Holiday rentals in San Mateo

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Top-rated holiday rentals in San Mateo

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

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Guest favourite

Guest house in San Carlos

4.99 out of 5 average rating, 594 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.

27 Jul – 3 Aug

€ 148 per night

Guest favourite

Guest house in Belmont

4.97 out of 5 average rating, 365 reviews

A Comfortable & Private Guest House

Attn: Promo Rate for Health Care Workers & First Responders on stays of ONE week, or more. Please alert us, so that we can offer you a promo rate. In light of these uncertain times, rest assured that we are doing everything to ensure the safety of our guests. Beautiful, Secluded, Safe, Fully Stocked, Comfortable, Newly Renovated, & Close to Public Transportation. In the heart of Silicon Valley with its own private entrance. It's 30 mins. N of San Jose, and 30 mins. S of San Francisco.

8–15 Mar

€ 113 per night

Guest favourite

Guest house in San Bruno

4.96 out of 5 average rating, 190 reviews

❤️Newly remodeled SFO Guesthouse, Private entrance

Detached, and perfectly situated cute guesthouse with a private entrance. Ideal for a vacation to explore San Francisco bay area/Silicon valley while staying in a safe and quiet neighborhood. Conveniently located 8 min drive from SFO Airport! 5 min drive to BART/Caltrain station, 2 min walking distance to bus stop and 4 min to EV charging station. Close access to 101, 280 freeway. 15 mins to San Francisco and 20 mins to Silicon Valley. 10 mins to the beautiful Highway 1, Pacifica.

23–30 Dec

€ 127 per night

Guest favourite

Guest suite in Belmont

4.95 out of 5 average rating, 103 reviews

Cozy private in-law suite, close to SFO, fast WiFi

Newly renovated, spacious in-law unit in the Belmont hills with a private entrance and Bay views. This adorable space is cozy and great for a weekend respite or remote work. SFO airport is just 15 mins away. Close by Stanford and San Carlos. Short drive to hiking trails and 30 mins away from the Pacific ocean. Easy access to San Francisco and San Jose, via freeway 101, 280, and 92. 🌞 Solar-powered through the day with battery 🔋 back-up at night. No outages and eco-friendly. 🌲

1–8 Jun

€ 132 per night

Guest favourite

Home in Burlingame

4.91 out of 5 average rating, 150 reviews

Cozy Modern Craftsman Retreat

Private studio with a large outdoor patio. Just a short walk to the dinning and shopping on Burlingame Avenue and also on historic Broadway. Caltrain and Bart are minutes away to get take you to wherever you need to go. Fast wifi and espresso maker provided. Enjoy fresh fruit from our orange tree, and a rosemary bush for those that enjoy cooking. Relax with our large queen bed, recessed dimmable lighting and a large flat panel 4K smart TV w/apps for Netflix, Amazon Video, etc.

12–19 Jul

€ 169 per night

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

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

24 Sep – 1 Oct

€ 123 per night

Guest favourite

Home in Belmont

4.93 out of 5 average rating, 326 reviews

Hidden French Gem for Fam/Biz~near Caltrain,SFO

Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

26 Aug – 2 Sep

€ 148 per night

Guest favourite

Cottage in San Mateo

4.95 out of 5 average rating, 466 reviews

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

Entire cottage with private entrance. * self check-in with codes * free parking on driveway * AC & heating * 1 queen bed, 1 sofa (converts into twin bed) * fiber speed WiFi * kitchenette with sink, dishes & utensils, microwave, oven, mini fridge, keurig coffee maker, water boiler, NO STOVE * 15 min drive to SFO * 10 min walk to Caltrain * walking distances to restaurants, bars & groceries * located at end of cul de sac in a safe & quiet neighborhood * TV with Chromecast

24 Sep – 1 Oct

€ 170 per night

Guest favourite

Guest suite in San Mateo

4.94 out of 5 average rating, 206 reviews

Luxury King Bed & Spa Bathroom

Our spacious guest suite has its own private entrance, comfortable pillow-top king size bed, work-friendly laptop desk, hi-speed wifi, spa bathroom with heated floor, mini fridge, microwave and a Keurig coffee maker. The guest suite is part of the main home, but there are no shared spaces and the areas are separated by a locked solid wood door & noise-dampening cushions. Our guest suite is ideal for couples visiting family in the neighborhood.

2–9 Jul

€ 201 per night

Guest favourite

Guest house in San Mateo

4.93 out of 5 average rating, 193 reviews

Charming Private Quiet Backyard Studio

This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

23–30 Jan

€ 133 per night

Guest favourite

Guest house in Hillsborough

4.95 out of 5 average rating, 814 reviews

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Due to the coronavirus, we are taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

19–26 Nov

€ 132 per night

Superhost

Guest house in Belmont

4.84 out of 5 average rating, 202 reviews

Charming Cottage Studio

Our place is small but comfy for solo adventurers and business travelers. Very safe neighborhood. Is close to public transportations CalTrains station, bus stops, restaurants and malls. Plenty of parking on the street. We are 30 min to San Jose, and 30 min to San Francisco. Very close to Oracle and to the 101 & 92 Highways. Only 20 min to the Ocean in Half Moon Bay.

2–9 Aug

€ 96 per night