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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chianti Region villas

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

1. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is NZ$263
includes taxes & fees
1 Oct - 2 Oct
Rooster House, cooking classes and opera
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

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$895
includes taxes & fees
1 Oct - 2 Oct
Villa Il Signorino
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

3. 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$765
includes taxes & fees
6 Oct - 7 Oct
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
An outdoor dining area with tables and chairs, surrounded by greenery and a view of trees and hills.

4. Villa with Pool - Two Bedrooms

Villa with Pool - Two Bedrooms
Rignano sull'Arno (Florence)
The price is NZ$407
includes taxes & fees
18 Oct - 19 Oct
Villa with Pool - Two Bedrooms
Exterior

5. 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$801
includes taxes & fees
18 Oct - 19 Oct
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Exterior

6. 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$949
includes taxes & fees
16 Oct - 17 Oct
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

7. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
Pool

8. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
Greve in Chianti
8.0 out of 10, Very good, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

9. 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 NZ$2,938
includes taxes & fees
6 Oct - 7 Oct
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Pool

10. 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$1,334
includes taxes & fees
21 Oct - 22 Oct
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
An outdoor patio with a stone wall, a wooden table, chairs, and a large umbrella. There are potted plants with red flowers and tall trees in the background.

11. Villa with Pool - 3 Bedrooms with independent bathroom

Villa with Pool - 3 Bedrooms with independent bathroom
Rignano sull'Arno
The price is NZ$662
includes taxes & fees
18 Oct - 19 Oct
Villa with Pool - 3 Bedrooms with independent bathroom
A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

12. Villa with Florence Pool / Breakfast, Quitedian housekeeping, AirCon whirlpool

Villa with Florence Pool / Breakfast, Quitedian housekeeping, AirCon whirlpool
Rignano sull'Arno
The price is NZ$9,940
includes taxes & fees
1 Oct - 2 Oct
Villa with Florence Pool / Breakfast, Quitedian housekeeping, AirCon whirlpool
A stone building with a swimming pool, wooden deck, and a tall tree.

13. 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$3,608
includes taxes & fees
4 Oct - 5 Oct
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A villa with a swimming pool, surrounded by lush greenery and vineyards.

14. 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 NZ$12,049
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A swimming pool with blue lounge chairs and umbrellas, surrounded by greenery and a view of distant hills.

15. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is NZ$11,084
includes taxes & fees
12 Oct - 13 Oct
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Bathroom

16. 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 NZ$1,150
includes taxes & fees
26 Oct - 27 Oct
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
A stone building with a large arched entrance, potted plants, and outdoor seating.

17. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 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$2,182
includes taxes & fees
26 Oct - 27 Oct
Exclusive Estate | Personal Concierge & Heated Pool
An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

18. 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$2,300
includes taxes & fees
6 Oct - 7 Oct
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
A covered balcony with a brick railing, a bench, and a view of lush greenery.

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 NZ$1,170
includes taxes & fees
1 Oct - 2 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is NZ$26,143
includes taxes & fees
1 Oct - 2 Oct
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
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

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"We had a lovely night stay at this villa in September. It is a 900 year-old hunting lodge that has been converted to spacious rooms many with balconies. The views are incredible, the rooms have been renovated with character fixtures, but includes excellent air-conditioning. The view from the pool was out of a storybook. Staff was attentive and very nice to deal with. The grounds have endless opportunities for photos at every turn. Try to explore the grounds a little - including the painters studio with is exquisite. It has only been open four months so there are a few bugs but overall, the stay was excellent. The one area they need to improve however is the food. The selections are pretty limited and the quality was not to the standard of the property. My recommendation is have the breakfast on site and lunch by the pool, but try the surrounding towns for dinner. Castellini in Chianti is a small town 15 minutes away with great choices. One Belvedere and their sister property Locanda are both within 2 kms and have high end dining. Overall I highly recommend this villa for a unique Tuscan experience."
Peter 2-night trip
Posted 14 hours ago
Fattoria di Vegi

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
135
Accommodation
477 Villas
Lowest Price
NZ$263
Highest Price
NZ$26,143

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between NZ$263 and NZ$26,143 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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