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433 Holiday homes in Siena Province

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433 Results  |  
23 Photos

Tower | 2 Bedrooms | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £62 /night

£430 - £491 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
The enchanting Torre Giordano will give you the unique opportunity to spend your vacations in a centuries-old tower!  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 5

Excellent 5/5 

5 Nights min stay

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from £44 /night

£307 - £368 / week

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Key info:

  • Nearest beach 75 km
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
HOME / COTTAGE INDEPENDENT OF NEW CONSTRUCTION IN THE OPEN COUNTRYSIDE panoramic view on San Gimignano Pets: maximum 2 (small)  …see more

11 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £51 /night

£356 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Immerso nella meravigliosa campagna toscana LA DOLCE VITA è un affittacamere all'interno di un antico casolare ristrutturato, circondato dall'atmosfera magica della natura incontaminata.  …see more

Featured properties

16 Photos

Farmhouse | 1 Bedroom | sleeps 4

Short stays welcome

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from £64 /night

£446 - £536 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Romantic one bedroom apartment in a converted traditional Tuscan farmhouse between San Gimignano and Volterra. Beautifully renovated farm building, Terraces with fantastic views, pool, ideal for rest and relaxation! Easy access Siena , Pisa and Florence.  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £91 /night

£631 - £1472 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Charming holiday apartment in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area.  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £118 /night

£820 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
On the sweet hills of the Chianti shire between vineyardand and olive groves, stands the "Podere il Pino". It offers a spectacular view on the beautiful medieval village of San Gimignano and it is very close to art cities as Florence, Siena, Pisa, Volterra and the sea.  …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

12 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

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from £75 /night

£522 - £552 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
“L'angolo di Pienza” for its central position is a good starting point to live an unique experience of life in a rich and delicious small country, with its lively community and its sights.  …see more

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 | 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 | 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

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 | 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

12 Photos

Apartment | 2 Bedrooms | sleeps 5

4 Nights min stay

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from £72 /night

£500 - £780 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Apartment in Tuscany , groundfloor, with special countryside vieuw from private terrace. At only 20 minutes from Siena. 2 km from village. Swimming pool in garden  …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

18 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £39 /night

£272 - £526 / week

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Key info:

  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £39 /night

£272 - £517 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
nice and comfortable apartments in walking distance from the village  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 7

Very Good 4/5 

3 Nights min stay

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from £84 /night

£587 - £1017 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Gorgeous holiday villa in Siena, just 5 minutes walking from the town. blloming garden, shared swimming pool, private car parking, internet (with flash drive), laundry room, chef for dinner or meal on request  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £106 /night

£736 - £1358 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Holiday Villa for 8 people 1 km from Siena, and 3.5 km from Piazza del Campo (sit of the Palio)  …see more

22 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £47 /night

£325 - £658 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £44 /night

£307 - £614 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £54 /night

£377 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
The house offers everything you need for a relaxing holiday and has free Wi-Fi, microwave oven, drip coffee maker, toaster and kettle as well as being supplied with all bedroom and bathroom linen.  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £32 /night

£220 - £439 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
nice and comfortable apartments in walking distance from the village  …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

19 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £37 /night

£259 - £500 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £32 /night

£220 - £439 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
nice and comfortable apartments in walking distance from the village .  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £39 /night

£272 - £517 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Nice and comfortable apartments in walking distance from the village  …see more

16 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £69 /night

£482 - £728 / 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 position of Tuscany. The apartment is furnished tastefully and with exclusive period furniture, fireplace, Sky TV, independent heating, external private space. Park, scenic swimming pool.  …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

19 Photos

House | 15 Bedrooms | sleeps 30

Min stay varies

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Poggiarello is a special place to spend a charming holiday in close contact with nature, where is possible to reach in few minutes Siena, San Gimignano, Firenze, Pisa, Lucca, Monteriggioni,Montalcino.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

Min stay varies

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from £114 /night

£798 - £1043 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. In our restaurant is possible to take: Breakfast Dinner Wine tasting  …see more

19 Photos

Farmhouse | 12 Bedrooms | sleeps 30

1 night min stay

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from £36 /night

£246 - £10119 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Our estate is composed of well equipped units: apartments with cooking corner, completely restored in typical tuscan style, maintaining intact the old original elements such as wooden-beam and arched ceilings, brickwork floors. Each unit disposes of private entrance A wide range of services and activities: walkings, ridings, excursions by byke, photo-tours, cooking-classes  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £53 /night

