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

4.94 out of 5 average rating, 182 reviews

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!

May 23 – 28

G$26,544 GYD per night
Guest favorite

Guest suite in San Mateo

4.92 out of 5 average rating, 295 reviews

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.

May 28 – Jun 4

G$32,154 GYD per night
Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 579 reviews

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.

Jun 18 – 25

G$32,124 GYD per night

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 San Bruno

4.96 out of 5 average rating, 209 reviews

Recently Remodeled Detached Quaint Studio

Apr 7 – 14

G$16,061 GYD per night
Guest favorite

Guesthouse in Redwood City

4.92 out of 5 average rating, 293 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Mar 26 – Apr 2

G$22,694 GYD per night
Guest favorite

Cottage in San Mateo

4.95 out of 5 average rating, 462 reviews

Entire Private Studio by SFO, AC/Heat/Free Parking

Jun 16 – 23

G$31,756 GYD per night
Guest favorite

Guesthouse in San Bruno

4.96 out of 5 average rating, 184 reviews

❤️Newly remodeled SFO Guesthouse, Private entrance

Jan 21 – 28

G$23,756 GYD per night
Guest favorite

Guest suite in Emerald Hills

4.92 out of 5 average rating, 145 reviews

Elegant retreat in Redwood City

Jan 9 – 16

G$25,842 GYD per night
Guest favorite

Guest suite in San Mateo

4.94 out of 5 average rating, 204 reviews

Luxury King Bed & Spa Bathroom

Jun 3 – 10

G$40,357 GYD per night
Guest favorite

Apartment in Pacifica

4.94 out of 5 average rating, 660 reviews

Seaside Private Studio! Near SFO, SF and Beach!

Jun 21 – 26

G$21,215 GYD per night
Guest favorite

Home in San Mateo

4.93 out of 5 average rating, 105 reviews

Lovely Mid-Century home near SF, SFO, & Peninsula

May 10 – 17

G$98,552 GYD per night
Superhost

Home in San Mateo

4.83 out of 5 average rating, 260 reviews

❤️ Delightful 1B/1B modern with a leisure garden

Apr 26 – May 3

G$34,495 GYD per night
Guest favorite

Guesthouse in Redwood City

4.88 out of 5 average rating, 153 reviews

Modern Studio Cottage with Private Entrance

Aug 20 – 27

G$26,299 GYD per night
Guest favorite

Guest suite in South San Francisco

4.93 out of 5 average rating, 364 reviews

Cozy Tiny studio 20Min to DwTn SF & 7min to SFO

Sep 4 – 11

G$20,278 GYD per night
Guest favorite

Guesthouse in Redwood City

4.94 out of 5 average rating, 171 reviews

Detached Guest House With Views

Dec 5 – 12

G$29,631 GYD per night

Other great vacation rentals in San Mateo

Guest favorite

Guest suite in San Bruno

4.88 out of 5 average rating, 864 reviews

Modern room & loft, private entrance

Jun 10 – 17

G$16,610 GYD per night
Guest favorite

Home in San Mateo

4.9 out of 5 average rating, 143 reviews

12-Min From SFO, Tastefully Designed, Work Station

Mar 19 – 26

G$55,544 GYD per night
Guest favorite

Home in Redwood City

4.97 out of 5 average rating, 288 reviews

Private suite

May 11 – 18

G$30,530 GYD per night
Guest favorite

Guesthouse in Sunnyvale

4.96 out of 5 average rating, 384 reviews

Private cottage in a garden

Nov 1 – 8

G$24,542 GYD per night
Guest favorite

Guesthouse in Emerald Hills

4.89 out of 5 average rating, 178 reviews

Serene Studio in Emerald Hills

May 5 – 12

G$20,498 GYD per night
Guest favorite

Guest suite in Redwood City

4.92 out of 5 average rating, 104 reviews

Private Elegant Studio in Silicon Valley

Nov 5 – 12

G$19,651 GYD per night
Guest favorite

Home in Redwood City

4.88 out of 5 average rating, 178 reviews

NEW! Beautiful Studio/Cottage

Sep 14 – 21

G$26,481 GYD per night
Guest favorite

Guest suite in Foster City

4.98 out of 5 average rating, 60 reviews

New modern 1 bedroom unit

Aug 23 – 30

G$27,115 GYD per night
Guest favorite

Place to stay in San Mateo

4.92 out of 5 average rating, 65 reviews

Cottage on the Water -SUP,Kayaking,Canoeing

Sep 2 – 9

G$31,499 GYD per night
Guest favorite

Condo in Hillsborough

5.0 out of 5 average rating, 7 reviews

Breathtaking View Modern 1b1b on Top of the World

May 2 – 9

G$34,930 GYD per night
Guest favorite

Guest suite in San Mateo

4.97 out of 5 average rating, 70 reviews

Luxurious 1-bedroom place with hot tub

Jan 1 – 8

G$29,669 GYD per night
Guest favorite

Guesthouse in San Mateo

4.82 out of 5 average rating, 57 reviews

Charming cottage in the Silicon Valley

Apr 25 – May 2

G$28,991 GYD 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

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 730 vacation rentals in Vintage Park, and over 720 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 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 house rentals in San Mateo have wifi?

    Absolutely! We offer over 280 house 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 Private Suite Rentals in San Mateo?

    Enhance your stay in our Private Suite Rentals with the most popular amenities: over 10 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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