Chianti Region villa rentals
We found 1,286 villa rentals — enter your dates for availability
Explore Chianti Region villa rentals
Showing deals for: 28 Oct - 31 Oct
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
Sleeps 12 · 6 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
The current price is AU$6,163
AU$6,163
for 3 nights, 1 villa
AU$2,054 per night
includes taxes & fees
Your panoramic house in Tuscany between vineyards and olive groves.
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
The current price is AU$1,401
AU$1,401
for 3 nights, 1 villa
AU$467 per night
includes taxes & fees
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Sleeps 12 · 6 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
The current price is AU$7,058
AU$7,058
for 3 nights, 1 villa
AU$2,353 per night
includes taxes & fees
Casale Tignano In Barberino Val d'elsa, Tuscany
Sleeps 10 · 5 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The current price is AU$2,369
AU$2,369
for 3 nights, 1 villa
AU$790 per night
includes taxes & fees
Made for gathering together, leave the rest to us - Villa 20 minutes to Florence
Sleeps 12 · 6 bedrooms · 7 bathrooms
1010 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
The current price is AU$9,628
AU$9,628
for 3 nights, 1 villa
AU$3,209 per night
includes taxes & fees
Villa in the Heart of Chianti
Sleeps 12 · 5 bedrooms · 7 bathrooms
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
The current price is AU$2,816
AU$2,816
for 3 nights, 1 villa
AU$939 per night
includes taxes & fees
Top rated villa rentals - Chianti Region
Beautiful Villa in a great central location
1010 out of 10
Exceptionalexceptional
114 reviews(114 reviews)
The Villa has everything you need for a more than comfortable stay. Centrally located for exploring many of the local Tuscany highlights with a quick tram to Florence.Worth staying in to enjoy the pool and surrounds when the weather is good. Great outdoor space! We were 15 adults.
Suzanne G.
Stayed May 2025
Amazing experience!
1010 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
The villa is absolutely stunning & our stay was an amazing experience. We had a small wedding ceremony with our guests followed by a home cooked Italian dinner which was the most perfect evening. Cate & her family were very accommodating and made us feel very welcome. Cate made our stay stress-free and was more than happy to help organise anything we may have needed for our stay. I can’t wait to stay again
Ashleigh R.
Stayed Mar 2025
Gorgeous tuscan villa
1010 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
Amazing villa, great check in process. Rooms gorgeous, living space's very comfortable. We stayed with 2 families over Christmas, very cosy. A car is very useful to see neighbouring towns.
Yolanda C.
Stayed Dec 2024
Great Venue and Host
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
We stayed 9 days with a group of four other couples for my 50th birthday. Wine is excellent, venue superb, and to a person all said it was the most relaxing part of extended trips. The pool was especially looked forward to by all after travelling. Leonardo has created a special enviroment and we look forward to another visit.
Ben C.
Stayed July 2024
A true Tuscan Villa
1010 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
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
Family holiday
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Our week at the Villa surpassed all expectations for our family get together! The Villa is truly special. Each room had its uniqueness! The breakfast service was a treat and meals prepared by in-house chef were wonderful. The outside table setting just perfect. Imprunetta village is only a short walk away (though need to be wary of cars)Domitila readily answered all queries leading up to our trip which made planning easy. We loved our tour of the vineyard, cellar and tasting. We really couldn’t fault our stay. Highly recommend. Thanks to Domitila and her team
Lisa M.
Stayed Sept 2023
Great time at Ripanera
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Sensational setting, perfect facilities, awesome grounds and pool, easy, comfortable feel to the house, A/C in bedrooms a godsend when every day was 35+.
On site manager was friendly, helpful, but not overly in your presence, so overall the experience was everything we sought and more.
Could not fault the villa.
Geoff P.
Stayed July 2019
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any holiday villa rentals in Chianti Region?
Choose one of the 1,286 villa rentals around Chianti Region and enjoy more space to spread out and relax than a hotel room. Check out properties in top cities like Val d'Elsa, San Gimignano and Montaione and get ready to explore like a local.
How much does it cost to stay in a villa rental in Chianti Region?
Stayz's filters make it a snap to find a villa rental in Chianti Region that fits your budget. Narrow your search by entering your maximum total or nightly price. Also think about when you go. Prices often vary based on peak seasons, major holidays or special events or festivals. You may find lower rates during months that are quieter.
When is the best time to rent a villa in Chianti Region?
Think about travelling in June, when the mercury ranges from around 13ºC to 26ºC. This is the most popular time of year to book a villa rental in Chianti Region.
Where can I rent a Chianti Region villa with great views?
A simple way to browse for a Chianti Region villa with views is to use our filters. Fine-tune your search by "Location" or click on "Guest rating" to see properties other guests highly recommend. After all, why book a room with a view when you can have a villa rental with gorgeous vistas?
Can I book a luxury villa in Chianti Region?
Take a look at our collection of luxury villa rentals in Chianti Region and prepare to holiday like an A-lister. We have high-end properties in cities like Val d'Elsa and Greve in Chianti that come with premium conveniences such as gourmet kitchens, plush décor and whole-home surround sound systems. For even more luxury, search for a villa with a pool or hot tub.
What are the top things to do in Chianti Region?
Do a quick search online to see what kind of attractions or nearby stops you can put on your itinerary. Want a change of pace from sightseeing? Take time to explore the area around your villa rental and talk to some locals to get a sense of life in Chianti Region.
Why should I book my villa holiday with Stayz?
When you choose a Stayz villa rental, the only people you have to share your space with are whoever you bring along. It's just you, your family and the entire place to yourselves. Our flexible cancellation policies also mean you can book your villa with confidence if you need to change your plans.