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
8.8 out of 10, Excellent, (13 reviews)
"Everyone was so friendly! And this place is so peaceful with the birds hobblying around. I def will be back to visit."
United States
Emann
The price is CA $204
CA $328 total
includes taxes & fees
May 12 - May 13
Mays Luxury Farm Stays

California Golden Dream C10

California Golden Dream C10
Adobe Meadow
The price is CA $135
CA $204 total
includes taxes & fees
May 14 - May 15
California Golden Dream C10

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

Cozy guest suite in Los Gatos - Beach in 30 min!
Los Gatos
8.8 out of 10, Excellent, (16 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 $164
CA $280 total
includes taxes & fees
May 12 - May 13
Cozy guest suite in Los Gatos - Beach in 30 min!

Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To Restaurants

Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To Restaurants
Miramar
7.2 out of 10, Good, (14 reviews)
"Parking was good. Short walk to the trail and beach. Accomodations were acceptable, not spectacular."
Canada
Wilma
The price is CA $68
CA $158 total
includes taxes & fees
May 18 - May 19
Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To Restaurants

Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more

Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more
El Granada
9.4 out of 10, Exceptional, (37 reviews)
"We loved our stay"
United States
Chris L.
The price is CA $305
CA $829 total
includes taxes & fees
May 21 - May 22
Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more

2BR Belmont Treehouse near SFO, Caltrain & Levi's

2BR Belmont Treehouse near SFO, Caltrain & Levi's
Belmont
9.6 out of 10, Exceptional, (7 reviews)
"The place was great! Clean, comfortable, and quiet for my family of 4. It had everything we needed for our 2 week stay so much so that we’ve booked again for another 2 weeks while we are in the middle of a move. Thank you Will!"
United States
Dash L.
The price is CA $206
CA $436 total
includes taxes & fees
May 17 - May 18
2BR Belmont Treehouse near SFO, Caltrain & Levi's

"Queens Palace" Studio Apt Business Ready - San Jose

"Queens Palace" Studio Apt Business Ready - San Jose
San Tomas
9.8 out of 10, Exceptional, (8 reviews)
"The room was cozy and quiet, perfect for a good night's sleep. Check-in and Check-out were super easy!"
United States
Joshua E.
The price is CA $176
CA $204 total
includes taxes & fees
May 13 - May 14
"Queens Palace" Studio Apt Business Ready - San Jose

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, (123 reviews)
"Cottage was quiet and comfortable. Great neighborhood. Amazing setup for dog. Well equiped kitchen and super easy walk to beach."
United States
Paul
The price is CA $244
CA $495 total
includes taxes & fees
May 26 - May 27
Small Beach Cottage near the Coastal Trail and The Ritz

Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

Stunning Oceanview Coastal Home – Beach, Trails, Family Activities
Montara
9.2 out of 10, Wonderful, (84 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 $164
CA $424 total
includes taxes & fees
May 12 - May 13
Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach

Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach
Pedro Point
9.4 out of 10, Exceptional, (11 reviews)
"great location and beautiful views. Clean and comfortable."
United States
David E.
The price is CA $154
CA $469 total
includes taxes & fees
Jun 11 - Jun 12
Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach

Palo Alto Cottage: Privacy, Comfort & Convenience

Palo Alto Cottage: Privacy, Comfort & Convenience
Midtown
9.6 out of 10, Exceptional, (18 reviews)
"Quiet, comfortable, and good location. "
United States
Kelsey P.
The price is CA $154
CA $282 total
includes taxes & fees
May 14 - May 15
Palo Alto Cottage: Privacy, Comfort & Convenience

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

@ Marbella Lane - 2BR Guest House |DTWN RWC| Pking
Palm Park
7.6 out of 10, Good, (19 reviews)
"Safe neighborhood and easy check in/out. The beds are very comfortable and everything was in place and worked as listed. Management was very responsive and attentive. We loved that it was walking distance from some local restaurants that were delicious! We would stay there again. "
United States
Angela C.
The price is CA $160
CA $550 total
includes taxes & fees
Jun 7 - Jun 8
@ Marbella Lane - 2BR Guest House |DTWN RWC| Pking

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
8.8 out of 10, Excellent, (9 reviews)
"We enjoyed the central location, and affordability of this this rental. Thank you!"
United States
Eric T.
The price is CA $109
CA $205 total
includes taxes & fees
May 12 - May 13
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House

lx51 History in Pescadero

lx51 History in Pescadero
Pescadero
10.0 out of 10, Exceptional, (4 reviews)
"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 $213
CA $670 total
includes taxes & fees
May 13 - May 14
lx51 History in Pescadero

Brand-new deluxe guesthouse with king bed in MPK, 1mi to Meta, 3mi to Stanford

Brand-new deluxe guesthouse with king bed in MPK, 1mi to Meta, 3mi to Stanford
Suburban Park - Lorelei Manor - Flood Park Triangle
The price is CA $367
CA $417 total
includes taxes & fees
May 13 - May 14
Brand-new deluxe guesthouse with king bed in MPK, 1mi to Meta, 3mi to Stanford

Luxury Spa Retreat Guest House with Ocean View

Luxury Spa Retreat Guest House with Ocean View
Moss Beach
9.6 out of 10, Exceptional, (40 reviews)
"We loved staying here! Such a beautiful home with beautiful views. Thank you!"
United States
Vita P.
The price is CA $362
CA $568 total
includes taxes & fees
Jun 1 - Jun 2
Luxury Spa Retreat Guest House with Ocean View

Mid Century Garden View Home Parking

Mid Century Garden View Home Parking
3.0 star property
Shoreview
8.6 out of 10, Excellent, (4 reviews)
"This is a very clean comfortable property! "
United States
Serena
The price is CA $253
CA $565 total
includes taxes & fees
May 17 - May 18
Mid Century Garden View Home Parking

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, (4 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
The price is CA $191
CA $455 total
includes taxes & fees
May 14 - May 15
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

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
9.0 out of 10, Wonderful, (21 reviews)
"The location of this rental is excellent. We enjoyed the hot tub and the coziness of the space. There were nice views and we had everything we needed to feel right at home."
United States
Letha S.
Seaside Escape: 1 block to Beach, Private Hot Tub, Fire Pit & BBQ

Cottage In The Woods

Cottage In The Woods
Woodside
10.0 out of 10, Exceptional, (52 reviews)
"Peaceful, cozy, perfect as always "
United States
Craig B.
The price is CA $274
CA $463 total
includes taxes & fees
May 25 - May 26
Cottage In The Woods
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?

Beachview Holiday Family Retreat | Steps to Sand: Visitors like this San Gregorio vacation home rental. It is located on the beach and offers a balcony, Netflix, and laundry facilities to help you feel perfectly comfortable 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.

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. Bean Hollow State Beach and Pelican Point Beach 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.