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.

Photo by SofiSabi

San Mateo County rentals with pool

We found 736 rentals with pool — enter your dates for availability

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December 2025

19

January 2026

Explore San Mateo County rentals with pools

Pool

Premier Host

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

Sleeps 12 · 4 bedrooms · 1+ bathroom

Serene canyon view with pool, hot tub & cedar barrel sauna

Premier Host

Serene Canyon Private Villa•Pool•HotTub•Sauna Retreat STR Permit Number:14614552

Sleeps 12 · 6 bedrooms · 3 bathrooms

Sunset from the deck

Premier Host

Rare Ocean-front near San Francisco. Sunsets, whale watching in seaside luxury

Sleeps 6 · 2 bedrooms · 2 bathrooms

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81339237-a0c9-6613-64ba-73b2338ec0bc3cd9f96e-4f89-426c-b73a-4981674ea631