A coastal landscape with a sandy beach, rocky cliffs, and the ocean.

Holiday Homes in San Mateo

  • 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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for San Mateo holiday homes

A living room with a flat-screen TV, grey sofas, a coffee table, and a small side table with a vase of flowers.

1. Cozy 3BR Home in San Mateo, Minutes to SFO & Downtown

Cozy 3BR Home in San Mateo, Minutes to SFO & Downtown
North Central
10.0 out of 10, Exceptional, (3 reviews)
"It was perfect for stay with a small kid! "
United States
Jan H.
The price is AU$661
includes taxes & fees
8 Nov - 9 Nov
Cozy 3BR Home in San Mateo, Minutes to SFO & Downtown
A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave.

2. Marbella Lane - Bright and Cozy Home near SFO

Marbella Lane - Bright and Cozy Home near SFO
North Central
The price is AU$1,026
includes taxes & fees
30 Nov - 1 Dec
Marbella Lane - Bright and Cozy Home near SFO
A staircase with wooden beams and large windows overlooking a beach.

3. 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 AU$589
includes taxes & fees
6 Nov - 7 Nov
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!
An aerial view of a coastal area with a beach, a pier, and a residential area with houses and roads.

4. Near SFO Premium Neighborhood Free Parking Private

Near SFO Premium Neighborhood Free Parking Private
Millbrae
8.0 out of 10, Very good, (5 reviews)
"Property was very clean and clearly marked. It was stocked well with waters. "
United States
Lauren T.
The price is AU$1,911
includes taxes & fees
30 Nov - 1 Dec
Near SFO Premium Neighborhood Free Parking Private
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.

5. 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 AU$451
includes taxes & fees
19 Nov - 20 Nov
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
A wooden deck with a grill, a round table with chairs, and a view of the ocean and hills.

6. 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 AU$455
includes taxes & fees
17 Nov - 18 Nov
Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach
A coastal landscape with a sandy beach, cliffs, and a field of wildflowers.

7. 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, (42 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 AU$886
includes taxes & fees
8 Nov - 9 Nov
Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more
A modern living room with a sofa, coffee table, and dining area.

8. Private Cottage House - Walk to Beaches, Harbor, Food, Trails, so much more

Private Cottage House - Walk to Beaches, Harbor, Food, Trails, so much more
El Granada
9.4 out of 10, Exceptional, (25 reviews)
"We loved our stay. Our only regret is not staying longer!"
United States
Anonymous traveller
Private Cottage House - Walk to Beaches, Harbor, Food, Trails, so much more
A modern living room with a brown sofa, a white coffee table, a black office chair, and a small white desk. There are two wall-mounted mirrors and a ceiling light.

9. Charming 1-bedroom house with AC, WiFi in delightful San Bruno

Charming 1-bedroom house with AC, WiFi in delightful San Bruno
San Bruno
6.4 out of 10, (7 reviews)
"Recommend."
United States
Max
The price is AU$304
includes taxes & fees
5 Nov - 6 Nov
Charming 1-bedroom house with AC, WiFi in delightful San Bruno
A modern kitchen with a central island, bar stools, and a dining area.

10. 2 Beds, 1 Bath, Kitchen private space, Furnished Stanford, Palo Alto, Menlo Park

2 Beds, 1 Bath, Kitchen private space, Furnished Stanford, Palo Alto, Menlo Park
Menlo Park
8.0 out of 10, Very good, (13 reviews)
"Great placeGreat location 10 minutes from everything Palo Alto and Menlo Park"
United States
Christopher W.
The price is AU$407
includes taxes & fees
4 Nov - 5 Nov
2 Beds, 1 Bath, Kitchen private space, Furnished Stanford, Palo Alto, Menlo Park
A beach with rocky cliffs and waves crashing onto the shore.

11. Luxury Spa Retreat Guest House with Ocean View

Luxury Spa Retreat Guest House with Ocean View
Moss Beach
9.8 out of 10, Exceptional, (55 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 AU$417
includes taxes & fees
12 Nov - 13 Nov
Luxury Spa Retreat Guest House with Ocean View
A coastal landscape with a sandy beach, cliffs, and a field of wildflowers.

