189+ San Polo in Chianti Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near San Polo in Chianti

Discover more than 189 holiday rentals in San Polo in Chianti. PickleTrip™ holiday homes has everything you need to find a place to stay near San Polo in Chianti, .

Whether you are looking for luxury villas in San Polo in Chianti, 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 Polo in Chianti with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in San Polo in Chianti 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 Polo in Chianti with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About San Polo in Chianti Holiday Rentals

There are a lot of options in San Polo in Chianti. If you plan on staying in the San Polo in Chianti 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 Polo in Chianti:

There are many holiday rentals available in San Polo in Chianti; however, here are a few of the most popular holiday homes listed in San Polo in Chianti 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 Polo in Chianti to find one that works for you.
Yes, there are 189 self-catering family homes and holiday rentals in San Polo in Chianti.
There are more than 189 luxury holiday homes in or near San Polo in Chianti, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 189 pet friendly rentals that are available in San Polo in Chianti.