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San Gregorio Vacation Rentals

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Our top choices for San Gregorio vacation rentals

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.
The price is CA $282
CA $474 total
includes taxes & fees
Oct 5 - Oct 6
Cottage In The Woods

2. Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.6 out of 10, Excellent, (30 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
The price is CA $166
CA $295 total
includes taxes & fees
Sep 27 - Sep 28
Mays Luxury Farm Stays

3. Adorable Romantic Private Getaway in Pescadero

Adorable Romantic Private Getaway in Pescadero
Pescadero
The price is CA $314
CA $512 total
includes taxes & fees
Sep 26 - Sep 27
Adorable Romantic Private Getaway in Pescadero

4. 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, (45 reviews)
"House was close to the beach, had everything we needed, felt warm and inviting"
United States
Elizabeth D.
The price is CA $608
CA $1,060 total
includes taxes & fees
Sep 28 - Sep 29
Beach Cottage Near the Coastal Trail and the Ritz

5. 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.
The price is CA $298
CA $538 total
includes taxes & fees
Sep 30 - Oct 1
Modern Coastal Retreat, Walk to Downtown HMB & Beach

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, (136 reviews)
"Great dog friendly well appointed tiny house."
United States
Deb L.
The price is CA $270
CA $528 total
includes taxes & fees
Oct 6 - Oct 7
Small Beach Cottage near the Coastal Trail and The Ritz

7. Oceanview Penthouse, Stylish, Walking to Beach

Oceanview Penthouse, Stylish, Walking to Beach
El Granada
10.0 out of 10, Exceptional, (51 reviews)
"Everything was absolutely perfect. It was the perfect getaway perfect area thank you so much."
United States
Don
The price is CA $207
CA $398 total
includes taxes & fees
Oct 4 - Oct 5
Oceanview Penthouse, Stylish, Walking to Beach

8. 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, (21 reviews)
"Great place to stay if visiting SF."
United States
Alex E.
The price is CA $613
CA $1,288 total
includes taxes & fees
Sep 28 - Sep 29
Elegant but practical retreat to maximize your enjoyment in beautiful HMB

9. 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, (17 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 traveller
The price is CA $324
CA $468 total
includes taxes & fees
Oct 12 - Oct 13
Modern Guesthouse Retreat in the Heart of Silicon Valley

10. Ocean View & Steps to Beach - Miramar Home - Roof Deck, Coastal Trail, Restaurants, Activities

Ocean View & Steps to Beach - Miramar Home - Roof Deck, Coastal Trail, Restaurants, Activities
Miramar
9.6 out of 10, Exceptional, (32 reviews)
"The location is the best! if you love the coast, but also want to go to SF and the Peninsula, this is your place. The host was so gracious and easy to communicate with. This place was perfect for our family."
United States
Janet M.
The price is CA $721
CA $1,335 total
includes taxes & fees
Oct 11 - Oct 12
Ocean View & Steps to Beach - Miramar Home - Roof Deck, Coastal Trail, Restaurants, Activities

11. 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
The price is CA $246
CA $683 total
includes taxes & fees
Sep 30 - Oct 1
Charming Garden Cottage- steps to historic Old Town Half Moon Bay

12. Miramar Oasis! Ocean View, Hot Tub, Steps2Beach, Roof Deck, Fire Pit, Coastal Trail

Miramar Oasis! Ocean View, Hot Tub, Steps2Beach, Roof Deck, Fire Pit, Coastal Trail
Miramar
9.2 out of 10, Wonderful, (15 reviews)
"Great location for a coastal vacation. Close to the trails and beach, easy to take a drive up and down the coast to restaurants and shopping. Loved the spacious kitchen/living area and spending time on the deck. "
United States
Julie H.
The price is CA $431
CA $900 total
includes taxes & fees
Oct 4 - Oct 5
Miramar Oasis! Ocean View, Hot Tub, Steps2Beach, Roof Deck, Fire Pit, Coastal Trail

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

Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more
El Granada
9.2 out of 10, Wonderful, (41 reviews)
"We had a wonderful time. There are beach views from both bedrooms and the porch is wonderful. We would recommend and would stay again."
United States
Aaron M.
The price is CA $273
CA $791 total
includes taxes & fees
Sep 27 - Sep 28
Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more

14. Luxury Spa Retreat Guest House with Ocean View

Luxury Spa Retreat Guest House with Ocean View
Moss Beach
9.8 out of 10, Exceptional, (52 reviews)
"Everything was as advertised. Had a great time. The host was very kind and easy to communicate with, and it was a very romantic get away for me and my partner. Would stay here again!"
United States
Sergio D.
The price is CA $336
CA $531 total
includes taxes & fees
Sep 27 - Sep 28
Luxury Spa Retreat Guest House with Ocean View

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

Marbella Lane - 2BR Guest House Dtwn RWC Pking
3.0 star property
Palm Park
Marbella Lane - 2BR Guest House Dtwn RWC Pking

16. Coastal Charm: Ocean Views, Hot Tub, Fire Pit Near Tide Pools, Surfing, & SFO

Coastal Charm: Ocean Views, Hot Tub, Fire Pit Near Tide Pools, Surfing, & SFO
Moss Beach
9.8 out of 10, Exceptional, (37 reviews)
"Such a pleasant stay Perfect home for relaxing with family - exceptionally clean home, a quiet neighborhood, especially helpful and welcoming hostFun end to our stay with s’mores (provided) at the fire pit "
United States
Linda C.
Coastal Charm: Ocean Views, Hot Tub, Fire Pit Near Tide Pools, Surfing, & SFO

17. 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.
The price is CA $235
CA $571 total
includes taxes & fees
Oct 6 - Oct 7
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!

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.
The price is CA $298
CA $839 total
includes taxes & fees
Oct 8 - Oct 9
Relax Coastal Retreat: Beautiful 2B Home Nr Beach

19. 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)
"The property is clean, convenient, and well-appointed. Owner communication was great. Would rent again in a heartbeat. "
United States
Carmela
The price is CA $60
CA $538 total
includes taxes & fees
Oct 4 - Oct 5
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

20. Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay

Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
Heritage Downtown
9.2 out of 10, Wonderful, (15 reviews)
"nice place...close to restaurants...easy parking!"
United States
Luz
The price is CA $102
CA $411 total
includes taxes & fees
Sep 30 - Oct 1
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
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.

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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.