Holiday Rentals in San Mateo, CA

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San Mateo, CA holiday rentals
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Best Holiday rentals and Airbnb offers in San Mateo, CA

Discover Central Holiday Rentals in San Mateo, CA

Coordinate an unforgettable urban break using private, independent holiday rentals for couples situated close to vibrant San Mateo, CA landmarks.

804- Sanmateo Comfortable 2br Home Wifi And Free Parking - San Mateo, CA
9.0 1 review

804- Sanmateo Comfortable 2br Home Wifi And Free Parking

house, San Mateo
This comfortable 2-bedroom property is situated in San Mateo, just 30km from San Francisco's Moscone Center and Union Square, providing easy access to the city while being located in a more relaxed suburban setting. The house has consistently received excellent ratings for location, cleanliness and user experience.
The property offers ample space for families or groups of friends, accommodating up to 7 guests. It provides amenities such as free parking, Wi-Fi access, and is a non-smoking accommodation.
Brand New Modern Luxury Unit  | Walk To Downtown - San Mateo, CA
9.9 27 reviews

Brand New Modern Luxury Unit | Walk To Downtown

apartment, San Mateo
This stylish San Mateo apartment, a short walk from the city centre and approximately 1.6km from the Caltrain station, offers easy access to San Francisco and other Bay Area destinations.
The one-bedroom, one-bathroom flat sleeps four guests comfortably, boasting a fully equipped kitchen, private patio, in-unit laundry, and high-speed fibre internet; perfect for business travellers or leisure visitors.
@ Marbella Lane - Modern Refreshing Home - San Mateo, CA
9.5 97 reviews

@ Marbella Lane - Modern Refreshing Home

apartment, San Mateo
This comfortable house is located in Central San Mateo, just 1.6km from Mills Health Center, Central Park, and Coyote Point Park. It has received excellent ratings for location, cleanliness, and user experience.
The property is a 3-bedroom, 2-bathroom home with a floor area of 114 square metres, suitable for up to 6 guests. It features a fully equipped kitchen, a garden, free Wi-Fi, and parking.
8 Br 8 Bath, Great For Groups/retreats, Complete New Renovation, Walk Downtown - San Mateo, CA
10 87 reviews

8 Br 8 Bath, Great For Groups/retreats, Complete New Renovation, Walk Downtown

apartment, San Mateo
This 8-bedroom house is located in a quiet neighbourhood in lower Baywood, San Mateo, a short walk from the downtown area and within 10 minutes of SFO. The property consistently receives excellent ratings for user experience, location, and cleanliness.
The house spans 320 square metres and features a large "Great Room" for group gatherings, eight en-suite bedrooms with smart TVs, two outdoor patios, a fully equipped kitchen, and a garden. Guests can enjoy amenities such as high-speed Wi-Fi, air conditioning, electric car charging, and 24/7 security.

Best San Mateo, CA holiday rentals with air conditioning

2139 3b Achome /Parking/wifi Fully Fenced Yard /Jacuzzi/ev Charger - San Mateo, CA
9.6 9 reviews

2139 3b Achome /Parking/wifi Fully Fenced Yard /Jacuzzi/ev Charger

apartment, San Mateo
This three-bedroom, two-bathroom house in East San Mateo offers convenient access to San Mateo city centre, Silicon Valley, and is within 10-13 minutes' drive (approximately 8-10 km) of San Francisco International Airport and attractions such as Coyote Point Park.
The property, sleeping up to six guests, features a fully equipped kitchen, private yard with jacuzzi and BBQ, driveway and garage parking, washer/dryer, fast Wi-Fi, and Smart TV with Netflix; nearby amenities include Hillsdale Shopping Centre.
Pets Are Welcome | 1br W/ Pet Spa - San Mateo, CA
No reviews

Pets Are Welcome | 1br W/ Pet Spa

apartment, Menlo Park
This apartment is in Menlo Park, a short drive from Facebook, Google, and Apple, and just 30 minutes from San Francisco and San Jose. The surrounding area is a mix of residential and commercial, with easy access to shops, restaurants, and parks.
The apartment is a one-bedroom flat with a floor area of 70 square metres and can comfortably accommodate up to three guests. It includes a range of amenities like a swimming pool, a terrace, and a garden, as well as a modern kitchen and air conditioning.
2 Queen Beds | Mini Fridge - San Mateo, CA
No reviews

