Search Villas in Chianti Region

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chianti Region villas

Villa in Figline Valdarno

Tuscany Garden Villa
10.0 out of 10, Exceptional, (2)
"Rymligt hus med bra toaletter! Väl utrustat kök. Saknade dock ac i ett av sovrummen"
Sweden
Gertrud R.
The price is ¥64,261
¥92,352 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Tuscany Garden Villa
10.0 out of 10, Exceptional, (3)
"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."
United States
Lidija M.
The price is ¥63,820
¥82,364 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
The price is ¥1,092,433
¥1,184,234 total
includes taxes & fees
Jan 2 - Jan 3, 2026
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
10.0 out of 10, Exceptional, (1)
"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 ¥322,424
¥439,687 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
7.0 out of 10, Good, (2)
"We arrived after dark, tired from long overnight flight. We had no water pressure upstairs and no hot water anywhere. This was corrected the next day. One on-suite toilette would not flush properly and leaked at the grinder motor. A "tech" was called in. He informed us that he could not fix it, they would need to call someone else. When we continued to report the issue to the host, she informed us that the "tech" said it was working OK. The "tech" informed us that it was not but he could not fix...
United States
Norman C.
The price is ¥532,000
¥633,507 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
10.0 out of 10, Exceptional, (1)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is ¥297,435
¥297,802 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
10.0 out of 10, Exceptional, (8)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
The price is ¥190,854
¥195,260 total
includes taxes & fees
Jan 8 - Jan 9, 2026
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Villa in Castellina in Chianti

Viniard Villa - Residence Le Rose in Chianti
The price is ¥58,753
¥120,700 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Viniard Villa - Residence Le Rose in Chianti
10.0 out of 10, Exceptional, (106)
"The Villa and grounds are absolutely beautiful! Caterina and her family members were the most gracious hosts. They could not do enough to make sure we had a "once in a lifetime" multi-generational family trip and truly made us feel like part of their family during our stay. We loved every second of our time in Tuscany and would highly recommend this amazing property."
United States
Charles S.
The price is ¥148,259
¥170,107 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Welcome home: Villa with concierge service and heated pool 20 minute to Florence
10.0 out of 10, Exceptional, (6)
"Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation"
United States
Frank V.
The price is ¥118,974
¥219,772 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Beautiful Tuscan home between Florence & Siena
10.0 out of 10, Exceptional, (12)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
The price is ¥235,011
¥269,161 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
United States
Ed M.
The price is ¥238,683
¥273,383 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
The price is ¥2,166,505
¥2,166,505 total
includes taxes & fees
Dec 31 - Jan 1, 2026
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
The price is ¥863,022
¥954,823 total
includes taxes & fees
Jan 12 - Jan 13, 2026
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
The price is ¥199,500
¥248,760 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
The price is ¥183,419
¥201,595 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
The price is ¥263,065
¥281,241 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Villa Torre Among the Hills of Siena
The price is ¥263,065
¥281,241 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Villa Capanna: A Window onto Tuscany

Villa in Foiano della Chiana

Artisti del Cavallo Tourism
8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
The price is ¥12,646
¥14,278 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Artisti del Cavallo Tourism

Villa in Sinalunga

Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (59)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is ¥27,248
¥30,920 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Il Poggio dell'Eremita
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chianti Region Hotel Reviews

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
222
Accommodation
566 Villas
Lowest Price
¥14,278
Highest Price
¥1,184,234

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between ¥14,278 and ¥1,184,234 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 566 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.

Explore a world of travel with Expedia