1+ Vacation Rentals Near San Mateo |
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Sailings Canada - Vacation Rentals in San Mateo

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Luxury Places to Stay in San Mateo

Over 253+ Luxury Places to Stay in or Near San Mateo
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Top-Rated Vacation Rentals with a Pool in San Mateo

Over 123+ Top-Rated Vacation Rentals with a Pool in or Near San Mateo
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Pet-Friendly Vacation Rentals in San Mateo

Over 65+ Pet-Friendly Vacation Rentals in or Near San Mateo
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Large Vacation Homes & Villas in San Mateo

Over 22+ Large Vacation Homes & Villas in or Near San Mateo
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Wheelchair Accessible Vacation Homes in San Mateo

Over 30+ Wheelchair Accessible Vacation Homes in or Near San Mateo
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San Mateo Vacation Rentals and Airbnb Places to Stay Under $200

Over 205+ San Mateo Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in San Mateo

Over 21+ Instantly Bookable Vacation Homes in or Near San Mateo
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About San Mateo Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sailings San Mateo, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in San Mateo. Places to stay near San Mateo with prices averaging US $26 a night.

Sailings makes it easy and safe to find and compare vacation rentals in San Mateo with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in San Mateo

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Use these Quick Filters to Find a Vacation Rental in San Mateo

★ Pro Tip: Sailings makes it easy to compare the best listings on Sailings homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sailings homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in San Mateo.

Weather in San Mateo

View the weather forecast for San Mateo before booking your San Mateo Vacation Rentals to confirm your best time to go.

December - February
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March - May
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June - August
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September - November
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San Mateo Vacation Rental Frequently Asked Questions

What are the top vacation rentals in San Mateo?

There are a lot of options in San Mateo. If you plan on staying in the San Mateo area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in San Mateo:

How many vacation rentals are available in San Mateo?

Currently, the total number of properties listed in 2026 is over 1 in the San Mateo area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in San Mateo.