San Mateo Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for San Mateo holiday rentals

Mid Century Garden View Home Parking

Mid Century Garden View Home Parking
3.0 star property
East San Mateo
8.6 out of 10, Excellent, (4 reviews)
"This is a very clean comfortable property! "
United States
Serena
The price is AU$498
includes taxes & fees
15 June - 16 June
Mid Century Garden View Home Parking

Lakefront Retreat WaterViews 3BR 1.5BA

Lakefront Retreat WaterViews 3BR 1.5BA
2.0 star property
East San Mateo
The price is AU$626
includes taxes & fees
7 June - 8 June
Lakefront Retreat WaterViews 3BR 1.5BA

Cozy 3BR Home in San Mateo, Minutes to SFO & Downtown

Cozy 3BR Home in San Mateo, Minutes to SFO & Downtown
Central San Mateo
10.0 out of 10, Exceptional, (2 reviews)
"It was perfect for stay with a small kid! "
United States
Jan H.
Cozy 3BR Home in San Mateo, Minutes to SFO & Downtown

Offsite family retreat property in the heart of Silicon Valley

Offsite family retreat property in the heart of Silicon Valley
East San Mateo
10.0 out of 10, Exceptional, (6 reviews)
"Very clean, well stocked, great deck, good location."
United States
Arvin K.
The price is AU$2,125
includes taxes & fees
16 June - 17 June
Offsite family retreat property in the heart of Silicon Valley

Sanmateo Cozy Central 3b1b Home Garage Parking AC

Sanmateo Cozy Central 3b1b Home Garage Parking AC
2.0 star property
Central San Mateo
The price is AU$691
includes taxes & fees
5 July - 6 July
Sanmateo Cozy Central 3b1b Home Garage Parking AC

Lakefront 3Beds/1.5Bath Retreat w/ Water Views • Walk to Shops • Near SF

Lakefront 3Beds/1.5Bath Retreat w/ Water Views • Walk to Shops • Near SF
East San Mateo
The price is AU$682
includes taxes & fees
7 June - 8 June
Lakefront 3Beds/1.5Bath Retreat w/ Water Views • Walk to Shops • Near SF

Beachfront California Coast Airstream_Luxury

Beachfront California Coast Airstream_Luxury
Heritage Downtown
9.4 out of 10, Exceptional, (10 reviews)
"This place is amazing, we had a great time and definitely will book this place again. "
United States
Theng X.
The price is AU$960
includes taxes & fees
8 June - 9 June
Beachfront California Coast Airstream_Luxury

Hills Cottage with Panoramic Views & Hot Tub. Pet Friendly!

Hills Cottage with Panoramic Views & Hot Tub. Pet Friendly!
Oakland
9.0 out of 10, Wonderful, (20 reviews)
"I really enjoyed my stay in this lovely and quiet cottage!"
United States
Tovah A.
The price is AU$318
includes taxes & fees
8 June - 9 June
Hills Cottage with Panoramic Views & Hot Tub. Pet Friendly!

BRAND NEW - ENTIRE FLOOR w/ OCEAN Beach View and PARKING!

BRAND NEW - ENTIRE FLOOR w/ OCEAN Beach View and PARKING!
Sunset District
9.6 out of 10, Exceptional, (99 reviews)
"Our second stay was just s good as the first. We will be back on our next trip out!"
United States
Heidi
The price is AU$354
includes taxes & fees
7 June - 8 June
BRAND NEW - ENTIRE FLOOR w/ OCEAN Beach View and PARKING!

Marbella Lane - 2BR Guest House Dtwn RWC Pking

Marbella Lane - 2BR Guest House Dtwn RWC Pking
3.0 star property
Palm Park
The price is AU$797
includes taxes & fees
24 June - 25 June
Marbella Lane - 2BR Guest House Dtwn RWC Pking

Coast PalmTree Yard 2BR Block from Beach

Coast PalmTree Yard 2BR Block from Beach
2.5 star property
Sharp Park
The price is AU$557
includes taxes & fees
8 June - 9 June
Coast PalmTree Yard 2BR Block from Beach

Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay

Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay
Heritage Downtown
9.2 out of 10, Wonderful, (7 reviews)
"The place was super cute and close to everything. I would definitely stay again! "
United States
Juliet M.
The price is AU$418
includes taxes & fees
28 June - 29 June
Miramar Penthouse – Coastal Elegance in the Heart of Half Moon Bay

