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472 Holiday homes in Siena Province

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Filters applied: Private pool (472)

472 Results  |  
13 Photos

Farmhouse | 1 Bedroom | sleeps 2

2 Nights min stay

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from £63 /night

£439 - £658 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
L'agriturismo è situato in modo da poter raggiungere con facilità i luoghi di maggiore interesse artistico : Siena, Volterra, Firenze, Monteriggioni, San Gimignano ecc... La zona è molto tranquilla, adatta al relax o a passeggiate  …see more

13 Photos

Cottage | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £212 /night

£1484 - £2067 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Podere Le Lame is an enchanting Tuscan Mill house, set in four hectares of olives - a house for complete peace and relaxation. All bedrooms have en suite bathrooms with power showers. There is a large hall/dining/kitchen with an open fire and French windows to a loggia.  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 5

Excellent 5/5 

3 Nights min stay

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from £154 /night

£1074 - £1621 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
3 BDR cosy house with patio,small pool,AC,Wifi, in the heart of Siena countryside, nestled in a village Please,ALWAYS enquiry about prices.  …see more

Featured properties

18 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £137 /night

£955 - £1831 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £189 /night

£1323 - £2439 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Self-catering Tuscan villa with private pool ideal for 8-12 persons. Each room with ensuite bathroom Private infinity swimming pool The skilful renovation of the premises has fully preserved the typical rustic Tuscan style.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

Very Good 4/5 

4 Nights min stay

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from £142 /night

£992 - £1984 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Self-catering villa with stunning views over Tuscany vineyards. Private pool. Shared tennis court with villa LisiDor (#44909, same owner). Internet. Bbq and shaded eating area. Fenced garden. Midway to Siena and Florence Typical Tuscan countryside with private pool and garden in silent position in the middle of Chianti hills  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

2 Nights min stay

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from £63 /night

£439 - £658 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
luogo molto tranquillo,adatto al relax o a passeggiate. L'agriturismo è situato in modo da poter raggiungere in poco tempo le principali città d'arte della Toscana : Siena, Firenze, San Gimignano, Volterra , Monteriggioni ecc...  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £218 /night

£1526 - £2064 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
A typical stone barn immersed in the Tuscan countryside of San Gimignano. A large garden overlooks the hills and surrounding countryside. Up to 7 people in a both modern and rustic atmosphere.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £182 /night

£1271 - £1621 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The villa is the ideal starting point to visit the Val di Chiana and Val d'Orcia with its wonderful medieval towns such as Cortona, Montepulciano, San Quirico d'Orcia, Pienza, as well as Montalcino and San Gimignano and the beautiful art cities of Siena and Florence.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 9

3 Nights min stay

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from £160 /night

£1116 - £2067 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Self-catering Tuscan villa with private pool ideal for 8-9 persons. Each room with ensuite bathroom Very close to the town  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £221 /night

£1541 - £3960 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
5 BDR beautiful indipendent house with pool,AC,WiFi in the Siena countryside, close to a village. Please,ALWAYS enquiry about prices.The house can be rented just in part (3BDR apt))  …see more

24 Photos

Farmhouse | 7 Bedrooms | sleeps 16

Very Good 4.5/5 

1 night min stay

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from £63 /night

£439 - £4030 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Swimming pool 15x5mt, cleaned using salt not chlorine. 3D archery range with wild animal targets, bow rental and trainer available. Try Alessandro's traditional cousine, it will surprise you! Our cellar and vineyards are open for visit, taste our Rosso di Montepulciano  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

Excellent 5/5 

3 Nights min stay

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from £447 /night

£3128 - £5007 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
8 BDR luxury historical villa with garden and pool in the heart of Siena countryside nestled in a village. Please,ALWAYS,enquiry about prices.The house can be rented just in part (4BDR).  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £261 /night

£1823 - £4643 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Splendid villa with breathtaking view over the Castle of Strozzavolta, in the Chianti, between Florence and Siena.  …see more

22 Photos

Tower | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £162 /night

£1131 - £2243 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • May take pets – please enquire
  • Private garden
Stunning medieval tower near San Gimignano for holiday rentals  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

3 Nights min stay

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from £188 /night

£1315 - £2191 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This enchanting holiday home is on a knoll overlooking the typical Tuscan countryside of the area around Pienza, San Quirico and Montalcino. In a very quiet position, only surrounded by a peaceful Tuscan countryside, this holiday accommodation consists of 4 apartments  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £188 /night

