A coastal lighthouse with a white tower, surrounded by residential buildings and rocky cliffs.

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. Mint House Menlo Park by Kasa

Mint House Menlo Park by Kasa
4.0 star property
Menlo Park
7.4 out of 10, Good, (39 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 NZ$276
includes taxes & fees
30 Oct - 31 Oct
Mint House Menlo Park by Kasa

2. 4Beds Private Unit Near BeachWalk Golf

4Beds Private Unit Near BeachWalk Golf
2.0 star property
Sharp Park
9.0 out of 10, Wonderful, (8 reviews)
"very nice stay for group or family very nice location "
United States
vincent
The price is NZ$702
includes taxes & fees
4 Nov - 5 Nov
4Beds Private Unit Near BeachWalk Golf

3. 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
The price is NZ$764
includes taxes & fees
20 Nov - 21 Nov
LakeFront Lavender House

4. @ Marbella Lane - Bright and Cozy Home Near SFO

@ Marbella Lane - Bright and Cozy Home Near SFO
3.0 star property
North Central
The price is NZ$834
includes taxes & fees
30 Oct - 31 Oct
@ Marbella Lane - Bright and Cozy Home Near SFO

5. 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, (26 reviews)
"Very pleasant in great location "
United States
Eric B.
The price is NZ$551
includes taxes & fees
3 Nov - 4 Nov
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!

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

Modern Coastal Retreat, Walk to Downtown HMB & Beach
Alsace Lorraine
10.0 out of 10, Exceptional, (33 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 NZ$691
includes taxes & fees
15 Nov - 16 Nov
Modern Coastal Retreat, Walk to Downtown HMB & Beach

7. Affordable Private Rooms with Shared Bath Kitchen near SFO (SA)

Affordable Private Rooms with Shared Bath Kitchen near SFO (SA)
2.5 star property
St. Francis
6.2 out of 10, (30 reviews)
"Nice quiet place a good neighborhood also"
United States
Terrell
The price is NZ$249
includes taxes & fees
29 Nov - 30 Nov
Affordable Private Rooms with Shared Bath Kitchen near SFO (SA)

8. 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, (15 reviews)
"nice place...close to restaurants...easy parking!"
United States
Luz
The price is NZ$567
includes taxes & fees
2 Nov - 3 Nov
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay

9. 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$534
includes taxes & fees
2 Nov - 3 Nov
Large and Cozy Home 2BD 2BA Near SF

10. 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 NZ$449
includes taxes & fees
2 Nov - 3 Nov
Oceanview Penthouse, Stylish, Walking to Beach

11. 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, (10 reviews)
"Clean,great location,super comfortable bed."
United States
michael
The price is NZ$645
includes taxes & fees
19 Nov - 20 Nov
Coastal Palm Tree 2BR Retreat Ocean View

12. 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$511
includes taxes & fees
29 Nov - 30 Nov
Maddux Homes near Westlake

13. Stunning Views by the Bay 2BR

Stunning Views by the Bay 2BR
2.0 star property
Uptown Brisbane
The price is NZ$995
includes taxes & fees
9 Nov - 10 Nov
Stunning Views by the Bay 2BR

14. 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$661
includes taxes & fees
15 Nov - 16 Nov
Coast PalmTree Yard 2BR Block from Beach

15. 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 NZ$580
includes taxes & fees
7 Nov - 8 Nov
Cottage In The Woods

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, (138 reviews)
"Great little place!"
United States
Jeffrey B.
The price is NZ$653
includes taxes & fees
1 Nov - 2 Nov
Small Beach Cottage near the Coastal Trail and The Ritz

17. Beautiful 2-bedroom Apt. Free parking, 5 minute to S.F AirPort and All business.

Beautiful 2-bedroom Apt. Free parking, 5 minute to S.F AirPort and All business.
San Bruno
10.0 out of 10, Exceptional, (3 reviews)
"The place was clean and located in a great spot. I walked my dogs around the neighborhood. We visited the beaches nearby with a 20 minute drive. Convenience stores are just across the block."
United States
Aaron R.
The price is NZ$973
includes taxes & fees
5 Nov - 6 Nov
Beautiful 2-bedroom Apt. Free parking, 5 minute to S.F AirPort and All business.

18. 214A - Cozy Studio with AC & Kitchen near Stanford

214A - Cozy Studio with AC & Kitchen near Stanford
Redwood City
9.0 out of 10, Wonderful, (8 reviews)
"Perfect stay for a quick get away! "
United States
Sylvia L.
The price is NZ$343
includes taxes & fees
5 Nov - 6 Nov
214A - Cozy Studio with AC & Kitchen near Stanford

19. Stylish Seaside Cottage - Walking to Beach

Stylish Seaside Cottage - Walking to Beach
El Granada
9.4 out of 10, Exceptional, (58 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$417
includes taxes & fees
2 Nov - 3 Nov
Stylish Seaside Cottage - Walking to Beach

20. Oceanview Sunset View 3BR Luxe Home Yard

Oceanview Sunset View 3BR Luxe Home Yard
3.0 star property
Westview
7.8 out of 10, Good, (6 reviews)
"Clean rooms, good location "
United States
David
The price is NZ$844
includes taxes & fees
8 Nov - 9 Nov
Oceanview Sunset View 3BR Luxe Home Yard
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$276 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.