List your home
Apply filters
£ to

Holiday homes 26

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Siena Clear
  • Castellina In Chianti Clear

Location

  • All locations

more +

less -

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties

Filters applied: Villa (26)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
26 Results   |  

Excellent 5/5 

24 Photos

Province of Siena / Castellina In Chianti

Villa / 7 Bedrooms / sleeps 14

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £388 / night

£2713 - £3274 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Sleeps 14 with possibility to add adjacent apartments up to total of 33. A beautiful 15th-century villa in the heart of the Chianti countryside, with 360° uninterrupted views of olives, vines and forests, with amazing sunset views over San Gimignano and the Apennine  …see more


23 Oct 2014

5/5

"Peaceful, Beautiful, Great hospitality"

Our hosts, Simon and Verity, were marvels of hosting. They made sure we were comfortable and knew the ins and outs. They were hospitable without being intrusive. A true skill. The accommodations w… More

See all reviews Continue

11 Photos

Province of Siena / Castellina In Chianti

Villa / 4 Bedrooms / sleeps 7

3 Nights min stay

Add to shortlist

from £147 / night

£1029 - £1774 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • No pets allowed
Il Torrino is a wonderful 4 bedroom villa set within a small and perfectly kept Tuscan medieval village and situated atop a hill with stunning views over the Chianti vineyards. Once a Medieval watch tower, the property oozes character and charm, but has been completely  …see more

22 Photos

Province of Siena / Castellina In Chianti

Villa / 6 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £476 / night

£3327 - £5114 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Enchanting typical Villa located in the very heart of Chianti between Siena and Firenze.  …see more

Featured properties

28 Photos

Province of Siena / Castellina In Chianti

Villa / 4 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £83 / night

£579 - £1171 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
Beautiful stone Tuscan hamlet dating back to the 16th century comprising 8 accommodations and nestling deep among the splendid Chianti Classico vineyards  …see more

Excellent 5/5 

24 Photos

Province of Siena / Castellina In Chianti

Villa / 3 Bedrooms / sleeps 7

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £139 / night

£969 - £1137 / week

View

Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
The Cypresses Villa is a real amazing place, peaceful, green, sunny, a great place for families and also for a small group of friends.There is a large list of sites to visit around, it is a perfect spot in between Sienna and Florence, an ideal postcard of Tuscany.  …see more


13 Mar 2015

5/5

"Charming staying and great location"

Cypresses Villa was the perfect house to stay for us, my wife and I had peaceful and relaxing time sitting outside, drinking a wine and reading, while the kids had great time in the fields, it was eve… More

See all reviews Continue

11 Photos

Province of Siena / Castellina In Chianti

Villa / 3 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £125 / night

£869 - £1135 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Quiet, nature and a 365° view of vineyards, olive groves and the valley. Unique location, only 5 min by car from the lovely village of Castellina in Chianti. Livingroom with fireplace, modern kitchen, study, two bathrooms, three bedrooms, sleeps 6 plus max 2 children.  …see more

Excellent 5/5 

30 Photos

Province of Siena / Castellina In Chianti

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £493 / night

£3446 - £6046 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This beautiful property belongs to the Campalli estate, a huge farm of 750 acres that produces Chianti Classico wine and includes the Castle of Campalli. La Corte di Campalli is an impressive stone-built farmhouse that dates back to the 16th century. It takes its name f  …see more


22 Aug 2014

5/5

"Wonderful Tuscan Villa"

La Corte di Campalli is a superb Tuscan villa on a working farm south of Castellina in Chianti. Simonetta and Ricardo are wonderful hosts, with the highlight of our week being the personal tour of th… More

See all reviews Continue

22 Photos

Province of Siena / Castellina In Chianti

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £472 / night

£3298 / week

View

Key info:

  • Nearest beach 193 km
  • Swimming pool
  • Not suitable for children
  • Car essential
  • Pets welcome
Everything about this property is classically Tuscan. If you dream of typical Tuscany as breathtaking panoramas, misty hills covered in precision lines of vineyards, olive groves, gravel roads and driveways shadily lined with pointy cypress trees, and grand villas with  …see more

30 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £228 / night

£1594 - £3476 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Santantimo Villa for rent with swimming pool in Castellina in Chianti  …see more

24 Photos

Province of Siena / Castellina In Chianti

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £472 / night

£3298 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Just 4 km from Castellina in Chianti Villa Rosa boasts unique views over the Chianti countryside from its romantic terrace and from whole of the villa. The classically furnished interior complete the picture.  …see more

16 Photos

Province of Siena / Castellina In Chianti

Villa / 4 Bedrooms / sleeps 8

2 Nights min stay

Add to shortlist

from £251 / night

£1752 - £3130 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
This beautiful, detached stone farmhouse, situated near Castellina in Chianti, was restored in 1995. Surrounded by ample private grounds, it sits in a panoramic position and is reached by its own driveway  …see more

16 Photos

Province of Siena / Castellina In Chianti

Villa / 6 Bedrooms / sleeps 11

2 Nights min stay

Add to shortlist

from £427 / night

£2987 - £4706 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Food and wine-lovers wanting a memorable holiday in Tuscany shouldn't look any further than Villa Fermini. This beautiful farmhouse lies at the centre of an agricultural estate that produces excellent Chianti Classico wines and extra virgin olive oil.  …see more

Excellent 5/5 

24 Photos

Province of Siena / Castellina In Chianti

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £195 / night

£1362 - £2270 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Casanovina is situated only a few kilometres from the town of Castellina in Chianti. The villa is set in a great location on a hillside overlooking the surrounding Chianti countryside. There are four bedrooms in total - two in the main house and two in the annexe.  …see more


