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40 Holiday homes in Montepulciano

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24 Photos

Farmhouse | 7 Bedrooms | sleeps 16

Very Good 4.5/5 

1 night min stay

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from £364 /night

£2544 - £3901 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • 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

23 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £76 /night

£530 - £944 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
2 bedroom beautiful 500 year old restored farmhouse. 7km outside of Montepulciano. Pool, terrace, garden area, patio, and BBQ. 5 minute drive to nearest supermarket, shops, bars and restaurants.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £68 /night

£475 - £586 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
The estate is near to other historical place, like Orvieto, Pienza, Arezzo, Siena, Florence , Rome. http://www.airport.umbria.it/en Ideal place to relax , in the middle of an agricultural estate were we produce wines red and white and oil.  …see more

Featured properties

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

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from £194 /night

£1357 - £1527 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Wonderful place to relax, make sports ( walking,archery and swimming) sip our good wine and enjoy our cousine. Our swimming pool is 15x5mt wide and is cleaned using salt and not chlorine.  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £61 /night

£424 - £509 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
single room in a Villa with only 7 rooms. Infinity pool sanitized using salt and not chlorine, far better for your skin and eyes. We are a winery where you may visit our cellar and taste our wine,Il Golo,Rosso di Montepulciano DOC, Grappa, Finocchiaccio and marmelades.  …see more

9 Photos

Farmhouse | 9 Bedrooms | sleeps 22

1 night min stay

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from £85 /night

£594 - £4156 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful estate were you can have organize a holiday in a private structure or bed and breakfast service.  …see more

15 Photos

Watermill | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £146 /night

£1018 - £2248 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Beutiful old structure located in one of the most unspoiled place of the area. this Villa , with two annex one just adjacent , the second at 100 meters , is ideal for family or friends groups.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £29 /night

£200 - £784 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
I Tigli is a splendid apartment with two bedrooms and two bathrooms which is part of a property with a total of 6 apartments sharing a pool.  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £218 /night

£1520 - £2880 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

22 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £120 /night

£840 - £1200 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
This little, two-storey, converted Tuscany farmhouse has been meticulously restored in a simple, rustic style, employing high-quality traditional materials.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £389 /night

£2720 - £3800 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Oliveto is the guest villa, and sits at the end of an olive grove known for producing one of Italy's premier extra virgin olive oils. The villa, the pool & the gardens are totally private - separated from the main house by a large expanse of olive grove.  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £286 /night

£2000 - £4800 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £486 /night

£3400 - £4400 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 16

7 Nights min stay

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from £500 /night

£3500 - £5500 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa San Biagio is situated close to Montepulciano. This magnificent country house is known for being the most exclusive and stunning farmhouse you can find in this area. It is the perfect choice if you are looking for a peaceful and relaxing holiday.  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £252 /night

£1760 - £3040 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Luxury Tuscan farmhouse and private pool, with stunning views over Montepulciano 4 double bedrooms all with en-suite marble bathrooms  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 23

7 Nights min stay

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from £546 /night

£3816 - £5936 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
Casale, montepulciano, villa, piscina, vigneti, matrimonio in toscana, matrimonio in Italia, Italy, Tuscany Antico casale, completamente restaurato e suddiviso in 7 accoglienti appartamenti  …see more

8 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £72 /night

£504 - £720 / week

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Key info:

  • Great for children of all ages 5
  • Car advised
  • No pets allowed
TV, iron and iron board, freezer, oven, high chair, facilities for disabled.  …see more

18 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £279 /night

£1951 - £4834 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
The villa is located 800 meters from a traditional Tuscan restaurant and four kilometers from the nearest village of Montepulciano where you'll find a few shops, restaurants, and a market. Nearby: Pienza, Montefollonico, Bagno Vignoni, Cortona, Orvieto, Castiglion del Lago, S.Quirico, Montalcino  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 6

Very Good 4.5/5 

1 night min stay

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from £67 /night

£467 - £721 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
Located in a wonderful area, along the wine road that leads from Montepulciano to Pienza, sorrounded by vineyards, olive trees, fields, woods. we offer self catering apartments , and also B&B service . new airport at 30 Km distance http://www.airport.umbria.it/en ASK AVAILABILITY we have apartment 4 people located in rustic farmhouses  …see more

22 Photos

Cottage | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £37 /night

£255 - £823 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
This charming rural cottage is a converted farm building in the heart of the countryside near Montepulciano. It is ideally situated with its own private garden space surrounded by hills and vineyards, where guests can relax and enjoy the peaceful surroundings. It is also only a few minutes away from the shops, restaurants and bars of the nearby villages.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £219 /night

£1527 - £2968 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Guest house | 7 Bedrooms | sleeps 14

Short stays welcome

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from £606 /night

£4240 - £6106 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa in the historical and cultural heart of Tuscany near the centre of Montepulciano, with restaurant, market and cafe/bar, all at our door step. We offer Internet connection, buffet breakfast, dinner in private terrace, wine tour, Jacuzzi and a wanderfull gaden. Ardene provides its guests with a high standard of accommodation. The private swimmingpool is wonderful!  …see more

7 Photos

B&B | 6 Bedrooms | sleeps 15

1 night min stay

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from £63 /night

£441 - £2968 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Bed and breakfast, rooms in this small and familiar structure are equipped with every comfort including breakfast buffet and Wi  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £517 /night

