A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region villas

1. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is NZ$257
includes taxes & fees
14 Aug - 15 Aug
Rooster House, cooking classes and opera

2. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is NZ$930
includes taxes & fees
11 Sept - 12 Sept
Villa Il Signorino

3. Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is NZ$1,605
includes taxes & fees
14 Aug - 15 Aug
Villa Marcolina

4. 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 NZ$740
includes taxes & fees
17 Aug - 18 Aug
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

5. 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, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is NZ$2,839
includes taxes & fees
1 Sept - 2 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

6. Pool Villa - Breakfast included

Pool Villa - Breakfast included
Rignano sull'Arno (Florence)
The price is NZ$606
includes taxes & fees
6 Sept - 7 Sept
Pool Villa - Breakfast included

7. 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 NZ$979
includes taxes & fees
8 Sept - 9 Sept
My Exclusive Italy - Classic Suite in a Luxury Wine Estate

8. 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 NZ$1,199
includes taxes & fees
15 Aug - 16 Aug
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

9. "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, (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 NZ$3,001
includes taxes & fees
11 Sept - 12 Sept
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

10. Apartments Florence - Villa Fonte Morgana with pool

Apartments Florence - Villa Fonte Morgana with pool
Impruneta
10.0 out of 10, Exceptional, (1 review)
"What a beautiful villa! We thoroughly enjoyed our stay in Tuscan countryside. All rooms were comfortable and large. We were surprised by the lack of body soap and shampoo."
United States
Christine B.
Apartments Florence - Villa Fonte Morgana with pool

11. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is NZ$2,597
includes taxes & fees
23 Aug - 24 Aug
The San Leonino House

12. 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
8.0 out of 10, Very good, (1 review)
"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"
Italy
Anonymous traveller
The price is NZ$2,325
includes taxes & fees
31 Aug - 1 Sept
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

13. Villa with Pool - 3 Bedrooms with independent bathroom

Villa with Pool - 3 Bedrooms with independent bathroom
Rignano sull'Arno
The price is NZ$1,011
includes taxes & fees
6 Sept - 7 Sept
Villa with Pool - 3 Bedrooms with independent bathroom

14. 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 NZ$1,166
includes taxes & fees
19 Aug - 20 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

15. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is NZ$2,765
includes taxes & fees
26 Aug - 27 Aug
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

16. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is NZ$3,801
includes taxes & fees
30 Aug - 31 Aug
Villa Torre Among the Hills of Siena

17. 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 NZ$6,159
includes taxes & fees
1 Sept - 2 Sept
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

18. 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 NZ$1,650
includes taxes & fees
14 Aug - 15 Aug
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate

19. Exclusive Estate | Heated Pool & Personal Concierge

Exclusive Estate | Heated Pool & Personal Concierge
impruneta
10.0 out of 10, Exceptional, (112 reviews)
"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 NZ$2,927
includes taxes & fees
21 Aug - 22 Aug
Exclusive Estate | Heated Pool & Personal Concierge

20. 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 NZ$4,243
includes taxes & fees
1 Sept - 2 Sept
Villa Milani with Shared Pool, Private Terrace & 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

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
136
Accommodation
477 Villas
Lowest Price
NZ$257
Highest Price
NZ$6,159

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between NZ$257 and NZ$6,159 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 477 villas to choose from. Enter your destination and dates and lock in your perfect trip today.
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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