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

San Gregorio Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for San Gregorio vacation rentals

Terrace/patio

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.
$310 nightly
The price is $338
Sep 21 - Sep 22
Total with taxes and fees
Cottage In The Woods
Yurt On Top - Swim, Hike, Glamp

2. Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.6 out of 10, Excellent, (29 reviews)
"This property is just what you need if you are looking for a peaceful place to escape to in the mountains. The host was very friendly and helpful. The chickens were adorable. And the view was breathtaking. We would definitely come back for another stay."
United States
Adrianna
$214 nightly
The price is $245
Sep 20 - Sep 21
Total with taxes and fees
Mays Luxury Farm Stays
Room

3. 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.
$356 nightly
The price is $403
Oct 6 - Oct 7
Total with taxes and fees
Small Beach Cottage near the Coastal Trail and The Ritz
Room

4. Adorable Romantic Private Getaway in Pescadero

Adorable Romantic Private Getaway in Pescadero
Pescadero
$363 nightly
The price is $363
Sep 26 - Sep 27
Total with taxes and fees
Adorable Romantic Private Getaway in Pescadero
Beach

5. 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)
"The property is clean, convenient, and well-appointed. Owner communication was great. Would rent again in a heartbeat. "
United States
Carmela
$354 nightly
The price is $360
Oct 4 - Oct 5
Total with taxes and fees
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
Property grounds

6. Oceanview Penthouse, Stylish, Walking to Beach

Oceanview Penthouse, Stylish, Walking to Beach
El Granada
10.0 out of 10, Exceptional, (51 reviews)
"Everything was absolutely perfect. It was the perfect getaway perfect area thank you so much."
United States
Don
$248 nightly
The price is $270
Sep 21 - Sep 22
Total with taxes and fees
Oceanview Penthouse, Stylish, Walking to Beach
Room

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

214A - Cozy Studio with AC & Kitchen near Stanford
Redwood City
9.2 out of 10, Wonderful, (7 reviews)
"Perfect stay for a quick get away! "
United States
Sylvia L.
$189 nightly
The price is $189
Oct 11 - Oct 12
Total with taxes and fees
214A - Cozy Studio with AC & Kitchen near Stanford
Interior

8. 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.
$341 nightly
The price is $355
Sep 30 - Oct 1
Total with taxes and fees
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!
Living area

9. 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)
"Great place, would stay again!"
United States
Marianna F.
$267 nightly
The price is $278
Sep 30 - Oct 1
Total with taxes and fees
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
Living area

10. Relax Coastal Retreat: Beautiful 2B Home Nr Beach

Relax Coastal Retreat: Beautiful 2B Home Nr Beach
El Granada
10.0 out of 10, Exceptional, (11 reviews)
"Great stay!"
United States
Jason M.
$551 nightly
The price is $591
Oct 8 - Oct 9
Total with taxes and fees
Relax Coastal Retreat: Beautiful 2B Home Nr Beach
Exterior

11. Modern Guesthouse Retreat in the Heart of Silicon Valley

Modern Guesthouse Retreat in the Heart of Silicon Valley
West Menlo Park
9.0 out of 10, Wonderful, (15 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 traveler
$330 nightly
The price is $330
Sep 19 - Sep 20
Total with taxes and fees
Modern Guesthouse Retreat in the Heart of Silicon Valley
Beach

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

Modern Coastal Retreat, Walk to Downtown HMB & Beach
Alsace Lorraine
10.0 out of 10, Exceptional, (28 reviews)
"Great location. An easy walk to the coastal trail."
United States
Barbara M.
$352 nightly
The price is $377
Sep 30 - Oct 1
Total with taxes and fees
Modern Coastal Retreat, Walk to Downtown HMB & Beach
Living area

13. 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
7.6 out of 10, Good, (20 reviews)
"Thanks for a great stay!"
United States
April M.
$170 nightly
The price is $170
Oct 8 - Oct 9
Total with taxes and fees
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
Interior

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

Marbella Lane - 2BR Guest House Dtwn RWC Pking
3.0 star property
Palm Park
Marbella Lane - 2BR Guest House Dtwn RWC Pking
Outdoor spa tub

15. 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, (63 reviews)
"Clean; cheerful! Wonderful location."
United States
Catherine
$447 nightly
The price is $475
Sep 24 - Sep 25
Total with taxes and fees
Charming Garden Cottage- steps to historic Old Town Half Moon Bay
Property grounds

16. 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
$313 nightly
The price is $341
Sep 17 - Sep 18
Total with taxes and fees
Secluded freestanding house in the delightful grape garden
Living area

17. 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, (22 reviews)
"We loved our stay. Our only regret is not staying longer!"
United States
Anonymous traveler
Private Cottage House - Walk to Beaches, Harbor,Food, Trials, so much more
Beach

18. 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.
$241 nightly
The price is $263
Oct 4 - Oct 5
Total with taxes and fees
Stylish Seaside Cottage - Walking to Beach
Classic House | Living area

19. Mid Century Garden View Home Parking

Mid Century Garden View Home Parking
3.0 star property
East San Mateo
7.2 out of 10, Good, (5 reviews)
"This is a very clean comfortable property! "
United States
Serena
$290 nightly
The price is $333
Sep 26 - Sep 27
Total with taxes and fees
Mid Century Garden View Home Parking
Room

20. Palo Alto Cottage: Privacy, Comfort & Convenience

Palo Alto Cottage: Privacy, Comfort & Convenience
Midtown
9.6 out of 10, Exceptional, (24 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.
$211 nightly
The price is $211
Sep 20 - Sep 21
Total with taxes and fees
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

Half Moon Bay Lodge

Half Moon Bay Lodge

8/10 Good
"We checked in for only 1 night but our room was meticulously cleaned and the bathroom is nice & big with lots of space. The beds are very comfortable and our room had a patio overlooking golf course. Although a little dated, the hotel is still very nice & in a quiet area. Another plus is a huge (free) parking lot with ample parking spots. There are also a lot of restaurants in the area plus a Starbucks down the road if you’re looking. Free continental breakfast in the morning but basic, nothing fancy. Nice place and highly recommend."
Carol 1-night trip
Posted less than an hour ago
Half Moon Bay Lodge

Find out more about San Gregorio

Everything you need to know about San Gregorio vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the San Gregorio vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

San Gregorio vacation 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 low season months. For more hustle and bustle, you may prefer to visit San Gregorio in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $170 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on San Gregorio rentals

At Expedia, we put the best San Gregorio vacation 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 vacation.

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.

Explore a world of travel with Expedia

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: You might want to consider this vacation rental near San Gregorio, which 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.