£1315 - £1884 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The villa near Pienza is elegantly furnished, in a perfect combination between comfort and tradition, with modern amenities such as internet Wi-Fi and Sat-TV. On two floors, the house can host up to 10 people.  …see more

20 Photos

Villa | 11 Bedrooms | sleeps 26

2 Nights min stay

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from £71 /night

£491 - £5958 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
On the ground floor there are large rooms, with fireplaces, which lead outside to a semi-circular parterre-solarium paved in terracotta.On the first floor there are 8 double rooms all with private bathrooms with shower, more rooms in the lemon house On the ground floor there's a double room with private bathroom with access to the swimming pool  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

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from £188 /night

£1315 - £2979 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
This beautiful villa in Siena is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beautiful attractions of the Chianti  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £44 /night

£303 - £745 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Perfect if you would like to visit San Gimignano by foot (15-30 minutes walk along the Francigena way)  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £251 /night

£1753 - £2103 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
As the house is part of a company that produces Brunello di Montalcino is possible to follow the stages of production or do a tasting tour to discover one of the best wines in the world in our cave.  …see more

19 Photos

Tower | 2 Bedrooms | sleeps 10

Very Good 4/5 

Short stays welcome

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from £107 /night

£745 - £2015 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
characterful and historic place with awesome view on the tuscan landscape; nice and quiet place; strategic spot to visit the whole Tuscany  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 11

5 Nights min stay

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from £248 /night

£1735 - £3715 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Basciano. The house position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £1502 /night

£10513 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The first floor of a Villa dating from around 1760, a commanding position within a protected area of outstanding natural beauty. Described as 'Manhattan in Tuscany' the compassionate treatment of the lovely old structure is supercharged by contemporary interior design. Bright, spacious and fully equipped for entertainment and comfort. A/C,Plasm TVs, WiFI, home theatre, stereo  …see more

11 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

Min stay varies

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Key info:

  • Nearest beach 62 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
L fienile di Colletalli is an ancient barn restored and converted into the most beautiful and unique spa resort. Is just five minutes by car from middle-age village Radicondoli. A large living room, a private and exclusive beautiful farm, a terrace, a garden, and a pool  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 25

Very Good 4.5/5 

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
"The Harvest Moon" holiday house, is a Tuscan country mansion with a spectacular pool overlooking the boundless valley. The whole property is available for more comfort and privacy. The whole property is available for more confort and privacy.  …see more

21 Photos

Farmhouse | 1 Bedroom | sleeps 4

Short stays welcome

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from £58 /night

£400 - £650 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Self catering Farmhouse with 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence, Siena and Pisa one hour from the house.  …see more

24 Photos

Villa | 12 Bedrooms | sleeps 23

Excellent 5/5 

3 Nights min stay

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from £338 /night

£2366 - £6308 / week

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Key info:

  • Nearest beach 170 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Private Villa with Pool, Tennis court and 5 hectare garden in the middle of Tuscany near Siena, Montepulciano, Pienza and many more! Perfect for Large groups up to 23 people to enjoy the holidays together or celebrate a Birthday, anniversary or reunion. Perfect place for groups, couples, Families! Your choice if self-catered or Hotel service!  …see more

16 Photos

Farmhouse | 8 Bedrooms | sleeps 19

2 Nights min stay

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from £285 /night

£1989 - £2988 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
A 17th century stone hamlet situated in one of the most wonderful positions of Tuscany. Four apartments and two bedrooms furnished with big taste and with exclusive period furniture, fireplace Sky TV independent heating external private space. Parking, scenic pool  …see more

23 Photos

Fort | 1 Bedroom | sleeps 3

3 Nights min stay

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from £108 /night

£751 - £834 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Romantic and charming 14th century fortress. Very authentic medieval atmosphere. Strategically located between Val d'Orcia and Crete Senesi, close to Montalcino, Montepulciano, Pienza and Siena. Shops at walking distance. Organic wine and extra virgin olive oil.  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 14

3 Nights min stay

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from £72 /night

£500 - £3000 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Italy, Tuscany, Siena , beautiful villa with swimming pool. Incredible views, perfect holiday location.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £201 /night

£1402 - £2191 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Colletalli is an ideal location to recharge ones energy away from the humdrum of daily life conveniently located within 1 hour motoring of Florence, Siena, Sangimignano, Volterra, sandy beaches  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £501 /night

£3505 - £4672 / week

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Key info:

