I drove from San Jose through Half Moon Bay, the drive was the best and there're many vista points to enjoy the view. I also spotted couple of dolphins.

San Mateo County rentals with pool

We found 742 rentals with pool — enter your dates for availability

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December 2025

4

January 2026

Explore San Mateo County rentals with pools

Showing deals for: 4 Mar - 7 Mar

Pool

Premier Host

Spacious 4BR Family Retreat with Indoor Pool, Jacuzzi & Movie Room – Near SFO

Sleeps 12 · 4 bedrooms · 1+ bathroom

for 3 nights, 1 home

NZ$1,255 per night

includes taxes & fees

front of house with large driveway. Additional parking across the street

4-5 Bedroom 4-5 Bath Luxury Home with Pool, Spa, fenced yard.

Sleeps 8 · 5 bedrooms · 4+ bathrooms

for 3 nights, 1 home

NZ$2,072 per night

includes taxes & fees

Interior

Premier Host

Stunning Alameda Beachfront Apt. Spectacular Dtown SF Views- Book Now on VRBO!

Sleeps 8 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

NZ$1,173 per night

includes taxes & fees

Living area

Private Pool & Hot Tub Retreat, Stunning City Views & Near SFO & Downtown

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 home

NZ$749 per night

includes taxes & fees

Find spaces that suit your style

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Holiday Rental options in San Mateo County

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