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.

Guest favorite
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!
Mar 31 – Apr 7
$108 per night
4.94 out of 5 average rating, 182 reviews
Guest favorite
Guest suite in San Mateo
San Mateo Getaway Private 2 Bedroom
Bright & spacious 2 bedroom apartment with beautiful backyard in San Mateo. In-law apartment with private entrance dedicated to hosting guests. Located in quiet residential neighborhood, but close to activities for families and singles. Amenities include wet bar area with toaster oven, coffee maker, mini fridge and microwave! Laundry available upon request. Easy access to San Francisco/San Jose via 280 & 101. Close to SFO, Cal train/BART and Downtown San Mateo. Lots of street parking.
Jun 5 – 12
$134 per night
4.92 out of 5 average rating, 294 reviews
Guest favorite
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.
May 27 – Jun 3
$134 per night
4.99 out of 5 average rating, 579 reviews

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

Other great vacation rentals in San Mateo

Guest favorite
Guesthouse in Belmont
Charming Cottage Studio
Aug 27 – Sep 3
$95 per night
4.84 out of 5 average rating, 199 reviews
Superhost
Apartment in Pacifica
Luxury Beach View Apartment
Nov 18 – 25
$130 per night
4.79 out of 5 average rating, 666 reviews
Guest favorite
Guesthouse in Redwood City
Soak up the Serenity on the Patio of a Charming Cottage
Dec 4 – 11
$94 per night
4.92 out of 5 average rating, 292 reviews
Guest favorite
Home in Burlingame
Cozy Modern Craftsman Retreat
May 25 – Jun 1
$135 per night
4.91 out of 5 average rating, 144 reviews
Guest favorite
Guest suite in Emerald Hills
Elegant retreat in Redwood City
Sep 10 – 17
$106 per night
4.92 out of 5 average rating, 141 reviews
Guest favorite
Guesthouse in Burlingame
Clean&Cozy Cottage near downtown Burlingame & SFO
Jun 3 – 8
$149 per night
4.98 out of 5 average rating, 284 reviews
Guest favorite
Home in San Mateo
❤️ Delightful 1B/1B modern with a leisure garden
Aug 24 – 31
$139 per night
4.83 out of 5 average rating, 260 reviews
Superhost
Guesthouse in San Mateo
Charming cozy studio King-sized bed
Sep 13 – 20
$142 per night
4.85 out of 5 average rating, 159 reviews
Guest favorite
Home in San Mateo
Lovely Mid-Century home near SF, SFO, & Peninsula
May 10 – 17
$436 per night
4.93 out of 5 average rating, 105 reviews
Guest favorite
Home in Montara
A private beachy pad in Montara
Apr 24 – May 1
$116 per night
4.98 out of 5 average rating, 266 reviews
Guest favorite
Guesthouse in Emerald Hills
Serene Studio in Emerald Hills
Apr 5 – 12
$89 per night
4.89 out of 5 average rating, 178 reviews
Guest favorite
Home in Redwood City
NEW! Beautiful Studio/Cottage
Sep 9 – 16
$109 per night
4.88 out of 5 average rating, 177 reviews

Other great vacation rentals in San Mateo

Guest favorite
Guest suite in South San Francisco
Cozy Tiny studio 20Min to DwTn SF & 7min to SFO
Jun 30 – Jul 7
$84 per night
4.93 out of 5 average rating, 362 reviews
Guest favorite
Guesthouse in Redwood City
Modern Studio Cottage with Private Entrance
Dec 4 – 11
$109 per night
4.88 out of 5 average rating, 150 reviews
Guest favorite
Home in San Mateo
Andulore Cottage - Near Burlingame Ave - Remodeled
Jan 21 – 28
$289 per night
4.94 out of 5 average rating, 128 reviews
Guest favorite
Home in Mountain View
391 - Mini studio in the heart of Silicon Valle
Mar 25 – Apr 1
$81 per night
4.92 out of 5 average rating, 330 reviews
Guest favorite
Place to stay in San Mateo
Cottage on the Water -SUP,Kayaking,Canoeing
Jul 19 – 26
$131 per night
4.92 out of 5 average rating, 66 reviews
Guest favorite
Guest suite in Foster City
New modern 1 bedroom unit
Aug 15 – 22
$113 per night
4.98 out of 5 average rating, 59 reviews
Guest favorite
Guest suite in San Mateo
Luxurious 1-bedroom place with hot tub
Nov 19 – 26
$122 per night
4.97 out of 5 average rating, 70 reviews
Guest favorite
Guest suite in Millbrae
Modern One Bedroom Suite in a Quiet Neighborhood
Aug 22 – 29
$94 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in San Mateo
Attached home(ADU) with great view and convenience
Jun 7 – 14
$116 per night
4.92 out of 5 average rating, 38 reviews
Guest favorite
Guest suite in Belmont
Cozy private in-law suite, close to SFO, fast WiFi
Aug 8 – 15
$96 per night
4.95 out of 5 average rating, 95 reviews
Guest favorite
Guesthouse in Belmont
Quaint Getaway in Belmont Hills
May 11 – 18
$102 per night
4.84 out of 5 average rating, 25 reviews
Guest favorite
Guest suite in San Mateo
Top floor private Suite with amazing views
Jun 7 – 14
$115 per night
5.0 out of 5 average rating, 26 reviews

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

100 properties have a pool

Pet-friendly rentals

150 properties allow pets

Family-friendly rentals

200 properties are a good fit for families

Total number of reviews

19K 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 600 vacation rentals in Hillsdale, over 720 vacation rentals in San Mateo Woods, and over 730 vacation rentals in Vintage Park.

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

    Four-legged friends are welcome in San Mateo. Choose from more than 150 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 100 vacation homes with pools in San Mateo, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in San Mateo have air conditioning?

    Absolutely! We offer over 100 house rentals with air conditioning in San Mateo. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in San Mateo have wifi?

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

  • 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.

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

    San Mateo has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in San Mateo have a gym?

    Absolutely! We offer over 70 apartment rentals with a gym in San Mateo. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in San Mateo?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 80 homes with air conditioning, over 160 homes with wifi, over 70 homes with a gym, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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