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408 Results  |  
16 Photos

Apartment / 2 Bedrooms / sleeps 6

3 Nights min stay

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from £108 / night

£752 - £1099 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Beautiful country house set in the heart of the Tuscan countryside  …see more

12 Photos

Villa / 6 Bedrooms / sleeps 12

2 Nights min stay

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from £1222 / night

£8553 - £10922 / week

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Key info:

  • Nearest beach 91 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Villa Chianti is everything you'd want a luxury villa in Italy. Set on a hill overlooking the Chianti landscape, it's a beautifully restored country house (the result, in fact, of a loving restoration that combines an ancient farmhouse and the main Villa).  …see more

23 Photos

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

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from £199 / night

£1387 - £2628 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano.  …see more

Featured properties

20 Photos

Apartment / 3 Bedrooms / sleeps 8

7 Nights min stay

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from £353 / night

£2470 - £3250 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Calpurnia is a charming two-story historical villa situated in the heart of the Tuscan countryside. It sleeps eight people. From Villa Calpurnia you will enjoy a spellbinding view of the Chianti hills and of the vineyards  …see more

11 Photos

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £84 / night

£584 - £701 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casale Oliveta is located in a little hamlet with a few houses up in the hills.  …see more

20 Photos

House / 2 Bedrooms / sleeps 4

5 Nights min stay

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from £182 / night

£1270 - £1550 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Emide D is a graceful apartment in a history-rich eighteenth-century estate. It sleeps four people. From Casa Emide D you will enjoy a marvelous view of the greenery. Casa Emide D is 80 square meters (860 square feet)  …see more

35 Photos

Apartment / 1 Bedroom / sleeps 4

2 Nights min stay

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from £84 / night

£584 - £876 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This charming country estate is located just 12 km south of Siena in the Val d'Arbia. It is perfect for those looking for an amazing holiday in the heart of the Tuscan countryside.  …see more

20 Photos

Cottage / 2 Bedrooms / sleeps 6

6 Nights min stay

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from £87 / night

£606 - £869 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Casa Porzia is a gracious cottage of 80 square meters (about 860 square feet) for six people, with garden and access to a pool of 7 X 14 meters (23 X 46 feet)  …see more

21 Photos

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

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from £66 / night

£460 - £584 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This property impresses at first sight with its superb location and its wonderful garden.  …see more

12 Photos

Villa / 5 Bedrooms / sleeps 10

Min stay varies

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from £354 / night

£2475 - £3643 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Podere Montepulciano sits on a hill just ten minutes drive away from captivating Renaissance town Pienza.  …see more

19 Photos

Farmhouse / 5 Bedrooms / sleeps 12

7 Nights min stay

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from £1033 / night

£7227 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Exceptional view. Exclusive décor. Published in many international magazines. Air conditioning in some of the bedrooms. Optional extra suite.  …see more

15 Photos

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £104 / night

£723 - £1068 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Apartment for 4 persons, with swimming pool , in Montepulciano  …see more

20 Photos

House / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £600 / night

£4200 - £5600 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Cherubina is a splendid sixteenth-century three-story villa located on top of a small hill. It sleeps 12 people. From Villa Cherubina you will enjoy a wonderful view of the Senesi hills. Villa Cherubina is 500 square meters (5380 square feet)  …see more

20 Photos

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

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from £2014 / night

£14098 - £15701 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car advised
  • Air conditioning
  • No pets allowed
Villa Le Cantine di Cerreto is one of our best villas in Italy for rent. Immersed in the heart of the countryside with beautiful swimming pool, this spectacular villa can comfortably sleep up to 14 people and is ideal for your vacation rental in Italy.  …see more

416 Photos

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £443 / night

£3095 - £4357 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This villa is an elegant 18th century mansion near Siena in the Chianti wine region, perfect for visiting Tuscany and relaxing by the pool during your holidays in Italy. The villa has a vantage position on a hill above the old town of Staggia Senese. From the ...  …see more

17 Photos

Villa / 10 Bedrooms / sleeps 20

7 Nights min stay

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from £407 / night

£2847 - £4365 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Large villa with private pool near Cortona  …see more

20 Photos

Farmhouse / 6 Bedrooms / sleeps 13

7 Nights min stay

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from £404 / night

£2825 - £4738 / week

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Key info:

  • Nearest beach 44 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Wonderful Tuscan villa with pool.  …see more

24 Photos

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £131 / night

£913 - £2738 / week

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Key info:

  • Nearest beach 130 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Demata is the beloved holiday home of a Florentine family with strong American connections as well as a great appreciation for the Tuscan country side and it's pleasures.  …see more

