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Our top choices for Chianti Region villas

1. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is ¥19,365
¥21,830 total
includes taxes & fees
Nov 22 - Nov 23
Rooster House, Cooking Classes, and Opera

2. Villa with Pool - 3 Bedrooms, each with a private bathroom

Villa with Pool - 3 Bedrooms, each with a private bathroom
Rignano sull'Arno
The price is ¥46,212
¥52,594 total
includes taxes & fees
Nov 22 - Nov 23
Villa with Pool - 3 Bedrooms, each with a private bathroom

3. Villa with Pool - Two Bedrooms

Villa with Pool - Two Bedrooms
Rignano sull'Arno (Florence)
The price is ¥26,407
¥32,569 total
includes taxes & fees
Nov 18 - Nov 19
Villa with Pool - Two Bedrooms

4. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
impruneta
10.0 out of 10, Exceptional, (117 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is ¥197,853
¥223,822 total
includes taxes & fees
Nov 18 - Nov 19
Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

5. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is ¥2,492,828
¥2,492,828 total
includes taxes & fees
Dec 15 - Dec 16
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

6. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
Vaggio
The price is ¥208,594
¥209,124 total
includes taxes & fees
Nov 17 - Nov 18
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

7. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is ¥953,934
¥954,641 total
includes taxes & fees
Nov 15 - Nov 16
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

8. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
Rignano sull'Arno
The price is ¥508,765
¥838,226 total
includes taxes & fees
Nov 15 - Nov 16
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

9. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
Vaggio
The price is ¥107,406
¥107,936 total
includes taxes & fees
Nov 16 - Nov 17
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

10. Villa in historic residence with swimming pool near Florence and Chianti

Villa in historic residence with swimming pool near Florence and Chianti
Figline Valdarno
The price is ¥167,822
¥240,957 total
includes taxes & fees
Nov 18 - Nov 19
Villa in historic residence with swimming pool near Florence and Chianti

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

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
7.4 out of 10, Good, (3 reviews)
"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...
United States
JIm B.
The price is ¥105,477
¥190,426 total
includes taxes & fees
Nov 16 - Nov 17
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

12. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is ¥223,857
¥262,898 total
includes taxes & fees
Nov 15 - Nov 16
Villa Torre Among the Hills of Siena

13. VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16

VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16
Firenze
The price is ¥375,214
¥375,214 total
includes taxes & fees
Nov 15 - Nov 16
VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16

14. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is ¥228,861
¥246,994 total
includes taxes & fees
Dec 15 - Dec 16
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

15. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is ¥223,857
¥262,898 total
includes taxes & fees
Nov 15 - Nov 16
Villa Capanna: A Window onto Tuscany

16. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is ¥269,352
¥273,577 total
includes taxes & fees
Nov 17 - Nov 18
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

17. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is ¥2,077,357
¥2,077,357 total
includes taxes & fees
Nov 29 - Nov 30
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

18. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"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 ¥286,180
¥286,533 total
includes taxes & fees
Nov 15 - Nov 16
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

19. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is ¥183,175
¥204,646 total
includes taxes & fees
Nov 17 - Nov 18
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

20. Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Rignano sull'Arno
7.0 out of 10, Good, (2 reviews)
"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 ¥257,631
¥354,961 total
includes taxes & fees
Nov 18 - Nov 19
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
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

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
175
Accommodation
541 Villas
Lowest Price
¥21,830
Highest Price
¥2,492,828

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between ¥21,830 and ¥2,492,828 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 541 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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