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57 Holiday homes in Montalcino

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57 Results  |  
24 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

1 night min stay

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from £225 /night

£1573 - £1936 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A really charming and full of style apartment in a XVI th century stone villa near Montalcino, Pienza, Siena, Montichiello. An enchanted garden and an amazing swimming pool with view on Montalcino for an unforgettable holiday: good food and wine, art, sport and relax..  …see more

21 Photos

Apartment | 4 Bedrooms | sleeps 9

Excellent 5/5 

1 night min stay

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from £214 /night

£1492 - £1775 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
An amazing holiday in the moast beautiful area of Tuscany, in the natural park of the Val d'Orcia, near Montalcino, Pienza, Siena, Montichiello, Bagno Vignoni. A quiete, relaxing garden with swimming pool, a charming, cosy and comfortable apartment in an ancient villa.  …see more

14 Photos

Apartment | 10 Bedrooms | sleeps 20

Excellent 5/5 

3 Nights min stay

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from £121 /night

£847 - £8468 / week

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Key info:

  • Nearest beach 68 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Wonderfull apartments for unforgettable holiday in Montalcino, Tuscany, Italy. Wine tasting in the neighbouring wineries and bicycle or hiking tours in the World Heritage Site Val d'Orcia - you have the choice!  …see more

Featured properties

18 Photos

Studio | sleeps 2

Excellent 5/5 

1 night min stay

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from £70 /night

£484 - £698 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjoy!  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 3

Excellent 5/5 

2 Nights min stay

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from £58 /night

£404 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Tuscan countryside, panoramic views, romantic suite, natural pool, beautiful garden  …see more

9 Photos

House | 3 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £70 /night

£484 / week

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Key info:

  • Nearest beach 55 km
  • Great for children of all ages
  • Pets welcome
  • Private garden
In una casa recentemente ristrutturata, nel comune di Montalcino, tra viti, olivi e macchia mediterranea, nella più assoluta tranquillità all'esterno come all'interno, l'agriturismo Villetta Caprili offre ospitalità fino a 8 persone con parcheggio privato.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

1 night min stay

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from £104 /night

£726 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Zafferano, ideal for a self catering holiday, is found in the hamlet of Vergelle, set amongst the peaceful countryside known as the Crete Senesi, south of Siena, in Tuscany. It is close to the hilltop town Montalcino with its world famous Brunello vineyards. This large 4 bedroomed villa is part of Vergelle’s old school building, and was fully renovated in 2008.  …see more

20 Photos

Farmhouse | 7 Bedrooms | sleeps 14

Good 3.5/5 

1 night min stay

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from £65 /night

£452 / week

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Key info:

  • Nearest beach 65 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
Appartamenti,camere,ristorante tipico,piscina,cantina,Brunello di Montalcino,Val d'Orcia VENDITA DIRETTA DI TUTTI I NOSTRI PRODOTTI AGRICOLI (VINO-,OLIO EXTRAVERGINE DI OLIVA,GRAPPA,ACETO,ORTAGGI)  …see more

18 Photos

Hotel apartment | 3 Bedrooms | sleeps 6

 

1 night min stay

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from £139 /night

£968 - £1371 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
An independent vacation surrounded by a magnificent Tuscan countryside.  …see more

13 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £363 /night

£2541 - £3468 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Villa Montepulciano sits on a hill just ten minutes drive away from Pienza, and overlooks the Orcia Valley, which has been proclaimed as a UNESCO World Heritage site.  …see more

19 Photos

House | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £153 /night

£1065 - £1690 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjoy!  …see more

21 Photos

Apartment | 4 Bedrooms | sleeps 9

1 night min stay

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from £185 /night

£1291 - £1492 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A really charming and cosy mansard in the ancient stone villa Pian dell'Asso near Montalcino, Pienza, Siena, Montichiello. An enchanted garden and an amazing swimming pool with view on Montalcino for a relaxing holiday: good food and wine, art and sport.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £121 /night

£847 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
Your home in downtown Montalcino to experience the everyday life of this true gem. Despite the notoriety from the famous Brunello wine, the town has remained authentic and charming. Discover our Dolce Vita...cheers!!  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

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from £185 /night

£1291 - £2259 / week

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Key info:

  • Suitable for children over 5
  • No pets allowed
The views from the terrace, the convenience of being right in the middle of things without needing a car to get food, lunch or dinner, and the beautifully renovated 17th century apartment.  …see more

22 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £108 /night

£750 - £1154 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjoy!  …see more

