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

4 bedroom luxury home on a quiet canal with pontoon rental available.

4 bedroom luxury home on a quiet canal with pontoon rental available.

Welaka
Located in Welaka, this vacation home is on the waterfront, within a 5-minute drive of Welaka Spring and Welaka Town Hall.
4 bedroom luxury home on a quiet canal with pontoon rental available.
Large Waterfront home w/dock

Large Waterfront home w/dock

Georgetown
Located in Georgetown, this vacation home is a 2-minute drive from Georgetown United Methodist Church and 6 minutes from Lake George.
Large Waterfront home w/dock
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
Save an average of 15% on thousands of hotels when you're signed in
Clean & Cozy 2-bedroom with sleeper sofa, parking available for boats or RVs.

Clean & Cozy 2-bedroom with sleeper sofa, parking available for boats or RVs.

Palatka
Located in Palatka, this vacation home is within a 5-minute drive of Palatka Welcome Center and Ravine Gardens State Park.
Clean & Cozy 2-bedroom with sleeper sofa, parking available for boats or RVs.
Boat Dock*Salt Water Heated Pool *Close to Beach

Boat Dock*Salt Water Heated Pool *Close to Beach

Palm Coast
Located in Palm Coast (Palm Harbor), this vacation home is within a 5-minute drive of Matanzas River and Trinity Presbyterian Church, Palm Coast.
Boat Dock*Salt Water Heated Pool *Close to Beach
Perfect for Family or Romantic Getaway*Modern*Vast*Comfy*Renovated*Heated Pool

Perfect for Family or Romantic Getaway*Modern*Vast*Comfy*Renovated*Heated Pool

Palm Coast
With a stay at this vacation home in Palm Coast (Palm Harbor), you'll be within a 5-minute drive of Palm Coast Lanes and Trinity Presbyterian Church, Palm ...
Perfect for Family or Romantic Getaway*Modern*Vast*Comfy*Renovated*Heated Pool
Stylish Family Retreat 🌴 with Heated Pool, Bikes & More Near Parks & Beaches🌴

Stylish Family Retreat 🌴 with Heated Pool, Bikes & More 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 Family Retreat 🌴 with Heated Pool, Bikes & More Near Parks & Beaches🌴
HEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Firepit & Games

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

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, Firepit & Games
Spacious Heated Pool Home with Pool & Ping Pong Table

Spacious Heated Pool Home with Pool & Ping Pong Table

Palm Coast
With a stay at this vacation home in Palm Coast, you'll be within a 5-minute drive of Grand Club Pine Lakes Golf Course and Belle Terre Park.
Spacious Heated Pool Home with Pool & Ping Pong Table
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
320 Holiday Homes
Lowest Price
AU$154
Highest Price
AU$245
Popular accommodation
4 bedroom luxury home on a quiet canal with pontoon rental available. , Large Waterfront home w/dock, Designer Heated Salt Water Pool Home - Close to Ocean-Modern, Clean & Cozy 2-bedroom with sleeper sofa, parking available for boats or RVs., Boat Dock*Salt Water Heated Pool *Close to Beach, Perfect for Family or Romantic Getaway*Modern*Vast*Comfy*Renovated*Heated Pool, Stylish Family Retreat 🌴 with Heated Pool, Bikes & More Near Parks & Beaches🌴, HEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Firepit & Games, Spacious Heated Pool Home with Pool & Ping Pong Table

Top trending hotels in San Mateo

Farmhouse Retreat Near St John’s River!

Farmhouse Retreat Near St John’s River!

San Mateo
The price is AU$245 per night from 21 Mar to 22 Mar
AU$245
includes taxes & fees
21 Mar - 22 Mar
When you stay at this farm stay in San Mateo, you'll be 15 minutes by car from Palatka Welcome Center.
Farmhouse Retreat Near St John’s River!
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$154 per night from 6 Apr to 7 Apr
AU$154
includes taxes & fees
6 Apr - 7 Apr
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$175 per night from 23 Mar to 24 Mar
AU$175
includes taxes & fees
23 Mar - 24 Mar
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
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$163 per night from 7 Apr to 8 Apr
AU$163
includes taxes & fees
7 Apr - 8 Apr
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
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.