San Mateo County Holiday Rentals

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Top Cities in San Mateo County

Half Moon Bay which includes a sandy beach and general coastal views as well as a small group of people
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Half Moon Bay

Half Moon Bay
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San Francisco

San Francisco

Our top choices for San Mateo County holiday rentals

Free WiFi
Peaceful 1BR Stay - Golf & Beach

Apartment in Sharp Park

Peaceful 1BR Stay - Golf & Beach
2.0 star property
The price is HK$490
HK$1,429 total
includes taxes & fees
22 Dec - 23 Dec
Peaceful 1BR Stay - Golf & Beach
Exterior
Stunning 2BR Ocean Mountain Sunset View

Apartment in Westview

Stunning 2BR Ocean Mountain Sunset View
2.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful place quiet and peaceful the view is amazing in the morning. "
United States
Astrid
The price is HK$951
HK$2,463 total
includes taxes & fees
31 Dec - 1 Jan 2026
Stunning 2BR Ocean Mountain Sunset View
Interior
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!

Holiday Home in Miramar

Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!
9.8 out of 10, Exceptional, (21)
"Excellent location, beautiful surroundings, thoroughly Zen. We loved it and will stay again!"
United States
Pamela C.
The price is HK$803
HK$2,483 total
includes taxes & fees
5 Jan - 6 Jan 2026
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!
Living area
Mid Century Garden View Home Parking

Holiday Home in East San Mateo

Mid Century Garden View Home Parking
2.0 star property
8.8 out of 10, Excellent, (3)
"This is a very clean comfortable property! "
United States
Serena
The price is HK$1,230
HK$2,975 total
includes taxes & fees
6 Jan - 7 Jan 2026
Mid Century Garden View Home Parking
Outdoor dining
Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach

Holiday Home in Pedro Point

Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach
9.6 out of 10, Exceptional, (4)
"This place had a great location beautiful view of the ocean it was very cozy "
United States
tammy k.
The price is HK$1,287
HK$3,149 total
includes taxes & fees
24 Dec - 25 Dec
Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach
Interior
Stunning 2 Bedroom 1 Bath Home near BART

Holiday Home in Daly City

Stunning 2 Bedroom 1 Bath Home near BART
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is HK$1,797
HK$3,218 total
includes taxes & fees
14 Jan - 15 Jan 2026
Stunning 2 Bedroom 1 Bath Home near BART
1 bedroom, iron/ironing board, WiFi, bed sheets
Small Beach Cottage near the Coastal Trail and The Ritz

Cottage in Arleta Park

Small Beach Cottage near the Coastal Trail and The Ritz
9.8 out of 10, Exceptional, (113)
"Great and cosy surfers cottage...my son and I were in HMB to attend a wedding."
United States
Charles C.
The price is HK$1,212
HK$2,261 total
includes taxes & fees
23 Dec - 24 Dec
Small Beach Cottage near the Coastal Trail and The Ritz
Beach
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

Holiday Home in South Downtown

Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
9.4 out of 10, Exceptional, (37)
"The stay was great, would recommend for quick getaway. "
United States
Kiera E.
The price is HK$225
HK$2,746 total
includes taxes & fees
22 Dec - 23 Dec
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
Interior
Stylish Seaside Cottage - Walking to Beach

Apartment in El Granada

Stylish Seaside Cottage - Walking to Beach
9.4 out of 10, Exceptional, (50)
"Great tiny place. "
United States
Laura M.
The price is HK$1,393
HK$2,140 total
includes taxes & fees
22 Dec - 23 Dec
Stylish Seaside Cottage - Walking to Beach
TV, fireplace
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay

Holiday Home in Heritage Downtown

Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
9.0 out of 10, Wonderful, (4)
"Awesome location and was beautiful inside. Wished there was AC and missing some small conveniences like salt and pepper but was overall a great experience "
United States
Lexi M.
The price is HK$328
HK$1,883 total
includes taxes & fees
12 Jan - 13 Jan 2026
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
Beach
Modern Coastal Retreat, Walk to Downtown HMB & Beach

Apartment in Alsace Lorraine

Modern Coastal Retreat, Walk to Downtown HMB & Beach
2.0 star property
10.0 out of 10, Exceptional, (7)
"Beach nearby. Very clean and nice vacation rental. The hosts really care about their guests and it shows. "
United States
Angela
The price is HK$1,366
HK$2,603 total
includes taxes & fees
4 Jan - 5 Jan 2026
Modern Coastal Retreat, Walk to Downtown HMB & Beach
Living area
Coastal Palm Tree 2BR Retreat Ocean View