17 Photos

Studio | sleeps 2

1 night min stay

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from £87 /night

£605 - £859 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
One large and cosy suite with a high ceiling with the typical wooden beams and wooden floor. There's a fully equipped kitchen, a small sitting area, a double bed with a restored big old Tuscan wardrobe. The private bathroom is with shower in travertine. The suite is equ  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

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from £87 /night

£605 - £940 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjoy!  …see more

19 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £865 /night

£6049 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Recently restored to the highest standard, the Villa is a deluxe country house in the beautiful Val D’Orcia in the South-Eastern part of the Siena province in Tuscany.  …see more

15 Photos

Villa | 3 Bedrooms | sleeps 8

Short stays welcome

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from £115 /night

£803 - £1170 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Sun baked stone walls, hand made terracotta floors, chestnut beamed ceilings, pergolas twisted with the perfume of jasmine and wisteria, sitting out on your terrace overlooking your swimming pool, Soaking up the radiant glow of the sun setting over the Val d'Orcia Valley.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 12

7 Nights min stay

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from £381 /night

£2662 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
This beautiful farm house is situated in fifty hectares of land with olive trees, a vineyard and also walnut trees. A very well appointed and furnished residence. Air conditioned in apartment four only. An independent farm house that sleeps 11+1.  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £60 /night

£419 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • No pets allowed
The apartment is about 90 square meters with a large living room with sofa, lounge chairs and dinner table, kitchen with good size refrigerator, gas burners, electric oven and all kinds of kitchenware. 1 double room with king size bed, 1 double room with queen size bed.  …see more

16 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £1021 /night

£7146 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Excellent furnished property set In a dominant position and close to the wonderful Castle of Velona, this property is on the top of a high hill overlooking the vineyards of Brunello. Historians will appreciate that its only 1 km from the magnificent abbey of Sant'Antimo  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

Short stays welcome

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from £81 /night

£561 - £803 / week

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Key info:

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

12 Photos

Villa | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £231 /night

£1613 - £1936 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

24 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £138 /night

£960 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Agriturismo Bonacchi in splendida posizione sui vigneti del Brunello - 2 Appartamenti indipendenti con cucine attrezzate, 3 camere e 10 posti letto totali  …see more

11 Photos

B&B | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £64 /night

£444 - £605 / week

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Key info:

  • Nearest beach 80 km
  • Not suitable for children
  • Car essential
  • No pets allowed
La posizione ed il luogo dove sorge la struttura consente al visitatore di ammirare paesaggi, le dolci colline, valloni e calanchi i cui colori variano con il cambio delle stagioni ed fonte d'attrazione e richiamo per i fotografi di tutto il mondo Strada Statale 146 - San Quirico d'Orcia 53027 San Quirico d'Orcia, Siena Latitudine 43.06 Longitudine 11.62  …see more

22 Photos

B&B | 3 Bedrooms | sleeps 8

1 night min stay

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from £201 /night

£1404 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Casa tradizionale toscana nel centro storico di Montalcino con 4 camere da letto tutte dotate di bagno , tv, asiugacapelli. Struttura tipica toscana nel centro del paese, si arriva a piedi in piazzetta principale, negozi, supermercato, enoteche, parcheggio. Possibilita' di organizzare winery tour e light lunch presso la cantina di famiglia , Parcheggio gratis  …see more

6 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £58 /night

£404 - £525 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
il casolare offre una vacanza immersa nella natura fra vigneti, uliveti ,boschi di macchia mediterranea ricca di fauna selvatica . Risulta strategicamente un punto importante per visitare a breve distanza le più belle località toscane (Siena Pienza Murlo San Antimo )  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £162 /night

£1130 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
2 Appartamenti indipendenti in splendida posizione sui vigneti del Brunello con cucine attrezzate e 3 camere, 10 posti letto totali  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

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from £65 /night

£452 / week

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Key info:

  • Nearest beach 80 km
  • Not suitable for children
  • Car essential
  • No pets allowed
La posizione ed il luogo dove sorge la struttura consente al visitatore di ammirare paesaggi, le dolci colline, valloni e calanchi i cui colori variano con il cambio delle stagioni ed fonte d'attrazione e richiamo per i fotografi di tutto il mondo. Strada Statale 146 - San Quirico d'Orcia 53027 San Quirico d'Orcia, Siena Latitudine 43.06 Longitudine 11.62  …see more

5 Photos

House | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £116 /night

£807 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Appartamenti dotati di confort ma senza perdere le caratteristiche del podere.  …see more

6 Photos

Apartment | 5 Bedrooms | sleeps 14

1 night min stay

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from £52 /night

£363 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
Ideale per che vuole passare dei giorni in pieno relax.  …see more

