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!

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

2 out of 5
Satsuma
Located in Satsuma, this vacation home is on the waterfront, within a 15-minute drive of Pomona Park Town Hall and Bronson-Mulholland House.
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

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

Satsuma
Located in Satsuma, this vacation home is on the waterfront, within a 15-minute drive of Pomona Park Town Hall and Bronson-Mulholland House.
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

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

Crescent City
Located in Crescent City, this vacation home is on the waterfront, a 1-minute drive from Crescent Lake and 5 minutes from St. John the Baptist Catholic ...
Tahiti Style 5 STAR OVER-WATER BUNGALOW + Lake House Blue + YouTube Video's PETS
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The Barefoot Bungalow | House in Palm Coast with an enclosed pool & grill

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

Palm Coast
With a stay at this vacation home in Palm Coast (Indian Trails), you'll be a 3-minute drive from Parkview Baptist Church and 5 minutes from Palm Coast United ...
The Barefoot Bungalow | House in Palm Coast with an enclosed pool & grill
Designer Heated Salt Water Pool Home - Close to Ocean-Modern

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

Palm Coast
Located in Palm Coast, this vacation home is within a 10-minute drive of Grand Club Pine Lakes Golf Course and Palm Coast United Methodist Church.
Designer Heated Salt Water Pool Home - Close to Ocean-Modern
Lakeside Retreat~ Large home with pool, dock, game room and balcony on lakefront

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

2 out of 5
Interlachen
Located in Interlachen, this vacation home is on the waterfront, within a 5-minute drive of Still Pond and Boll Green Lake.
Lakeside Retreat~ Large home with pool, dock, game room and balcony on lakefront
Escape to our Cozy Home with Crystal-Clear Springs and Trails

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

Fort McCoy
With a stay at this vacation home in Fort McCoy, you'll be within a 15-minute walk of Ocala National Forest and Lake George.
Escape to our Cozy Home with Crystal-Clear Springs and Trails
Charming 1930's house only a few blocks from the St. Johns River!

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

Welaka
With a stay at this vacation home in Welaka, you'll be on a river, just a 1-minute walk from Welaka Town Hall and 8 minutes by foot from Welaka National Fish ...
Charming 1930's house only a few blocks from the St. Johns River!
Modern Poolside Getaway w Games, Fire pit & Family Fun

Modern Poolside Getaway w Games, Fire pit & Family Fun

Palm Coast
Located in Palm Coast (Palm Harbor), this vacation home is within a 5-minute drive of Trinity Presbyterian Church, Palm Coast and Matanzas River.
Modern Poolside Getaway w Games, Fire pit & Family Fun
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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
417 Holiday Homes
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

Top trending hotels in San Mateo

Red Roof Inn PLUS+ Palm Coast

Red Roof Inn PLUS+ Palm Coast

2.5 out of 5
10 Kingswood Dr, Palm Coast, FL
Fully refundableReserve now, pay when you stay
A stay at Red Roof Inn PLUS+ Palm Coast places you in the heart of Palm Coast, within a 15-minute walk of Let's Play Indoor Playground and Palm Coast Lanes.
Red Roof Inn PLUS+ Palm Coast
Microtel Inn & Suites by Wyndham Palm Coast I-95

Microtel Inn & Suites by Wyndham Palm Coast I-95

2 out of 5
16 Kingswood Dr, Palm Coast, FL
Fully refundableReserve now, pay when you stay
When you stay at Microtel Inn & Suites by Wyndham Palm Coast I-95 in Palm Coast, you'll be in a state park, within a 5-minute drive of Let's Play Indoor Playground ...
Microtel Inn & Suites by Wyndham Palm Coast I-95
Fairfield Inn & Suites Palm Coast I-95

Fairfield Inn & Suites Palm Coast I-95

2.5 out of 5
400 Old Kings Rd, Palm Coast, FL
Fully refundableReserve now, pay when you stay
With a stay at Fairfield Inn & Suites Palm Coast I-95 in Palm Coast, you'll be near the beach, a 4-minute walk from Let's Play Indoor Playground and a 2-minute ...
Fairfield Inn & Suites Palm Coast I-95
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Express & Suites Palm Coast I95 by IHG

Holiday Inn Express & Suites Palm Coast I95 by IHG

3 out of 5
120 Garden St N, Palm Coast, FL
Fully refundable
When you stay at Holiday Inn Express & Suites Palm Coast I95 by IHG in Palm Coast, you'll be in the suburbs, within a 5-minute drive of Palm Coast United Methodist ...
Holiday Inn Express & Suites Palm Coast I95 by IHG
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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.