24 Photos

Villa / 8 Bedrooms / sleeps 14

7 Nights min stay

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from £452 / night

£3160 - £5793 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
stunning villa, located in Tuscany Italy, has a max. capacity of 14 people. This stunning villa is perfect for families and friends  …see more

7 Photos

Farmhouse / 1 Bedroom / sleeps 2

3 Nights min stay

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from £78 / night

£543 - £779 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Farmhouse Graziano Stalla is one of 3 independent country homes located on a vast farm estate, where stately cypress trees welcome you to a captivating Tuscan experience.andnbsp;The house is at the medieval town of San Gimignano with its well-known towers, as well as a  …see more

20 Photos

Villa / 1 Bedroom / sleeps 21

7 Nights min stay

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from £384 / night

£2687 - £4157 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Farmhouse divided into apartments set in 10 hectares of private forest and with a large swimming pool. sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

24 Photos

Villa / 11 Bedrooms / sleeps 22

3 Nights min stay

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from £585 / night

£4092 - £5763 / week

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Key info:

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

24 Photos

Villa / 11 Bedrooms / sleeps 22

7 Nights min stay

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from £574 / night

£4015 - £5694 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Originally a country estate dating back to 1795, this superb Leopoldine villa blends outstanding elegance and comfort with traditional rustic features which reflect its long history.  …see more

22 Photos

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

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from £42 / night

£289 - £552 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany. Gaiole is in the Chianti Classico area, ideal to taste and enjoy the best wine and food in Italy.  …see more

24 Photos

Villa / 11 Bedrooms / sleeps 22

7 Nights min stay

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from £730 / night

£5110 - £9344 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Halfway between Siena and Florence in the splendid Tuscan is the Villa Azzurra. The location of the villa is in a strategic position where it is easy to admire the most important Tuscan cities without having to renounce a relaxing and tranquil holiday in the countryside  …see more

24 Photos

Villa / 8 Bedrooms / sleeps 16

7 Nights min stay

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from £663 / night

£4640 - £5850 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden

Centred around a pretty garden, Casa Vittorio is a notable, historic residence set over several levels and elegantly furnished. It is in a village location, just a short stroll from a restaurant, the castle and the truffle museum.

 …see more

24 Photos

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

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from £612 / night

£4280 - £4790 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden

This charming Italian property has been carefully restored by the owner as a fine example of Tuscan rural 18th century style.

 …see more

24 Photos

Villa / 18 Bedrooms / sleeps 35

7 Nights min stay

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from £5103 / night

£35720 - £46140 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden

Total Luxury - Italy special occasion villa with services - this magnificent 14th century estate is situated in the heart of rural Tuscany between San Gimignano and Siena. The villa's hilltop position offers wonderful 360 degree views of the surrounding countryside

 …see more

16 Photos

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £73 / night

£508 - £1092 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Beautiful newly restored two bedroom house with large kitchen, living room, garden and a swimming pool. Incredible unbroken 360 views over the Val D'Orcia valley. Sun-baked stone walls hand made terracotta floors, chestnut beams, pergolas twisted with wisteria. Located in the Val d'Orcia region south of Siena.  …see more

21 Photos

Apartment / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £93 / night

£645 - £845 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
A characteristic apartment in the heart of Tuscany sleeping 6 guests with pool. Ideal to reach Moltacino, Siena and Chianti. 3 double bedrooms, 2 bathrooms, gated parking.  …see more

35 Photos

Apartment / 2 Bedrooms / sleeps 6

3 Nights min stay

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from £73 / night

£511 - £716 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
These apartments are situated in extensive parks including a swimming pool and lake in rural Tuscany. They can accommodate between 2 and 8 guests and are a short distance from famous historical towns such as Montepulciano, Pienza and Montichiello.  …see more

35 Photos

Apartment / 2 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £73 / night

£511 - £716 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
These apartments are situated in extensive parks including a swimming pool and lake in rural Tuscany. They can accommodate between 2 and 8 guests and are a short distance from famous historical towns such as Montepulciano, Pienza and Montichiello.  …see more

36 Photos

Apartment / 3 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £154 / night

£1073 - £1431 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
These apartments are situated in extensive parks including a swimming pool and lake in rural Tuscany. They can accommodate between 2 and 8 guests and are a short distance from famous historical towns such as Montepulciano, Pienza and Montichiello.  …see more

35 Photos

Apartment / 1 Bedroom / sleeps 4

3 Nights min stay

Add to shortlist

from £52 / night

£358 - £511 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
These apartments are situated in extensive parks including a swimming pool and lake in rural Tuscany. They can accommodate between 2 and 8 guests and are a short distance from famous historical towns such as Montepulciano, Pienza and Montichiello.  …see more