4 Photos

Villa | 2 Bedrooms | sleeps 6

1 night min stay

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from £116 /night

£807 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa in the middle of Val D'Orcia, typical tuscany house on the top of the hill. Close to Montalcino , Pienza and Thermal baths.  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

Short stays welcome

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from £86 /night

£600 - £1200 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
The villa is a large 3 bedroom property, which provides comfortable accommodation for up to 8 people. It is a beautiful bright and spacious house spread over three floors and includes a private outdoor garden and patio area and a large shared swimming pool.  …see more

25 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

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from £119 /night

£831 - £1384 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Charming farmhouse with garden + pool in a loosely layout hamlet - the castle estate of Vivo d'Orcia. Absolute privacy. Spectacular view over the Orcia valley below. Sleeps 4  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

Excellent 5/5 

7 Nights min stay

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from £542 /night

£3791 - £6371 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
This spacious, stylishly furnished villa is set in extensive grounds, which offer a choice of venues for outdoor relaxation and dining. It is tucked away in a very secluded spot, amid gently rolling wooded hills.  …see more

13 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £633 /night

£4428 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
La Giocosa is located in the most desirable region south of Siena, in the Val d'Orcia, an enchanting and miraculously unspoilt valley in southern Tuscany, listed as UNESCO world heritage in 2004.  …see more

20 Photos

House | 6 Bedrooms | sleeps 16

7 Nights min stay

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from £537 /night

£3759 - £6283 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Elegant country décor. Airy and spacious rooms. Air conditioning in the first floor bedrooms. Optional guest house.  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £665 /night

£4654 - £7759 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Argiano with 5 bedrooms sleeps 10  …see more

14 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £173 /night

£1210 - £1775 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • No pets allowed
This large apartment is on the exclusive wine estate dei Vini. The farm with a chapel which it is part of dates from the 17th century and has been renovated in style. You look out on a graceful hillside where some of the best wines of Italy come from. 7 persons.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £202 /night

£1412 - £1815 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
A holiday at Borgo Brunello provides something for everyone: 3km from Montalcino for culture vultures and wine fans, beautiful landscape offering sporting and recreational possibilities as well as infinite calm for a romantic or family getaway.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 14

2 Nights min stay

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from £540 /night

£3777 - £5488 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Perfect place to enjoy a relaxing holiday, combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. The villa is nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden  …see more

23 Photos

Cottage | 1 Bedroom | sleeps 2

7 Nights min stay

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from £83 /night

£581 - £726 / week

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Key info:

  • Nearest beach 70 km
  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Situated on the castle estate of Vivo d'Orcia, Casa Gallinaio is a charming restored former chicken coop for 2 with terrace and private garden. View onto the medieval hamlet and the Monte Amiata.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

1 night min stay

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from £287 /night

£2009 - £3944 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Bandini is located only 300 meters from the hamlet of Lucignano d'Asso on top of a hill on the border between the Val d'Orcia and the Sienese clay hills. Lucignano d'Asso is a medieval ancient hamlet which, since the XV century, has belonged to the Piccolomini fam  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 7

7 Nights min stay

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from £217 /night

£1516 - £2404 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This property is a stunning villa set in Tuscany Italy. It has 4 bedrooms and 3 bathrooms, and it is ideal for those who are looking for a memorable experience. This property features: a swimming Pool, air Conditioning .  …see more

11 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £84 /night

£586 - £587 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This beautiful first floor holiday apartment, one of three, along with ITS541, is accessed via rough track and forms part of a stone-built hamlet dating back to the early 16th century in the heart of Tuscany, set amongst olive groves and vineyards. Located in a peace...  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £89 /night

£621 - £706 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
2 Double beds, 1 Single bed, 2 Bedrooms, 2 Bathroom, 1 Living room, 1 Kitchen (75 sqm)  …see more

15 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £104 /night

£726 - £968 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • No pets allowed
This apartment is located on the exclusive wine estate Dei Vini (20 ha). You will stay in a farmhouse with adjoining chapel dating from the 17th century and renovated in style. The area offers a harmonious landscape and produces some of the best wines of Italy. 4 pers.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

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from £271 /night

£1896 - £2178 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
A holiday at Borgo Brunello provides something for everyone: 3km from Montalcino for culture vultures and wine fans, beautiful landscape offering sporting and recreational possibilities as well as infinite calm for a romantic or family getaway.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £271 /night

£1896 - £2178 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
A holiday at Borgo Brunello provides something for everyone: 3km from Montalcino for culture vultures and wine fans, beautiful landscape offering sporting and recreational possibilities as well as infinite calm for a romantic or family getaway.  …see more

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