Top Castellina in Chianti villa rentals - Tuscany

Explore Castellina in Chianti villa rentals

Beautiful view of the entire property - main house + 2 guesthouses

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Sleeps 23 · 11 bedrooms · 11+ bathrooms

End of a exiting afternoon. Some drinks at the Pool.

Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa

Sleeps 10 · 4 bedrooms · 5 bathrooms

Luxury converted barn with hilltop views in chianti wine region, Tuscany

Sleeps 6 · 3 bedrooms · 3 bathrooms

Top rated villa rentals - Castellina in Chianti

Premier Host

A very special experience

We loved our time here. Views were amazing, house comfortable and close to beautiful towns. You need a car to experience the most amazing food and scenery A very memorable holiday indeed

Marietta R.

Stayed May 2025

Premier Host

Spectacular!

Would highly recommend! The property is stunning - perfect for our extended family, with everything you could need for young and old. The views are breathtaking! Gaia was incredibly communicative and a generous and responsive host. Thank you for such a wonderful stay!

Simone L.

Stayed Sept 2024

Premier Host

Relaxing and scenic authentic Chianti experience

This is one of those conflicted reviews. I’d like to keep Le Bagnaie secret so we can book in future but I can’t resist posting about the experience. I can’t fault anything about the stay. The check in instructions were easy, property is well appointed and spotless, spectacular views, great pool and beautiful district. We drove around the surrounding towns and wineries. The meal from Serena was a real highlight. We didn’t want to leave

Damian H.

Stayed Sept 2024

A true Tuscan Villa

The property views are even better in real life. The villa, grounds and pool are well looked after. Amazing stay. Just a note for those that may need to know…all the bedrooms are upstairs. There is one bathroom downstairs and 2 upstairs. Alessio was a fantastic host. We loved our stay! Thank you

Michelle L.

Stayed June 2024

Premier Host

Fabulous in Chianti

Great villa - perfect for large family stay

John S.

Stayed May 2024

Amazing

Our stay was incredible! Everything as per pictures, Sergio and Elena were very helpful!! Would definitely recommend this place ! You can’t get a better view or place than this!!

Jenelle C.

Stayed Apr 2019

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Frequently asked questions

Are there any holiday villa rentals in Castellina in Chianti?

Browse our 666 villa rentals in Castellina in Chianti that are often set in stunning and exclusive locations. Whether you'd like to stay in San Leonino, Villa, Badesse or another popular neighbourhood, you'll discover the perfect villa on Stayz.

How much does it cost to stay in a villa rental in Castellina in Chianti?

Stayz's filters make it a cinch to find a villa rental in Castellina in Chianti that matches your budget. Fine-tune your search by entering your maximum total or nightly price. Also consider when you go. Prices often vary based on major local holidays or special events or festivals. Villas may be cheaper when it's less busy.

When is the best time to rent a villa in Castellina in Chianti?

It can all depend on the weather conditions you like most, among other things. Many visitors to Chianti Region get a Castellina in Chianti villa rental in May, when temperatures range from 9ºC to 21ºC.

Where can I rent a Castellina in Chianti villa with great views?

Villa rentals with views of medieval areas are just one of the types of stays available to book in Castellina in Chianti. If you're looking for villas full of charm that offer vistas worth remembering, Stayz can help you find them.

Can I book a luxury villa in Castellina in Chianti?

Featuring a host of amenities like swimming pools, courtyards and advanced in-home entertainment, Stayz's luxurious villa rentals in Castellina in Chianti promise a top-tier travel experience. Look forward to the best in modern and comfortable furnishings, ample room and a setting that ensures privacy and tranquility for you and your guests.

What are the top things to do in Castellina in Chianti?

Siena Cathedral, Torre del Mangia and Piazza del Campo are terrific attractions that'll keep the whole crew occupied in Castellina in Chianti. There's nothing like travel to bring everyone together, so check out our villa rentals in this vibrant destination.

Why should I book my villa holiday with Stayz?

Booking your villa rental with Stayz means you'll have the entire place for your exclusive use — your own private sanctuary, without any interruptions from others. Not only that, our flexible payment and cancellation policies allow you to modify your plans if you need to.