Search Vacation Homes in San Mateo

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Homes in San Mateo

Newly built, charming cozy and quiet river home
Property grounds

Newly built, charming cozy and quiet river home

9.8 out of 10, Exceptional, (6)
Newly built, charming cozy and quiet river home
Tahiti Style 5 STAR OVER-WATER BUNGALOW + Lake House Blue + YouTube Video's PETS
Aerial view

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

10.0 out of 10, Exceptional, (336)
"Nothing cheap about this place views are amazing loved every minute of our stay here. Dean was a great host.wanted for nothing. Would absolutely recommend this gem to anyone. "
Tahiti Style 5 STAR OVER-WATER BUNGALOW + Lake House Blue + YouTube Video's PETS
Perfect for Family or Romantic Getaway*Modern*Vast*Comfy*Renovated*Heated Pool
Sun loungers, beach towels

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

9.2 out of 10, Wonderful, (42)
"Nice property. We had a nice stay there!!"
Perfect for Family or Romantic Getaway*Modern*Vast*Comfy*Renovated*Heated Pool
GameRoom | Canal | Large Dock | Pool | Pets OK! 6 beds
Terrace/patio

GameRoom | Canal | Large Dock | Pool | Pets OK! 6 beds

10.0 out of 10, Exceptional, (2)
"The home was in a quiet neighborhood and the canal view was exceptional. It was in a convenient location, easy drive to the beach and St. Augustine. The home had everything we needed."
$611 nightly
The price is $667
Oct 2 - Oct 3
Total with taxes and fees
GameRoom | Canal | Large Dock | Pool | Pets OK! 6 beds
**EXCLUSIVE 3-bedroom w/heated private pool**
Smart TV

**EXCLUSIVE 3-bedroom w/heated private pool**

8.0 out of 10, Very Good, (16)
"What a beautiful house this is. We couldn’t have asked for more whilst visiting family in Florida. The house had everything we needed, lovely location in a quiet street, close to amenities, and beaches. We will definitely be back again. Thank you Camille. "
**EXCLUSIVE 3-bedroom w/heated private pool**
Tranquility Home Near Historical Flagler Beach
Smart TV

Tranquility Home Near Historical Flagler Beach

10.0 out of 10, Exceptional, (14)
"Came into town for the Daytona 500 and to spend a week in Florida. Place was as advertised, plenty of space, quiet neighborhood, and close to anything that you'd need during your stay. Important note for those who like to watch tv in bed, there are no TVs in the bedrooms themselves, just the living room.Would stay again."
$169 nightly
The price is $187
Oct 2 - Oct 3
Total with taxes and fees
Tranquility Home Near Historical Flagler Beach
Stylish Family Retreat with Heated Pool, Bikes & More Near Parks & Beaches
Beach nearby, sun loungers, beach towels

Stylish Family Retreat with Heated Pool, Bikes & More Near Parks & Beaches

10.0 out of 10, Exceptional, (62)
"The house was very comfortable and accommodating. We are considering staying there again in the future."
$454 nightly
The price is $502
Oct 2 - Oct 3
Total with taxes and fees
Stylish Family Retreat with Heated Pool, Bikes & More Near Parks & Beaches
Charming 3-bedroom house in Palm Coast: Near Beach
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in Palm Coast: Near Beach

9.6 out of 10, Exceptional, (5)
"Easy to find, accommodated our family while we were in town for a wedding. House was very clean and comfortable."
$319 nightly
The price is $353
Oct 17 - Oct 18
Total with taxes and fees
Charming 3-bedroom house in Palm Coast: Near Beach
Heated Pool Oasis in Palm Coast
Dining

Heated Pool Oasis in Palm Coast

9.8 out of 10, Exceptional, (33)
"Property is an excellent facility located in quiet area. It is well furnished and decorated. Pool and hot tub are also excellent. I would recommend it to anyone."
$564 nightly
The price is $584
Oct 5 - Oct 6
Total with taxes and fees
Heated Pool Oasis in Palm Coast
Private Dock, Fishing, Chef's Kitchen-Sleeps 8
Fridge, oven, stovetop, dishwasher

Private Dock, Fishing, Chef's Kitchen-Sleeps 8

10.0 out of 10, Exceptional, (18)
"We were only there a few days - we will book longer next year - Area rich in history"
Private Dock, Fishing, Chef's Kitchen-Sleeps 8
Fisherman’s Paradise
Microwave, oven, stovetop, dishwasher

