San Casciano in Val di Pesa villa rentals

We found 174 villa rentals — enter your dates for availability
Discover a selection of 25 homes, 26 villas and holiday rentals in San Casciano in Val di Pesa that are perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as parking and a washer and dryer. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Explore San Casciano in Val di Pesa villa rentals

Image of "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C
Premier Host

1. "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

Sleeps 18 · 9 bedrooms · 8+ bathrooms
10 out of 10
exceptional
(143 reviews)
More information about "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C, opens in a new tab

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently Asked Questions

Are there any holiday villa rentals in San Casciano in Val di Pesa?

Choose one of our 272 villa rentals in San Casciano in Val di Pesa and you'll have an ideal base for your next family or group adventure. Calzaiolo, Massanera and San Quirico in Collina are among the city's most popular neighbourhoods.

How much does it cost to stay in a villa rental in San Casciano in Val di Pesa?

Where you stay, when you want to travel and the length of your escape will determine how much you pay for a villa rental in San Casciano in Val di Pesa. Key in your travel details on Stayz to compare options and then pick the best one for you.

When is the best time to rent a villa in San Casciano in Val di Pesa?

It can all depend on the weather conditions you like most, among other factors. Many people visiting Chianti Region book a San Casciano in Val di Pesa villa rental in April, when average temperatures range from 6ºC to 18ºC.

Where can I rent a San Casciano in Val di Pesa villa with great views?

Stayz has a range of character-filled villa rentals in San Casciano in Val di Pesa, including escapes with views of historic areas. In between seeing the sights, kick back and gaze at vistas that are an attraction in themselves.

Can I book a luxury villa in San Casciano in Val di Pesa?

Take your holiday to the next level with one of our villa rentals in San Casciano in Val di Pesa. Offering premium conveniences such as fully-equipped kitchens, advanced in-home entertainment systems and quality furnishings, you and your guests will feel like A-listers. Use our filter tool to display the properties with first-rate perks like hot tubs and pools for that added layer of opulence and luxury.

What are the top things to do in San Casciano in Val di Pesa?

One of the first things to do after locking in your villa rental is to fill your itinerary with awesome activities and sights. There's loads of them in San Casciano in Val di Pesa, with some of the leading family-friendly attractions including Cathedral of Santa Maria del Fiore, Ponte Vecchio and Uffizi Gallery.

Why should I book my villa holiday with Stayz?

With 24/7 customer support, peace of mind is guaranteed when you book through Stayz. As soon as you lock in your villa rental to even after your adventure is over, we'll be by your side. It's all part of our Book with Confidence Guarantee. What's more, we also have benefits like payment protection and flexible cancellation policies