12. 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)
"Beautiful location and space. Location was perfect and exactly what we needed"
United States
Patricia D.
The price is AU$638
includes taxes & fees
4 Nov - 5 Nov
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
A beach with a large rock in the foreground and a red bridge in the background.

13. Spacious SF Haven: Cozy Bedrooms & Modern Kitchen - Safest neighborhood in SF

Spacious SF Haven: Cozy Bedrooms & Modern Kitchen - Safest neighborhood in SF
Richmond District
9.8 out of 10, Exceptional, (33 reviews)
"Awesome location. Great property. Strongly recommend for a stay in San Francisco."
United States
Christopher S.
The price is AU$1,497
includes taxes & fees
24 Nov - 25 Nov
Spacious SF Haven: Cozy Bedrooms & Modern Kitchen - Safest neighborhood in SF
A courtyard with outdoor seating, a bicycle, and a building with a shop entrance.

14. Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay

Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay
Heritage Downtown
9.6 out of 10, Exceptional, (22 reviews)
"Great location and comfortable bed"
United States
Karly G.
The price is AU$395
includes taxes & fees
4 Nov - 5 Nov
Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay
A modern hotel room with a grey sofa, two armchairs, a bed, a round mirror, and a large painting on the wall.

15. 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 AU$449
includes taxes & fees
17 Nov - 18 Nov
Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay
A living room with a flat-screen TV, fireplace, two armchairs, a coffee table, and decorative items.

16. 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 AU$437
includes taxes & fees
10 Nov - 11 Nov
Large and Cozy Home 2BD 2BA Near SF
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.

17. Beachview Holiday Family Retreat | Steps to Sand

Beachview Holiday Family Retreat | Steps to Sand
Miramar
9.4 out of 10, Exceptional, (62 reviews)
"Great location, comfortable home"
United States
Patricia W.
The price is AU$1,485
includes taxes & fees
10 Nov - 11 Nov
Beachview Holiday Family Retreat | Steps to Sand
A spacious living room with a grey armchair, a blue sofa, and a round coffee table.

18. Walk to Beach - Remodeled Coastal 3 Beds Home Safe Town Highway 1 Near SF / SFO

Walk to Beach - Remodeled Coastal 3 Beds Home Safe Town Highway 1 Near SF / SFO
Linda Mar
10.0 out of 10, Exceptional, (28 reviews)
"Great house for our family to stay and see the city!"
United States
Brad A.
The price is AU$630
includes taxes & fees
5 Nov - 6 Nov
Walk to Beach - Remodeled Coastal 3 Beds Home Safe Town Highway 1 Near SF / SFO
A kitchen with white cabinets, a round glass table, and dark wooden chairs.

19. RUSTIC/MODERN DESIGN, OASIS CITY GETAWAY/NEAR SFO

RUSTIC/MODERN DESIGN, OASIS CITY GETAWAY/NEAR SFO
Downtown South San Francisco
9.6 out of 10, Exceptional, (20 reviews)
"This is the second time I booked this place, great location, close to the airport, very clean and comfortable. "
United States
Jeremy M.
The price is AU$527
includes taxes & fees
21 Nov - 22 Nov
RUSTIC/MODERN DESIGN, OASIS CITY GETAWAY/NEAR SFO
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top San Mateo Hotel Reviews

Chancellor Hotel on Union Square

Chancellor Hotel on Union Square

8/10 Good
"Perfect location, right on Union Square so perfect for the city. Rooms were clean - a bit small but they all are in SF. There was a big cupboard in the room to store luggage which was good. Beds were basic doubles so felt quite small. and a bit soft for my liking. But bathroom was fine. Nice touch was the free water and cookies in reception. It was great value for money"
Simon 2-night trip
Posted 3 hours ago
Chancellor Hotel on Union Square

Find out more about San Mateo

San Mateo Holiday Homes information

Number of reviews
358
Accommodation
872 Holiday Homes
Lowest Price
AU$304
Highest Price
AU$1,911

Explore a world of travel with Expedia