Fisherman’s Paradise

10.0 out of 10, Exceptional, (1)
"It was clean and welcoming but be advised there is no water there. That wasn’t why we were there. I appreciated the little touches like snacks and coffee pods. The house is secure but it is Putnam County FL so it was a mixed neighborhood. Thank you Kimberley, it was the base we needed. "
Fisherman’s Paradise
Cozy & Family-Friendly
Beach

Cozy & Family-Friendly

10.0 out of 10, Exceptional, (3)
"The house and property was absolutely amazing conveniently located to everything extremely clean and comfortable Marcos was a fabulous host I can’t say enough about this home will rent again absolutely love "
Cozy & Family-Friendly
HEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Games & Firepit
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (74)
"Property owner was very responsive, home has everything you could need and more. Will definitely be staying here again."
HEATED Saltwater POOL, Harry Potter, BBQ, Lake, Fishing, Gazebo, Games & Firepit
Sandy Toes Paradise Palm Coast
Beach towels

Sandy Toes Paradise Palm Coast

9.8 out of 10, Exceptional, (23)
"Staying at Sandy Toes was the perfect home to relax and enjoy the Palm Coast area. It is very clean, owners quick to respond to questions and quiet neighborhood. Many parks and access to the beach."
Sandy Toes Paradise Palm Coast
Luxury defined - Beautiful 5BR 3Ba Home Perfect for entire family vacation
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (44)
"Very clean, and owner was very helpful. Very nice place to stay."
$281 nightly
The price is $311
Oct 6 - Oct 7
Total with taxes and fees
Luxury defined - Beautiful 5BR 3Ba Home Perfect for entire family vacation
Escape to our Cozy Home with Crystal-Clear Springs and Trails
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (38)
"Quiet, cozy. great area. "
Escape to our Cozy Home with Crystal-Clear Springs and Trails
Your Home away from home!
Fridge, microwave, oven, stovetop

Your Home away from home!

10.0 out of 10, Exceptional, (5)
"Place was great! Clean, modern, everything worked and the process was super simple. My group was very pleased. Highly recommend!"
$318 nightly
The price is $352
Oct 2 - Oct 3
Total with taxes and fees
Your Home away from home!
Stunning Lake house,heated pool, pet friendly,close to beach, restaurants ,bars
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (26)
"The house was beautiful!! And the host leyla was super nice and responds very quick!! She lets us check in early because the house was ready!!! The house has every utensil and cooking supply you can think about. Will definitely be coming back!!! "
Stunning Lake house,heated pool, pet friendly,close to beach, restaurants ,bars
Flamingo 🦩 PRIVATE HEATED POOL House: Short Drive to St Augustine, Daytona Beach
Outdoor pool, a heated pool

Flamingo 🦩 PRIVATE HEATED POOL House: Short Drive to St Augustine, Daytona Beach

9.8 out of 10, Exceptional, (65)
"We loved our stay at the flamingo pool house. We enjoyed all the area had to offer. One of the neighbors had to complain about my kids enjoying the pool but everything else was awesome."
Flamingo 🦩 PRIVATE HEATED POOL House: Short Drive to St Augustine, Daytona Beach
Waterfront,new dock;relax& fun:sleeps six,two full baths. Allow one sm - med dog
2 bedrooms, desk, iron/ironing board, free WiFi

Waterfront,new dock;relax& fun:sleeps six,two full baths. Allow one sm - med dog

9.2 out of 10, Wonderful, (38)
"The stay was great!! "
Waterfront,new dock;relax& fun:sleeps six,two full baths. Allow one sm - med dog
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top San Mateo Hotel Reviews

Old Town Inn - St Augustine South

Old Town Inn - St Augustine South

10/10 Excellent
"The best hotel. I’ve stayed at in St. John’s and the Elkton area family oriented beyond clean, amazingly comfortable beds, spacious rooms, quiet and very safe."
Holly 1-night trip
Posted 2 days ago
Old Town Inn - St Augustine South

Find out more about San Mateo

Find out more about San Mateo

San Mateo Vacation Homes information

Number of reviews
797
Accommodation
393 Vacation Homes
Lowest Price
$187
Highest Price
$667

Explore a world of travel with Expedia

Explore a world of travel with Expedia