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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for San Gregorio vacation rentals

Beach

1. Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
South Downtown
9.4 out of 10, Exceptional, (42 reviews)
"The property is clean, convenient, and well-appointed. Owner communication was great. Would rent again in a heartbeat. "
United States
Carmela
$359 nightly
The price is $364
Aug 27 - Aug 28
Total with taxes and fees
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
Yurt On Top - Swim, Hike, Glamp | Minibar (free items), laptop workspace, WiFi (free)

2. Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.4 out of 10, Very Good, (25 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
$212 nightly
The price is $242
Aug 27 - Aug 28
Total with taxes and fees
Mays Luxury Farm Stays
Terrace/patio

3. Cottage In The Woods

Cottage In The Woods
Woodside
10.0 out of 10, Exceptional, (58 reviews)
"The cabin was perfect for the two of us. The soothing sound of the stream and view of redwoods from the deck was wonderful."
United States
Jay
$292 nightly
The price is $318
Aug 20 - Aug 21
Total with taxes and fees
Cottage In The Woods
1 bedroom, iron/ironing board, WiFi, bed sheets

4. 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, (9 reviews)
"The place was super cute and close to everything. I would definitely stay again! "
United States
Juliet M.
$259 nightly
The price is $267
Aug 26 - Aug 27
Total with taxes and fees
Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay
1 bedroom, WiFi, bed sheets

5. 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.
$189 nightly
The price is $189
Sep 4 - Sep 5
Total with taxes and fees
214B - Cozy Studio with AC & Kitchen near Stanford
1 bedroom, iron/ironing board, WiFi, bed sheets

6. 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, (132 reviews)
"A beautiful place perfect for our stay in Half Moon Bay. Convenient to the beach, cute, clean and very comfortable. We will definitely stay here again!"
United States
Tami S.
$325 nightly
The price is $369
Aug 26 - Aug 27
Total with taxes and fees
Small Beach Cottage near the Coastal Trail and The Ritz
1 bedroom, WiFi, bed sheets

7. Adorable Romantic Private Getaway in Pescadero

Adorable Romantic Private Getaway in Pescadero
Pescadero
$368 nightly
The price is $368
Aug 20 - Aug 21
Total with taxes and fees
Adorable Romantic Private Getaway in Pescadero
Interior

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

Marbella Lane - 2BR Guest House Dtwn RWC Pking
3.0 star property
Palm Park
$408 nightly
The price is $460
Aug 23 - Aug 24
Total with taxes and fees
Marbella Lane - 2BR Guest House Dtwn RWC Pking
2 bedrooms, desk, iron/ironing board, WiFi (free)

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

@ Marbella Lane - 2BR Guest House |DTWN RWC| Pking
Palm Park
7.4 out of 10, Good, (20 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.
$331 nightly
The price is $368
Aug 23 - Aug 24
Total with taxes and fees
@ Marbella Lane - 2BR Guest House |DTWN RWC| Pking
1 bedroom, in-room safe, desk, iron/ironing board

10. 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
Aug 26 - Aug 27
Total with taxes and fees
Palo Alto Cottage: Privacy, Comfort & Convenience
TV, fireplace

11. 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, (12 reviews)
"Great place, would stay again!"
United States
Marianna F.
$215 nightly
The price is $219
Aug 30 - Aug 31
Total with taxes and fees
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
Smart TV, DVD player

12. 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.
$676 nightly
The price is $726
Aug 26 - Aug 27
Total with taxes and fees
Relax Coastal Retreat: Beautiful 2B Home Nr Beach
TV

13. Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill

Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill
Belmont
9.4 out of 10, Exceptional, (3 reviews)
"Great quiet location. Well maintained"
United States
Vishal M.
$354 nightly
The price is $354
Aug 24 - Aug 25
Total with taxes and fees
Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill
Property grounds

14. Secluded freestanding house in the delightful grape garden

Secluded freestanding house in the delightful grape garden
Emerald Hills
7.0 out of 10, Good, (7 reviews)
"Location and views were amazing! "
United States
Richelle
$373 nightly
The price is $405
Aug 23 - Aug 24
Total with taxes and fees
Secluded freestanding house in the delightful grape garden
1 bedroom, desk, WiFi, bed sheets

15. 214A - Cozy Studio with AC & Kitchen near Stanford

214A - Cozy Studio with AC & Kitchen near Stanford
Redwood City
9.0 out of 10, Wonderful, (6 reviews)
"Perfect stay for a quick get away! "
United States
Sylvia L.
$192 nightly
The price is $192
Sep 3 - Sep 4
Total with taxes and fees
214A - Cozy Studio with AC & Kitchen near Stanford
Interior

16. 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.
$368 nightly
The price is $383
Aug 31 - Sep 1
Total with taxes and fees
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!
Beach

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

Modern Coastal Retreat, Walk to Downtown HMB & Beach
Alsace Lorraine
10.0 out of 10, Exceptional, (27 reviews)
"Better than most 5 star hotel suites at a fraction of the cost. In a nice neighborhood, 2 blocks from the beach and close to downtown, it was quiet, clean, had modern appliances, and a very nice shower for 2 (no tub). Would definitely stay again."
United States
Ken B.
$398 nightly
The price is $427
Aug 31 - Sep 1
Total with taxes and fees
Modern Coastal Retreat, Walk to Downtown HMB & Beach
Outdoor spa tub

18. 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, (62 reviews)
"Close to everything, pet friendly "
United States
Gary B.
$478 nightly
The price is $507
Aug 30 - Aug 31
Total with taxes and fees
Charming Garden Cottage- steps to historic Old Town Half Moon Bay
1 bedroom, desk, WiFi (free), bed sheets

19. 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
$302 nightly
The price is $334
Aug 20 - Aug 21
Total with taxes and fees
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette
House, 2 Bedrooms, Patio, Lake View | Exterior

20. LakeFront Lavender House

LakeFront Lavender House
2.0 star property
East San Mateo
8.0 out of 10, Very Good, (1 review)
"The listing provided showed a listing of a differently painted house, although the inside was clean the outside needs cleaning. The inside smelled like strong cleaning supplies so airing it out was necessary. The door for one of the bedrooms was locked and were told to find a way to open it on our own, so if you need immediate support for anything related to the house, expect you will need to do it yourself. The futon couch that they have is broken and don’t let them charge for it. If it’s a...
United States
Luis
$286 nightly
The price is $328
Aug 20 - Aug 21
Total with taxes and fees
LakeFront Lavender House
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

Crowne Plaza San Francisco Airport by IHG

Crowne Plaza San Francisco Airport by IHG

8/10 Good
"Over the past few years, we've stayed at this hotel several times & enjoyed our stays. However & this past weekend, we noticed the a few things about our stay: 1. We waited for 50 mins. at the airport for the hotel shuttle. I called the hotel twice but it still took 50 mins. 2. The hotel restaurant only offered a buffet for breakfast. The breakfast was decent but 1 person in our party only wanted coffee, orange juice & toast. She had to pay for the buffet to get the few items she wanted. 3. The sidewalks of the hotel entrance & also the rug at the entrance to the restaurant were littered with leaves for the 4 days of our stay! I think it's time for us to select another property on our next visit!"
David 3-night trip
Posted less than an hour ago
Crowne Plaza San Francisco Airport by IHG

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 $171 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?

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. Pescadero 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.