Book Holiday Homes in San Mateo
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Featured Holiday Homes in San Mateo

FREE BOAT to use, Fish from the dock, Make lasting memories. Fur babies welcome!

Beautiful Oasis on the Creek with Pool; 2 houses and backyard paradise

Tahiti Style 5 STAR OVER-WATER BUNGALOW + Lake House Blue + YouTube Video's PETS

The Barefoot Bungalow | House in Palm Coast with an enclosed pool & grill

Designer Heated Salt Water Pool Home - Close to Ocean-Modern

Lakeside Retreat~ Large home with pool, dock, game room and balcony on lakefront

Escape to our Cozy Home with Crystal-Clear Springs and Trails

Charming 1930's house only a few blocks from the St. Johns River!

Modern Poolside Getaway w Games, Fire pit & Family Fun
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 | 417 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | FREE BOAT to use, Fish from the dock, Make lasting memories. Fur babies welcome!, Beautiful Oasis on the Creek with Pool; 2 houses and backyard paradise, Tahiti Style 5 STAR OVER-WATER BUNGALOW + Lake House Blue + YouTube Video's PETS, The Barefoot Bungalow | House in Palm Coast with an enclosed pool & grill, Designer Heated Salt Water Pool Home - Close to Ocean-Modern, Lakeside Retreat~ Large home with pool, dock, game room and balcony on lakefront, Escape to our Cozy Home with Crystal-Clear Springs and Trails, Charming 1930's house only a few blocks from the St. Johns River!, Modern Poolside Getaway w Games, Fire pit & Family Fun |
Holiday Homes in San Mateo
More accommodations in San Mateo
Top trending hotels in San Mateo

Red Roof Inn PLUS+ Palm Coast

Microtel Inn & Suites by Wyndham Palm Coast I-95

Fairfield Inn & Suites Palm Coast I-95

Holiday Inn Express & Suites Palm Coast I95 by IHG
More ways to explore San Mateo
Top picks
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^Subject to availability and chosen travel dates.