Air conditioned apartments and villas to rent in Province of Siena

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926 Holiday homes

Filters applied: Air conditioning (929)

(11) Excellent 

21

charming cottage in peaceful country setting - Gracciano cottage sleeps 6

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
The cottage is opposite the owner's house and consists of two double bedrooms, two bathrooms and a large living room with cooking area. The living area opens onto a patio and pergola and the downstairs bedroom also opens onto a small patio. There is access for the disa  …see more

from £69 / night

£380 - £1776 / week

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from £69 / night

(8) Very Good 

5

TuscanFlat - Siena apartment sleeps 4

Province of Siena / Siena

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 105 km
  • Car not necessary
  • Air conditioning
This very stylish 430-square-foot apartment a few minutes walk from Piazza del Campo.You will need to walk up 66 steps to access this apartment, but the effort is amply rewarded by two amazing terraces and their spectacular views. The main living space here is a large,  …see more

from £87 / night

£664 - £966 / week

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from £87 / night

32

Leccetino - Trequanda villa sleeps 6

Province of Siena / Trequanda

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Villa Leccetino Tuscany Arriving at Leccetino, down a short tree covered road is like arriving at a very secret location. Tucked into the hillside surrounded by olive trees, this is a spectacular masonry villa, made with stones dug up from the ground on this terraced p  …see more

from £278 / night

£1940 - £3440 / week

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from £278 / night

(41) Excellent 

19

Stunning farmhouse apartment located between Tuscan cities of San Gimignano and Volterra, shared pool, private garden, sleeps 6 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Azzurra is an apartment in Poderra Torrichi, a gated community of three farm buildings, which is located between the medieval cities of San Gimignano and Volterra. Podera Torrichi is newly renovated and has retained the charm of the traditional Tuscan farm buildings, wi  …see more

from £185 / night

£1000 - £1462 / week

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from £185 / night

(21) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

 …see more

from £48 / night

£289 - £419 / week

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from £48 / night

48

La Grancia Country Resort Apt4 - Montisi fort sleeps 3

Province of Siena / Montisi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
La Grancia Country Resort is a romantic and charming 14th century fortress used as a "Grancia", a granary for the storage of the produce grown on the property. Perched next to the delightful hilltop village of Montisi, it overlooks the surrounding Tuscany coun  …see more

from £107 / night

£739 - £821 / week

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from £107 / night

(4) Very Good 

7

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from £35 / night

£311 - £328 / week

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from £35 / night

(3) Very Good 

17

Province of Siena / Siena

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from £87 / night

£561 / week

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from £87 / night

(3) Excellent 

20

Granaio 7 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 6 people (4+2) in total. The apartment is next to Granaio nr 6 (nr 277512) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San Gimignan  …see more

from £35 / night

£242 - £828 / week

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from £35 / night

20

Cypress Villa (v008) - Pienza farmhouse sleeps 13

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Nearest beach 44 km
  • Swimming pool
  • Child friendly
Ground floor: a large living room with fireplace, small kitchen, a double bedroom with a separate entrance from the outside with an en-suite bathroom with washing machine.First floor: a double bedroom with Jacuzzi inside the room and en-suite bathroom with shower, a dou  …see more

from £355 / night

£2483 - £4423 / week

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from £355 / night

100

Emma - Laghetto - Bagno Vignoni apartment sleeps 4

Province of Siena / Bagno Vignoni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
On the first floor of the barns can be found Laghetto apartment. This apartment includes one double bedroom and a double sofa bed and therefore can accommodate up to four guests. It has a very fresh feel with light rooms and neutral colours. A four-poster bed with drapi  …see more

from £69 / night

£423 - £604 / week

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from £69 / night

(43) Excellent 

21

La Casina Toscana, central with parking and wi-fi - Montepulciano cottage sleeps 5

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 km
  • Child friendly
  • Air conditioning
Placed in the countryside of Montepulciano, near the most important historical towns such as Pienza, Montalcino and Bagno Vignoni, the Casina Toscana is a historical residence of the nineteenth century, which allows guests to enjoy the tranquility and relaxation that th  …see more

from £61 / night

£345 - £604 / week

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from £61 / night

13

Traditional stone-built villa in Tuscan province of Siena with swimming pool, terrace and barbecue - Montisi villa sleeps 6

