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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for San Gregorio vacation 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.
$288 nightly
The price is $314
Oct 5 - Oct 6
Total with taxes and fees
Cottage In The Woods
A cozy bedroom with a wooden ceiling, a bed with white linens, and a textured blanket.

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 dog friendly well appointed tiny house."
United States
Deb L.
$372 nightly
The price is $422
Oct 19 - Oct 20
Total with taxes and fees
Small Beach Cottage near the Coastal Trail and The Ritz
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
$323 nightly
The price is $338
Oct 26 - Oct 27
Total with taxes and fees
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
A coastal view with a rocky shoreline, waves crashing onto the beach, and a clear sky.

4. 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.
$335 nightly
The price is $359
Oct 6 - Oct 7
Total with taxes and fees
Modern Coastal Retreat, Walk to Downtown HMB & Beach
A hot tub in a backyard with a wooden deck, outdoor furniture, and a wooden fence.

5. 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
$445 nightly
The price is $469
Nov 4 - Nov 5
Total with taxes and fees
Charming Garden Cottage- steps to historic Old Town Half Moon Bay
A wooden deck with a white bathtub, wooden pergola, and a blue wall with a sign.

6. Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.6 out of 10, Excellent, (33 reviews)
"I'll be back"
United States
Billy
$199 nightly
The price is $228
Nov 2 - Nov 3
Total with taxes and fees
Mays Luxury Farm Stays
A coastal landscape with a sandy beach, cliffs, and a field of wildflowers.

7. 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.
$514 nightly
The price is $537
Oct 26 - Oct 27
Total with taxes and fees
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
A wooden lattice structure with a sofa and a small table, surrounded by plants and a patterned rug.

8. 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
$260 nightly
The price is $283
Oct 12 - Oct 13
Total with taxes and fees
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.

9. 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.
$190 nightly
The price is $190
Oct 23 - Oct 24
Total with taxes and fees
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.

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.
$238 nightly
The price is $259
Oct 7 - Oct 8
Total with taxes and fees
Stylish Seaside Cottage - Walking to Beach
A living room with a sectional sofa, a wooden coffee table, and a colorful striped rug.

11. 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.
$170 nightly
The price is $170
Oct 13 - Oct 14
Total with taxes and fees
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
A wooden dining table with wicker chairs, surrounded by lush greenery and vines.

12. 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
$319 nightly
The price is $348
Oct 7 - Oct 8
Total with taxes and fees
Secluded freestanding house in the delightful grape garden
A two-story house with a gabled roof and a front porch.

13. 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, (18 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
$328 nightly
The price is $328
Oct 12 - Oct 13
Total with taxes and fees
Modern Guesthouse Retreat in the Heart of Silicon Valley
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.

14. 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.
$211 nightly
The price is $211
Oct 11 - Oct 12
Total with taxes and fees
Palo Alto Cottage: Privacy, Comfort & Convenience
A modern hotel room with a grey sofa, two armchairs, a bed, a round mirror, and a large painting on the wall.

15. 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.
$319 nightly
The price is $336
Oct 20 - Oct 21
Total with taxes and fees
Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay
A spacious living room with a fireplace, a television, and comfortable seating.

16. 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, (47 reviews)
"House was close to the beach, had everything we needed, felt warm and inviting"
United States
Elizabeth D.
$558 nightly
The price is $632
Oct 18 - Oct 19
Total with taxes and fees
Beach Cottage Near the Coastal Trail and the Ritz
A hotel room with two beds, each with white bedding and a red accent. There are two wall-mounted lamps providing light.

17. 2 Queen Beds | Mini Fridge

2 Queen Beds | Mini Fridge
Belmont
$98 nightly
The price is $113
Oct 9 - Oct 10
Total with taxes and fees
2 Queen Beds | Mini Fridge
A modern living room with a large bean bag, a fireplace, and a television.

18. 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.
$482 nightly
The price is $516
Oct 8 - Oct 9
Total with taxes and fees
Relax Coastal Retreat: Beautiful 2B Home Nr Beach
Lounge

19. Mint House Menlo Park by Kasa

Mint House Menlo Park by Kasa
4.0 star property
Menlo Park
7.6 out of 10, Good, (37 reviews)
"The property was beautiful and looked exactly like the photos. It was in a very nice clean area, pet friendly, and had a lot of space to work. We did not get to check out the gym but it looked very nice as well! Definitely looking forward to staying at other Kasa properties in the future!"
United States
Tiffanie
$289 nightly
The price is $334
Oct 24 - Oct 25
Total with taxes and fees
Mint House Menlo Park by Kasa
A bedroom with two beds, a ceiling fan, a window with curtains, and a nightstand with a lamp.

20. Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette
Cupertino
9.6 out of 10, Exceptional, (5 reviews)
"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
$298 nightly
The price is $330
Oct 5 - Oct 6
Total with taxes and fees
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette
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

Hotel Aluxor SFO

Hotel Aluxor SFO

8/10 Good
"This could be a lovely hotel. The room was clean and very comfortable. The gentlemen who checked me in was very helpful; however the gentleman who checked me out made me wait for 8 minutes while he continued his phone call. It was very hard to find help after I checked in. I purchased some water and a bag of chips. No staff was available to take my payment . I finally left the money in the room key return slot. I would consider staying here again . I give it a 3.5 out of 5. Score is based on the lack of staff to assist."
Teresa 1-night trip
Posted 1 hour ago
Hotel Aluxor SFO

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.

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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.