Book Holiday Homes in San Mateo

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in San Mateo

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

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

St. Augustine
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 ...
HEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Games & Firepit
East Palatka Home on St Johns River w/ Boat Dock!

East Palatka Home on St Johns River w/ Boat Dock!

East Palatka
Located in East Palatka, this vacation home is on the waterfront, within a 15-minute drive of Bronson-Mulholland House and Palatka Welcome Center.
East Palatka Home on St Johns River w/ Boat Dock!
Home near the beach with private pool, inviting patio, streaming & AC

Home near the beach with private pool, inviting patio, streaming & AC

Palm Coast
With a stay at this vacation home in Palm Coast (Indian Trails), you'll be within a 5-minute drive of Parkview Baptist Church and Palm Coast United Methodist ...
Home near the beach with private pool, inviting patio, streaming & AC
Save an average of 15% on thousands of hotels when you're signed in
Relaxing Modern 3 br home with HEATED POOL

Relaxing Modern 3 br home with HEATED POOL

Palm Coast
When you stay at this vacation home in Palm Coast, you'll be next to a golf course, within a 5-minute drive of Belle Terre Park and St. Elizabeth Ann Seton Catholic ...
Relaxing Modern 3 br home with HEATED POOL
Stylish house🌴 w/heated pool, bikes&moore for family fun near parks & beaches🏖

Stylish house🌴 w/heated pool, bikes&moore for family fun near parks & beaches🏖

Palm Coast
With a stay at this vacation home in Palm Coast (Palm Harbor), you'll be within a 5-minute drive of Trinity Presbyterian Church, Palm Coast and Palm Coast ...
Stylish house🌴 w/heated pool, bikes&moore for family fun near parks & beaches🏖
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
The price is AU$324 per night from 26 Nov to 27 Nov
AU$324
includes taxes & fees
26 Nov - 27 Nov
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!
Beautiful, Pet-Friendly Coastal Getaway

Beautiful, Pet-Friendly Coastal Getaway

Palm Coast
Located in Palm Coast, this vacation home is on a river, a 4-minute drive from Grand Club Pine Lakes Golf Course and 5 minutes from Belle Terre Park.
Beautiful, Pet-Friendly Coastal Getaway
Enjoy  yourself at Fat Bastard's Getaway on Crescent Lake!

Enjoy yourself at Fat Bastard's Getaway on Crescent Lake!

Crescent City
Located in Crescent City, this vacation home is on a lake, within a 5-minute drive of Crescent Lake and St. John the Baptist Catholic Church.
Enjoy yourself at Fat Bastard's Getaway on Crescent Lake!
Satsuma Home w/ Fire Pit + Dunns Creek Access!

Satsuma Home w/ Fire Pit + Dunns Creek Access!

Satsuma
Located in Satsuma, this vacation home is within a 15-minute drive of Pomona Park Town Hall and Bronson-Mulholland House.
Satsuma Home w/ Fire Pit + Dunns Creek Access!
Don't see what you're looking for?
See all available properties in San Mateo
View all properties
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
334 Holiday Homes
Lowest Price
AU$128
Highest Price
AU$324
Popular accommodation
HEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Games & Firepit, East Palatka Home on St Johns River w/ Boat Dock!, Home near the beach with private pool, inviting patio, streaming & AC, Relaxing Modern 3 br home with HEATED POOL, Stylish house🌴 w/heated pool, bikes&moore for family fun near parks & beaches🏖, Charming 1930's house only a few blocks from the St. Johns River!, Beautiful, Pet-Friendly Coastal Getaway, Enjoy yourself at Fat Bastard's Getaway on Crescent Lake!, Satsuma Home w/ Fire Pit + Dunns Creek Access!

Top trending hotels in San Mateo

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$133 per night from 15 Dec to 16 Dec
AU$133
includes taxes & fees
15 Dec - 16 Dec
When you stay at Quality Inn & Suites Palatka Riverfront in Palatka, you'll be on the Strip and 30 mi (48.2 km) from St. Augustine Beach.
Quality Inn & Suites Palatka Riverfront
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
The price is AU$128 per night from 9 Dec to 10 Dec
AU$128
includes taxes & fees
9 Dec - 10 Dec
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
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$145 per night from 26 Nov to 27 Nov
AU$145
includes taxes & fees
26 Nov - 27 Nov
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
Save an average of 15% on thousands of hotels when you're signed in
Fairfield Inn and Suites by Marriott

Fairfield Inn and Suites by Marriott

2.5 out of 5
400 Old Kings Rd, Palm Coast, FL
Fully refundableReserve now, pay when you stay
The price is AU$204 per night from 26 Nov to 27 Nov
AU$204
includes taxes & fees
26 Nov - 27 Nov
With a stay at Fairfield Inn and Suites by Marriott 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 and Suites by Marriott
Don't see what you're looking for?
See all available properties in San Mateo
View all properties
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.