San Leo pickleball Stays, Resort Rentals, & Homes
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Luxury Places to Stay in San Leo
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Top-Rated Villas with a Pool in San Leo
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Pet-Friendly Villas in San Leo
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Large Private Villas in San Leo
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San Leo Villas, Airbnb and Holiday Homes Under $200
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Book a Last Minute Place to Stay in San Leo
About San Leo Vacation Rentals
Discover over 23 amazing vacation rental options in San Leo 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 Leo.
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 876.92 ft², with prices averaging US $949 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 Leo.
Top Pickleball-Ready Accommodation Types in San Leo
| Type | Count |
|---|---|
| Vacation Homes | 8 |
| Holiday Apartments | 5 |
| Villas | 3 |
Use these Quick Filters to Find a Vacation Rental in San Leo
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★ 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 Leo with PickleTrip™.
Weather in San Leo, IT
View the weather forecast for San Leo before booking your San Leo Vacation Rentals to confirm your best time to go.
Top Attractions Around San Leo, IT
PickleTrip offers a large selection of top attractions around San Leo . Research things to do on your vacation before you visit San Leo.
Other Places to Stay in San Leo, IT
Frequently Asked Questions About San Leo?
What are the top vacation rentals, resorts, and hotels in San Leo 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 Leo. 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 Leo!
- Casa Giogano
- Suite Valmarecchia
- Newly renovated Italian villa with external hot tub and heated swimming pool
- Farmhouse in the valleys of Montefeltro 5 miles from San Leo
- TERRALUNA Villa Vacanze San Leo - San Marino
- Palazzo Serre - Natura & Piscina
- Le Cicale
- Casa Vacanze in pietra del '700
- Casa Giogano
- Giardino in piazza, casa in pietra a San Leo
How many PickleTrip vacation rentals or resorts are available in San Leo?
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 23 properties listed in San Leo in 2026, 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.
