Book Holiday Homes in San Mateo

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Featured Holiday Homes in San Mateo

Tranquil house with beautiful garden in Emeryville

Tranquil house with beautiful garden in Emeryville

Emeryville CA
Stay at this holiday home in Emeryville. Enjoy a garden, laundry facilities and patios. Popular attractions Jack London Square and Bay Street are located ...
Opens in a new windowTranquil house with beautiful garden in Emeryville
Modern Guesthouse Retreat in the Heart of Silicon Valley

Modern Guesthouse Retreat in the Heart of Silicon Valley

Menlo Park CA
The price is NZ$506 per night from 1 Jan to 2 Jan
NZ$506
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this holiday home in Menlo Park. Enjoy a garden, housekeeping and air conditioning. Popular attractions Allied Arts Guild and Rodin Sculpture Garden ...
Opens in a new windowModern Guesthouse Retreat in the Heart of Silicon Valley
Contemporary 3bedrooms 2bathrooms in private top floor locates@safe neighborhood

Contemporary 3bedrooms 2bathrooms in private top floor locates@safe neighborhood

San Francisco CA
The price is NZ$805 per night from 16 Dec to 17 Dec
NZ$805
16 Dec - 17 Dec
includes taxes & fees
Stay at this family-friendly holiday home in San Francisco. Enjoy an in-room coffee maker and housekeeping. Popular attractions Golden Gate Park and Golden Gate ...
Opens in a new windowContemporary 3bedrooms 2bathrooms in private top floor locates@safe neighborhood
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Oceanview Family Retreat with Saltwater Hot Tub – Steps from the Beach

Oceanview Family Retreat with Saltwater Hot Tub – Steps from the Beach

Pedro Point, Pacifica CA
Stay at this holiday home in Pacifica. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Pacifica State Beach and Rockaway Beach are located ...
Opens in a new windowOceanview Family Retreat with Saltwater Hot Tub – Steps from the Beach
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

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

Half Moon Bay California
Stay at this holiday home in Half Moon Bay. Enjoy a garden, patios and cable/satellite TV service. Popular attractions Poplar Beach and Half Moon Bay State Beach ...
Opens in a new windowNantucket Penthouse - walk to restaurants, beaches, activies & so much more
Upscale stylish entire 4B2B house with amazing views

Upscale stylish entire 4B2B house with amazing views

Daly City CA
Stay at this holiday home in Daly City. Enjoy laundry facilities. Popular attractions Golden Gate Park and Chase Center are located nearby.
Opens in a new windowUpscale stylish entire 4B2B house with amazing views
Test Property - E2E Vrbo

Test Property - E2E Vrbo

Oakland CA
The price is NZ$139 per night from 15 Jan to 16 Jan
NZ$139
15 Jan - 16 Jan 2026
includes taxes & fees
Stay at this holiday home in Oakland. Enjoy laundry facilities and air conditioning. Popular attractions Jack London Square and Oakland Arena are located ...
Opens in a new windowTest Property - E2E Vrbo
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House

Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House

Half Moon Bay CA
The price is NZ$250 per night from 16 Dec to 17 Dec
NZ$250
16 Dec - 17 Dec
includes taxes & fees
Stay at this holiday home in Half Moon Bay. Popular attractions Francis Beach and Poplar Beach are located nearby.
Opens in a new windowAffordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
Distinguished Oceanfront Point Estate with Iconic Beach + Mountain Vistas

Distinguished Oceanfront Point Estate with Iconic Beach + Mountain Vistas

2 out of 5
Montara CA
Stay at this beach holiday home in Montara. Enjoy a beach locale, a sauna and a garden. Popular attractions Montara State Beach and Gray Whale Cove State Beach ...
Opens in a new windowDistinguished Oceanfront Point Estate with Iconic Beach + Mountain Vistas
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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.

San Mateo Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our San Mateo vacation homes are the perfect way for you to wing it.

Holiday houses in San Mateo let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of San Mateo in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local San Mateo adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in San Mateo with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of San Mateo vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

San Mateo Holiday Homes essential information

Accommodation
1207 Holiday Homes
Lowest Price
NZ$139
Highest Price
NZ$805
Popular accommodation
Tranquil house with beautiful garden in Emeryville, Modern Guesthouse Retreat in the Heart of Silicon Valley, Contemporary 3bedrooms 2bathrooms in private top floor locates@safe neighborhood, Oceanview Family Retreat with Saltwater Hot Tub – Steps from the Beach, Nantucket Penthouse - walk to restaurants, beaches, activies & so much more, Upscale stylish entire 4B2B house with amazing views, Test Property - E2E Vrbo, Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House, Distinguished Oceanfront Point Estate with Iconic Beach + Mountain Vistas

Top trending hotels in San Mateo

Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
2500 Mason St San Francisco CA
Fully refundableReserve now, pay when you stay
The price is NZ$319 per night from 17 Dec to 18 Dec
NZ$319
17 Dec - 18 Dec
includes taxes & fees
Stay at this business-friendly hotel in San Francisco. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Our guests praise the breakfast and the ...
Opens in a new windowHotel Riu Plaza Fisherman's Wharf
Fairmont San Francisco

Fairmont San Francisco

5 out of 5
950 Mason Street Atop Nob Hill San Francisco CA
Fully refundableReserve now, pay when you stay
The price is NZ$527 per night from 21 Dec to 22 Dec
NZ$527
21 Dec - 22 Dec
includes taxes & fees
Stay at this luxury hotel in San Francisco. Enjoy a full-service spa, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowFairmont San Francisco
Holiday Inn Golden Gateway by IHG

Holiday Inn Golden Gateway by IHG

3.5 out of 5
1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
The price is NZ$241 per night from 16 Dec to 17 Dec
NZ$241
16 Dec - 17 Dec
includes taxes & fees
Stay at this business-friendly hotel in San Francisco. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the pool and the ...
Opens in a new windowHoliday Inn Golden Gateway by IHG
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Hyatt Place San Francisco Downtown

Hyatt Place San Francisco Downtown

3 out of 5
701 3rd St San Francisco CA
Fully refundableReserve now, pay when you stay
The price is NZ$326 per night from 4 Jan to 5 Jan
NZ$326
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this hotel in San Francisco. Enjoy free Wi-Fi, breakfast (surcharge) and parking (surcharge). Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowHyatt Place San Francisco Downtown
Don't see what you're looking for?
See all available properties in San Mateo
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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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^Subject to availability and chosen travel dates.