Province of Siena / Montisi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Three bed stone built home with all the traditional and style of an old tuscan home yet all the modern comforts.Air Conditioning is a must in Tuscany.This property has air conditioning in all rooms and is remotly controlled in each room.Two large bathrooms one with a ba  …see more

from £123 / night

£858 - £1250 / week

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from £123 / night

(4) Excellent 

21

La Chiesina - Casaglia villa sleeps 6

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
The villa was an ancient historical structure going back to before the year 1200, originally the chapel "Santa Maria Church", near the burg of Casaglia. Over the centuries, the chapel was deconsecrated to become, first a watchtower, and then a place where the  …see more

from £130 / night

£863 - £1983 / week

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from £130 / night

(5) Excellent 

23

Pure 5 star Luxury in Tuscany-Jacuzzi-AC-wifi-S - Pienza apartment sleeps 8

Province of Siena / Pienza

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
New lower price - one of the nicest flat in Tuscany 5 star standard !!The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. Private parking, large roof terrace (55m2) with great views over  …see more

from £121 / night

£845 / week

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from £121 / night

(43) Excellent 

25

Lovingly restored stone-built Tuscan barn - San Gimignano house sleeps 4

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
Podere Torricchi is a small collection of beautifully renovated 16th Century farm buildings converted into houses and apartments. Set on a hill the entire site has stunning views of the rolling Tuscan countryside. I'l Granario' is a house set on two floors, tastefully r  …see more

from £90 / night

£625 - £900 / week

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from £90 / night

(8) Excellent 

24

Delightful 2 bedroom farmhouse with beautiful private grounds and pool - Sarteano farmhouse sleeps 5

Province of Siena / Sarteano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Agriturismo Sferracavalli is the best way to enjoy Italian genuine food, which can be gathered in the back garden, and to feel compleatly plunged in peace and relax among Tuscany nature. Medieval villages complete the perfect Tuscany atmosphere all around, so that w  …see more

from £108 / night

£647 - £949 / week

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from £108 / night

20

Villa Olmo - Radicofani villa sleeps 14

Province of Siena / Radicofani

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies in a hilly location with stunning panoramic views of the surrounding hills and mountains, about 8 km from the village of Radicofani. It is an ideal starting point for enjoying the tranquility of the surrounding mountainous landscape and on the other to ma  …see more

from £432 / night

£2069 - £3018 / week

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from £432 / night

(1) Excellent 

29

Province of Siena / Montepulciano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £233 / night

£1207 - £1897 / week

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from £233 / night

(15) Excellent 

22

Casacorvo Minore *Late Booking Discounts* - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships.The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style with sol  …see more

from £85 / night

£525 - £725 / week

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from £85 / night

20

The Spring (v024) - Pienza villa sleeps 12

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below. The house, built in the first half of the eighteenth century, has been renovated carefully by the couple  …see more

from £488 / night

£3414 - £3966 / week

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from £488 / night

4

Self catering large apartment with heated pool - San Fabiano apartment sleeps 5

Monteroni d'Arbia / San Fabiano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Large apartment at the ground floor of the villa.Vaulted ceilings, large rooms, all comforts. Large master bedroom om with king size bed, living room with two beds, large dining and cooking room, bathroom with shower.The area is famous for the Dante Alighieri Divina Com  …see more

from £130 / night

£690 - £1035 / week

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from £130 / night

9

Gaiole Suites 8 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartmen  …see more

from £42 / night

£290 - £483 / week

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from £42 / night

(7) Excellent 

15

Holiday farmhouse apartment rental in Tuscany, property features beautiful garden and private fishing lake - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats inside an old barn that were recently restructured.Both the apartments can accommodate up to 4 people and are composed of a bedroom with bathroom, a small bedroom and a dining room/k  …see more

from £61 / night

£414 - £785 / week

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from £61 / night

55

Province of Siena / Cetona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £104 / night

£604 - £733 / week

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from £104 / night

17

Appartamento Ginestra - Castelnuovo Berardenga apartment sleeps 2

Province of Siena / Castelnuovo Berardenga

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Le Rocche di Valiano is an ancient village situated in the heart of Chianti region near Siena.The structure, completely surrounded by olives groves, enjoys a spectacular view of the typical Tuscany landscape made by sweet hills and of the vast vineyards.The apartment Gi  …see more

from £36 / night

£248 - £507 / week

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from £36 / night

19

Suite Artista: Cannavacciuolo - Montalcino apartment sleeps 3

Province of Siena / Montalcino

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Suite d'Artista is a perfect place to enjoy a relaxing holiday combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming p  …see more

from £125 / night

£875 / week

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from £125 / night

(5) Excellent 

46

Villa Sangimignano - Montauto farmhouse sleeps 5

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The 200 sqm villa is a typical stone barn in an early '900 style, characterized by the tranquility of the Tuscan countryside of San Gimignano in which it is immersed.It can be accessed via a large private and completely fenced garden of 2,000 sqm.The house is the r  …see more

from £200 / night

£1466 - £1983 / week

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from £200 / night

25

Appartamento Glicine - Castelnuovo Berardenga apartment sleeps 7

Province of Siena / Castelnuovo Berardenga

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Le Rocche di Valiano is an ancient village situated in the heart of Chianti area near Siena. The structure, completely surrounded by olives groves, enjoys a spectacular view of the typical Tuscany landscape made by sweet hills and of the vast vineyards. The apartment  …see more

from £55 / night

£381 - £767 / week

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from £55 / night

(1) Excellent 

13

Province of Siena / Asciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £95 / night

