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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for San Gregorio holiday rentals

A wooden deck with a metal railing overlooking a forested area.

1. 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 AU$473
includes taxes & fees
25 Oct - 26 Oct
Cottage In The Woods
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.

2. 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, (15 reviews)
"nice place...close to restaurants...easy parking!"
United States
Luz
The price is AU$431
includes taxes & fees
26 Oct - 27 Oct
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
A wooden deck with a bench, surrounded by a garden with mulch and stepping stones, leading to a house with a gray exterior and a purple door.

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

Modern Coastal Retreat, Walk to Downtown HMB & Beach
Alsace Lorraine
10.0 out of 10, Exceptional, (33 reviews)
"Great location. An easy walk to the coastal trail."
United States
Barbara M.
The price is AU$468
includes taxes & fees
1 Nov - 2 Nov
Modern Coastal Retreat, Walk to Downtown HMB & Beach
A living room with a sectional sofa, a wooden coffee table, and a colorful striped rug.

4. 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, (23 reviews)
"Thanks for a great stay!"
United States
April M.
The price is AU$195
includes taxes & fees
26 Oct - 27 Oct
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
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, (137 reviews)
"Great little place!"
United States
Jeffrey B.
The price is AU$526
includes taxes & fees
2 Nov - 3 Nov
Small Beach Cottage near the Coastal Trail and The Ritz
A wooden deck with a hot tub, a wooden fence, and a large tree.

6. Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.8 out of 10, Excellent, (38 reviews)
"though a bit off the beaten path--accomodations were great, relaxing after a hard day work on the deck and the welcome addition and unexpected treat of farm fresh eggs!"
United States
Mark
The price is AU$290
includes taxes & fees
23 Nov - 24 Nov
Mays Luxury Farm Stays
A living room with a flat-screen TV mounted above a fireplace, a wall-mounted decorative item, and a framed picture.

7. 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 AU$382
includes taxes & fees
26 Oct - 27 Oct
Oceanview Penthouse, Stylish, Walking to Beach
A hotel room with a bed, a desk with a chair, a television, and a large window with curtains.

8. 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 AU$274
includes taxes & fees
5 Nov - 6 Nov
214B - Cozy Studio with AC & Kitchen near Stanford
A covered patio with outdoor furniture, a wooden deck, and a white pergola.

9. 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 AU$697
includes taxes & fees
26 Oct - 27 Oct
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
A bedroom with a skylight, a bed, a desk with a chair, and a wardrobe.

10. Stylish Seaside Cottage - Walking to Beach

Stylish Seaside Cottage - Walking to Beach
El Granada
9.4 out of 10, Exceptional, (58 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 AU$363
includes taxes & fees
26 Oct - 27 Oct
Stylish Seaside Cottage - Walking to Beach
A hot tub in a backyard with a wooden deck, outdoor furniture, and a wooden fence.

11. 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, (66 reviews)
"Clean; cheerful! Wonderful location."
United States
Catherine
The price is AU$661
includes taxes & fees
16 Nov - 17 Nov
Charming Garden Cottage- steps to historic Old Town Half Moon Bay
A staircase with wooden beams and large windows overlooking a beach.

12. 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, (26 reviews)
"Very pleasant in great location "
United States
Eric B.
The price is AU$534
includes taxes & fees
3 Nov - 4 Nov
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!
A covered porch with a table and chairs, a view of the ocean, and a large tree.

13. 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, (42 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 AU$737
includes taxes & fees
26 Oct - 27 Oct
Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more
A modern hotel room with a grey sofa, two armchairs, a bed, a round mirror, and a large painting on the wall.

14. 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, (10 reviews)
"The place was super cute and close to everything. I would definitely stay again! "
United States
Juliet M.
The price is AU$454
includes taxes & fees
3 Nov - 4 Nov
Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay
A wooden dining table with wicker chairs, surrounded by lush greenery and vines.

15. 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 AU$518
includes taxes & fees
2 Nov - 3 Nov
Secluded freestanding house in the delightful grape garden
A bedroom with a bed, a bedside lamp, an air conditioning unit, a window with blinds, and a ceiling light.

16. Marbella Lane - 2BR Guest House Dtwn RWC Pking

Marbella Lane - 2BR Guest House Dtwn RWC Pking
3.0 star property
Palm Park
The price is AU$666
includes taxes & fees
27 Oct - 28 Oct
Marbella Lane - 2BR Guest House Dtwn RWC Pking
A spacious living room with a fireplace, a television, and comfortable seating.

17. Beach Cottage Near the Coastal Trail and the Ritz

Beach Cottage Near the Coastal Trail and the Ritz
Arleta Park
10.0 out of 10, Exceptional, (49 reviews)
"So grateful to get to bring our dogs with us! This was a wonderful getaway, great communication, and such a lovely beach cottage. Easy walk to the beach to either enjoy the view from the bluff or walk down the stairs to the sand. We all remarked on how much if felt like somewhere we would want to call home."
United States
Stacey D.
The price is AU$888
includes taxes & fees
5 Nov - 6 Nov
Beach Cottage Near the Coastal Trail and the Ritz
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.

18. Palo Alto Cottage: Privacy, Comfort & Convenience

Palo Alto Cottage: Privacy, Comfort & Convenience
Midtown
9.4 out of 10, Exceptional, (27 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 AU$309
includes taxes & fees
26 Oct - 27 Oct
Palo Alto Cottage: Privacy, Comfort & Convenience
A bedroom with a bed, a desk, a chair, a window, and a door.

19. 214A - Cozy Studio with AC & Kitchen near Stanford

214A - Cozy Studio with AC & Kitchen near Stanford
Redwood City
9.0 out of 10, Wonderful, (8 reviews)
"Perfect stay for a quick get away! "
United States
Sylvia L.
The price is AU$248
includes taxes & fees
20 Nov - 21 Nov
214A - Cozy Studio with AC & Kitchen near Stanford
A bedroom with a bed, a bedside table with a lamp, a trash bin, and a painting on the wall.

20. @ Marbella Lane - 2BR Guest House |DTWN RWC| Pking

@ Marbella Lane - 2BR Guest House |DTWN RWC| Pking
Palm Park
7.4 out of 10, Good, (20 reviews)
"Nice clean quiet place to spend the night while on a short business trip."
United States
Don
The price is AU$529
includes taxes & fees
27 Oct - 28 Oct
@ Marbella Lane - 2BR Guest House |DTWN RWC| Pking
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

Good Nite Inn - Redwood City

Good Nite Inn - Redwood City

10/10 Excellent
"wonderful staff, clean room with air conditioning!!!"
Dawit 2-night trip
Posted less than an hour ago
Good Nite Inn - Redwood City

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$195 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?

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.