Holiday rentals in Old Gilroy

Guest suite in Scotts Valley

4.96 out of 5 average rating, 728 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, 732 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.

4.97 out of 5 average rating, 147 reviews

Home in Watsonville

Magical hilltop 3-bedroom with spectacular views

Stay at this bright, beautiful home at the top of the Pajaro Valley, with balcony views of Big Sur, Monterey Bay & Mt. Madonna. The open concept fully equipped kitchen/living room will make you feel at home, while the patio/grill & fireplace will help you relax. Replace the sounds of the city with the natural tones of the countryside. From horse whinnies, to the neighbouring sheep, you’ll be fully immersed in a one of a kind modern country experience. Contact for booking related questions.

5 out of 5 average rating, 63 reviews

Centrally Located Home King Bed/Patio/Fenced Yard

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 small family! ▪️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!

Superhost

4.86 out of 5 average rating, 102 reviews

STYLISH GUEST HOUSE ON A BEAUTIFUL ESTATE

This Stylish and Private Guest House is located on a 1.2 Acre Estate with beautiful Landscaped Grounds. This Guest House Offers a Private Entrance & Two Private Balconies. This Unit is Fully Furnished & Tastefully Decorated with current trending Styles. This property is on the border of Gilroy and San Martin. Conveniently located near Gilroy Outlets, Restaurants, Costco, Walmart, and Target. This property is centrally located between San Francisco & Monterey. Please request longer stays!

4.96 out of 5 average rating, 69 reviews

Guest house 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!

Guest house in San Martin

4.91 out of 5 average rating, 11 reviews

Farms & Vineyards Stay with view: 3 BR, Game Room.

This beautifully remodeled 3-bedroom, 1-bathroom with game room space offers modern amenities in a peaceful ranch setting right in Silicon Valley. The home features a full kitchen with stainless steel appliances, an open living area, gym, washer/dryer, and outdoor BBQ space. Enjoy access to an equestrian arena and stables. Located in a safe, gated community, this space offers a blend of rural tranquility and modern convenience on a 10-acre private estate. Your perfect retreat awaits!

4.99 out of 5 average rating, 100 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, 142 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, 786 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 the first & 3rd Weekend of every month from 12-4:30. We usually have live music, wine tasting is in the same vicinity as the Cottage.

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Other great holiday rentals in Old Gilroy

4.53 out of 5 average rating, 68 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.

Campervan/Motorhome in Monterey County

4.86 out of 5 average rating, 14 reviews

Cozy Glamping Experience

EdwardRating, 5 stars1 month ago

Thank you loves the spot an location was perfectly in middle of Monterey bay 👌 would love to stay again

Shipping container in Gilroy

5 out of 5 average rating, 3 reviews

Countryside Container Home

OscarRating, 5 stars1 week ago

Thank you for providing a place to stay for me and my wife and pets. You had an amazing time and willing to visit in the future thank you.

4.98 out of 5 average rating, 106 reviews

Private room in Gilroy

Clean and comfy private room for rent

ChristopherRating, 5 stars2 weeks ago

Monty and his Partner are some of the nicest host we have ever come across. They made sure to make you feel welcomed and are very gracious host! I would definitely stay here again! The bed was comfortable, the TV was nice and big and it felt very private.

5 out of 5 average rating, 3 reviews

Contemporary Lifestyle

JosselynRating, 5 stars2 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.

Private room in San Martin

4.97 out of 5 average rating, 315 reviews

Beautiful, warm and cozy room on a country acre!

chrisRating, 5 stars1 week ago

It was a lovely experience and everything was perfect! Breakfast was great; fresh fruit and eggs, and it was so nice to sit outside and eat. And fun to chat with Madelyn. What a gem!

4.68 out of 5 average rating, 44 reviews

Cozy Gilroy Retreat Near Wineries & Attractions!

ChristianRating, 5 stars2 weeks ago

This Airbnb spot is definitely a new favorite! It was very clean and easy to check in and check out. The privacy and closeness to the freeway was also a great plus.