Vacation rentals in San Mateo County

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Top-rated vacation rentals in San Mateo County

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

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

Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

Mar 26 – Apr 2

€ 116 per night
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

€ 146 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

€ 153 per night

Popular amenities for San Mateo County vacation rentals

Other great vacation rentals in San Mateo County

Superhost

Guesthouse in San Mateo

4.92 out of 5 average rating, 145 reviews

Cozy Studio 1B/1B w A/C No Pet in San Mateo

May 21 – 28

€ 118 per night
Guest favorite

Guest suite in Boulder Creek

4.89 out of 5 average rating, 889 reviews

Redwood Riverfront Getaway

Aug 29 – Sep 5

€ 120 per night
Guest favorite

Guesthouse in Woodside

4.97 out of 5 average rating, 143 reviews

SkyHigh Redwoods Retreat with Bay Views

Nov 14 – 21

€ 203 per night
Superhost

Apartment in Pacifica

4.79 out of 5 average rating, 671 reviews

Luxury Beach View Apartment

Mar 14 – 21

€ 175 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

€ 463 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

€ 123 per night
Guest favorite

Guest suite in Palo Alto

5.0 out of 5 average rating, 167 reviews

Savvy Studio ❤︎ Palo Alto ❤︎ of Silicon Valley

Sep 1 – 8

€ 150 per night
Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 804 reviews

Little Cottage on the Hill

Oct 12 – 19

€ 135 per night
Guest favorite

Cabin in Woodside

4.97 out of 5 average rating, 338 reviews

Kings Mountain Studio Cabin

May 16 – 23

€ 189 per night
Guest favorite

Apartment in Palo Alto

4.95 out of 5 average rating, 137 reviews

Private Studio Apartment with private entrance.

Dec 11 – 18

€ 122 per night
Guest favorite

Guesthouse in Woodside

4.97 out of 5 average rating, 90 reviews

Private cottage in the woods

Jun 4 – 11

€ 122 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

€ 150 per night

Destinations to explore