  • Nearest beach 74 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Ancient and noble mansion of the XVIII century overlooking Chianti hills, for a luxury and leisure stay in the hearth of Tuscany... Its location in the centre of Tuscany, a few km from the highway Firenze-Siena.  …see more

20 Photos

Farmhouse | 5 Bedrooms | sleeps 9

3 Nights min stay

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from £128 /night

£893 - £1686 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Comfortable country house with private pool to rent near San Casciano dei Bagni – sleeps 9 From 1080€ to 2040€ a week  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £213 /night

£1488 - £2976 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Holiday villa with private pool and sauna within walking distance from Cetona – sleeps 9 From 1800€ to 3600€ a week  …see more

21 Photos

Castle | 6 Bedrooms | sleeps 16

4 Nights min stay

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from £390 /night

£2728 - £3182 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Romantic castle with pool to rent near Montepulciano – sleeps 14+2 From 3300€ to 3850€ a week  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £355 /night

£2480 - £3720 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Large mansion with private pool to rent near Monteroni d'Arbia - sleeps 11 From 3000€ to 4500€ a week  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £231 /night

£1612 - £3100 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Elegant air-conditioned villa with private pool to rent close to Montepulciano – sleeps 6 From 2160€ to 3480€ a week  …see more

17 Photos

Villa | 1 Bedroom | sleeps 4

Short stays welcome

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from £138 /night

£964 - £1227 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Wonderful Villa with private pool overlooking the castle of Monteriggioni  …see more

22 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £271 /night

£1894 - £2581 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Magical Tuscan farmhouse with pool overlooking the stunning Siena countryside. Enjoying the most beautiful and tranquil of settings Le Contessine offers both a relaxing escape and a strategic location for touring the whole of Tuscany and Umbria with ease. 4 bedrooms.  …see more

13 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £756 /night

£5290 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
Is the perfect mix of luxury and rustic Italian, with a relaxed feel perfect for a holiday with friends and family or for a special celebration! Stomennano's got so much character and charm and you'll be amazed by the beauty of the Villa and the gardens.  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £179 /night

£1247 - £1986 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • No pets allowed
The old style restoerd flats can offer a perfect feeling of Tuscany. The large garen with view will grant you of unforgettable sunsets over the hills. A large garden with 6x12 mt swimming pool and a very nice barbeque area are at the guest's disposal. In summertime is absolutely nice to go by bike/walking/jogging, it's very easy to find people doing the same  …see more

21 Photos

Villa | 8 Bedrooms | sleeps 12

Short stays welcome

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from £401 /night

£2804 - £5073 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

22 Photos

Apartment | 3 Bedrooms | sleeps 4

3 Nights min stay

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from £114 /night

£798 - £1402 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 75 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
"Casa Serena" is located in a panoramic position, blessed with mesmerising views over the Chianti vineyards and enchanting hamlets. Quiet location but not isolated. Local assistant 24 H in case of need - english speaking  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £152 /night

£1060 - £1696 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Private viila and swimming pool deeped in nature and quiet.We rent out the whole house,so you could enjoy your holiday without any disturb.  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £182 /night

£1271 - £1534 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
Charming farmhouse in Tuscany, the ideal starting point to visit the Val di Chiana and Val d'Orcia with its wonderful medieval towns such as Cortona, Montepulciano, San Quirico d'Orcia, Pienza, as well as Montalcino and San Gimignano and the beautiful art town of Siena. Situated in the heart of Tuscany, near the centre of the little town of Sinalunga.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £86 /night

£601 - £1276 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
"BACCHINO IN THE CHIANTI" is located in the center of the Chianti geographic area where they produce the famous and superb wine Chianti Gallo Nero, between Gaiole in Chianti (5 km), Radda in Chianti (7 km) and Castellina in Chianti.  …see more

19 Photos

Farmhouse | 6 Bedrooms | sleeps 12

1 night min stay

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from £126 /night

£877 - £2191 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Beautiful Tuscan country house and cottage set on a natural terrace with commanding views of the Tuscan hills. Deep in the countryside with easy day trips to Florence, Sienna and Perugia.  …see more

11 Photos

Farmhouse | 6 Bedrooms | sleeps 12

Min stay varies

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from £376 /night

£2629 - £3943 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Renaissance Villa with private swimming pool on the Tuscan hills.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £226 /night

£1577 - £3067 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
The place is peaceful, outside in the garden; you have the possibility to relax under the trees or to eat under the stars. Beautiful structure for a relaxing holiday in the tuscany area . ask for availability we have several solution for you. also self catering apartments with breakfast service.  …see more