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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.

Apartment in San Mateo
Fabulous apartment in downtown San Mateo
Relax away from the hustle of the city in your apartment in downtown San Mateo. Located only two blocks from the San Mateo Caltrain, you can get to or from SF or SJ in 30 minutes. Our home has a separate entrance for the guest apartment on the second floor. Tuck yourself away in the California King sized bed, or explore downtown on foot. With over 100 restaurants in walking distance, you will not have a shortage of delicious dining. Eat out or enjoy a meal in the comfort of your home. Welcome!
$104 per night
Guesthouse in San Carlos
Private Garden Cottage
Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.
$134 per night
Apartment 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
$123 per night

Stay near San Mateo's top sights

Hillsdale Shopping Center150 locals recommend
San Mateo County Event Center16 locals recommend
Whole Foods Market158 locals recommend
Trader Joe's21 locals recommend
Safeway148 locals recommend
CuriOdyssey35 locals recommend

San Mateo apartment rentals

Apartment in Pacifica
Luxury Beach View Apartment
$159 per night
Apartment in Burlingame
Home away from home in wonderful Burlingame
$135 per night
Apartment in Pacifica
Seaside Private Studio! Near SFO, SF and Beach!
$95 per night
Apartment in Mill Valley
Floating condo 'A' on Sausalito's Richardson Bay.
$184 per night
Apartment in San Carlos
Beauty in San Carlos! 1 large bedroom apartment
$202 per night
Apartment in Richmond
Point Richmond Top Floor Studio with Bay views
$134 per night
Apartment in San Francisco
Chic Urban Stay with View - Walk to Shops & Eats
$113 per night
Apartment in Menlo Park
Beautiful Spacious Living w/Resort Like Feel
$160 per night
Apartment in Brisbane
Exceptional Value!
$98 per night
Apartment in Half Moon Bay
Coastal Zen Cottage - Walk To Beach!
$140 per night
Apartment in Burlingame
Cozy Artists Studio in downtown Burlingame
$175 per night
Apartment in San Carlos
Chic Studio: King Bed, Walker's Paradise
$124 per night

Quick stats about vacation rentals in San Mateo

Total rentals

620 properties

Rentals with dedicated workspaces

320 properties have a dedicated workspace

Rentals with a pool

110 properties have a pool

Pet-friendly rentals

160 properties allow pets

Family-friendly rentals

190 properties are a good fit for families

Total number of reviews

18K 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.

Destinations to explore

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