2 Queen Beds | Mini Fridge

apartment, Belmont
This apartment in Belmont is conveniently located approximately 21 kilometres from San Francisco International Airport and 40 kilometres from the San Mateo County Event Centre, with direct access to a lake and the San Francisco Bay for boating and swimming.
This 19 square metre flat accommodates up to four guests, offering air conditioning, complimentary WiFi, an outdoor swimming pool, and on-site parking, with a launderette available for guest use.
Marbella Lane - Adorable And Quiet Studio - San Mateo, CA
No reviews

Marbella Lane - Adorable And Quiet Studio

studio, San Mateo
This studio apartment is located in Hillsborough Park, 5 kilometres from San Francisco International Airport and 27 kilometres from San Francisco City Hall and Moscone Centre.
This 46 square metre studio offers a kitchenette with a fridge and microwave, a private entrance, and parking for up to three guests, with free WiFi available throughout.

Frequently asked questions about holiday rentals in San Mateo, CA

  • What are the top family-friendly attractions in San Mateo, CA?

    The San Mateo County Fair is a great option for families, with rides, games, and live entertainment. The Exploratorium is a hands-on science museum that's perfect for kids of all ages. The Central Park is a great place for a family picnic or to let the kids run around.
  • What are the best Airbnb and holiday rentals in San Mateo, CA?

  • When is the best time to book a vacation rental in San Mateo, CA?

    The best time to book a vacation rental in San Mateo is during the shoulder seasons, from April to May or September to October, when the weather is pleasant and the prices are more affordable. You can avoid the crowds and enjoy a more relaxed experience.
  • What are the most popular Airbnbs in San Mateo, CA?

  • What events or festivals should visitors check out in and around San Mateo, CA?

    The San Mateo County Fair is a popular event held annually in June, offering a variety of entertainment and attractions. The Half Moon Bay Art & Pumpkin Festival is another popular event, held in October, with art, crafts, and pumpkins galore.
  • What are the best holiday rentals with a pool in San Mateo, CA?

  • What are the best budget-friendly activities in San Mateo, CA?

    Take a walk or cycle along the San Francisco Bay Trail, which offers stunning views of the bay. Visit the San Mateo Public Library, which offers free events and programs. Enjoy a picnic in the Central Park, a beautiful green space in the heart of the city.
  • What are the best rentals for families and kids in San Mateo, CA?

  • What are the best restaurants with local dishes in San Mateo, CA?

    For a taste of authentic Filipino cuisine, try Balay Dako. The Creamery is a local favourite for its delicious burgers and milkshakes. The Old Pro is a classic American restaurant with a warm and inviting atmosphere.
  • What are the best rentals or Airbnbs with a jacuzzi in San Mateo, CA?

  • What are the best walking or cycling routes in San Mateo, CA?

    The San Francisco Bay Trail is a popular option for walking or cycling, offering scenic views of the bay and access to various parks and attractions. The Central Park is a great place for a leisurely stroll or a bike ride.
  • Are there pet-friendly attractions in San Mateo, CA?

    The Central Park is a great place to take your dog for a walk or to play fetch. The San Mateo County Fair is also pet-friendly, allowing well-behaved dogs on leashes.
  • What are the benefits of choosing a vacation rental in San Mateo, CA?

    Vacation rentals offer more space and privacy compared to hotels. They often come with kitchen facilities, allowing you to prepare your own meals. You can also find rentals in different locations, giving you more flexibility to explore the area.
  • What are the top sports attractions and facilities in San Mateo, CA?

    The College of San Mateo has a variety of sporting facilities, including a football stadium, baseball field, and tennis courts. The San Mateo Recreation Center offers a range of fitness classes, a swimming pool, and other amenities.

Popular destinations

Choose the Right Holiday Rentals with a Balcony in San Mateo, CA

A terrace with city skyline views is a fantastic reason to book a holiday rental in San Mateo, CA. View our top picks and start comparing now.

