65+ San Mateo Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near San Mateo

Discover more than 65 holiday rentals in San Mateo. PickleTrip™ holiday homes has everything you need to find a place to stay near San Mateo, FL.

Whether you are looking for luxury villas in San Mateo, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to San Mateo with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in San Mateo for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in San Mateo with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About San Mateo Holiday Rentals

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 Holiday Home Rentals in San Mateo:

There are many holiday rentals available in San Mateo; however, here are a few of the most popular holiday homes listed in San Mateo on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in San Mateo to find one that works for you.
Yes, there are 65 self-catering family homes and holiday rentals in San Mateo.
There are more than 65 luxury holiday homes in or near San Mateo, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 65 pet friendly rentals that are available in San Mateo.