San Gregorio Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for San Gregorio vacation rentals

A wooden deck with a metal railing overlooking a forested area.

1. Cottage In The Woods

Cottage In The Woods
Woodside
10.0 out of 10, Exceptional, (65 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 AED 735
AED 1,188 total
includes taxes & fees
15 Nov - 16 Nov
Cottage In The Woods
A spacious loft-style room with a high ceiling, a wooden staircase, a bed with a blue upholstered headboard, a kitchen area with a wooden countertop, and a skylight.

2. 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, (138 reviews)
"Great little place!"
United States
Jeffrey B.
The price is AED 795
AED 1,436 total
includes taxes & fees
18 Nov - 19 Nov
Small Beach Cottage near the Coastal Trail and The Ritz
A coastal view with a rocky shoreline, waves crashing onto the beach, and a clear sky.

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

Modern Coastal Retreat, Walk to Downtown HMB & Beach
Alsace Lorraine
10.0 out of 10, Exceptional, (36 reviews)
"Excellent host and house! Home was exceptionally clean, amazing bathroom, and short walk to the beach. We truly loved our stay!"
United States
Cortney P.
The price is AED 694
AED 1,233 total
includes taxes & fees
18 Nov - 19 Nov
Modern Coastal Retreat, Walk to Downtown HMB & Beach
A spacious living room with a large wooden coffee table, a sofa with patterned cushions, and a view of the outside through a large window.

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

Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
Heritage Downtown
9.8 out of 10, Exceptional, (17 reviews)
"nice place...close to restaurants...easy parking!"
United States
Luz
The price is AED 289
AED 1,072 total
includes taxes & fees
15 Nov - 16 Nov
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
A hot tub in a backyard with a wooden deck, outdoor furniture, and a wooden fence.

5. 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, (67 reviews)
"Clean; cheerful! Wonderful location."
United States
Catherine
The price is AED 484
AED 1,543 total
includes taxes & fees
16 Nov - 17 Nov
Charming Garden Cottage- steps to historic Old Town Half Moon Bay
A coastal landscape with a sandy beach, cliffs, and a field of wildflowers.

6. 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, (44 reviews)
"The stay was great, would recommend for quick getaway. "
United States
Kiera E.
The price is AED 427
AED 1,743 total
includes taxes & fees
16 Nov - 17 Nov
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
A spacious living room with a fireplace, a television, and comfortable seating.

7. 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, (50 reviews)
"We had an amazing week staying at this adorable cottage. It was clean, bright and welcoming. The outdoor shower was clutch post beach time and the yard allowed for our dog to enjoy the trip as much as we did. Add in the access to the coastal trail and it was unbeatable. We would love to stay here again for another adventure in Half Moon Bay!"
United States
rita m.
The price is AED 1,325
AED 2,319 total
includes taxes & fees
23 Nov - 24 Nov
Beach Cottage Near the Coastal Trail and the Ritz
Lounge

8. Mint House Menlo Park by Kasa

Mint House Menlo Park by Kasa
4.0 star property
Menlo Park
7.4 out of 10, Good, (40 reviews)
"The property was beautiful and looked exactly like the photos. It was in a very nice clean area, pet friendly, and had a lot of space to work. We did not get to check out the gym but it looked very nice as well! Definitely looking forward to staying at other Kasa properties in the future!"
United States
Tiffanie
The price is AED 493
AED 570 total
includes taxes & fees
4 Dec - 5 Dec
Mint House Menlo Park by Kasa
A distillery with outdoor seating and a metal structure in the center.

9. Stylish Seaside Cottage - Walking to Beach

Stylish Seaside Cottage - Walking to Beach
El Granada
9.4 out of 10, Exceptional, (60 reviews)
"Clean and cozy, enjoyed our stay.Rollyn"
United States
Rollyn K.
The price is AED 372
AED 792 total
includes taxes & fees
15 Nov - 16 Nov
Stylish Seaside Cottage - Walking to Beach
A narrow brick pathway flanked by walls with colorful tile patterns, leading to a doorway.

10. Secluded freestanding house in the delightful grape garden

Secluded freestanding house in the delightful grape garden
Emerald Hills
7.4 out of 10, Good, (8 reviews)
"Location and views were amazing! "
United States
Richelle
The price is AED 572
AED 1,320 total
includes taxes & fees
15 Nov - 16 Nov
Secluded freestanding house in the delightful grape garden
A wooden deck with a white bathtub, wooden pergola, and a blue wall with a sign.

11. Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.8 out of 10, Excellent, (42 reviews)
"though a bit off the beaten path--accomodations were great, relaxing after a hard day work on the deck and the welcome addition and unexpected treat of farm fresh eggs!"
United States
Mark
The price is AED 432
AED 768 total
includes taxes & fees
15 Nov - 16 Nov
Mays Luxury Farm Stays
A couple on a balcony with a table, chairs, and a view of the sea.

12. Oceanview Penthouse, Stylish, Walking to Beach

Oceanview Penthouse, Stylish, Walking to Beach
El Granada
9.8 out of 10, Exceptional, (52 reviews)
"Everything was absolutely perfect. It was the perfect getaway perfect area thank you so much."
United States
Don
The price is AED 459
AED 873 total
includes taxes & fees
2 Dec - 3 Dec
Oceanview Penthouse, Stylish, Walking to Beach
A hotel room with a bed, a desk with a chair, a television, and a large window with curtains.

13. 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.
The price is AED 312
AED 662 total
includes taxes & fees
14 Nov - 15 Nov
214B - Cozy Studio with AC & Kitchen near Stanford
A coastal landscape with a sandy beach, cliffs, and a field of wildflowers.

14. 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, (43 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 AED 787
AED 2,142 total
includes taxes & fees
19 Nov - 20 Nov
Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more
A modern living room with a grey sofa, a coffee table, and a TV mounted on the wall. There is a large window with a view of the countryside.

15. Beachview Holiday Family Retreat | Steps to Sand

Beachview Holiday Family Retreat | Steps to Sand
Miramar
9.6 out of 10, Exceptional, (62 reviews)
"Just steps from the beach !!"
United States
maxwell
The price is AED 1,723
AED 4,174 total
includes taxes & fees
3 Dec - 4 Dec
Beachview Holiday Family Retreat | Steps to Sand
A beach with rocky cliffs and waves crashing onto the shore.

16. Luxury Spa Retreat Guest House with Ocean View

Luxury Spa Retreat Guest House with Ocean View
Moss Beach
9.8 out of 10, Exceptional, (58 reviews)
"This little place is so cute and the view is spectacular. The host was super quick to respond when we had a hiccup with the wifi. Everything was clean and well stocked. Nice towels, comfy bed. My only complaint isthat I had to leave."
United States
Paula B.
The price is AED 661
AED 1,076 total
includes taxes & fees
15 Nov - 16 Nov
Luxury Spa Retreat Guest House with Ocean View
A bedroom with a bed, a bedside table with a lamp, a trash bin, and a painting on the wall.

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

Marbella Lane - 2BR Guest House Dtwn RWC Pking
3.0 star property
Palm Park
The price is AED 584
AED 1,757 total
includes taxes & fees
2 Dec - 3 Dec
Marbella Lane - 2BR Guest House Dtwn RWC Pking
A backyard with a swimming pool, outdoor furniture, and a patio area.

18. Luxury Silicon Valley Work and Wellness Oasis

Luxury Silicon Valley Work and Wellness Oasis
Los Altos Hills
10.0 out of 10, Exceptional, (5 reviews)
"Excellent property and very responsive host. Would definitely recommend!"
United States
J S.
The price is AED 995
AED 1,679 total
includes taxes & fees
16 Nov - 17 Nov
Luxury Silicon Valley Work and Wellness Oasis
A modern hotel room with a grey sofa, two armchairs, a bed, a round mirror, and a large painting on the wall.

19. 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, (10 reviews)
"The place was super cute and close to everything. I would definitely stay again! "
United States
Juliet M.
The price is AED 484
AED 1,294 total
includes taxes & fees
29 Nov - 30 Nov
Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay
A modern kitchen with a large island, built-in oven, and a view of the ocean through large windows.

20. 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 AED 1,469
AED 3,049 total
includes taxes & fees
8 Dec - 9 Dec
Elegant but practical retreat to maximize your enjoyment in beautiful HMB
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.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
apart-hotel image
Aparthotels
Aparthotels

Top San Gregorio Hotel Reviews

A hotel with a courtyard, arched walkways, and a sign reading "Half Moon Bay Lodge".
Half Moon Bay Lodge

Half Moon Bay Lodge

Half Moon Bay Lodge
Ocean Colony

10/10 Excellent

We appreciated the heated pool and spa. Nice breakfast.
United States
Sandy
Reviewed November 18, 2024
Half Moon Bay Lodge

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.