcome to your oasis of tranquility and natural beauty!

4.99 out of 5 average rating, 102 reviews

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

Superhost

Farm stay in San Martin

4.87 out of 5 average rating, 143 reviews

Private Barn in a farm.

A full size barn turned it a beautiful living space with a well equipped trailer inside is waiting for you. Outdoor TV, lounge area, well lit foosball table area, lazy fun chairs, barbecue and fire pit are all for you. Separate electric gate will give you a separate entrance and privacy. Enjoy room in the barn or strolling on the small farm, chickens horses goats and accessional One bunk bed (two twin size beds) plus a separate room with full bed. 4 people total.

4.91 out of 5 average rating, 787 reviews

Yurt in Watsonville

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.

4.95 out of 5 average rating, 225 reviews

Cottage in Morgan Hill

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.

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Gilroy holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Gilroy

Guest suite in Gilroy

4.82 out of 5 average rating, 109 reviews

Private guest suite with pool and stunning views

JerryRating, 5 stars1 month ago

Deric’s place was a perfect peaceful getaway from the daily bustle. The surroundings were serene, the outdoor space was well maintained, and the picturesque nature of everything was appreciated from the charming gazebo to the beautiful pool.

4.54 out of 5 average rating, 69 reviews

Remodeled & Cozy Gilroy Guest House Near Downtown!

LucieRating, 5 stars1 month ago

it was what I wanted, we wanted to be away from the city and it was comfortable. My kids were happy. It was spacious, it was what I expected pictures were accurate. Easy to access, I felt safe. The only thing was only one burner turned on, it didn't bother me. Just took a little longer to make breakfast. I told them and they were going to check it, they were responsive. Overall, I was very pleased.

Shipping container in Gilroy

5 out of 5 average rating, 4 reviews

Countryside Container Home

DanielRating, 5 stars2 weeks ago

Christina was very accommodating host.

Guest suite in Watsonville, Santa Cruz County

4.95 out of 5 average rating, 132 reviews

Gracious garden Guest Suite - sunny Corralitos

RebeccaRating, 5 stars2 weeks ago

We were very busy coming and going, yet found the Gracios garden guest suite to be clean, comfortable, and close to our family get together in Watsonville. The shower area was clean, functioned well, and gorgeous tile work, also Kris supplied plenty of welcoming snacks 😊 Grandson enjoyed Milo the friendly dog:) Thank you, Nick & Rebecca

5 out of 5 average rating, 3 reviews

Contemporary Lifestyle

JosselynRating, 5 stars3 weeks ago

I wanted to express my sincere appreciation for Alexis hospitality during our recent stay. She was extremely responsive to our questions and made sure we felt right at home. The home's cleanliness and organization contributed to a comfortable atmosphere, especially with two toddlers. We particularly appreciated the availability of Netflix, which was a great asset for keeping the toddlers entertained. The ample space in the home also provided a convenient and relaxing environment for our family. Basic necessities were provided and more! Thank you again for providing a welcoming and family-friendly space. We look forward to the opportunity to stay again in the future.

4.86 out of 5 average rating, 154 reviews

Guest suite in Gilroy

Full Guest House in the Foothills

JenniferRating, 5 stars1 week ago

We love staying at Paul and Stefania's! They have a laid back vibe and a beautiful property. It is wonderful to be able to enjoy the view and take things at a slower pace. The space where we stay is fully equipped and comfortable. We love it!! Thank you!

5 out of 5 average rating, 5 reviews

Home in Morgan Hill

Charming Vineyard Rose Cottage

VeronicaRating, 5 stars2 weeks ago

We had a lovely stay at the Rose Cottage - the place was clean and comfortable, the kitchen had everything we needed, and there was a great DVD collection! Beyond that, the property is gorgeous with the vineyard in the front and a babbling creek out back. Lucy and Davorin were friendly, responsive, and even went out of their way to mail us back our toddler's swimsuit and toy that we accidentally left behind. We would absolutely stay again if back in the area.