906 Brand New Townhome Sleeps 10 - San Mateo, CA
9.3 3 reviews

906 Brand New Townhome Sleeps 10

apartment, Redwood City
This Redwood City townhome, a spacious four-bedroom property, is conveniently located 18km from the Shoreline Amphitheatre and 23km from San Francisco International Airport.
The 190 square metre dwelling boasts three bathrooms, sleeps up to twelve guests, and includes a fully equipped kitchen, private balcony with city views, and free Wi-Fi; a garden is also available.
Luxury 4br4ba Basketball Court, Hot Tub Spa, Foosball, Pool Table, Tesla Charger - San Mateo, CA
10 8 reviews

Luxury 4br4ba Basketball Court, Hot Tub Spa, Foosball, Pool Table, Tesla Charger

house, San Mateo
This luxurious villa is located in South San Mateo, a quiet and safe neighbourhood just 8 kilometres from Hillsdale Mall and downtown San Mateo. It is conveniently close to major highways and a 20-minute drive to San Francisco International Airport.
The property offers 307 square metres of living space with four bedrooms and four bathrooms, accommodating up to eight guests. The house features a hot tub spa, a Tesla charger, a basketball court, a pool table, a foosball table, and a garden.
Peaceful Family Friendly 2br 2ba Entire Apt Unit In Belmont Hill - San Mateo, CA
9.5 2 reviews

Peaceful Family Friendly 2br 2ba Entire Apt Unit In Belmont Hill

apartment, Belmont
This Belmont flat is located 25.7 kilometres from Shoreline Amphitheatre and 14.9 kilometres from San Francisco International Airport.
This 102 square metre, two-bedroom, two-bathroom apartment accommodates up to nine guests and features a fully equipped kitchen, a private balcony, complimentary Wi-Fi, and access to an indoor swimming pool.
Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit In Belmont Hill - San Mateo, CA
9.6 4 reviews

Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit In Belmont Hill

apartment, Belmont
This two-bedroom flat in Belmont offers a peaceful retreat within a low-traffic residential area, providing easy access to Belmont Downtown, Caltrain for Silicon Valley commutes, and is located 22 kilometres from San Francisco International Airport (SFO).
This entire apartment, suitable for five guests, features a kitchen with a fridge, microwave oven, and dishwasher, alongside a swimming pool, terrace/balcony, and parking, with nearby attractions including the Museum of San Carlos History and Hiller Aviation Museum.

Popular Family-Friendly Holiday Rentals in San Mateo, CA

Family holidays in San Mateo, CA work best when your holiday rental is properly set up with space and city attractions within easy reach.

New Renovation 7bd/3ba Whole House -Deck Views! - San Mateo, CA
9.5 161 reviews

New Renovation 7bd/3ba Whole House -Deck Views!

apartment, Daly City
This seven-bedroom home is located in Serramonte, Daly City, just 1.6 kilometres from the Santa Cruz Mountains and 3.2 kilometres from Serramonte Centre. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The spacious house features a private garden, a terrace, and a fireplace for cosy evenings. Guests can enjoy a fully equipped kitchen, free Wi-Fi, and parking on-site.
Vintage San Francisco Bay Area Home - San Mateo, CA
9.2 99 reviews

Vintage San Francisco Bay Area Home

apartment, South San Francisco
This vintage-style apartment is located in Paradise Valley, South San Francisco, about 24 kilometres south of Downtown San Francisco, close to the San Bruno Mountains, SFO Airport, and the Bay Area Bio-tech hub. The accommodation has received excellent ratings from previous guests, highlighting its unique retro aesthetic, spacious backyard, and convenient location.
This three-bedroom flat can accommodate up to six guests and features a large backyard with a palm tree, seating, and a garden. The property has modern amenities such as fast Wi-Fi, a Smart TV, a record player, and a microwave oven, as well as a range of vintage books and San Francisco-themed trinkets.
Upscale Cottage: First Block From The Beach - San Mateo, CA
9.9 115 reviews

Upscale Cottage: First Block From The Beach

apartment, Half Moon Bay
This charming cottage is located just 15 kilometres from the centre of Half Moon Bay, offering a peaceful retreat close to the Pacific Ocean and the Pacific Coast Trail. It has received excellent ratings for location, cleanliness, and overall user experience.
The cottage spans 93 square metres and can accommodate up to four guests in its two bedrooms and one bathroom. It features a fully equipped kitchen, a spacious garden, a tennis court, and a range of outdoor amenities including a ping pong table and barbecue.
@ Marbella Lane 3br House In Downtown Redwood City - San Mateo, CA
8.4 181 reviews

@ Marbella Lane 3br House In Downtown Redwood City

apartment, Redwood City
This five-bedroom property is located in Downtown Redwood City, just 18 kilometres from the Shoreline Amphitheatre and 39 kilometres from the San Jose Convention Center. This home has received excellent ratings for its location, cleanliness, and overall experience.
The house has five bedrooms, offering ample space for families or groups of friends. Guests can enjoy a fully equipped kitchen, air conditioning, a private garden, a swimming pool, and free Wi-Fi access.

