Book Holiday Homes in San Mateo

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Featured Holiday Homes in San Mateo

Relaxing Miramar Beach House-- directly on bike path, 5 minutes to the beach!

Relaxing Miramar Beach House-- directly on bike path, 5 minutes to the beach!

Half Moon Bay
Stay at this vacation home in Half Moon Bay. Enjoy WiFi, onsite parking, and an onsite playground. Popular attractions Miramar Beach and Waterfront Coastside ...
Relaxing Miramar Beach House-- directly on bike path, 5 minutes to the beach!
Come enjoy this Beautiful Home ! Sunsets Optional !

Come enjoy this Beautiful Home ! Sunsets Optional !

San Francisco
The price is NZ$1,133 per night from 30 Apr to 1 May
NZ$1,133
per night
30 Apr - 1 May
Stay at this family-friendly vacation home in San Francisco. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Golden Gate Park and Presidio ...
Come enjoy this Beautiful Home ! Sunsets Optional !
Clean & Lovely house close to everywhere

Clean & Lovely house close to everywhere

Oakland
Stay at this vacation home in Emeryville. Enjoy WiFi, 2 bathrooms, and 3 bedrooms. Popular attractions Fox Theater and Greek Theater are located nearby. Discover ...
Clean & Lovely house close to everywhere
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Private Studio , spectacular  Ocean View , bathroom , kitchenette, Very Quiet

Private Studio , spectacular Ocean View , bathroom , kitchenette, Very Quiet

Half Moon Bay
Stay at this vacation home in Half Moon Bay. Enjoy WiFi, onsite parking, and a garden. Popular attractions Pillar Piont Beach and Vallejo Beach are located nearby. ...
Private Studio , spectacular Ocean View , bathroom , kitchenette, Very Quiet
Oceanfront Oasis, Sunsets & Crashing Waves

Oceanfront Oasis, Sunsets & Crashing Waves

Moss Beach
Stay at this vacation home in Moss Beach. Enjoy WiFi, onsite parking, and a garden. Popular attractions JV Fitzgerald Marine Reserve and Montara State Beach ...
Oceanfront Oasis, Sunsets & Crashing Waves
Oceanfront Coastal Home w/ Breathtaking Views – Hiking, Beaches & More

Oceanfront Coastal Home w/ Breathtaking Views – Hiking, Beaches & More

Moss Beach
Stay at this vacation home in Moss Beach. Enjoy WiFi, onsite parking, and a patio. Popular attractions JV Fitzgerald Marine Reserve and Montara State Beach are ...
Oceanfront Coastal Home w/ Breathtaking Views – Hiking, Beaches & More
Luxury beach house with private hot tub, enclosed yard, BBQ, & fireplace

Luxury beach house with private hot tub, enclosed yard, BBQ, & fireplace

Half Moon Bay
Stay at this vacation home in Half Moon Bay. Enjoy onsite parking, barbecue grills, and a patio. Popular attractions Waterfront Coastside Trail and Vallejo Beach ...
Luxury beach house with private hot tub, enclosed yard, BBQ, & fireplace
Modern 3BR Oasis, Free Parking!

Modern 3BR Oasis, Free Parking!

Oakland
Stay at this vacation home in Emeryville. Enjoy free WiFi, onsite parking, and a patio. Popular attractions Fox Theater and Jack London Square are located nearby. ...
Modern 3BR Oasis, Free Parking!
Beach Front 6000SF  10b/6bth  Luxury House 7 Miles  to SF

Beach Front 6000SF 10b/6bth Luxury House 7 Miles to SF

Pacifica
Stay at this family-friendly vacation home in Pacifica. Enjoy onsite parking, an arcade/game room, and an in-room DVD player. Popular attractions Rockaway Beach ...
Beach Front 6000SF 10b/6bth Luxury House 7 Miles to SF
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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
778 Holiday Homes
Lowest Price
NZ$223
Highest Price
NZ$1,133
Popular accommodation
Relaxing Miramar Beach House-- directly on bike path, 5 minutes to the beach!, Come enjoy this Beautiful Home ! Sunsets Optional !, Clean & Lovely house close to everywhere, Private Studio , spectacular Ocean View , bathroom , kitchenette, Very Quiet, Oceanfront Oasis, Sunsets & Crashing Waves, Oceanfront Coastal Home w/ Breathtaking Views – Hiking, Beaches & More, Luxury beach house with private hot tub, enclosed yard, BBQ, & fireplace, Modern 3BR Oasis, Free Parking!, Beach Front 6000SF 10b/6bth Luxury House 7 Miles to SF

Top trending hotels in San Mateo

Holiday Inn Golden Gateway, an IHG Hotel

Holiday Inn Golden Gateway, an IHG Hotel

3.5 out of 5
1500 Van Ness Ave, San Francisco, CA
Fully refundable
The price is NZ$255 per night from 27 May to 28 May
NZ$255
per night
27 May - 28 May
Stay at this business-friendly hotel in San Francisco. Enjoy free WiFi, a 24-hour fitness center, and onsite parking. Our guests praise the pool and the helpful ...
Holiday Inn Golden Gateway, an IHG Hotel
Hyatt Regency San Francisco

Hyatt Regency San Francisco

4 out of 5
5 Embarcadero Center, San Francisco, CA
Fully refundable
The price is NZ$391 per night from 2 May to 3 May
NZ$391
per night
2 May - 3 May
Stay at this business-friendly hotel in San Francisco. Enjoy free WiFi, breakfast, and room service. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency San Francisco
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$239 per night from 30 Apr to 1 May
NZ$239
per night
30 Apr - 1 May
Stay at this business-friendly hotel in San Francisco. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Hotel Riu Plaza Fisherman's Wharf
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Club Quarters Hotel in San Francisco

Club Quarters Hotel in San Francisco

4 out of 5
424 Clay St, San Francisco, CA
Fully refundableReserve now, pay when you stay
The price is NZ$223 per night from 10 May to 11 May
NZ$223
per night
10 May - 11 May
Stay at this 4-star business-friendly hotel in San Francisco. Enjoy free WiFi, breakfast, and room service. Our guests praise the restaurant and the helpful ...
Club Quarters Hotel in San Francisco
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.