£3618 - £6822 / week

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Key info:

  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
Villa Zingo is an exception idyllic Tuscan retreat nestled in the charming town Chiamciano.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £591 /night

£4135 - £7649 / week

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Key info:

  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
Contemporary five bedroom property with three doubles and two twin bedrooms. The villa is situated in the wonderful province of Siena, rich in history and culture.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £271 /night

£1896 - £3708 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Maramai, now a charming country house, used to be a small farm with 3 separate buildings. It is named after the Tuscan farmer’s family who lived there until the early ’70s.  …see more

7 Photos

Hotel apartment | 7 Bedrooms | sleeps 22

1 night min stay

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from £97 /night

£679 - £4156 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • Pets welcome
  • Private garden
It is the second structure that we have opened. Half way up the main street of Montepulciano, a few meters from Piazza delle Erbe and the Tower of Pulcinella, “La Dimora” provides large space and is equipped with every comfort, air conditioning and Wi-Fi included. On t  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £61 /night

£424 - £1272 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Agriturismo nel sud della Toscana , a Montepulciano , tra la Val d'Orcia e la Valdichiana , a conduzione familiare , di piccole dimensioni ,vicino al centro storico, con vista panoramica , coltivazioni biologiche di uva , olivi , alberi da frutta IL Sorbo è assolutamente indipendente e gode di una splendida vista sulla tipica campagna toscana  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 7

2 Nights min stay

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from £53 /night

£365 - £509 / week

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Key info:

  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Ideale per famiglie e per chi vuole una vacanza rigenerante all'insegna dell'arte  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £61 /night

£424 - £594 / week

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Key info:

  • Nearest beach 158 km
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villetta indipendente con giardino e parcheggio esclusivi. immersa nel verde della campagna toscana a soli 5 minuti a piedi dal centro storico di Montepulciano, dall'autostazione e dal supermercato. Camere climatizzate con uso gratuito della connessione internet wi-fi. Interni in autentico stile toscano: travi in legno, nicchie e l'antico focolare caratterizzano la struttura.  …see more

22 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £59 /night

£408 - £526 / week

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Key info:

  • Great for children of all ages 5
  • Car advised
  • No pets allowed
Brand new apartment, functional, quiet, well furnished, with parking and garden, free wifi, close to the owners, close to the supermarket and at a great wine restaurant near Montepulciano, Pienza, Siena, Val d'Orcia, Cortona, Arezzo , Perugia, Assisi. Car recommended. There is NO swimming pool in the house, but nearby there are swimming pools, spas and natural hot springs.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £51 /night

£357 - £424 / week

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Key info:

  • Great for children of all ages 5
  • Car advised
  • No pets allowed
Brand new apartment, functional, quiet, well furnished, with parking and garden, free wifi, close to the owners, close to the supermarket and at a great wine restaurant near Montepulciano, Pienza, Siena, Val d'Orcia, Cortona, Arezzo , Perugia, Assisi. Car recommended. There is NO swimming pool in the house, but nearby there are swimming pools, spas and natural hot springs.  …see more

4 Photos

House | 4 Bedrooms | sleeps 6

2 Nights min stay

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from £43 /night

£297 / week

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Key info:

  • Nearest beach 200 km
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
Cas colonica immersa nella campagna toscana con possibilità di escursioni, itinerari turistici ed enogastronomici, soggiorni nelle terme vicine di Rapolano e Bagnovignoni. Escursioni e visite dei siti della Val D'orcia e dei siti Etruschi di Chiusi.  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £55 /night

£382 - £509 / week

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Key info:

  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Delizioso appartamento totalmente ristrutturato nel 2011 nel centro storico di uno dei paesi toscani più belli.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £61 /night

£424 / week

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Key info:

  • Great for children of all ages 5
  • No pets allowed
L'appartamento è stato ristrutturato pochi anni fa', è spazioso, confortevole e munito di tutto quello che può servire in una casa. Dalle finestre si vede un panorama mozzafiato. La sua ubicazione 100 metri da Piazza Grande lo rende unico nel suo genere.  …see more

15 Photos

B&B | 3 Bedrooms | sleeps 9

Min stay varies

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Key info:

  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
b&b nella campagna di Montepulciano, Punto strategico per visitare sia la Toscana che l'Umbria.  …see more

23 Photos

House | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £73 /night

£509 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Casa indipendente con ampio giardino esterno, vicinissima al centro storico di Montepulciano, ma allo stesso tempo in piena campagna.  …see more

5 Photos

B&B | 4 Bedrooms | sleeps 12

2 Nights min stay

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from £146 /night

£1018 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Agriturismo biologico, bed and breakfast,fattoria biologica, cucina vegetariana e vegana,  …see more

10 Photos

Villa | 13 Bedrooms | sleeps 27

2 Nights min stay

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from £85 /night

£594 - £764 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
E' possibile gustare la squisita cucina locale e nel contempo immergersi nella cultura artistica di Siena e della vicina Firenze o semplicemente in "un dolce far niente". Tutto questo è "Casa al Bosco", luogo ideale per chiunque voglia vivere una vacanza all'insegna del  …see more

18 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Ancient farmhouse in Tuscany, just 1,5km from the center of Montepulciano with a wonderful view on Valdichiana.Up to 6 people rented all the year. 25 hectars of property with wineyard, olives, trees and truffles. 3 bedrooms, 1 big saloon with central fireplace, big kitc  …see more