A coastal landscape with a sandy beach, rocky cliffs, and the ocean.

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

1. Mid Century Garden View Home Parking

Mid Century Garden View Home Parking
3.0 star property
East San Mateo
7.2 out of 10, Good, (5 reviews)
"This is a very clean comfortable property! "
United States
Serena
The price is NZ$565
includes taxes & fees
26 Sept - 27 Sept
Mid Century Garden View Home Parking

2. Mid Century Garden View Home Parking

Mid Century Garden View Home Parking
East San Mateo
The price is NZ$571
includes taxes & fees
10 Oct - 11 Oct
Mid Century Garden View Home Parking

3. 20%OFF! Chic Home with Expansive big Backyard

20%OFF! Chic Home with Expansive big Backyard
East San Mateo
8.0 out of 10, Very good, (9 reviews)
"Complimentary goodies, clean, warm, departure gift. "
United States
Osvaldo D.
The price is NZ$598
includes taxes & fees
7 Oct - 8 Oct
20%OFF! Chic Home with Expansive big Backyard

4. Lakefront Retreat WaterViews 3BR 1.5BA

Lakefront Retreat WaterViews 3BR 1.5BA
2.0 star property
East San Mateo
The price is NZ$733
includes taxes & fees
23 Sept - 24 Sept
Lakefront Retreat WaterViews 3BR 1.5BA

5. LakeFront Lavender House

LakeFront Lavender House
2.0 star property
East San Mateo
8.0 out of 10, Very good, (1 review)
"The listing provided showed a listing of a differently painted house, although the inside was clean the outside needs cleaning. The inside smelled like strong cleaning supplies so airing it out was necessary. The door for one of the bedrooms was locked and were told to find a way to open it on our own, so if you need immediate support for anything related to the house, expect you will need to do it yourself. The futon couch that they have is broken and don’t let them charge for it. If it’s a...
United States
Luis
The price is NZ$640
includes taxes & fees
4 Oct - 5 Oct
LakeFront Lavender House

6. 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, (3 reviews)
"It was perfect for stay with a small kid! "
United States
Jan H.
The price is NZ$862
includes taxes & fees
29 Sept - 30 Sept
Cozy 3BR Home in San Mateo, Minutes to SFO & Downtown

7. Sanmateo Cozy Central 3b1b Home Garage Parking AC

Sanmateo Cozy Central 3b1b Home Garage Parking AC
2.0 star property
Central San Mateo
Sanmateo Cozy Central 3b1b Home Garage Parking AC

8. @ Marbella Lane - Bright and Cozy Home Near SFO

@ Marbella Lane - Bright and Cozy Home Near SFO
3.0 star property
Central San Mateo
The price is NZ$644
includes taxes & fees
22 Sept - 23 Sept
@ Marbella Lane - Bright and Cozy Home Near SFO

9. Marbella Lane - Bright and Cozy Home near SFO

Marbella Lane - Bright and Cozy Home near SFO
Central San Mateo
Marbella Lane - Bright and Cozy Home near SFO

10. 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
8.0 out of 10, Very good, (1 review)
"the housekeeper was there when we arrived and slowed our check-in. the floors looked clean but weren't. the pillows are horrible. be sure to bring your own. the location is convenient and the view is lovely."
United States
Kymberly G.
The price is NZ$855
includes taxes & fees
23 Sept - 24 Sept
Lakefront 3Beds/1.5Bath Retreat w/ Water Views • Walk to Shops • Near SF

11. @ Marbella Lane - Bright and Cozy Home near SFO

@ Marbella Lane - Bright and Cozy Home near SFO
Central San Mateo
7.0 out of 10, Good, (4 reviews)
"Very cute and cozy. Great location."
United States
Daisy V.
@ Marbella Lane - Bright and Cozy Home near SFO

12. Lakefront Lavender House • 2BR w/ Water Views & Backyard • Near SF

Lakefront Lavender House • 2BR w/ Water Views & Backyard • Near SF
East San Mateo
The price is NZ$750
includes taxes & fees
4 Oct - 5 Oct
Lakefront Lavender House • 2BR w/ Water Views & Backyard • Near SF

13. Modern Pacifica Studio Near Beaches & SF

Modern Pacifica Studio Near Beaches & SF
2.5 star property
Westview
The price is NZ$351
includes taxes & fees
21 Sept - 22 Sept
Modern Pacifica Studio Near Beaches & SF

14. Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay

Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
Heritage Downtown
9.6 out of 10, Exceptional, (14 reviews)
"nice place...close to restaurants...easy parking!"
United States
Luz
The price is NZ$506
includes taxes & fees
30 Sept - 1 Oct
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay

15. Coast PalmTree Yard 2BR Block from Beach

Coast PalmTree Yard 2BR Block from Beach
2.5 star property
Sharp Park
10.0 out of 10, Exceptional, (1 review)
The price is NZ$557
includes taxes & fees
21 Sept - 22 Sept
Coast PalmTree Yard 2BR Block from Beach

16. Oceanview Penthouse, Stylish, Walking to Beach

Oceanview Penthouse, Stylish, Walking to Beach
El Granada
10.0 out of 10, Exceptional, (51 reviews)
"Everything was absolutely perfect. It was the perfect getaway perfect area thank you so much."
United States
Don
The price is NZ$415
includes taxes & fees
21 Sept - 22 Sept
Oceanview Penthouse, Stylish, Walking to Beach

17. 214A - Cozy Studio with AC & Kitchen near Stanford

214A - Cozy Studio with AC & Kitchen near Stanford
Redwood City
9.2 out of 10, Wonderful, (7 reviews)
"Perfect stay for a quick get away! "
United States
Sylvia L.
The price is NZ$337
includes taxes & fees
3 Oct - 4 Oct
214A - Cozy Studio with AC & Kitchen near Stanford

18. Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
South Downtown
9.2 out of 10, Wonderful, (43 reviews)
"The property is clean, convenient, and well-appointed. Owner communication was great. Would rent again in a heartbeat. "
United States
Carmela
The price is NZ$679
includes taxes & fees
4 Oct - 5 Oct
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

19. Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!

Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!
Miramar
9.8 out of 10, Exceptional, (25 reviews)
"Very pleasant in great location "
United States
Eric B.
The price is NZ$822
includes taxes & fees
25 Sept - 26 Sept
Seaside Art Gallery Loft: Inspire Your Creativity with Breathtaking Views!

20. Sunny side Bayview heights

Sunny side Bayview heights
Bayview
9.6 out of 10, Exceptional, (60 reviews)
"Great value for a good size suite close to downtown SF. Having laundry was nice and the bunk beds in the separate closet room was ideal for a child. Excellent suite overall and only minor issue was we could hear a lot of footsteps upstairs at night and early morning."
Canada
hong dean
The price is NZ$322
includes taxes & fees
19 Oct - 20 Oct
Sunny side Bayview heights
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our San Mateo holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up San Mateo. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in San Mateo. Seeing all the best attractions is bound to make you fall in love with San Mateo. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in San Mateo short-term rentals, that won’t be hard to do.

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?

Spacious 4BR Family Retreat with Indoor Pool, Jacuzzi & Movie Room – Near SFO: This holiday home rental outside of San Mateo offers an indoor pool, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a pool table and 1 hot tub.

How many holiday rentals are there in San Mateo?

Expedia has 44 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 Sawyer Camp Trail are a couple of great spots to enjoy the outdoors. In the wider area, you’ll find popular places such as Pier 39 and Oracle Park.

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.