Vacation rentals in San Mateo

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Top-rated vacation rentals in San Mateo

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Guest favourite
Home in San Mateo
Lovely Mid-Century home near SF, SFO, & Peninsula
Walk through the enclosed atrium sporting a custom mural and stunning red maple in this home dating back to 1956. The spacious house boasts mid-century furniture and art with a wall of glass overlooking the deck with a backdrop of fruit trees. Spacious 2 bedrooms & den with TV converts to a sofa bed. You also have a private office if you're working from home, right off the atrium. Enjoy a lovely dinner in back garden on a cool summer night. Though we love children, our home is not childproof, and we prefer not to host children under 12 years of age, thank you for understanding. This home was built in 1956 by Joseph Eichler and completely remodeled in 2017 with the goal of staying true to its original Mid-Century design while updating the house for modern living. It features a collection of beautiful Mid-Century furniture and art made by the owner and friends. Guests enter through an enclosed atrium that sports a custom mural and stunning red maple. The back yard features a large dining area with a backdrop of fruit tree and a spacious deck overlooking thousands of acres of open space and the Coastal Range. This home has two bedrooms with queen size beds and one bedroom with a full size sofa-bed. The master bedroom has an en suite bathroom with walk-in shower, the other two rooms share a bathroom with a deep tub. There is a spacious, well lit office for your use. One of the best features of this home is it's great room with a wood-burning fireplace, dining room, and kitchen--perfect for entertaining a small group. The backyard features an 8 person outdoor dining table and 6 burner BBQ for your use, as well a large outdoor sofa surrounding a fire pit. The front atrium is another well lit modern get away where you can to sit back and enjoy nature and art. Guests will have access to the entire property including the house and gardens. There is a washer and drier for guest use in the garage. I have a co-host who will be there for you 24/7. The house is in the Highlands neighborhood, which was developed by Joseph Eichler in the mid-1950s. The community center across the street from the property features a great playground for children. San Francisco Airport is 15 minutes away. - Caltrain (Goes up and down to San Francisco and San Jose) - BART (Goes to Downtown San Francisco and East Bay) - Lyft (Use referral code JEN573431) - Uber (Use referral code jcc271ue) Parking in the drive way only (no garage use for cars). TV in one of the bedrooms, not the living room. No parties or events allowed. No curtains in two of the bedrooms, but no one can see into these room as a building wall hides them. 20 minutes to downtown San Francisco We take cleaning in this climate very seriously, we are in full compliance with the cleaning guidelines approved by WHO (Worldwide Health Organization) CDC (Center for Disease Control) and the EPA (Environmental Protection Agency)
May 10 – 17
$718 CAD per night
4.93 out of 5 average rating, 105 reviews
Guest favourite
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.
Apr. 19 – 26
$208 CAD per night
4.92 out of 5 average rating, 294 reviews
Guest favourite
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
$213 CAD 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 favourite
Home in San Mateo
Serene Modern Home w/Private Yard
Aug. 21 – 28
$736 CAD per night
4.92 out of 5 average rating, 198 reviews
Superhost
Apartment in Pacifica
Luxury Beach View Apartment
Oct. 28 – Nov. 4
$242 CAD per night
4.79 out of 5 average rating, 666 reviews
Guest favourite
Home in Burlingame
Cozy Modern Craftsman Retreat
May 25 – Jun. 1
$246 CAD per night
4.91 out of 5 average rating, 144 reviews
Guest favourite
Guesthouse in Redwood City
Quiet , Private Studio / Cottage
Feb. 23 – Mar. 2
$176 CAD per night
4.98 out of 5 average rating, 374 reviews
Superhost
Guesthouse in San Mateo
Cozy & huge studio w/ full kitchen & bath
Jan. 20 – 27
$249 CAD per night
4.86 out of 5 average rating, 35 reviews
Guest favourite
Place to stay in San Mateo
Cottage on the Water -SUP,Kayaking,Canoeing
Jul. 19 – 26
$218 CAD per night
4.92 out of 5 average rating, 66 reviews
Guest favourite
Guest suite in Foster City
New modern 1 bedroom unit
Aug. 11 – 18
$182 CAD per night
4.98 out of 5 average rating, 59 reviews
Guest favourite
Home in San Mateo
Attached home(ADU) with great view and convenience
May 19 – 26
$221 CAD per night
4.92 out of 5 average rating, 38 reviews
Guest favourite
Guest suite in San Mateo
Luxurious 1-bedroom place with hot tub
Nov. 19 – 26
$236 CAD per night
4.97 out of 5 average rating, 70 reviews
Guest favourite
Guesthouse in Belmont
Quaint Getaway in Belmont Hills
Apr. 2 – 9
$161 CAD per night
4.84 out of 5 average rating, 25 reviews
Guest favourite
Guest suite in Belmont
Cozy private in-law suite, close to SFO, fast WiFi
Aug. 15 – 22
$168 CAD per night
4.95 out of 5 average rating, 95 reviews
Guest favourite
Home in San Mateo
Lagoon Living Offsite + Family Retreat!
Aug. 28 – Sep. 4
$983 CAD per night
4.98 out of 5 average rating, 42 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

Destinations to explore

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  3. California
  4. San Mateo County
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