Book Holiday Homes in San Mateo

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Featured Holiday Homes in San Mateo

Luxury defined - Beautiful 5BR 3Ba Home Perfect for entire family vacation

Luxury defined - Beautiful 5BR 3Ba Home Perfect for entire family vacation

Palm Coast FL
Located in Palm Coast (Belle Terre), this vacation home is within a 5-minute drive of Belle Terre Park and St. Elizabeth Ann Seton Catholic Church.
Opens in a new windowLuxury defined - Beautiful 5BR 3Ba Home Perfect for entire family vacation
Unbeatable Waterfront Deal: Special Offers on 4BR Luxury Canal Retreat

Unbeatable Waterfront Deal: Special Offers on 4BR Luxury Canal Retreat

Welaka FL
Located in Welaka, this vacation home is on the waterfront, within a 5-minute drive of Welaka Spring and Welaka Town Hall.
Opens in a new windowUnbeatable Waterfront Deal: Special Offers on 4BR Luxury Canal Retreat
Pristine Palms | House in Palm Coast with enclosed pool & full kitchen

Pristine Palms | House in Palm Coast with enclosed pool & full kitchen

2 out of 5
Palm Coast FL
With a stay at this vacation home in Palm Coast (Palm Harbor), you'll be a 4-minute drive from Hammock Dunes Creek Course and 6 minutes from Matanzas River.
Opens in a new windowPristine Palms | House in Palm Coast with enclosed pool & full kitchen
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Newly built, charming cozy and quiet river home

Newly built, charming cozy and quiet river home

Palatka FL
With a stay at this vacation home in Palatka, you'll be on the waterfront, and 10.3 mi (16.6 km) from Palatka Welcome Center and 10.8 mi (17.4 km) from Ravine ...
Opens in a new windowNewly built, charming cozy and quiet river home
Boat Dock*Salt Water Heated Pool *Close to Beach

Boat Dock*Salt Water Heated Pool *Close to Beach

Palm Coast FL
With a stay at this vacation home in Palm Coast (Palm Harbor), you'll be a 1-minute drive from Matanzas River and 7 minutes from Hammock Dunes Creek Course.
Opens in a new windowBoat Dock*Salt Water Heated Pool *Close to Beach
Reunion - Sleeps 26 hot tub 10 br 8 ba 6 mile beach

Reunion - Sleeps 26 hot tub 10 br 8 ba 6 mile beach

Palm Coast FL
With a stay at this vacation home in Palm Coast (Indian Trails), you'll be within a 5-minute drive of Palm Coast United Methodist Church and Parkview Baptist ...
Opens in a new windowReunion - Sleeps 26 hot tub 10 br 8 ba 6 mile beach
Stunning Lake house,heated pool, pet friendly,close to beach, restaurants ,bars

Stunning Lake house,heated pool, pet friendly,close to beach, restaurants ,bars

Palm Coast FL
With a stay at this vacation home in Palm Coast (Quail Hollow), you'll be within a 15-minute drive of Cypress Knoll Golf Club and AdventHealth Palm Coast.
Opens in a new windowStunning Lake house,heated pool, pet friendly,close to beach, restaurants ,bars
HEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Games & Firepit

HEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Games & Firepit

St. Augustine FL
With a stay at this vacation home, you'll be centrally located in St. Augustine, within a 15-minute drive of Flagler College and Castillo de San Marcos National ...
Opens in a new windowHEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Games & Firepit
Luxury near St. Augustine & Daytona! 30% off monthly booking

Luxury near St. Augustine & Daytona! 30% off monthly booking

Palm Coast FL
With a stay at this vacation home in Palm Coast (Matanzas Woods), you'll be within a 10-minute drive of Matanzas River and Parkview Baptist Church.
Opens in a new windowLuxury near St. Augustine & Daytona! 30% off monthly booking
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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
384 Holiday Homes
Lowest Price
AU$108
Highest Price
AU$155
Popular accommodation
Luxury defined - Beautiful 5BR 3Ba Home Perfect for entire family vacation, Unbeatable Waterfront Deal: Special Offers on 4BR Luxury Canal Retreat, Pristine Palms | House in Palm Coast with enclosed pool & full kitchen, Newly built, charming cozy and quiet river home, Boat Dock*Salt Water Heated Pool *Close to Beach, Reunion - Sleeps 26 hot tub 10 br 8 ba 6 mile beach, Stunning Lake house,heated pool, pet friendly,close to beach, restaurants ,bars, HEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Games & Firepit, Luxury near St. Augustine & Daytona! 30% off monthly booking

Top trending hotels in San Mateo

Old Town Inn - St Augustine South

Old Town Inn - St Augustine South

2625 State Rd 207 Elkton FL
Fully refundableReserve now, pay when you stay
The price is AU$110 per night from 21 Dec to 22 Dec
AU$110
21 Dec - 22 Dec
includes taxes & fees
With a stay at Old Town Inn - St Augustine South in Elkton, you'll be within a 15-minute drive of St. Augustine Premium Outlets and Flagler College.
Opens in a new windowOld Town Inn - St Augustine South
Quality Inn & Suites Palatka Riverfront

Quality Inn & Suites Palatka Riverfront

2.5 out of 5
201 N 1st Street Palatka FL
Fully refundableReserve now, pay when you stay
The price is AU$155 per night from 4 Jan to 5 Jan
AU$155
4 Jan - 5 Jan 2026
includes taxes & fees
When you stay at Quality Inn & Suites Palatka Riverfront in Palatka, you'll be on the riverwalk and 30 mi (48.2 km) from St. Augustine Beach.
Opens in a new windowQuality Inn & Suites Palatka Riverfront
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
The price is AU$108 per night from 23 Dec to 24 Dec
AU$108
23 Dec - 24 Dec
includes taxes & fees
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.
Opens in a new windowRed Roof Inn PLUS+ Palm Coast
Save an average of 15% on thousands of hotels when you're signed in
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
The price is AU$150 per night from 24 Dec to 25 Dec
AU$150
24 Dec - 25 Dec
includes taxes & fees
Located in Palm Coast, Fairfield Inn & Suites Palm Coast I-95 is within a 10-minute drive of Ocean Hammock Golf Club and Washington Oaks Gardens State Park.
Opens in a new windowFairfield Inn & Suites Palm Coast I-95
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.