£368 - £859 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. In our restaurant is possible to take: Breakfast Dinner Wine tasting  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £76 /night

£526 - £1227 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday suite apartment in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes from Siena, San Gimignano and Florence. Fantastic view from terrace. Shared pool  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £53 /night

£368 - £1963 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. In our restaurant is possible to enjoy: Breakfast Dinner Wine tasting  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £80 /night

£554 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
Staying in the Old Town is the best you could want from a holiday, everything is at hand, quaint shops for shopping, restaurants, taverns, museums and art galleries. Remember that the center is a pedestrian zone, calm and quiet  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

Add to shortlist

from £149 /night

£1043 - £1831 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

20 Photos

Barn | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £99 /night

£693 - £1131 / 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
This is the most informal apartment of Piaggione of Serravalle, smaller than the other two, for this reason it's undoubtedly the coziest and most intimate. It's located in an independent structure from the main farmhouse, to which it's linked externally to La Loggia. The Piaggione of Serravalle is a lively farm that is in constant action and that brings forth its daily acti  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

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from £59 /night

£412 - £552 / 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 position of Tuscany. The apartment is furnished tastefully and with period furniture, fireplace, Sky TV, independent heating external, private space. Park, scenic swimming pool.  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 25

Very Good 4.5/5 

Min stay varies

Add to shortlist

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

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

16 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £99 /night

£689 - £954 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Il Pozzo is an apartment which is part of a converted farmhouse from the eighteenth-century, entirely in stone, that was recently the subject of a careful and passionate restoration. A park of three hectares surrounds the property. There is also a swimming pool on-site  …see more

19 Photos

Castle | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £53 /night

£368 - £1139 / week

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Key info:

  • Nearest beach 75 km
  • Suitable for over 5s only
  • Car advised
  • Pets welcome
  • Private garden
Holidays in an original Castle near Siena! Castello di Capria offers the perfect location for history and nature loving guests. Space for up to 10 people in comfortable rooms, self catered or with catering. Special Getaway for smaller groups for up to 10 people. Golf nearby, Horse riding nearby, swimming nearby.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £113 /night

£789 - £6308 / 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
Private Apartment in historic Villa with swimming pool, tennis court and 5 hectare garden. Near Siena, Montepulciano, Cortona etc. 4 bedrooms (or more if needed) with 2 bathrooms, 1 separate WC, 1 kitchen, 1 living room, private terrace and garden!  …see more

11 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

5 Nights min stay

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from £47 /night

£323 - £810 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
The large apartment (116 sqm) is situated in the historical centre of Montepulciano. Inside the house the guests will appreciate its peaceful and warm atmosphere. The apartment has been recently restored with the intention of giving its guests the best comfort.  …see more

23 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Min stay varies

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from £88 /night

£614 - £1402 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
CHIANTI , WINE , COOKING CLASS , AGRITURISMO , LANDSCAPE , VIEW  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £282 /night

£1972 - £2891 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Lovely villa, South of Siena, perfect base for the exploration of Tuscany. Private pool, isolated, complete privacy. Ideal for families or groups: rates for 7, 12 and - adding a small apartment - 16people (price on request). Children and pets are welcome.  …see more

15 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Min stay varies

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from £72 /night

£501 - £667 / week

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Key info:

  • Nearest beach 75 km
  • Suitable for over 5s only
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
The village is located in a strategic position, 25 km from Siena and 50 km from the seaside; along the way to the coast, the old Massetana way, you will have the chance to visit the extraordinary San Galgano Abbey, the Montesiepi hermitage, villages, ancient churches. Sail with us on board of Free Will to the Tuscan Archipelago, Sardinia, Corsica.  …see more

24 Photos

Farmhouse | 10 Bedrooms | sleeps 20

Short stays welcome

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from £526 /night

£3680 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The Wine Estate of Castelnuovo Tancredi has 3 stone farmhouses that compose an antique Borgo with a shared pool overlooking the gorgeous countryside. Each farmhouse is unique, and varies in size from 2 to 4 bedrooms. Ideal for families, weddings and family reunions. You haven't seen the real Tuscany until you see the Val d'Orcia. Wine tastings and cooking classes on site.  …see more