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San Mateo vacation rentals

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Top-rated vacation rentals in San Mateo

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Private room in San Mateo
Autumn Season! Large Beautiful Private Suite
Summer Special! A gorgeous spacious Suite with lots of light & privacy, a walk-in closet, luxury shower & separate tub, a coffee bar, microwave, mini-refrigerator, AC, fan & TV, computer workspace + WiFi. No smoking/drinking inside the room. Front stairs into the house. Steep staircase to a very private suite. No access to washer/dryer or main kitchen. Located 1/2 way between San Fran (Oracle & Chase Stadium) & Silicon Valley (Stanford Univ). Train nearby. Close to freeways (101 & 280), shop.
$79 per night
Guest suite in Millbrae
Private 1 bedroom guest suite for SFO trip 1 guest
1 bedroom 1 bathroom guest suite with private entrance. Good for a short SFO trip. But be aware it might not fit family vacation need! Newly remodeled kitchen, full bathroom, Wi-Fi, gas cooktop, coffee maker, toaster, microwave. Soft foam topper queen bed. Convenient for Bay Area commuter, 15 mins driving to SFO airport. Close to 101, 280 freeway. 30 mins driving to San Francisco or 50 mins to San Jose. 15 mins walk to grocery store, Starbucks and restaurants. Easy and free street parking.
$92 per night
Rental unit in San Mateo
Cozy Studio 1B/1B w A/C No Pet in San Mateo
This cozy studio is good for a couple vacation. It is also suitable for business trip with high speed WIFI. It is well equipped with all the amenities you need to enjoy your stay! 15 minutes walk to San Mateo Downtown. 11 minutes walk to Cal Train Station, which takes you to San Francisco in 30 min, and San Jose 45 min. If you have a car, you can reach those popular destinations easily: Hwy 101: 3 min San Francisco Airport: 9 min Apple Palo Alto: 12 miles Stanford: 17 miles
$132 per night

Stay near San Mateo's top sights

Hillsdale Shopping Center150 locals recommend
San Mateo County Event Center16 locals recommend
Whole Foods Market159 locals recommend
Safeway148 locals recommend
Trader Joe's21 locals recommend
Copenhagen Bakery & Cafe24 locals recommend

Other great vacation rentals in San Mateo

Private room in San Mateo
Fantastic 1 bed / 1 bath!
$70 per night
Rental unit in San Mateo
Junior 1 Bedroom, Walk to Caltrain, San Mateo I8
$99 per night
Guesthouse in San Mateo
Modern guest house in great location
$142 per night
Private room in San Mateo
Cozy Private BR in ventilated Apartment
$57 per night

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

Are there family-friendly vacation rentals in San Mateo?

Yes! We have over 90 homes with more than 2 bedrooms perfect for families looking for a comfortable and convenient stay in San Mateo.

How much does it cost to stay in an apartment in San Mateo?

Experience the best of San Mateo with our apartment vacation rentals, averaging about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Are there pet-friendly vacation rentals in San Mateo?

Yes! Four-legged friends are welcome too! Select from over 170 pet-friendly vacation rentals in San Mateo, so your furry family members can join in on the adventure.

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

Yes! Work meets play with ease at over 270 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 120 vacation homes with pools in San Mateo, available on Airbnb. Make a splash and soak up the sun in style!

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 1,500 vacation rentals in San Mateo Woods, over 1,500 vacation rentals in Vintage Park, and over 630 vacation rentals in Hillsdale.
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