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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Chianti Region villas

Property grounds

VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.

VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.
Rosano - Florence
9.8 out of 10, Exceptional, (31 reviews)
"Local sights and food"
United States
Brian W.
The price is ￥56,162
￥88,211 total
includes taxes & fees
May 6 - May 7
VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is ￥127,130
￥141,341 total
includes taxes & fees
Apr 29 - Apr 30
Villa Marcolina
Pool

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is ￥872,570
￥966,173 total
includes taxes & fees
Apr 22 - Apr 23
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Exterior

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is ￥2,209,039
￥2,209,039 total
includes taxes & fees
Apr 22 - Apr 23
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Property grounds

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (8 reviews)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
The price is ￥168,486
￥172,979 total
includes taxes & fees
Apr 25 - Apr 26
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Exterior

Luxury Tuscan Villa Collalto with 18 rooms -Perfect for Exclusive Events

Luxury Tuscan Villa Collalto with 18 rooms -Perfect for Exclusive Events
Colle di Val d'Elsa
The price is ￥1,591,257
￥1,771,911 total
includes taxes & fees
May 5 - May 6
Luxury Tuscan Villa Collalto with 18 rooms -Perfect for Exclusive Events
Exterior

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
The price is ￥71,582
￥78,741 total
includes taxes & fees
Apr 26 - Apr 27
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Outdoor dining

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (3 reviews)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
The price is ￥56,012
￥73,984 total
includes taxes & fees
Apr 22 - Apr 23
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is ￥88,317
￥97,149 total
includes taxes & fees
Apr 23 - Apr 24
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Exterior

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is ￥2,642,756
￥2,642,756 total
includes taxes & fees
Apr 29 - Apr 30
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Exterior

Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is ￥251,381
￥292,754 total
includes taxes & fees
Apr 22 - Apr 23
Villa Capanna: A Window onto Tuscany
Exterior

Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
10.0 out of 10, Exceptional, (2 reviews)
"Nice place 👌 "
United States
Avi A.
The price is ￥50,546
￥73,385 total
includes taxes & fees
Apr 24 - Apr 25
Villa Il Signorino
Exterior

Dedicated Concierge service, heated pool, ensuite bathrooms, few min to Florence

Dedicated Concierge service, heated pool, ensuite bathrooms, few min to Florence
impruneta
10.0 out of 10, Exceptional, (107 reviews)
"We had an incredible stay at this Tuscan villa over the Christmas holidays with a group of 10, and the home was perfect in every way. The villa was spacious, comfortable, and ideal for a large group. Caterina and her sister Cecilia were exceptionally responsive, warm, and a pleasure to work with from start to finish. Caterina truly went above and beyond with our requests—it genuinely felt like having a five-star hotel concierge at our disposal. The pizza class and in-home dining experience were...
United States
Bernie K.
The price is ￥235,416
￥269,675 total
includes taxes & fees
May 12 - May 13
Dedicated Concierge service, heated pool, ensuite bathrooms, few min to Florence
Exterior

My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate

My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is ￥129,965
￥142,961 total
includes taxes & fees
Apr 23 - Apr 24
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Exterior

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (7 reviews)
"From the moment we entered to our last day everything was perfect. Group of 15 and we all fit comfortably. "
United States
Debra P.
The price is ￥336,972
￥465,770 total
includes taxes & fees
Apr 22 - Apr 23
Beautiful Tuscan home between Florence & Siena
Outdoor dining

Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
Exterior

Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is ￥321,247
￥362,620 total
includes taxes & fees
May 5 - May 6
Villa Torre Among the Hills of Siena
Pool

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (1 review)
"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."
Poland
Anonymous traveler
The price is ￥210,038
￥329,604 total
includes taxes & fees
Apr 25 - Apr 26
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
Empoli
10.0 out of 10, Exceptional, (1 review)
"The villa is divided into 4 apartments and was perfect for our group of eleven. The property was beautiful and it is convenient to the Empoli train station."
United States
Vicki C.
The price is ￥242,740
￥289,009 total
includes taxes & fees
Apr 26 - Apr 27
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
Pool

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
The price is ￥270,538
￥303,251 total
includes taxes & fees
May 15 - May 16
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chianti Region Hotel Reviews

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"L’ambiance est exceptionnelle, le service est chaleureux et prévenant, et le restaurant est aussi excellent. Je recommande chaleureusement."
Chantal 1-night trip
Posted 2 days ago
Villa Casagrande Resort & SPA

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
160
Accommodation
540 Villas
Lowest Price
￥73,385
Highest Price
￥2,642,756

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between ￥73,385 and ￥2,642,756 per night. These escapes offer the privacy of your own space at a price that doesn't break the bank. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Chianti Region?
Chianti Region has 540 villas to choose from. Enter your destination and dates and lock in your perfect trip today.
Why book your villa in Chianti Region with Expedia?
We think arranging a vacation should be a breeze, so if you're looking for villas at a great price, Expedia delivers. Keep costs down and choose an all-inclusive stay, or splurge on a plush villa to spoil the ones you love most. Our handy filters make it easy to find a property in Chianti Region that matches your needs.
How can I find cheap villas in Chianti Region?
With Expedia's user-friendly filter tool, scoring cheap villas in Chianti Region has never been easier. To find stays that won't break the bank, fine-tune your search by star rating, budget and amenities.
What is there to do near my villa in Chianti Region?
Whether you love food, shopping, history or sightseeing, Chianti Region offers something for everyone! The major city of San Gimignano boasts lots of things to do, including Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery, Historical Torture Museum and Ornithological Museum. If you're headed to Radda in Chianti, Castello di Albola, Castello di Radda Winery and Borgo di Vescine - Tenute di Castelvecchi shouldn't be missed.

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