31 Jan 2015

5/5

"Ideal family base for relaxation, exploration, and wine tasting"

We had a lovely week in Casanovina - a really relaxing time enjoying the spectacular views, wine and food! Booking and service prior to going was great, as were our hosts over there, who live in the … More

See all reviews Continue

Excellent 5/5 

22 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 9

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £269 / night

£1880 - £3398 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casale Cipressi is an exclusive Tuscan country house 2.7km from Castellina in Chianti furnished to a high standard and consists of two floors. Stone built with traditional terracotta tiled floors and chestnut wooden beams gracing the old style ceilings.  …see more


2 Jul 2014

5/5

"Beautiful Tuscan Villa in the heart of Chianti - A winner!"

We booked this villa to accommodate 2 familys - 9 of us in total. We loved our week in Tuscany and it was the perfect base for all that we wanted to see in and around the Chianti region. The views we… More


22 Jan 2012

5/5

"Heaven...this is the place I want to come to to die!!"

We were reallocated to this wonderful place at very short notice by 'To Tuscany' when the place we had booked had a small fire...divine intervention? This was the most magnificent place we have eve… More

See all reviews Continue

30 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £228 / night

£1594 - £3476 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Pets welcome
The villa in Chianti (400 m2) was built in the early 16th century as an ancient oratory. In 1876 it underwent its first transformation into a farmhouse and only today, thanks to a skilful restoration project that brought the structure back to its original beauty, a coun  …see more

Excellent 5/5 

12 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

Min stay varies

Add to shortlist

from £249 / night

£1738 - £2696 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Beautiful independent restored villa (400 sqm) sleeping 10 with private pool, astro turf tennis court, gardens. Located in panoramic position on a Chianti Hillside only 5km from Castellini in Chianti. The property is surrounded by a well-maintained large garden.  …see more


2 Mar 2014

5/5

"Fabulous Villa Masseto"

My family and I spent a week in the fabulous Villa Masseto in Tuscany. We had a dream week in this house which is very big and yet cosy and warm. Decorated with great taste and all the comfort you n… More

See all reviews Continue

Very Good 4/5 

49 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 10

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £233 / night

£1626 - £1877 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This grand house, with 5 bedrooms and 5 bathrooms can host 10 people, so it is ideal for large families. Located in Tuscany Italy, this house offers a swimming Pool, an internet Connection .  …see more


31 May 2015

4/5

"Séjour reposant au coeur du Chianti"

Nous avons aimé le cadre magnifique de cette grande et ancienne propriété en plein coeur du Chianti. De beaux volumes, un salon confortable, une cuisine à disposition pour y prendre nos repas froi… More

See all reviews Continue

Excellent 5/5 

46 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 9

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £486 / night

£3401 - £4940 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Nestled within the hills and woods of the Chianti Classico, this beautiful villa rental is the ideal place to spend a relaxing holiday. There is an extremely large garden with a private swimming pool and a covered terrace with a table and chairs where you and your famil  …see more


22 Oct 2011

5/5

"John's review of Villa Consorzio"

Our stay at Villa Consorzio was outstanding! From the morning we were greeted by Maria, to the day we left, our experiences were awesome! Hard to rank the the amenities and experiences of the Villa -… More

See all reviews Continue

23 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £236 / night

£1652 - £3450 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Situated in a small hamlet around the Castellina region this villa looks out over the heart of the Chianti countryside. An elegant villa completely restored and renovated from an ancient farmhouse set in a private garden with swimming pool and stunning views overlookin  …see more

45 Photos

Province of Siena / Castellina In Chianti

Villa / 8 Bedrooms / sleeps 16

7 Nights min stay

Add to shortlist

from £322 / night

£2254 - £3073 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
elegant house sleeps 16 people, so it is perfect for a large group of friends and is located in Tuscany Italy. This property is ideal if you seek a relaxing holiday. The villa features: a swimming Pool, air Conditioning, an internet Connection .  …see more

12 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £262 / night

£1834 - £3444 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa in Castellina In Chianti with 5 bedrooms sleeps 12  …see more

44 Photos

Province of Siena / Castellina In Chianti

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £377 / night

£2634 - £3830 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This luxury villa for 8 in beautiful Chianti is ideally located between Florence and Siena. It is a truly stunning property set in peaceful grounds including a swimming pool, gardens and olive grove. Inside it is just attractive featuring 4 large en  …see more

48 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £286 / night

£1996 - £2895 / week

View

Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This extraordinary villa welcomes up to 12 people in its ample common areas and bedrooms, and it has a wonderful garden and swimming pool. It is ideal for large families or groups of friends.  …see more

24 Photos

Province of Siena / Castellina In Chianti

Villa / 8 Bedrooms / sleeps 16

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
elegant house sleeps 16 people, so it is ideal for a large group of friends to enjoy an unforgettable trip to Chianti. The villa offers a swimming pool and an internet Connection.  …see more

25 Photos

Province of Siena / Castellina In Chianti

Villa / 2 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £132 / night

£922 - £1383 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This elegant house, with 2 bedrooms and 3 bathrooms can accomodate 6 people, so it is perfect for a large group of friends. Located in Tuscany Italy, this house offers a swimming Pool, air Conditioning .  …see more

48 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £380 / night

£2660 - £3869 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Located in Tuscany Italy, this gorgeous accommodation is the perfect place for your holidays. The accommodation features: a swimming Pool, air Conditioning .  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page