Vacation rentals in Old Gilroy

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Top-rated vacation rentals in Old Gilroy

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Scotts Valley

4.96 out of 5 average rating, 629 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!

Oct 9 – 16

G$15,819 GYD per night

Guest favorite

Cabin in Los Gatos

4.99 out of 5 average rating, 788 reviews

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.

Apr 7 – 14

G$35,968 GYD per night

Guest favorite

Apartment in Carmel-by-the-Sea

4.87 out of 5 average rating, 825 reviews

Private romantic 1 br in Carmel Woods- love dogs

Dog friendly! Private entrance to 2 rm studio overlooking the forest w/ floor to ceiling windows. Queen memory-foam bed, bathroom w/shower & amenities, kitchenette w/ dishes, microwave/convection oven, burner, toaster, coffee.Far ocean view, sunsets, deck, gas grill. Quiet, fireplace, complimentary wood, free internet, TV, DVDs, LPS, All amenities. Beach towels/mats, ottoman/cot, free parking. Peaceful. Let us know about dogs when booking. note: ceilings are low in spots & there are some steps.

Apr 6 – 13

G$28,004 GYD per night

Guest favorite

Guest suite in Boulder Creek

4.98 out of 5 average rating, 428 reviews

Enjoy Private Redwoods from Your Bed or the Deck

Come and visit our own private slice of the REDWOOD FOREST with over 40 trees and large deck to enjoy them. Wake up to fresh mountain air, a view of nature and coffee. After a day of WINE tasting, HIKING, BEACHES, or exploration, bring a bottle back and sprawl in comfort reflecting, chatting, or sipping on the deck. The perfect little getaway spot. Treat yourself to some nature with us. A winter fireplace, easy walking and parking makes this scene. 1.5 miles to downtown Boulder Creek and fun!

Aug 30 – Sep 6

G$28,811 GYD per night

Guest favorite

Guest suite in Santa Cruz

4.92 out of 5 average rating, 141 reviews

Cute Pleasure Point Studio - Walk to the Surf

In the heart of Pleasure Point, this remodeled, private studio is a short walk to the best surf spots in Santa Cruz. 3-minute walk to the stairs by O'Neill's house, and ~6 different breaks also within walking distance. Short stroll to coffee shops, restaurants and more. Walk or ride bikes (2 provided) almost everywhere. Quick drive to Capitola, Boardwalk & downtown Santa Cruz. Open to singles or couples (baby OK) that understand that our family lives in adjoining property. No pets allowed.

Sep 1 – 8

G$25,036 GYD per night

Guest favorite

Home in Watsonville

4.82 out of 5 average rating, 271 reviews

Remarkable Reader's Garden Retreat in the Country

Remarkable Reader’s Retreat in a quiet country location, halfway between Santa Cruz and Monterey. Sited in a large country garden with herbs, historic fruit and citrus trees. A farmhouse kitchen with cooking fireplace and antique oak floors. The library is a lovely retreat, with leaded glass windows, Turkish carpets, and treasures from a lifetime of travel. Located along a beautiful country road with great walking and biking. A quiet oasis retreat, guarded by red-tail hawks and hummingbirds.

May 6 – 13

G$32,963 GYD per night

Guest favorite

Guest suite in Los Gatos

4.93 out of 5 average rating, 252 reviews

Remote Mountain Suite with Hot Tub

One-bedroom attached in-law suite with private entrance- relaxing den with large leather couch, flat screen tv (Roku/no cable) kitchenette w/hot plate and private bath. Supplied with bottle of wine and breakfast essentials. Mountain location 2.5 miles down a very narrow scenic ridge-top road on 6 beautiful acres of lush vegetation and towering redwood trees. Ideal for a couple or small family looking to explore the Santa Cruz county Mountains, Bay Area and coast without breaking the bank.

Jul 8 – 15

G$25,319 GYD per night

Guest favorite

Cottage in Morgan Hill

4.95 out of 5 average rating, 201 reviews

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 Sat & 3rd Weekend of every month from 11:30-4:30. We usually have live music, wine tasting is in the same vicinity as the Cottage. When your stay is on those weekends you get a comp tasting for two.

Sep 9 – 16

G$66,977 GYD per night

Superhost

Farm stay in San Martin

4.9 out of 5 average rating, 105 reviews

Private Barn in a farm.

A full size barn turned it a beautiful living space with a new 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 total privacy. Enjoy room in the barn or strolling on the farm, chickens horses goats and accessional bunnies. Outdoor play area and picnic tables. Parties up to 50 people can be arranged. different pricing.

Oct 3 – 10

G$22,892 GYD per night

Guest favorite

Bungalow in San Martin

4.99 out of 5 average rating, 104 reviews

Moose Mountain Vineyards Bungalow

Relax in an elegant 2 bed bungalow sitting atop Moose Mountain Vineyards. Enjoy the panoramic view of San Martin as well as the 13,000 grape vines growing on property. Relax in the hot tub or infinity pool, or sip estate wine on one of our four decks as the sunset takes your breath away. Enjoy a complimentary whole food plant-based breakfast with ingredients sourced onsite. This stay offers many opportunities to explore the inner workings of Moose Mountain Vineyards.

Apr 3 – 10

G$91,548 GYD per night

Guest favorite

Farm stay in San Martin

5.0 out of 5 average rating, 129 reviews

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 at Harvey Bear Park! Minutes away from lovely wineries and Gilroy Premium Outlets! Our property also houses a small farm with friendly goats, sheep, ducks, a goose and free range chickens of various colors! You can also check out our 120+ fruit orchard. IG: barrelcreekfarm

Mar 24 – 31

G$55,861 GYD per night

Guest favorite

Yurt in Watsonville

4.92 out of 5 average rating, 714 reviews

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.

Feb 12 – 19

G$26,271 GYD per night