San Gregorio Holiday Rentals

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Holiday Rentals in San Gregorio

Holiday Home in East San Mateo

2.0 star property
8.8 out of 10, Excellent, (3)
"This is a very clean comfortable property! "
United States
Serena
The price is AU$503
includes taxes & fees
28 Dec - 29 Dec
Mid Century Garden View Home Parking

Holiday Home in Half Moon Bay

9.4 out of 10, Exceptional, (37)
"The stay was great, would recommend for quick getaway. "
United States
Kiera E.
The price is AU$543
includes taxes & fees
28 Dec - 29 Dec
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

Apartment in Half Moon Bay

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 AU$472
includes taxes & fees
7 Dec - 8 Dec
Modern Coastal Retreat, Walk to Downtown HMB & Beach

Cabin in Los Gatos

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great Location with comfortable beds and a stunning view from the porch and windows. Loved feeding the koi. "
United States
Bryce
The price is AU$371
includes taxes & fees
8 Dec - 9 Dec
Mays Luxury Farm Stays

Apartment in San Tomas

10.0 out of 10, Exceptional, (5)
"Good clean property and check in was easy"
United States
Brij P.
The price is AU$182
includes taxes & fees
12 Dec - 13 Dec
"Queens Palace" Studio Apt Business Ready - San Jose

Holiday Home in Pedro Point

9.6 out of 10, Exceptional, (4)
"This place had a great location beautiful view of the ocean it was very cozy "
United States
tammy k.
The price is AU$470
includes taxes & fees
15 Dec - 16 Dec
Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach

Cottage in Half Moon Bay

9.8 out of 10, Exceptional, (113)
"We had an amazing stay! Perfect for what we needed and very close to everything in Half Moon Bay. Matt and Guliz were very responsive and friendly. We would absolutely stay again."
United States
Patrick C.
The price is AU$478
includes taxes & fees
30 Dec - 31 Dec
Small Beach Cottage near the Coastal Trail and The Ritz

Holiday Home in Pescadero

10.0 out of 10, Exceptional, (1)
"Great location and the backyard was so relaxing. It was a lovely getaway and we look forward to staying there in the future "
United States
jess w.
The price is AU$760
includes taxes & fees
18 Dec - 19 Dec
lx51 History in Pescadero

Apartment in El Granada

9.4 out of 10, Exceptional, (50)
"Great tiny place. "
United States
Laura M.
The price is AU$417
includes taxes & fees
7 Dec - 8 Dec
Stylish Seaside Cottage - Walking to Beach

Apartment in El Granada

10.0 out of 10, Exceptional, (35)
"This place is amazing.. great place to stay and enjoy your anniversary "
United States
anthony
The price is AU$494
includes taxes & fees
9 Dec - 10 Dec
Oceanview Penthouse, Stylish & Walking to Beach

Holiday Home in Saratoga

The price is AU$14,232
includes taxes & fees
7 Dec - 8 Dec
Spacious estate near charming downtown Saratoga and the Montalvo Arts Center.

Holiday Home in Millbrae

9.6 out of 10, Exceptional, (56)
"Very clean and quiet stay."
United States
Bobby N.
The price is AU$271
includes taxes & fees
7 Dec - 8 Dec
3 bedroom (6 people) residential home in lovely safe town near SFO/SF Bay Area

Holiday Home in Jackson Park

2.0 star property
The price is AU$229
includes taxes & fees
12 Dec - 13 Dec
Luxury Private Bedroom steps from DT Mt View

Holiday Home in Boulder Creek

9.8 out of 10, Exceptional, (123)
"Very clean home. Beautifully furnished. Nice stay!"
United States
Tran
The price is AU$845
includes taxes & fees
8 Dec - 9 Dec
Cozy Home - in the redwoods with hot tub!

Cottage in Belmont

9.0 out of 10, Wonderful, (2)
"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.
The price is AU$442
includes taxes & fees
20 Dec - 21 Dec
2 Bedroom Treehouse Cottage

Holiday Home in Ben Lomond

8.0 out of 10, Very good, (11)
"Could have used a few repairs. But kitchen was great."
United States
Karen G.
The price is AU$535
includes taxes & fees
6 Jan - 7 Jan 2026
Redwoods near Los Gatos and Santa Cruz beach

Holiday Home in Montara

10.0 out of 10, Exceptional, (8)
"Such a cute property and outdoor space . Easy communication and location is great for central planning. "
United States
Emily P.
Coastal Charm: Inviting 3 BR Montara Home

Holiday Home in Montara

9.8 out of 10, Exceptional, (56)
"Gorgeous place A perfect stay"
United States
Matt H.
The price is AU$680
includes taxes & fees
10 Dec - 11 Dec
Ocean & Mountain View Home - Walk to Trails, Beach, Family Activities

Cottage in Cupertino

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 AU$502
includes taxes & fees
14 Dec - 15 Dec
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Cabin in Boulder Creek

2.0 star property
10.0 out of 10, Exceptional, (12)
"Beautiful location, perfect for a peaceful get away.Great hosts!"
United States
Cristina W.
The price is AU$632
includes taxes & fees
23 Dec - 24 Dec
Either Way Hideaway
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, 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 favourite 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 depend 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 AU$323 per night. Entering your travel dates in the search wizard might find you 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?

Marbella Lane Duplex Redwood City: This holiday home rental outside of San Gregorio is located near the airport, and has a patio, a private garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a microwave and a coffee maker, so that you can cook with friends or family.

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

San Gregorio State Beach and Pomponio State Beach are a couple of lovely local spots to get outside and enjoy nature. Pescadero State Beach and Pelican Point 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.