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San Mateo vacation rentals

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Popular amenities for San Mateo vacation rentals

Stay near San Mateo's top sights

Hillsdale Shopping Center150 locals recommend
San Mateo County Event Center16 locals recommend
Whole Foods Market158 locals recommend
San Mateo Central Park29 locals recommend
Trader Joe's21 locals recommend
Marina Plaza Shopping Center3 locals recommend

Quick stats about vacation rentals in San Mateo

  • Total rentals

    590 properties

  • Rentals with dedicated workspaces

    320 properties have a dedicated workspace

  • Rentals with a pool

    90 properties have a pool

  • Pet-friendly rentals

    130 properties allow pets

  • Family-friendly rentals

    190 properties are a good fit for families

  • Total number of reviews

    17K reviews

Your guide to San Mateo

All About San Mateo

Nestled between the hilly metropolis of San Francisco and urban San Jose, with the sweeping sands of Half Moon Bay to the west, the city of San Mateo boasts easy access to cultural hotspots, natural beauty, and a world-class food scene.

People are drawn here to admire nearly 45,000 artworks at the Cantor Arts Center at Stanford University, hike among the dramatic scenery at either end of Purisima Creek, and savor hard-to-beat ramen and crab nigiri at one of San Mateo’s established cluster of Japanese restaurants. There’s also public art to enjoy all around town, with vivid murals on numerous buildings, including the 1963 mosaic mural on South El Camino Real.

Less than half an hour west of San Mateo, Half Moon Bay boasts Surfers’ Beach for beginners and Mavericks for seasoned pros who want to take on wild waves. The same distance north, you can taqueria-hop in San Francisco’s Mission District and ride the city’s famous cable cars.


The best time to stay in a vacation rental in San Mateo

San Mateo is known for its mild, damp winters and dry summers. A lot of activities are outdoors, from kayaking in the bay to hiking and biking, so the summer and fall seasons are the best times to book San Mateo vacation rentals. Temperatures are at their most comfortable from April through October, and the changing colors of the leaves bring a range of pumpkin beers from the region’s breweries.

Layers are important in the colder months, as drizzle and searing sunshine are both possibilities in different parts of the Bay Area at any one time. You can see gray whales at Pacifica between February and April.


Top things to do in San Mateo

Japanese Tea Garden

The Japanese Tea Garden is one of the main attractions in Central Park, San Mateo’s main community park. The garden covers over 16 acres of manicured lawns, including a pagoda tower, a koi pond, and a teahouse for a quiet afternoon among delicate cherry blossoms. This serene site was designed by the landscape architect who worked on the Tokyo Imperial Palace.

Coyote Point

Less than 20 minutes from downtown by bike or road, Coyote Point is a popular spot for activities like windsurfing and sailing. If you’re cycling, the San Francisco Bay Trail crosses the park, so you can extend your ride north all the way to San Francisco or south to Palo Alto. At the water’s edge, you’ll find a marina and a beach, backing onto an 18-hole golf course.

Filoli Historic House & Garden

A 15-minute drive from San Mateo, this Georgian Revival house and its pristine landscaped gardens span over 650 acres. Wander around the terraces for commanding views of the Santa Cruz Mountains and cross Fault Creek Bridge to step over the famous San Andreas Fault. A spring visit will be rewarded with fragrant cherry and apple blossom.

Frequently Asked Questions

  • Where should I stay in San Mateo?

    Make yourself at home in San Mateo by choosing from our most frequently booked neighborhoods. We have over 580 vacation rentals in Hillsdale, over 700 vacation rentals in Vintage Park, and over 700 vacation rentals in San Mateo Woods.

  • Are there pet-friendly vacation rentals in San Mateo?

    Four-legged friends are welcome in San Mateo. Choose from more than 130 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in San Mateo?

    Yes! Work meets play with ease at over 320 vacation rentals in San Mateo featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there San Mateo vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 90 vacation homes with pools in San Mateo, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly house rentals in San Mateo?

    San Mateo has more than 130 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do private suite rentals in San Mateo have wifi?

    Absolutely! We offer over 30 private suite rentals with wifi in San Mateo. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in San Mateo have air conditioning?

    Absolutely! We offer over 10 guesthouse rentals with air conditioning in San Mateo. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in San Mateo have a gym?

    Absolutely! We offer over 60 apartment rentals with a gym in San Mateo. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in guesthouse rentals in San Mateo?

    Experience the best of San Mateo with our guesthouse rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in San Mateo have a bbq area?

    Absolutely! We offer over 20 apartment rentals with a bbq area in San Mateo. Enjoy a tailored experience with all the comforts you desire.

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