San Gregorio Vacation Rentals

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Our top choices for San Gregorio vacation rentals

Mays Luxury Farm Stays

Mays Luxury Farm Stays
2.0 star property
Los Gatos
10.0 out of 10, Exceptional, (7 reviews)
"We had a great time and really enjoyed it "
United States
Sripan
The price is CA $156
CA $275 total
includes taxes & fees
Apr 26 - Apr 27
Mays Luxury Farm Stays

Mid Century Garden View Home Parking

Mid Century Garden View Home Parking
2.0 star property
East San Mateo
8.6 out of 10, Excellent, (4 reviews)
"This is a very clean comfortable property! "
United States
Serena
The price is CA $236
CA $549 total
includes taxes & fees
Mar 31 - Apr 1
Mid Century Garden View Home Parking

Steps to Ocean: Luxe Family Home in Half Moon Bay!

Steps to Ocean: Luxe Family Home in Half Moon Bay!
3.0 star property
Arleta Park
The price is CA $667
CA $1,361 total
includes taxes & fees
Mar 29 - Mar 30
Steps to Ocean: Luxe Family Home in Half Moon Bay!

Oceanview Penthouse, Stylish & Walking to Beach

Oceanview Penthouse, Stylish & Walking to Beach
El Granada
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful views and having two private decks was really nice. Parking was easy and safe. "
United States
Heather
The price is CA $303
CA $446 total
includes taxes & fees
Mar 29 - Mar 30
Oceanview Penthouse, Stylish & Walking to Beach

497-Upscale Home w/AC & Patio near Meta & Stanford

497-Upscale Home w/AC & Patio near Meta & Stanford
Menlo Park
8.8 out of 10, Excellent, (8 reviews)
"Had 5 people staying at the property and it was great that everyone had dedicated space/bathroom. Parking is a little tricky but overall great experience "
United States
Robert H.
The price is CA $728
CA $1,421 total
includes taxes & fees
Mar 28 - Mar 29
497-Upscale Home w/AC & Patio near Meta & Stanford

@ Marbella Lane - Bright and Cozy Home Near SFO

@ Marbella Lane - Bright and Cozy Home Near SFO
3.0 star property
North Central
The price is CA $339
CA $706 total
includes taxes & fees
Mar 31 - Apr 1
@ Marbella Lane - Bright and Cozy Home Near SFO

491-Luxury Home w/ AC & Patio near Meta & Stanford

491-Luxury Home w/ AC & Patio near Meta & Stanford
Menlo Park
8.8 out of 10, Excellent, (3 reviews)
"The location is very conveniently located, easy drive to grab coffee in downtown every morning. Bed is too soft and pillows were too hard for us so we couldn’t sleep well, but got better when we bought our own pillows. The washer "
United States
Sarah L.
The price is CA $688
CA $1,368 total
includes taxes & fees
Mar 28 - Mar 29
491-Luxury Home w/ AC & Patio near Meta & Stanford

Elegant but practical retreat to maximize your enjoyment in beautiful HMB

Elegant but practical retreat to maximize your enjoyment in beautiful HMB
El Granada
10.0 out of 10, Exceptional, (13 reviews)
"Great place"
United States
Joseph F.
The price is CA $546
CA $1,021 total
includes taxes & fees
Mar 29 - Mar 30
Elegant but practical retreat to maximize your enjoyment in beautiful HMB

Charming 3-bedroom Guesthouse with WiFi in Sunnyvale

Charming 3-bedroom Guesthouse with WiFi in Sunnyvale
San Miguel
The price is CA $483
CA $1,075 total
includes taxes & fees
Mar 30 - Mar 31
Charming 3-bedroom Guesthouse with WiFi in Sunnyvale

Spacious 4-bedroom house in charming Newark with AC

Spacious 4-bedroom house in charming Newark with AC
Newark
The price is CA $601
CA $1,370 total
includes taxes & fees
Apr 12 - Apr 13
Spacious 4-bedroom house in charming Newark with AC

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, (57 reviews)
"Close to everything, pet friendly "
United States
Gary B.
The price is CA $240
CA $662 total
includes taxes & fees
Apr 12 - Apr 13
Charming Garden Cottage- steps to historic Old Town Half Moon Bay

