Chianti Region Vacation Homes from ￥10,547

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Our top choices for Chianti Region vacation homes

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

1. 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

￥26,900 total

includes taxes & fees

Nov 13 - Nov 14

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

2. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

￥23,021 total

includes taxes & fees

Nov 12 - Nov 13

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

￥22,513 total

includes taxes & fees

Nov 17 - Nov 18

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

4. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

￥30,667 total

includes taxes & fees

Nov 14 - Nov 15

A garden with various plants and flowers, a pathway, and a swing set.

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

Toscana

Robert M.

￥23,789 total

includes taxes & fees

Nov 12 - Nov 13

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

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.

￥57,078 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a tiled backsplash, a dining area with a table and chairs, and a staircase with a plant shelf.

7. A cozy little house

Loro Ciuffenna

￥14,536 total

includes taxes & fees

Dec 1 - Dec 2

A room with a view of a vineyard through an arched window, a bottle of wine, and a plate of fruit.

8. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

Tavarnelle Val di Pesa

￥40,947 total

includes taxes & fees

Nov 29 - Nov 30

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

9. Casa Marisa in Castellina in Chianti

Castellina in Chianti

￥47,860 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

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

Figline Valdarno

￥20,119 total

includes taxes & fees

Nov 17 - Nov 18

An outdoor patio with a table, chairs, a grill, and a large umbrella.

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

Tavarnelle Val di Pesa

Ramona S.

￥49,766 total

includes taxes & fees

Nov 12 - Nov 13

A wooden table with two wine glasses and a bottle of wine, set outdoors with a view of greenery and hills.

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

Rignano sull'Arno

Anonymous traveler

￥32,262 total

includes taxes & fees

Dec 1 - Dec 2

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

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

Impruneta

￥27,476 total

includes taxes & fees

Nov 16 - Nov 17

A stone building with a tiled roof, a small window, and a door.

14. Mhateria Relais

Rignano Sull' Arno

Thomas K.

￥47,063 total

includes taxes & fees

Nov 13 - Nov 14

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

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

Impruneta

￥30,773 total

includes taxes & fees

Dec 1 - Dec 2

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

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

Montespertoli

￥49,492 total

includes taxes & fees

Nov 12 - Nov 13

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

17. 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.

￥71,436 total

includes taxes & fees

Nov 29 - Nov 30

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

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

San Gimignano

Anne-Marie M.

￥86,203 total

includes taxes & fees

Nov 15 - Nov 16

A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

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

Montevarchi

￥59,205 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with white cabinets, a wooden dining table, and a built-in oven.

20. Casa San Martino between Florence and Siena with Pool

Tavarnelle Val di Pesa

"Pros: Wat hebben we een heerlijke tijd gehad in dit prachtige vakantiehuis in Barberino Tavarnelle! De ligging is fantastisch: rustig, sfeervol en helemaal ondergedompeld in de mooie Toscaanse omgeving. Het huis is comfortabel en van alles voorzien wat je nodig hebt voor een ontspannen verblijf. Met name de airco tijdens warme dagen was erg fijn. Een extra groot compliment voor Susanna. Ze is ontzettend gastvrij, vriendelijk en betrokken, en denkt echt met je mee. Ze was bovendien heel...

Anonymous traveler

￥143,228 total

includes taxes & fees

Nov 23 - Nov 24

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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 pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

Casa Vacanze Le Case

San Gimignano

10/10 Excellent

Andrew

A terrace with a table set for breakfast, a chair, and a large umbrella.

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

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

2. Agriturismo La Ferrozzola

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

4. Chianti Craft House Badia a Passignano

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

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

7. A cozy little house

8. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

9. Casa Marisa in Castellina in Chianti

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

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

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

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

14. Mhateria Relais

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

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

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

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

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

20. Casa San Martino between Florence and Siena with Pool

Learn more about Chianti Region

Top reviews in Chianti Region

Agriturismo La Ferrozzola

10/10 Excellent

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