Photo by Stefany Mathias-Butler

Holiday Rentals in San Gregorio

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Our top choices for San Gregorio holiday rentals

Holiday Home in East San Mateo

Mid Century Garden View Home Parking
2.0 star property
8.8 out of 10, Excellent, (3)
"This is a very clean comfortable property! "
United States
Serena
The price is €338
includes taxes & fees
6 Jan - 7 Jan
Mid Century Garden View Home Parking

Cabin in Los Gatos

Mays Luxury Farm Stays
2.0 star property
10.0 out of 10, Exceptional, (5)
"Great Location with comfortable beds and a stunning view from the porch and windows. Loved feeding the koi. "
United States
Bryce
The price is €210
includes taxes & fees
6 Jan - 7 Jan
Mays Luxury Farm Stays
2.0 star property
10.0 out of 10, Exceptional, (7)
"Beach nearby. Very clean and nice vacation rental. The hosts really care about their guests and it shows. "
United States
Angela
The price is €259
includes taxes & fees
6 Jan - 7 Jan
Modern Coastal Retreat, Walk to Downtown HMB & Beach
10.0 out of 10, Exceptional, (36)
"The studio is in a great location and is centrally located within walking distance to shops and restaurants. Pictures were accurate and the place was spotless; would definitely stay here again."
United States
Steven D.
The price is €285
includes taxes & fees
6 Jan - 7 Jan
Oceanview Penthouse, Stylish & Walking to Beach
9.6 out of 10, Exceptional, (4)
"This property is located in a residential and quiet neighborhood with a nice park within walking distance! Great place for someone who is traveling by themselves!"
United States
Kevin
The price is €288
includes taxes & fees
5 Feb - 6 Feb
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette
9.4 out of 10, Exceptional, (38)
"The stay was great, would recommend for quick getaway. "
United States
Kiera E.
The price is €417
includes taxes & fees
9 Jan - 10 Jan
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
8.2 out of 10, Very good, (11)
"We had a wonderful stay at Eric's lovely home. The view is not to be believed, and the rooms were comfortable and clean. We hope to return as soon as possible. Thanks Eric!"
United States
Susan & David S.
The price is €189
includes taxes & fees
23 Jan - 24 Jan
Cozy guest suite in Los Gatos - Beach in 30 min!
2.0 star property
The price is €132
includes taxes & fees
6 Jan - 7 Jan
Luxury Private Bedroom steps from DT Mt View
10.0 out of 10, Exceptional, (5)
"Good clean property and check in was easy"
United States
Brij P.
The price is €140
includes taxes & fees
12 Jan - 13 Jan
"Queens Palace" Studio Apt Business Ready - San Jose
8.4 out of 10, Very good, (7)
"Location, clean rooms,"
United States
Sheridan D.
The price is €128
includes taxes & fees
6 Jan - 7 Jan
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
9.8 out of 10, Exceptional, (113)
"Great and cosy surfers cottage...my son and I were in HMB to attend a wedding."
United States
Charles C.
The price is €256
includes taxes & fees
12 Jan - 13 Jan
Small Beach Cottage near the Coastal Trail and The Ritz
9.2 out of 10, Wonderful, (52)
"Host was great and very communicative during our stay! Home was clean and felt very cozy! "
United States
Gisselle
The price is €224
includes taxes & fees
6 Jan - 7 Jan
Luxury stay near Santana Row for vacation/business
8.6 out of 10, Excellent, (4)
"Clean, simple, well stocked!"
United States
Ben
The price is €158
includes taxes & fees
7 Jan - 8 Jan
214A - Cozy Studio with AC & Kitchen near Stanford
10.0 out of 10, Exceptional, (21)
"Very clean, comfortable and quiet."
United States
John
The price is €230
includes taxes & fees
6 Jan - 7 Jan
Stunning and unique AirStream on the Coastal Trail and near Poplar Beach
9.6 out of 10, Exceptional, (5)
"This place had a great location beautiful view of the ocean it was very cozy "
United States
tammy k.
The price is €268
includes taxes & fees
8 Jan - 9 Jan
Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach

Cabin in Boulder Creek

Either Way Hideaway
2.0 star property
10.0 out of 10, Exceptional, (15)
"We had a beautiful stay here. Everything was just as described and the surroundings were amazing. "
United States
Vita P.
The price is €342
includes taxes & fees
2 Feb - 3 Feb
Either Way Hideaway
9.6 out of 10, Exceptional, (25)
"We had such a wonderful experience here for our 1 week stay. The beds were so comfortable, the house was super clean and the kitchen had everything we needed to cook for our group. Seamless check in and our host was always ready to assist if we needed it! Would definately recommend!!!"
United States
Susan
The price is €376
includes taxes & fees
6 Jan - 7 Jan
Remote work, visitor's Love 4B with 2x suites /3BR- Levis, Kaiser, Great America

Cottage in Belmont

2 Bedroom Treehouse Cottage
8.8 out of 10, Excellent, (3)
"The house is very comfortable and very clean. It contains everything a traveler needs. We arrived at night and had difficulty to locate the place, as there are other residences on the same lot. The Tree House is at the very top, so requires walking up four flights of stairs (65 steps in all), which we did not realize when we first arrived. But it is unique and a fun place to stay, in a nice area. We saw deer around the property three times during our short stay. Still, stores, restaurants...
United States
Jay S.
2 Bedroom Treehouse Cottage
9.4 out of 10, Exceptional, (9)
"This rental was all that I hoped for and I'll try to book it again when I visit my children nearby"
United States
Nancy A.
The price is €242
includes taxes & fees
16 Jan - 17 Jan
Modern little poolside house By Downtown Mountain View!
10.0 out of 10, Exceptional, (43)
"Our stay was great! This was a perfect guest house for our trip! Very clean and in a good neighborhood! "
United States
Shayna C.
The price is €221
includes taxes & fees
30 Jan - 31 Jan
Brand New! Guest House - Modern Stylish & Central
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top San Gregorio Hotel Reviews

Find out more about San Gregorio

Everything you need to know about San Gregorio holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Gregorio holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Gregorio holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

San Gregorio holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Gregorio. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Gregorio holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Gregorio holiday rentals we have selected for you start as low as €182 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on San Gregorio rentals

At Expedia, we put the best San Gregorio holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top San Gregorio rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Gregorio holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Gregorio. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in San Gregorio?

Yes, there are holiday rentals close to the most popular sights in San Gregorio, or you can select a more secluded option if you're looking for a relaxing stay. San Gregorio is known for its beaches and restaurants.

What are some of the best holiday rentals that San Gregorio has to offer?

Oceanview Family Retreat with Saltwater Hot Tub – Steps from the Beach: This holiday home rental outside of San Gregorio is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

What’s there to see and do in San Gregorio?

Explore the area and family-friendly sights such as JV Fitzgerald Marine Reserve, or get out into nature at a spot like Pomponio State Beach. Pescadero State Beach and Bean Hollow State Beach are a couple of places you'll find in the wider area.

What’s a holiday rental in San Gregorio like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Gregorio. Holiday rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for family trips.