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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 €135
includes taxes & fees
27 Oct - 28 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 €456
includes taxes & fees
26 Oct - 27 Oct
Villa Il Signorino
An outdoor dining area with tables and chairs, surrounded by greenery and a view of trees and hills.

3. Villa with Pool - Two Bedrooms

Villa with Pool - Two Bedrooms
Rignano sull'Arno (Florence)
The price is €185
includes taxes & fees
26 Oct - 27 Oct
Villa with Pool - Two Bedrooms
A modern house with a swimming pool, outdoor seating, and a view of mountains.

4. 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 €706
includes taxes & fees
2 Nov - 3 Nov
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
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.

5. 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 €313
includes taxes & fees
15 Nov - 16 Nov
Villa with Pool - 3 Bedrooms, each with a private bathroom
A stone building with a large arched entrance, potted plants, and outdoor seating.

6. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 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 €966
includes taxes & fees
1 Nov - 2 Nov
Exclusive Estate | Personal Concierge & Heated Pool
A modern outdoor space with a rectangular pool, a wooden bench, and a well-maintained lawn.

7. 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 €1,037
includes taxes & fees
2 Nov - 3 Nov
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

8. 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 €1,554
includes taxes & fees
3 Nov - 4 Nov
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

9. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is €13,027
includes taxes & fees
27 Oct - 28 Oct
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

10. Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~

Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (4 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 €393
includes taxes & fees
28 Oct - 29 Oct
Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
Exterior

11. 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 €399
includes taxes & fees
26 Oct - 27 Oct
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
A stone building with a swimming pool, wooden deck, and a tall tree.

12. 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 €1,078
includes taxes & fees
2 Nov - 3 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

13. 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 €473
includes taxes & fees
26 Oct - 27 Oct
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

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 €1,954
includes taxes & fees
2 Nov - 3 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Pool

15. Villa Sunset, in the heart of Chianti area

Villa Sunset, in the heart of Chianti area
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 area
A villa with a swimming pool, surrounded by lush greenery and vineyards.

16. 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 €5,404
includes taxes & fees
26 Oct - 27 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
An outdoor seating area with a sofa, chairs, and a table, surrounded by greenery and a stone wall.

17. Florence Apartments - Villa Fonte Morgana with Pool

Florence Apartments - 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.
Florence Apartments - Villa Fonte Morgana with Pool
A building with a large entrance, potted plants, and a statue in the foreground.

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 €1,622
includes taxes & fees
1 Nov - 2 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

19. 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 €5,189
includes taxes & fees
26 Oct - 27 Oct
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
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

Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti

10/10 Excellent
"Staff was super helpful and attentive. Beautiful stay"
Elsa 4-night trip
Posted 1 day ago
Salvadonica - Borgo del Chianti

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
178
Accommodation
529 Villas
Lowest Price
€135
Highest Price
€13,027

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between €135 and €13,027 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 529 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 holiday 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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