£647 - £914 / week

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from £95 / night

(5) Very Good 

23

Spacious Chianti apartment with pool access, terrace and outdoor dining area - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
This is a spacious fully furnished 2 bedroom apartment in Borgo di Gaiole in the village of Gaiole in Chianti. Gaiole is in the heart of the Chianti Classico Region of Tuscany.The property has stunning views over the village and to the vineyards overlooking the village  …see more

from £150 / night

£600 - £850 / week

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from £150 / night

(1) Excellent 

24

Casa Giovanni - San Giovanni d'Asso villa sleeps 5

Province of Siena / San Giovanni d'Asso

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Italian village rental - This charming historic residence is part of a larger building, located in the village of San Giovanni d'Asso, just beyond the original castle walls and a short walk to the centre.With origins dating back to the 15th century this property ce  …see more

from £240 / night

£1680 - £2360 / week

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from £240 / night

13

Province of Siena / San Gimignano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £173 / night

£992 - £2845 / week

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from £173 / night

(3) Excellent 

22

Granaio 6 - San Gimignano apartment sleeps 7

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 7 (5+2) people in total. The apartment is next to Granaio nr 7 (advert nr 277234 ) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San  …see more

from £36 / night

£250 - £854 / week

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from £36 / night

(32) Excellent 

24

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS - Gaiole in Chianti apartment sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Ideal for couples looking for a relaxing romantic holiday, we provide everything you need in our fully equipped and tastefully decorated apartment, see our reviews. FREE WI-FI Walking distance to local restaurants. The large private garden for your exclusive use overlo  …see more

from £60 / night

£420 - £665 / week

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from £60 / night

27

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £179 / night

£1250 - £1682 / week

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from £179 / night

5

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £113 / night

£604 / week

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from £113 / night

24

Casa Chianti - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
A cosy and lovingly furnished 1 bedroom apartment located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful SienaT  …see more

from £45 / night

£311 - £535 / week

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from £45 / night

(6) Excellent 

26

Just 5 minutes from the centre of the Gaiolie, wonderful apartment with pool and breathtaking terrace, sleeps 6 - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The apartment is just 5 minutes walk from the center of Gaiole, where you will find all the services you need. Like restaurants, bars, wineshops, banks, food shop, hairdressers etc.Gaiole is one of several traditional Chianti villages in the region. Others worth visitin  …see more

from £85 / night

£595 - £944 / week

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from £85 / night

17

Holiday Resort in Montepulciano M - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearest village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from £48 / night

£332 - £694 / week

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from £48 / night

Top Destination reviews

Villa Galardini
Great location in heart of Tuscany; wonderful property and very friendly owners

Property is peaceful, clean and ideally located for daytrips to the many nearby villages and Sienna. Grocery stores and restaurants conveniently located in nearby Buonconvento . This was a 50th Birthday celebration vacation to Tuscany with spouse a … see more
Villa Vianci
Best vacation ever!

Our entire experience at Villa Vianci was beyond expectations. We travelled with 4 generations, ages 3 1/2 to 85! The villa was spectacular, spacious & immaculate. The pictures on line don't do it justice. Tommasso & Chiara were the best, any que … see more
Podere Val delle Corti
Very nice and total clean appartment

Beautiful property within a lovely environment Very nice and total clean appartment Landlady and the whole proprietor familiy are very friendly an helpful No kind of weakness has been discovered, at all … see more
La Casina Toscana, central with parking and wi-fi
Clean, comfortable and cozy house with privacy and convenience to Montepuciano

We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close enough to walk to the Montepulciano town. The place was very clean and thoughtf … see more
Agriturismo Sammonti
Perfect week in Tuscany

All previous positive reviews reflect our experience. Beautiful, quiet location. Lovely hosts. The house was cosy and a great place to come home to after sightseeing. It was also very easy to spend a whole day in the local area or enjoying the pool … see more
Villa PetrAlexa, Tuscany cottage in Chianti area
Villa PetrAlexa - excellent leisure facility

This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfectly prepared. The house was heated up and foo … see more

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