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 $249
CA $381 total
includes taxes & fees
May 3 - May 4
Mays Luxury Farm Stays

214B - Cozy Studio with AC & Kitchen near Stanford

214B - Cozy Studio with AC & Kitchen near Stanford
Redwood City
10.0 out of 10, Exceptional, (1 review)
"Comfortable and easy. It had everything that I needed. Communication was clear. "
United States
Anastasia and Tom L.
The price is CA $122
CA $247 total
includes taxes & fees
Apr 6 - Apr 7
214B - Cozy Studio with AC & Kitchen near Stanford

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, (117 reviews)
"The property was tucked away in a quiet neighborhood and it felt like a very private oasis all to myself. It was exceptionally clean and perfectly cozy for me to stay in for a few days. I would definitely stay again if I am ever in the area! "
United States
Courtney D.
The price is CA $249
CA $450 total
includes taxes & fees
Apr 5 - Apr 6
Small Beach Cottage near the Coastal Trail and The Ritz

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 $166
CA $284 total
includes taxes & fees
Apr 7 - Apr 8
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
7.4 out of 10, Good, (13 reviews)
"Very clean, host was a great communicator."
United States
Nicolaus O.
The price is CA $69
CA $160 total
includes taxes & fees
Apr 19 - Apr 20
Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To 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 $216
CA $679 total
includes taxes & fees
Apr 6 - Apr 7
lx51 History in Pescadero

Luxury Spa Retreat Guest House with Ocean View

Luxury Spa Retreat Guest House with Ocean View
Moss Beach
9.8 out of 10, Exceptional, (38 reviews)
"We had a great stay, bed was comfortable, place was clean, although the pillows seemed a bit flat. The host was quick at replying to questions. The host made sure we felt safe and had what we needed. The only thing we didn’t care for was the stability of the WiFi at the place and the area. "
United States
Nikki
The price is CA $287
CA $477 total
includes taxes & fees
Apr 6 - Apr 7
Luxury Spa Retreat Guest House with Ocean View

Cottage In The Woods

Cottage In The Woods
Woodside
10.0 out of 10, Exceptional, (49 reviews)
"Fantastic location for hiking in Redwood forests."
United States
Walter C.
The price is CA $251
CA $439 total
includes taxes & fees
Apr 4 - Apr 5
Cottage In The Woods

Mid Century Garden View Home Parking

Mid Century Garden View Home Parking
3.0 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 $237
CA $551 total
includes taxes & fees
Apr 7 - Apr 8
Mid Century Garden View Home Parking

Relax Coastal Retreat: Beautiful 2B Home Nr Beach

Relax Coastal Retreat: Beautiful 2B Home Nr Beach
El Granada
10.0 out of 10, Exceptional, (9 reviews)
"Great stay!"
United States
Jason M.
Relax Coastal Retreat: Beautiful 2B Home Nr Beach

Palo Alto Cottage: Privacy, Comfort & Convenience

Palo Alto Cottage: Privacy, Comfort & Convenience
Midtown
9.8 out of 10, Exceptional, (16 reviews)
"Quiet, comfortable, and good location. "
United States
Kelsey P.
The price is CA $162
CA $297 total
includes taxes & fees
Apr 9 - Apr 10
Palo Alto Cottage: Privacy, Comfort & Convenience

California Golden Dream C10

California Golden Dream C10
Adobe Meadow
The price is CA $137
CA $207 total
includes taxes & fees
Apr 9 - Apr 10
California Golden Dream C10

Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

Stunning Oceanview Coastal Home – Beach, Trails, Family Activities
Montara
9.2 out of 10, Wonderful, (83 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 $215
CA $493 total
includes taxes & fees
May 3 - May 4
Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

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
8.6 out of 10, Excellent, (8 reviews)
"We enjoyed the central location, and affordability of this this rental. Thank you!"
United States
Eric T.
The price is CA $111
CA $209 total
includes taxes & fees
Apr 19 - Apr 20
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House

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, (7 reviews)
"Had a great stay. Location is perfect. Clean and comfortable. Would stay again."
United States
Bill P.
The price is CA $62
CA $354 total
includes taxes & fees
Apr 14 - Apr 15
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay

"Queens Palace" Studio Apt Business Ready - San Jose

"Queens Palace" Studio Apt Business Ready - San Jose
San Tomas
10.0 out of 10, Exceptional, (7 reviews)
"Good clean property and check in was easy"
United States
Brij P.
The price is CA $179
CA $207 total
includes taxes & fees
Apr 23 - Apr 24
"Queens Palace" Studio Apt Business Ready - San Jose

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 $269
CA $708 total
includes taxes & fees
Apr 16 - Apr 17
Charming Garden Cottage- steps to historic Old Town Half Moon Bay

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 $194
CA $462 total
includes taxes & fees
Apr 9 - Apr 10
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Nice one bedroom apartment for short getaways or temporary housing w/ fast WiFi

Nice one bedroom apartment for short getaways or temporary housing w/ fast WiFi
East Palo Alto
8.4 out of 10, Very good, (19 reviews)
"Perfect location for a short stay in the area! Thank you!"
United States
Joshua A.
The price is CA $152
CA $398 total
includes taxes & fees
Apr 8 - Apr 9
Nice one bedroom apartment for short getaways or temporary housing w/ fast WiFi

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 $334
CA $621 total
includes taxes & fees
Apr 23 - Apr 24
Either Way Hideaway
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. Manhattan 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.