36 Photos

Apartment / 1 Bedroom / sleeps 4

3 Nights min stay

Add to shortlist

from £52 / night

£358 - £511 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
These apartments are situated in extensive parks including a swimming pool and lake in rural Tuscany. They can accommodate between 2 and 8 guests and are a short distance from famous historical towns such as Montepulciano, Pienza and Montichiello.  …see more

36 Photos

Apartment / 1 Bedroom / sleeps 4

3 Nights min stay

Add to shortlist

from £52 / night

£358 - £511 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
These apartments are situated in extensive parks including a swimming pool and lake in rural Tuscany. They can accommodate between 2 and 8 guests and are a short distance from famous historical towns such as Montepulciano, Pienza and Montichiello.  …see more

18 Photos

Villa / 1 Bedroom / sleeps 7

Min stay varies

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from £183 / night

£1278 - £1825 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautifully restored villa with swimming pool on the edge of a small hamlet. sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

20 Photos

Farmhouse / 7 Bedrooms / sleeps 14

Min stay varies

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from £626 / night

£4380 - £6278 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Fantastic farmhouse with heated pool. Activities organized and chef, babysitter and driver available.  …see more

20 Photos

House / 5 Bedrooms / sleeps 10

2 Nights min stay

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from £471 / night

£3292 - £5319 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
This beautifully restored 14th century farmhouse sits within a farming estate on a hilltop with magnificent views over the soft hills of the Arbia river valley.  …see more

23 Photos

Villa / 5 Bedrooms / sleeps 10

2 Nights min stay

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from £1158 / night

£8106 - £10316 / week

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Key info:

  • Ask owner if suitable for children
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Born from the careful restoration of an ancient manor, this enchanting property comprises two restored historic farmhouses: the manor's farmhouse and the independent (but equally gorgeous! guest house.  …see more

20 Photos

Villa / 6 Bedrooms / sleeps 12

2 Nights min stay

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from £301 / night

£2106 - £4000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Toiano is a quaint, lovingly decorated property. The stones and the old ceiling beams have been incorporated into a beautifully-finished new country home that oozes personality and charm.  …see more

16 Photos

Villa / 10 Bedrooms / sleeps 20

7 Nights min stay

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from £4813 / night

£33688 - £39875 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Villa Il Casale is an outstanding country villa located in the Chianti just minutes from Siena and nearby Montalcino.  …see more

24 Photos

Villa / 9 Bedrooms / sleeps 14

7 Nights min stay

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from £1508 / night

£10550 - £14675 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden

Large air conditioned villa near Siena - Villa Santa Caterina is an imposing fully restored 13th-century monastery, subsequently used as a farmhouse, which has been transformed into an elegant country holiday house.

 …see more

13 Photos

Villa / 3 Bedrooms / sleeps 6

3 Nights min stay

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from £104 / night

£727 - £1311 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful Three bedroom stone house spread over three floors with the master bedroom on the top floor entered by a spiral staricase. Fully fitted kitchen with fridge freezr, dishwasher, oven and hob with all of the cooking equipment supplied.  …see more

24 Photos

Villa / 7 Bedrooms / sleeps 14

3 Nights min stay

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from £1355 / night

£9480 - £13692 / week

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Key info:

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

24 Photos

Villa / 5 Bedrooms / sleeps 12

7 Nights min stay

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from £133 / night

£928 - £1446 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This is an ample villa sleeping up to 12 people, fully fitted and featuring its own garden and swimming pool. Cities such as Pisa and Florence are nearby, and that makes this large villa a perfect starting point for exploring the entire Tuscan region  …see more

24 Photos

Villa / 14 Bedrooms / sleeps 27

7 Nights min stay

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from £1559 / night

£10913 - £21679 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This exclusive luxury villa nestled in the hills of the Tuscan countryside in the south of the province of Siena offers top-quality accommodation completed by first-class services and panoramic views in a natural biogenetic reserve in the Val di Merse.  …see more

6 Photos

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £76 / night

£529 - £925 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Apartment for 4 persons, with swimming pool , in San Gimignano  …see more

20 Photos

Apartment / 1 Bedroom / sleeps 2

3 Nights min stay

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from £94 / night

£657 - £730 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Leopoldo C is a romantic 65-square-meter (about 700 square feet) apartment which sleeps two people. It features a view to the hills famous as 'Crete Senesi '. There is also a shared swimming pool and shared gardens  …see more

20 Photos

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £68 / night

£475 - £621 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Monia D is a welcoming cottage made of stone. It sleeps four people. From Casa Monia D you will have a pleasant view of the Tuscan hills. Casa Monia D is 50 square meters (540 square feet)  …see more

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