992+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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San Mateo pickleball Stays, Resort Rentals, & Homes

About San Mateo Vacation Rentals

Discover over 992 amazing vacation rental options in San Mateo with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in San Mateo.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 505.41 ft², with prices averaging US $320 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in San Mateo.

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Top Pickleball-Ready Accommodation Types in San Mateo

Type Count
Holiday Apartments 633
Vacation Homes 207
Villas 30

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

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in San Mateo with PickleTrip™.

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Frequently Asked Questions About San Mateo?

What are the top vacation rentals, resorts, and hotels in San Mateo with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in San Mateo. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in San Mateo!

How many pickleball-ready properties have private pools in San Mateo?

Discover 15 accommodations with private or nearby pickleball courts in San Mateo. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in San Mateo is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in San Mateo? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in San Mateo?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 992 properties listed in San Mateo in 2025, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.

Nearby Neighborhood (3) 
Neighborhood Property Count
Parque Vacation Rentals in San Mateo, PR 121
Hipodromo Vacation Rentals in San Mateo, PR 29
Sagrado Corazon Vacation Rentals in San Mateo, PR 4052

People Also Ask

There are 992 San Mateo, PR Vacation Rentals

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