A beach with waves crashing onto the shore under a clear blue sky.

San Gregorio Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for San Gregorio holiday rentals

A coastal landscape with a sandy beach, cliffs, and a field of wildflowers.

1. Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
South Downtown
9.2 out of 10, Wonderful, (43 reviews)
"Beautiful location and space. Location was perfect and exactly what we needed"
United States
Patricia D.
The price is NZ$675
includes taxes & fees
4 Oct - 5 Oct
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
A wooden deck with a white bathtub, wooden pergola, and a blue wall with a sign.

2. Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.6 out of 10, Excellent, (32 reviews)
"I'll be back"
United States
Billy
The price is NZ$369
includes taxes & fees
29 Sept - 30 Sept
Mays Luxury Farm Stays
A spacious living room with a large wooden coffee table, a sofa with patterned cushions, and a view of the outside through a large window.

3. Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay

Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
Heritage Downtown
9.6 out of 10, Exceptional, (14 reviews)
"nice place...close to restaurants...easy parking!"
United States
Luz
The price is NZ$507
includes taxes & fees
30 Sept - 1 Oct
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
A wooden deck with a metal railing overlooking a forested area.

4. Cottage In The Woods

Cottage In The Woods
Woodside
10.0 out of 10, Exceptional, (61 reviews)
"We really enjoyed our stay here! One of the best equipped houses we’ve ever rented , and the lovey creek babbling by the porch , it was awesome."
United States
Donna M.
The price is NZ$587
includes taxes & fees
5 Oct - 6 Oct
Cottage In The Woods
A cozy bedroom with a wooden ceiling, a bed with white linens, and a textured blanket.

5. Small Beach Cottage near the Coastal Trail and The Ritz

Small Beach Cottage near the Coastal Trail and The Ritz
Arleta Park
9.8 out of 10, Exceptional, (136 reviews)
"Great dog friendly well appointed tiny house."
United States
Deb L.
The price is NZ$654
includes taxes & fees
6 Oct - 7 Oct
Small Beach Cottage near the Coastal Trail and The Ritz
A hot tub in a backyard with a wooden deck, outdoor furniture, and a wooden fence.

6. Charming Garden Cottage- steps to historic Old Town Half Moon Bay

Charming Garden Cottage- steps to historic Old Town Half Moon Bay
Heritage Downtown
9.8 out of 10, Exceptional, (64 reviews)
"Clean; cheerful! Wonderful location."
United States
Catherine
The price is NZ$840
includes taxes & fees
30 Sept - 1 Oct
Charming Garden Cottage- steps to historic Old Town Half Moon Bay
A hotel room with a bed, a desk with a chair, a television, and a large window with curtains.

7. 214B - Cozy Studio with AC & Kitchen near Stanford

214B - Cozy Studio with AC & Kitchen near Stanford
Redwood City
10.0 out of 10, Exceptional, (2 reviews)
"Comfortable and easy. It had everything that I needed. Communication was clear. "
United States
Anastasia and Tom L.
The price is NZ$328
includes taxes & fees
3 Oct - 4 Oct
214B - Cozy Studio with AC & Kitchen near Stanford
A round wooden table with a white pot containing a plant, flanked by two blue chairs with gold legs, on a light-colored wooden floor.

8. Stylish Seaside Cottage - Walking to Beach

Stylish Seaside Cottage - Walking to Beach
El Granada
9.4 out of 10, Exceptional, (57 reviews)
"Clean, cozy, comfortable and as described. Very comfortable bed too! Close to HMB restaurants and shops, will stay again!"
United States
Chase T.
The price is NZ$423
includes taxes & fees
4 Oct - 5 Oct
Stylish Seaside Cottage - Walking to Beach
A living room with a sectional sofa, a wooden coffee table, and a colorful striped rug.

9. Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House

Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
Heritage Downtown
7.8 out of 10, Good, (22 reviews)
"Thanks for a great stay!"
United States
April M.
The price is NZ$300
includes taxes & fees
13 Oct - 14 Oct
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
A narrow brick pathway flanked by walls with colorful tile patterns, leading to a doorway.

10. Secluded freestanding house in the delightful grape garden

Secluded freestanding house in the delightful grape garden
Emerald Hills
7.4 out of 10, Good, (8 reviews)
"Location and views were amazing! "
United States
Richelle
The price is NZ$626
includes taxes & fees
29 Sept - 30 Sept
Secluded freestanding house in the delightful grape garden
A rocky coastline with a cave-like formation and waves crashing onto the shore.

11. Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

Stunning Oceanview Coastal Home – Beach, Trails, Family Activities
Montara
9.2 out of 10, Wonderful, (87 reviews)
"Great host! Big fenced in yard for the dogs as well. Located near many awesome hikes. We would definitely stay again! "
United States
Brent J.
The price is NZ$576
includes taxes & fees
4 Oct - 5 Oct
Stunning Oceanview Coastal Home – Beach, Trails, Family Activities
A modern hotel room with a grey sofa, two armchairs, a bed, a round mirror, and a large painting on the wall.

12. Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay

Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay
Heritage Downtown
9.2 out of 10, Wonderful, (9 reviews)
"The place was super cute and close to everything. I would definitely stay again! "
United States
Juliet M.
The price is NZ$460
includes taxes & fees
30 Sept - 1 Oct
Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay
A wooden lattice structure with a sofa and a small table, surrounded by plants and a patterned rug.

13. Oceanview Penthouse, Stylish, Walking to Beach

Oceanview Penthouse, Stylish, Walking to Beach
El Granada
9.8 out of 10, Exceptional, (52 reviews)
"Everything was absolutely perfect. It was the perfect getaway perfect area thank you so much."
United States
Don
The price is NZ$483
includes taxes & fees
4 Oct - 5 Oct
Oceanview Penthouse, Stylish, Walking to Beach
A coastal view with a rocky shoreline, waves crashing onto the beach, and a clear sky.

14. Modern Coastal Retreat, Walk to Downtown HMB & Beach

Modern Coastal Retreat, Walk to Downtown HMB & Beach
Alsace Lorraine
10.0 out of 10, Exceptional, (29 reviews)
"Great location. An easy walk to the coastal trail."
United States
Barbara M.
The price is NZ$628
includes taxes & fees
7 Oct - 8 Oct
Modern Coastal Retreat, Walk to Downtown HMB & Beach
A staircase with wooden beams and large windows overlooking a beach.

15. Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!

Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!
Miramar
9.8 out of 10, Exceptional, (25 reviews)
"Very pleasant in great location "
United States
Eric B.
The price is NZ$685
includes taxes & fees
7 Oct - 8 Oct
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!
A black leather sectional sofa with patterned cushions, a glass coffee table with a floral design, and a small sign with the word "joy".

16. Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill

Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill
Belmont
9.6 out of 10, Exceptional, (4 reviews)
"Great quiet location. Well maintained"
United States
Vishal M.
Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill
A two-story house with a gabled roof and a front porch.

17. Modern Guesthouse Retreat in the Heart of Silicon Valley

Modern Guesthouse Retreat in the Heart of Silicon Valley
West Menlo Park
9.2 out of 10, Wonderful, (17 reviews)
"We weren’t actually able to stay at this lovely-looking property, but the hosts were kind and communication was great. "
United States
Anonymous traveller
The price is NZ$572
includes taxes & fees
1 Oct - 2 Oct
Modern Guesthouse Retreat in the Heart of Silicon Valley
A modern living room with a sofa, coffee table, and dining area.

18. Private Cottage House - Walk to Beaches, Harbor,Food, Trials, so much more

Private Cottage House - Walk to Beaches, Harbor,Food, Trials, so much more
El Granada
9.4 out of 10, Exceptional, (24 reviews)
"We loved our stay. Our only regret is not staying longer!"
United States
Anonymous traveller
Private Cottage House - Walk to Beaches, Harbor,Food, Trials, so much more
A coastal landscape with a sandy beach, cliffs, and a field of wildflowers.

19. Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more

Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more
El Granada
9.2 out of 10, Wonderful, (41 reviews)
"We had a wonderful time. There are beach views from both bedrooms and the porch is wonderful. We would recommend and would stay again."
United States
Aaron M.
The price is NZ$1,038
includes taxes & fees
22 Oct - 23 Oct
Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more
A modern, well-lit room with a bed, a dining area with a table and chairs, a TV mounted on the wall, and a large window providing natural light.

20. Palo Alto Cottage: Privacy, Comfort & Convenience

Palo Alto Cottage: Privacy, Comfort & Convenience
Midtown
9.6 out of 10, Exceptional, (25 reviews)
"It was a great cozy space and perfect for our trip to the area! Super accessible, but also very private. Absolutely worth the trip here!"
United States
Cera B.
The price is NZ$374
includes taxes & fees
29 Sept - 30 Sept
Palo Alto Cottage: Privacy, Comfort & Convenience
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

Hyatt Regency San Francisco Airport

Hyatt Regency San Francisco Airport

10/10 Excellent
"beautiful place, great location"
Yingsha 1-night trip
Posted 1 hour ago
Hyatt Regency San Francisco Airport

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 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 NZ$300 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?

Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more: This holiday home rental outside of San Gregorio is located on the beach, and has a balcony, a pool table and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Half Moon Bay Golf Links 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.