Handpicked Self-Catering Rentals with Parking in San Mateo, CA

Park up and enjoy the city centre. These holiday rentals in San Mateo, CA come with a free car park on-site. Start comparing now.

Luxury Spacious Studio In Woodside Plaza - San Mateo, CA
9.8 286 reviews

Luxury Spacious Studio In Woodside Plaza

studio, Redwood City
Explore Redwood Citys Downtown Nr Eateries & Entertainment - San Mateo, CA
No reviews

Explore Redwood Citys Downtown Nr Eateries & Entertainment

apartment, Menlo Park
Poplar House | 3br 2nd Floor | Near Downtown - San Mateo, CA
No reviews

Poplar House | 3br 2nd Floor | Near Downtown

apartment, San Mateo
Marbella Lane - 2br Guest House Dtwn Rwc Pking - San Mateo, CA
No reviews

Marbella Lane - 2br Guest House Dtwn Rwc Pking

house, Redwood City

Compare Luxury Holiday Rentals in San Mateo, CA

Upscale holiday rentals in San Mateo, CA offer a refined stay you will want to return to. Enjoy premium amenities and attentive service.

Fetching Cozy Studio Close To Everything - San Mateo, CA
10 2 reviews

Fetching Cozy Studio Close To Everything

studio, San Mateo

Explore Pet-Friendly Holiday Rentals in San Mateo, CA

Your dog is as welcome as you are. These pet-friendly holiday rental and Airbnbs in San Mateo, CA provide easy access to local dog parks and city walks. See what's available.

1 Queen Bed|mobil Access|nsmk|kitchen - San Mateo, CA
No reviews

1 Queen Bed|mobil Access|nsmk|kitchen

apartment, Belmont
Mavericks Penthouse  Downtown Luxury On Main Street, Half Moon Bay - San Mateo, CA
9.4 20 reviews

Mavericks Penthouse Downtown Luxury On Main Street, Half Moon Bay

apartment, Half Moon Bay
Rustic/modern Design, Oasis City Getaway/near Sfo - San Mateo, CA
9.6 20 reviews

Rustic/modern Design, Oasis City Getaway/near Sfo

apartment, South San Francisco
Newly Furnished! Recently Renovated! Cute Space! Close To Sfo! - San Mateo, CA
9.5 111 reviews

Newly Furnished! Recently Renovated! Cute Space! Close To Sfo!

cottage, South San Francisco

Find the Best Holiday Rentals with a Pool in San Mateo, CA

Pool access at your holiday rental makes a proper swim in the heart of the city part of your daily routine in San Mateo, CA.

1 King Bed - San Mateo, CA
8.0 1 review

1 King Bed

apartment, Belmont
2 Full Beds  Non-smoking Kitchen - San Mateo, CA
No reviews

2 Full Beds Non-smoking Kitchen

apartment, Belmont
1 Queen Bed  Mobil Access Tub Nsmk Kitchen - San Mateo, CA
No reviews

1 Queen Bed Mobil Access Tub Nsmk Kitchen

apartment, Belmont
Hillsborough Haven: Private Pool, Hot Tub & Scenic Views In A Gated House. - San Mateo, CA
9.8 6 reviews

Hillsborough Haven: Private Pool, Hot Tub & Scenic Views In A Gated House.

apartment, Hillsborough

Check Out Holiday Rentals with a Hot Tub in San Mateo, CA

A holiday rental with a hot tub in San Mateo, CA is perfect for unwinding in private after exploring the city. Browse our top-rated options.

Modern Luxury Living In Menlo Park With Pool, Spa & Gym - San Mateo, CA
No reviews

Modern Luxury Living In Menlo Park With Pool, Spa & Gym

apartment, Menlo Park
.5mi From Poplar Beach And Main Street - San Mateo, CA
10 39 reviews

.5mi From Poplar Beach And Main Street

apartment, Half Moon Bay
Luxury Condos At Anton Menlo W Pool & Amenities - San Mateo, CA
9.8 900 reviews

Luxury Condos At Anton Menlo W Pool & Amenities

apartment, Menlo Park
Modern Living In Silicon Valley: 2br Condo Near Facebook - San Mateo, CA
No reviews

Modern Living In Silicon Valley: 2br Condo Near Facebook

apartment, Menlo Park
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