Chianti Region Vacation Homes from ￥10,475

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Our top choices for Chianti Region vacation homes

A stone building with a tiled roof, surrounded by greenery and a large terracotta pot.

1. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

￥22,863 total

includes taxes & fees

Nov 16 - Nov 17

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

2. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

￥26,715 total

includes taxes & fees

Nov 16 - Nov 17

An outdoor patio with a table, chairs, and a view of a landscape.

3. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

Toscana

Kim

￥24,260 total

includes taxes & fees

Nov 16 - Nov 17

A swimming pool with clear blue water, surrounded by trees and a wooden deck.

4. Apartment House with garden Tuscany Chianti , Florence 15km.

Toscana

Robert M.

￥25,527 total

includes taxes & fees

Nov 21 - Nov 22

A view through a wooden door of a courtyard with stone walls and potted plants.

5. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

￥29,400 total

includes taxes & fees

Nov 17 - Nov 18

6. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

￥56,687 total

includes taxes & fees

Nov 16 - Nov 17

A rustic stone building with a large arched doorway, surrounded by lush greenery and a cobblestone path.

7. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

Tavarnelle Val di Pesa

￥31,020 total

includes taxes & fees

Nov 16 - Nov 17

A bedroom with a bed, bedside tables, a dresser, and wall art.

8. A cozy little house

Loro Ciuffenna

￥14,436 total

includes taxes & fees

Dec 1 - Dec 2

A room with stone walls, a grey sofa, a black chair, a radiator, and a view of an outdoor patio.

9. Casa FILI Cozy Tuscany House

San Vincenzo A Torri

Anonymous traveler

￥23,414 total

includes taxes & fees

Nov 16 - Nov 17

A brick building with a garden, a metal fence, and a clear sky.

10. Casa Marisa in Castellina in Chianti

Castellina in Chianti

￥47,532 total

includes taxes & fees

Nov 17 - Nov 18

A patio with a stone barbecue grill, a table with a black bowl, and a tree providing shade.

11. Holiday Home 'Il Piccolo Rifugio' with Pool, Garden and Wi-Fi

Figline Valdarno

￥19,981 total

includes taxes & fees

Nov 17 - Nov 18

A rectangular swimming pool with a metal fence, surrounded by trees and a clear sky.

12. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

Tavarnelle Val di Pesa

Ramona S.

￥49,425 total

includes taxes & fees

Nov 16 - Nov 17

A rural property with a gravel path leading to a building marked 'FELCIOLIANA.'

13. Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence

Rignano sull'Arno

Anonymous traveler

￥32,040 total

includes taxes & fees

Dec 1 - Dec 2

A stone building with a tiled roof, a swimming pool, and a garden with various plants.

14. Mhateria Relais

Rignano Sull' Arno

Thomas K.

￥44,980 total

includes taxes & fees

Nov 17 - Nov 18

An aerial view of a traditional villa with multiple buildings, surrounded by lush greenery and trees.

15. Nice apartment for 6 people with pool, WIFI, A/C, TV, balcony and pets allowed, close to Florence

Impruneta

￥30,562 total

includes taxes & fees

Dec 1 - Dec 2

A living room with a TV, a sofa, and a dining area with chairs.

16. House with a separate entrance on the outskirts of Florence and Chianti

Impruneta

￥27,287 total

includes taxes & fees

Nov 16 - Nov 17

A house with a tiled roof, surrounded by a garden and trees, with a view of distant hills.

17. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Montevarchi

￥58,800 total

includes taxes & fees

Nov 16 - Nov 17

A garden pathway leading to a stone building with a brick wall, a pergola, and a small brick structure in the background.

18. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...

Marianne H.

￥70,947 total

includes taxes & fees

Nov 29 - Nov 30

A stone building with a covered outdoor seating area and a brick pathway.

19. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

San Gimignano

Anne-Marie M.

￥85,612 total

includes taxes & fees

Nov 16 - Nov 17

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

20. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

￥49,152 total

includes taxes & fees

Nov 16 - Nov 17

View all properties

Learn more about Chianti Region

Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages.

See all hotels in Chianti Region

Terraced vineyards on a hillside, a small village, and rolling green hills.

Top reviews in Chianti Region

Agriturismo La Ferrozzola

Castellina in Chianti

10/10 Excellent

Kai

A large, multi-story building surrounded by lush greenery and trees.

Villa La Stella - Casa per Ferie

Le Cure

10/10 Excellent

Unique property up in the hills. Glad I stayed here. After arrivingin Florence by train, I found a news stand across the street and purchased some bus tickets for 1.50 Euros (A pack of 10 for 14 Euros). Found the stop for bus #7 and was on my way.A scenic 20 minute ride left me at the base of the hotel. The next 50 uphill meters were a struggle, hauling 50 pounds of luggage in the midday heat, but it was worth it. Arrived at a beautiful property in a scenic setting. The staff was very polite and...

Javier

A stone building with a pool and outdoor seating, surrounded by greenery and a view of distant mountains.

Casa Vacanze Le Case

San Gimignano

10/10 Excellent

Andrew

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San Gimignano Vacations
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Car rental Greve in Chianti
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Search Vacation Homes in Chianti Region

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Chianti Region vacation homes

1. Agriturismo La Ferrozzola

2. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

3. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

4. Apartment House with garden Tuscany Chianti , Florence 15km.

5. Chianti Craft House Badia a Passignano

6. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

7. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

8. A cozy little house

9. Casa FILI Cozy Tuscany House

10. Casa Marisa in Castellina in Chianti

11. Holiday Home 'Il Piccolo Rifugio' with Pool, Garden and Wi-Fi

12. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

13. Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence

14. Mhateria Relais

15. Nice apartment for 6 people with pool, WIFI, A/C, TV, balcony and pets allowed, close to Florence

16. House with a separate entrance on the outskirts of Florence and Chianti

17. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

18. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

19. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

20. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Learn more about Chianti Region

Top reviews in Chianti Region

Agriturismo La Ferrozzola

10/10 Excellent

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