Apartment in Sharp Park

Coastal Palm Tree 2BR Retreat Ocean View
3.0 star property
9.0 out of 10, Wonderful, (6)
"Clean,great location,super comfortable bed."
United States
michael
The price is HK$1,416
HK$3,003 total
includes taxes & fees
2 Jan - 3 Jan 2026
Coastal Palm Tree 2BR Retreat Ocean View
1 bedroom, desk, WiFi, bed sheets
214A - Cozy Studio with AC & Kitchen near Stanford

Apartment in Redwood City

214A - Cozy Studio with AC & Kitchen near Stanford
8.6 out of 10, Excellent, (4)
"Clean, simple, well stocked!"
United States
Ben
The price is HK$895
HK$1,618 total
includes taxes & fees
4 Jan - 5 Jan 2026
214A - Cozy Studio with AC & Kitchen near Stanford
Living area
Oceanview Sunset View 3BR Luxe Home Yard

Apartment in Westview

Oceanview Sunset View 3BR Luxe Home Yard
3.0 star property
8.0 out of 10, Very good, (1)
"place is very good. Also area is really great. Very close to the ocean."
United States
Ajit
The price is HK$1,354
HK$3,383 total
includes taxes & fees
23 Dec - 24 Dec
Oceanview Sunset View 3BR Luxe Home Yard
Terrace/patio
Oceanview Penthouse, Stylish & Walking to Beach

Apartment in El Granada

Oceanview Penthouse, Stylish & Walking to Beach
10.0 out of 10, Exceptional, (36)
"I loved this little place so much!!! I would definitely recommend this to a solo traveler or a couple! It was darling and the plants on the property were so amazingly beautiful! I wish I never had to leave! Bed was super comfy and the bathroom was super nice!Thank you for everything!Kimberly"
United States
Kimberly O.
The price is HK$1,704
HK$2,498 total
includes taxes & fees
22 Dec - 23 Dec
Oceanview Penthouse, Stylish & Walking to Beach
Interior
Coastal Charm: Inviting 3 BR Montara Home

Holiday Home in Montara

Coastal Charm: Inviting 3 BR Montara Home
10.0 out of 10, Exceptional, (8)
"What a charming cozy cottage on the coast! Me and my mom enjoyed our stay and wished it was a longer stay. We’ll definitely stay again in the future. Thank you for hosting us!"
United States
Dennis A.
The price is HK$1,313
HK$3,502 total
includes taxes & fees
7 Jan - 8 Jan 2026
Coastal Charm: Inviting 3 BR Montara Home
Fridge, microwave, coffee/tea maker, electric kettle
Brand new cozy apartment! Massage chair, two fireplaces with heaters

Apartment in Westlake

Brand new cozy apartment! Massage chair, two fireplaces with heaters
10.0 out of 10, Exceptional, (41)
"Great stay! "
United States
Asha M.
The price is HK$1,066
HK$2,870 total
includes taxes & fees
6 Jan - 7 Jan 2026
Brand new cozy apartment! Massage chair, two fireplaces with heaters
Exterior
Stunning and unique AirStream on the Coastal Trail and near Poplar Beach

Mobile Home in Arleta Park

Stunning and unique AirStream on the Coastal Trail and near Poplar Beach
10.0 out of 10, Exceptional, (21)
"Very clean, comfortable and quiet."
United States
John
The price is HK$1,360
HK$2,311 total
includes taxes & fees
30 Dec - 31 Dec
Stunning and unique AirStream on the Coastal Trail and near Poplar Beach
Beach nearby
Luxury Spa Retreat Guest House with Ocean View

Holiday Home in Moss Beach

Luxury Spa Retreat Guest House with Ocean View
9.8 out of 10, Exceptional, (35)
"Had an incredibly pleasant stay at this place. It feels very private but has a beautiful view of the ocean. The amenities including the hot tub, sauna, bike, and fire pit were thoroughly enjoyable and added very positively to the experience. The house was very clean and well stocked with supplies. The host provided welcome instructions in a timely manner and included nearby recommendations for local restaurants and sights. I would absolutely stay here again!"
United States
emily h.
The price is HK$1,611
HK$2,635 total
includes taxes & fees
22 Dec - 23 Dec
Luxury Spa Retreat Guest House with Ocean View
Beach
Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To Restaurants

Holiday Home in Miramar

Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To Restaurants
6.4 out of 10, (10)
"Great location. "
United States
Lea M.
The price is HK$389
HK$899 total
includes taxes & fees
22 Dec - 23 Dec
Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To Restaurants
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

Best Western Plus Grosvenor Airport Hotel

Best Western Plus Grosvenor Airport Hotel

10/10 Excellent
"Good"
francois 1-night trip
Posted 14 hours ago
Best Western Plus Grosvenor Airport Hotel