Holiday rentals in San Mateo County

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Top-rated holiday rentals in San Mateo County

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

Guest favourite

Guest house 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.

12–19 Mar

€ 116 per night
Guest favourite

Flat 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!

1–6 Apr

€ 140 per night
Guest favourite

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.

18–25 Apr

€ 143 per night

Popular amenities for San Mateo County holiday rentals

Other great holiday rentals in San Mateo County

Superhost

Guest house in San Mateo

4.92 out of 5 average rating, 145 reviews

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

21–28 May

€ 118 per night
Guest favourite

Guest house in Hillsborough

4.95 out of 5 average rating, 804 reviews

Little Cottage on the Hill

16–23 Sep

€ 136 per night
Guest favourite

Guest suite in Boulder Creek

4.98 out of 5 average rating, 420 reviews

Enjoy Private Redwoods from Your Bed or the Deck

28 Aug – 4 Sep

€ 151 per night
Guest favourite

Home in San Mateo

4.93 out of 5 average rating, 105 reviews

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

10–17 May

€ 462 per night
Guest favourite

Guest suite in Boulder Creek

4.89 out of 5 average rating, 889 reviews

Redwood Riverfront Getaway

29 Aug – 5 Sep

€ 120 per night
Guest favourite

Guest house in Woodside

4.97 out of 5 average rating, 143 reviews

SkyHigh Redwoods Retreat with Bay Views

10–17 Dec

€ 203 per night
Superhost

Flat in Pacifica

4.79 out of 5 average rating, 670 reviews

Luxury Beach View Apartment

13–20 Mar

€ 174 per night
Guest favourite

Guest suite in San Mateo

4.94 out of 5 average rating, 204 reviews

Luxury King Bed & Spa Bathroom

24–31 May

€ 196 per night
Guest favourite

Flat in Palo Alto

4.95 out of 5 average rating, 136 reviews

Private Studio Apartment with private entrance.

5–12 Mar

€ 122 per night
Guest favourite

Guest house in San Bruno

4.96 out of 5 average rating, 184 reviews

❤️Newly remodeled SFO Guesthouse, Private entrance

27 Sep – 4 Oct

€ 123 per night
Guest favourite

Guest house in Woodside

4.97 out of 5 average rating, 90 reviews

Private cottage in the woods

18–25 Jun

€ 121 per night
Guest favourite

Place to stay in San Mateo

4.92 out of 5 average rating, 65 reviews

Cottage on the Water -SUP,Kayaking,Canoeing

12–19 Nov

€ 149 per night

Destinations to explore