Coastal Palm Tree 2BR Retreat Ocean View

Coastal Palm Tree 2BR Retreat Ocean View
3.0 star property
Sharp Park
8.6 out of 10, Excellent, (9 reviews)
"I loved everything about the place. Really clean and homey vibe"
United States
Christian
The price is AU$548
includes taxes & fees
11 June - 12 June
Coastal Palm Tree 2BR Retreat Ocean View

Small Beach Cottage near the Coastal Trail and The Ritz

Small Beach Cottage near the Coastal Trail and The Ritz
Arleta Park
9.8 out of 10, Exceptional, (125 reviews)
"Cottage was quiet and comfortable. Great neighborhood. Amazing setup for dog. Well equiped kitchen and super easy walk to beach."
United States
Paul
The price is AU$531
includes taxes & fees
8 June - 9 June
Small Beach Cottage near the Coastal Trail and The Ritz

Oceanview Penthouse, Stylish & Walking to Beach

Oceanview Penthouse, Stylish & Walking to Beach
El Granada
10.0 out of 10, Exceptional, (42 reviews)
"Great little spot, awesome view and location. "
United States
Jessie k.
The price is AU$447
includes taxes & fees
14 June - 15 June
Oceanview Penthouse, Stylish & Walking to Beach

Palo Alto Cottage: Privacy, Comfort & Convenience

Palo Alto Cottage: Privacy, Comfort & Convenience
Midtown
9.6 out of 10, Exceptional, (20 reviews)
"Quiet, comfortable, and good location. "
United States
Kelsey P.
The price is AU$322
includes taxes & fees
1 July - 2 July
Palo Alto Cottage: Privacy, Comfort & Convenience

Enjoy a stylish experience at this Kick back and relax in a calm stylish space

Enjoy a stylish experience at this Kick back and relax in a calm stylish space
Paradise Park
8.4 out of 10, Very good, (26 reviews)
"The place was great. Location was safe and close to several attractions. Only negative is some confusion in the vrbo listing- I think they confused check in and check out times (said 3pm checkout) and we were kicked out at 11. Also said only 1 bedroom but there were 2 so that was a nice surprise!"
United States
Ben M.
The price is AU$375
includes taxes & fees
8 June - 9 June
Enjoy a stylish experience at this Kick back and relax in a calm stylish space

Sunny side Bayview heights

Sunny side Bayview heights
Bayview
9.4 out of 10, Exceptional, (48 reviews)
"Easy parking close enough to the city center, hot shower, fridge, microwave, everything we needed for our dogs and a comfortable bed. Happy with our stay, will stay again. "
United States
Esmeralda
The price is AU$278
includes taxes & fees
29 June - 30 June
Sunny side Bayview heights

Marbella Lane - 2BR Guest House Dtwn RWC Pking

Marbella Lane - 2BR Guest House Dtwn RWC Pking
3.0 star property
El Granada
The price is AU$856
includes taxes & fees
8 June - 9 June
Marbella Lane - 2BR Guest House Dtwn RWC Pking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top San Mateo Hotel Reviews

Find out more about San Mateo

Everything you need to know about San Mateo holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Mateo holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Mateo holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

San Mateo holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Mateo. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Mateo holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Mateo holiday rentals we have selected for you start as low as AU$133 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on San Mateo rentals

At Expedia, we put the best San Mateo holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top San Mateo rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Mateo holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Mateo. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find a holiday rental in San Mateo?

Yes, there are holiday rentals in San Mateo close to Coyote Point Park, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in San Mateo. You can also check out the festivals while you're visiting.

What are some of the best holiday rentals that San Mateo has to offer?

Vintage San Francisco Bay Area Home: This holiday home rental outside of San Mateo offers a garden, a selection of books and a Smart TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a stovetop, a microwave and a coffee maker, so that you can cook with friends or family.

How many holiday rentals are there in San Mateo?

Expedia has 48 holiday rentals for your stay in San Mateo.

What’s there to see and do in San Mateo?

Family-friendly attractions include Coyote Point Park and CuriOdyssey, whereas San Francisco Bay and Shoreview Park are a couple of great spots to enjoy the outdoors. In the wider area, you’ll find popular places such as Oracle Park and Pier 39.

What’s a holiday rental in San Mateo like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in San Mateo. Holiday rentals offer extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family getaway.