Panorama of the Pacific ocean on sandy Cowell Ranch State beach surrounded by sea cliffs, rocky headlands on sunny day in San Mateo County, California

San Mateo Holiday Rentals

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Our top choices for San Mateo holiday rentals

@ 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$606
includes taxes & fees
2 July - 3 July
@ Marbella Lane - Bright and Cozy Home Near SFO

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 NZ$691
includes taxes & fees
15 June - 16 June
Mid Century Garden View Home Parking

LakeFront Lavender House

LakeFront Lavender House
2.0 star property
East San Mateo
The price is NZ$698
includes taxes & fees
11 July - 12 July
LakeFront Lavender House

ANDULORE COTTAGE - Near Burlingame Ave - Remodeled - Spacious Backyard Retreat

ANDULORE COTTAGE - Near Burlingame Ave - Remodeled - Spacious Backyard Retreat
Central San Mateo
10.0 out of 10, Exceptional, (85 reviews)
"Great stay, great location, great time. "
United States
greg d.
The price is NZ$1,281
includes taxes & fees
29 June - 30 June
ANDULORE COTTAGE - Near Burlingame Ave - Remodeled - Spacious Backyard Retreat

Lakefront Retreat WaterViews 3BR 1.5BA

Lakefront Retreat WaterViews 3BR 1.5BA
2.0 star property
East San Mateo
The price is NZ$1,178
includes taxes & fees
6 July - 7 July
Lakefront Retreat WaterViews 3BR 1.5BA

Marbella Lane - Adorable and Quiet Studio

Marbella Lane - Adorable and Quiet Studio
Central San Mateo
The price is NZ$749
includes taxes & fees
2 July - 3 July
Marbella Lane - Adorable and Quiet Studio

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 NZ$901
includes taxes & fees
5 July - 6 July
Sanmateo Cozy Central 3b1b Home Garage Parking AC

Panoramic Bayview 4BR · Single-Level · 1Gbps WiFi

Panoramic Bayview 4BR · Single-Level · 1Gbps WiFi
South San Mateo
The price is NZ$2,180
includes taxes & fees
15 June - 16 June
Panoramic Bayview 4BR · Single-Level · 1Gbps WiFi

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 NZ$1,622
includes taxes & fees
12 July - 13 July
Offsite family retreat property in the heart of Silicon Valley

Marbella Lane - Bright and Cozy Home near SFO

Marbella Lane - Bright and Cozy Home near SFO
Central San Mateo
The price is NZ$1,058
includes taxes & fees
8 July - 9 July
Marbella Lane - Bright and Cozy Home near SFO

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$717
includes taxes & fees
7 July - 8 July
Lakefront Lavender House • 2BR w/ Water Views & Backyard • Near SF

@ Marbella Lane - Bright and Cozy Home near SFO

@ Marbella Lane - Bright and Cozy Home near SFO
Central San Mateo
6.8 out of 10, (3 reviews)
"Very cute and cozy. Great location."
United States
Daisy V.
The price is NZ$728
includes taxes & fees
29 June - 30 June
@ Marbella Lane - Bright and Cozy Home near SFO

Marbella Lane Cozy 2BR Studio Duplex Home

Marbella Lane Cozy 2BR Studio Duplex Home
Central San Mateo
The price is NZ$1,499
includes taxes & fees
8 July - 9 July
Marbella Lane Cozy 2BR Studio Duplex Home

@ Marbella Lane – Cozy 2BR + Studio Duplex Home

@ Marbella Lane – Cozy 2BR + Studio Duplex Home
Central San Mateo
@ Marbella Lane – Cozy 2BR + Studio Duplex Home

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

@ Marbella Lane - Adorable and Quiet Studio

@ Marbella Lane - Adorable and Quiet Studio
Central San Mateo
4.0 out of 10, (4 reviews)
"I rented this unit for my son who is visiting from New York. It workedc out perfect for us. We would run it again."
United States
Bob S.
The price is NZ$505
includes taxes & fees
2 July - 3 July
@ Marbella Lane - Adorable and Quiet Studio

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 NZ$380
includes taxes & fees
15 June - 16 June
Hills Cottage with Panoramic Views & Hot Tub. Pet Friendly!

Sunny Spacious House in Vibrant Berkeley/Oakland Rockridge

Sunny Spacious House in Vibrant Berkeley/Oakland Rockridge
Oakland
9.4 out of 10, Exceptional, (82 reviews)
"Comfortable accommodations"
United States
Charles P.
The price is NZ$675
includes taxes & fees
28 June - 29 June
Sunny Spacious House in Vibrant Berkeley/Oakland Rockridge

@ Marbella Lane - Convenient Home 9-min to Levi's

@ Marbella Lane - Convenient Home 9-min to Levi's
3.0 star property
Sunnyvale
The price is NZ$1,275
includes taxes & fees
29 June - 30 June
@ Marbella Lane - Convenient Home 9-min to Levi's

@ Marbella Lane - Convenient Home 9-Min to Levi's

@ Marbella Lane - Convenient Home 9-Min to Levi's
Sunnyvale
9.4 out of 10, Exceptional, (13 reviews)
"Great location, enjoyed our stay."
United States
Michael W.
The price is NZ$963
includes taxes & fees
29 June - 30 June
@ Marbella Lane - Convenient Home 9-Min to Levi's
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.
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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?

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 an electric kettle, so that you can cook with friends or family.

How many holiday rentals are there in San Mateo?

Expedia has 47 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.