A lighthouse on a cliff by the sea during sunset.

San Mateo County Holiday Rentals

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Top Cities in San Mateo County

Our top choices for San Mateo County holiday rentals

1. Modern Pacifica Studio Near Beaches & SF

Modern Pacifica Studio Near Beaches & SF
2.5 star property
Westview
The price is NZ$365
includes taxes & fees
20 Sept - 21 Sept
Modern Pacifica Studio Near Beaches & SF

2. Beachy 1BR Escape with SofaBed Golf

Beachy 1BR Escape with SofaBed Golf
2.0 star property
Sharp Park
8.0 out of 10, Very good, (2 reviews)
"Pet friendly, nice quiet neighborhood next to the beach."
United States
Amatullah
The price is NZ$396
includes taxes & fees
16 Sept - 17 Sept
Beachy 1BR Escape with SofaBed Golf

3. 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 NZ$719
includes taxes & fees
27 Sept - 28 Sept
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

4. Stunning 2 Bedroom 1 Bath Home near BART

Stunning 2 Bedroom 1 Bath Home near BART
3.0 star property
Daly City
10.0 out of 10, Exceptional, (1 review)
The price is NZ$437
includes taxes & fees
20 Sept - 21 Sept
Stunning 2 Bedroom 1 Bath Home near BART

5. 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, (13 reviews)
"Great place, would stay again!"
United States
Marianna F.
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay

6. Oceanview 2BR 1Bath Balcony Sunset Views

Oceanview 2BR 1Bath Balcony Sunset Views
2.5 star property
Westview
The price is NZ$636
includes taxes & fees
10 Oct - 11 Oct
Oceanview 2BR 1Bath Balcony Sunset Views

7. 214A - Cozy Studio with AC & Kitchen near Stanford

214A - Cozy Studio with AC & Kitchen near Stanford
Redwood City
9.2 out of 10, Wonderful, (7 reviews)
"Perfect stay for a quick get away! "
United States
Sylvia L.
The price is NZ$318
includes taxes & fees
10 Oct - 11 Oct
214A - Cozy Studio with AC & Kitchen near Stanford

8. Coast PalmTree Yard 2BR Block from Beach

Coast PalmTree Yard 2BR Block from Beach
2.5 star property
Sharp Park
10.0 out of 10, Exceptional, (1 review)
The price is NZ$647
includes taxes & fees
15 Oct - 16 Oct
Coast PalmTree Yard 2BR Block from Beach

9. Coastal Palm Tree 2BR Retreat Ocean View

Coastal Palm Tree 2BR Retreat Ocean View
3.0 star property
Sharp Park
8.6 out of 10, Excellent, (9 reviews)
"Clean,great location,super comfortable bed."
United States
michael
Coastal Palm Tree 2BR Retreat Ocean View

10. Oceanview Penthouse, Stylish, Walking to Beach

Oceanview Penthouse, Stylish, Walking to Beach
El Granada
9.8 out of 10, Exceptional, (50 reviews)
"Great little spot, awesome view and location. "
United States
Jessie k.
The price is NZ$484
includes taxes & fees
4 Oct - 5 Oct
Oceanview Penthouse, Stylish, Walking to Beach

11. 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 NZ$665
includes taxes & fees
20 Sept - 21 Sept
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!

12. Stylish Seaside Cottage - Walking to Beach

Stylish Seaside Cottage - Walking to Beach
El Granada
9.4 out of 10, Exceptional, (57 reviews)
"Clean, cozy, comfortable and as described. Very comfortable bed too! Close to HMB restaurants and shops, will stay again!"
United States
Chase T.
The price is NZ$471
includes taxes & fees
4 Oct - 5 Oct
Stylish Seaside Cottage - Walking to Beach

13. Tranquil 2BR with Coastal Mountain Views

Tranquil 2BR with Coastal Mountain Views
2.0 star property
Westview
8.0 out of 10, Very good, (1 review)
"The space."
United States
Elizabeth
The price is NZ$590
includes taxes & fees
19 Sept - 20 Sept
Tranquil 2BR with Coastal Mountain Views

14. Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

Stunning Oceanview Coastal Home – Beach, Trails, Family Activities
Montara
9.2 out of 10, Wonderful, (86 reviews)
"The sounds of the ocean as you look at the stars from your room…enough said. Thank you! "
United States
NATALIE T.
The price is NZ$484
includes taxes & fees
24 Sept - 25 Sept
Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

15. Large and Cozy Home 2BD 2BA Near SF

Large and Cozy Home 2BD 2BA Near SF
2.5 star property
Bayshore Heights
The price is NZ$568
includes taxes & fees
21 Sept - 22 Sept
Large and Cozy Home 2BD 2BA Near SF

16. 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, (135 reviews)
"Great dog friendly well appointed tiny house."
United States
Deb L.
The price is NZ$691
includes taxes & fees
6 Oct - 7 Oct
Small Beach Cottage near the Coastal Trail and The Ritz

17. Mid Century Garden View Home Parking

Mid Century Garden View Home Parking
3.0 star property
East San Mateo
7.2 out of 10, Good, (5 reviews)
"This is a very clean comfortable property! "
United States
Serena
The price is NZ$663
includes taxes & fees
10 Oct - 11 Oct
Mid Century Garden View Home Parking

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

Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach
Pedro Point
9.2 out of 10, Wonderful, (12 reviews)
"Fantastic Host, amazing view and a wonderful VRBO property!"
United States
Jason A.
The price is NZ$550
includes taxes & fees
20 Sept - 21 Sept
Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach

19. Maddux Homes near Westlake

Maddux Homes near Westlake
3.0 star property
Broadmoor
5.6 out of 10, (4 reviews)
"The place was a little dusty and not fully clean. Also, the drain in the shower was backed up but wasn’t terrible. "
United States
Jaime
The price is NZ$520
includes taxes & fees
5 Oct - 6 Oct
Maddux Homes near Westlake

20. Cottage In The Woods

Cottage In The Woods
Woodside
10.0 out of 10, Exceptional, (61 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
The price is NZ$531
includes taxes & fees
15 Sept - 16 Sept
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 Mateo County Hotel Reviews

Find out more about San Mateo County

Everything you need to know about San Mateo County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Mateo County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Mateo County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

San Mateo County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Mateo County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Mateo County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Mateo County holiday rentals we have selected for you start as low as NZ$292 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on San Mateo County rentals

At Expedia, we put the best San Mateo County holiday 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 Mateo County 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 Mateo County holiday.

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 Mateo County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.