601-Lavish Home w/ AC & Patio near Meta & Stanford

601-Lavish Home w/ AC & Patio near Meta & Stanford
Menlo Park
9.2 out of 10, Wonderful, (15 reviews)
"I enjoyed the place and the location. There are plenty of nice restaurants and very close to Stanford University."
United States
Marco S.
The price is CA $780
CA $1,492 total
includes taxes & fees
Mar 28 - Mar 29
601-Lavish Home w/ AC & Patio near Meta & Stanford

Luxury stay near Santana Row for vacation/business

Luxury stay near Santana Row for vacation/business
West San Jose
9.4 out of 10, Exceptional, (57 reviews)
"The room was good and convenient for my work trip. "
United States
Pavani
The price is CA $214
CA $353 total
includes taxes & fees
Mar 30 - Mar 31
Luxury stay near Santana Row for vacation/business

Cozy guest suite in Los Gatos - Beach in 30 min!

Cozy guest suite in Los Gatos - Beach in 30 min!
Los Gatos
8.6 out of 10, Excellent, (14 reviews)
"Amazing views from the back porch. Very easy to check in and check out. The property is beautiful. Lots of great places nearby to eat, drink, or grab a cup of coffee.Would recommend."
United States
Immanuel D.
The price is CA $165
CA $283 total
includes taxes & fees
Apr 7 - Apr 8
Cozy guest suite in Los Gatos - Beach in 30 min!

Private Home with Breathtaking Ocean Views - walk to Beaches, Restaurants

Private Home with Breathtaking Ocean Views - walk to Beaches, Restaurants
Miramar
9.2 out of 10, Wonderful, (47 reviews)
"Location was great! Walked to the beach, dinner and breakfast. Short drive to hiking and down town half moon bay. "
United States
Julie W.
The price is CA $925
CA $1,623 total
includes taxes & fees
Apr 9 - Apr 10
Private Home with Breathtaking Ocean Views - walk to Beaches, Restaurants

lx51 History in Pescadero

lx51 History in Pescadero
Pescadero
10.0 out of 10, Exceptional, (1 review)
"Great location and the backyard was so relaxing. It was a lovely getaway and we look forward to staying there in the future "
United States
jess w.
The price is CA $215
CA $676 total
includes taxes & fees
Apr 3 - Apr 4
lx51 History in Pescadero

Either Way Hideaway

Either Way Hideaway
Boulder Creek
10.0 out of 10, Exceptional, (15 reviews)
"We had a beautiful stay here. Everything was just as described and the surroundings were amazing. "
United States
Vita P.
The price is CA $288
CA $565 total
includes taxes & fees
Apr 20 - Apr 21
Either Way Hideaway

W. Menlo Luxurious executive mansion over 4000sqft

W. Menlo Luxurious executive mansion over 4000sqft
West Menlo Park
9.6 out of 10, Exceptional, (21 reviews)
"Mike was very responsive and welcoming. The house was perfect for our 13 person group and ideally located for the wedding we were attending at Stanford. It was an excellent and comfortable stay. "
United States
Richard W.
The price is CA $1,048
CA $1,691 total
includes taxes & fees
Apr 14 - Apr 15
W. Menlo Luxurious executive mansion over 4000sqft

Luxury Silicon Valley Work and Wellness Oasis

Luxury Silicon Valley Work and Wellness Oasis
Los Altos Hills
The price is CA $392
CA $682 total
includes taxes & fees
Apr 7 - Apr 8
Luxury Silicon Valley Work and Wellness Oasis

Los Gatos Guest Cottage: 2 Mi to Netflix HQ!

Los Gatos Guest Cottage: 2 Mi to Netflix HQ!
Monte Sereno
10.0 out of 10, Exceptional, (1 review)
"This cottage provided a wonderful stay for us. The host was so attentive and the accommodations felt more like a boutique hotel than a rental property. The home and property were beautiful and we would highly recommend staying here!"
United States
Jennifer
The price is CA $412
CA $752 total
includes taxes & fees
Mar 30 - Mar 31
Los Gatos Guest Cottage: 2 Mi to Netflix HQ!
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.

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?

San Francisco Bay area: Elegant Pacific Ocean View, sleeps 10, gourmet kitchen: Visitors like this San Gregorio vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a hot tub, and a selection of books so you can immerse yourself in your vacation.

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. Pelican Point 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.