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San Gregorio Vacation Rentals

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Our top choices for San Gregorio vacation rentals

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 CA $284
CA $486 total
includes taxes & fees
Oct 20 - Oct 21
Cottage In The Woods

2. 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 little place!"
United States
Jeffrey B.
The price is CA $294
CA $563 total
includes taxes & fees
Oct 19 - Oct 20
Small Beach Cottage near the Coastal Trail and The Ritz

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, (32 reviews)
"Great location. An easy walk to the coastal trail."
United States
Barbara M.
The price is CA $270
CA $503 total
includes taxes & fees
Oct 19 - Oct 20
Modern Coastal Retreat, Walk to Downtown HMB & Beach

4. Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay

Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay
Heritage Downtown
9.4 out of 10, Exceptional, (20 reviews)
"Great location and comfortable bed"
United States
Karly G.
The price is CA $156
CA $497 total
includes taxes & fees
Oct 19 - Oct 20
Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay

5. Seaside Escape: 1 block to Beach, Private Hot Tub, Fire Pit & BBQ

Seaside Escape: 1 block to Beach, Private Hot Tub, Fire Pit & BBQ
Miramar
8.6 out of 10, Excellent, (26 reviews)
"Great location, clean and private space."
United States
Alec H.
The price is CA $281
CA $619 total
includes taxes & fees
Oct 18 - Oct 19
Seaside Escape: 1 block to Beach, Private Hot Tub, Fire Pit & BBQ

6. 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 CA $142
CA $243 total
includes taxes & fees
Oct 19 - Oct 20
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House

7. Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.8 out of 10, Excellent, (36 reviews)
"The owner is incredibly respectful and empathetic. They welcome you with great respect and do everything possible to make you feel wonderful. I would definitely go back! A wonderful nature getaway! Thank you for such kindness."
United States
Mirna
The price is CA $183
CA $316 total
includes taxes & fees
Nov 5 - Nov 6
Mays Luxury Farm Stays

8. 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 CA $222
CA $778 total
includes taxes & fees
Oct 26 - Oct 27
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

9. 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, (65 reviews)
"Clean; cheerful! Wonderful location."
United States
Catherine
The price is CA $228
CA $675 total
includes taxes & fees
Nov 16 - Nov 17
Charming Garden Cottage- steps to historic Old Town Half Moon Bay

10. 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 CA $217
CA $414 total
includes taxes & fees
Oct 26 - Oct 27
Oceanview Penthouse, Stylish, Walking to Beach

11. 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 CA $211
CA $524 total
includes taxes & fees
Oct 19 - Oct 20
Secluded freestanding house in the delightful grape garden

12. 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 CA $221
CA $415 total
includes taxes & fees
Nov 4 - Nov 5
Stylish Seaside Cottage - Walking to Beach

13. 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 CA $139
CA $264 total
includes taxes & fees
Oct 23 - Oct 24
214B - Cozy Studio with AC & Kitchen near Stanford

14. 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, (48 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 CA $490
CA $909 total
includes taxes & fees
Oct 29 - Oct 30
Beach Cottage Near the Coastal Trail and the Ritz

15. 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 CA $308
CA $875 total
includes taxes & fees
Oct 22 - Oct 23
Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more

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 CA $203
CA $653 total
includes taxes & fees
Oct 19 - Oct 20
Marbella Lane - 2BR Guest House Dtwn RWC Pking

17. 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 CA $129
CA $462 total
includes taxes & fees
Nov 3 - Nov 4
Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay

18. 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 CA $205
CA $496 total
includes taxes & fees
Oct 18 - Oct 19
Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

19. 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 CA $166
CA $304 total
includes taxes & fees
Oct 24 - Oct 25
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

Find out more about San Gregorio

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with San Gregorio. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there vacation rentals in San Gregorio?

Yes, we have vacation rentals close to the most popular points of interest in San Gregorio, or you can select a more secluded option if you're looking for relaxation. San Gregorio is known for its beaches and restaurants.

What are some of the best vacation home rentals in San Gregorio?

Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more: Visitors like this San Gregorio vacation home rental. It 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 larger area.

What’s a vacation rental in San Gregorio like?

Vacation rentals are private properties where you can stay for a couple of days or more in San Gregorio. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a family trip.