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89 Holiday homes in Montepulciano

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89 Results  |  
24 Photos

Farmhouse | 7 Bedrooms | sleeps 16

Very Good 4.5/5 

1 night min stay

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from £367 /night

£2565 - £3933 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £10 /night

£69 - £428 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
we rent house in center of Montepulciano. Flat (apartment) of roughly 60 sq m (646 sq ft), located in via Cagnano 9. Restored in 2011 it is has high quality finishes and exposed beams. It consists of a large living room/kitchen, two bedrooms (one of which is a master b  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

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from £196 /night

£1368 - £1539 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

Featured properties

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £62 /night

£428 - £513 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

12 Photos

Farmhouse | 1 Bedroom | sleeps 4

1 night min stay

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from £57 /night

£399 - £570 / 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
Farmhouse apartment with seasonal outdoor pool, in Montepulciano Tuscany country estate surrounded with the wonderful Nobile-Vineyards.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

4 Nights min stay

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from £54 /night

£377 - £471 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
holiday apartments in Montepulciano. Farm stay in a wine estate in Montepulciano  …see more

9 Photos

Farmhouse | 9 Bedrooms | sleeps 22

1 night min stay

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from £86 /night

£599 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • 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

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £392 /night

£2742 - £3831 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • 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

24 Photos

Villa | 8 Bedrooms | sleeps 16

4 Nights min stay

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from £490 /night

£3428 - £3952 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • 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

23 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £289 /night

£2017 - £4839 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • 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 | 7 Bedrooms | sleeps 16

3 Nights min stay

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from £505 /night

£3529 - £5545 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • 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

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £219 /night

£1533 - £2904 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • 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

23 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £29 /night

£202 - £799 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • 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 | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £121 /night

£847 - £1210 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • 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

24 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £43 /night

£300 - £471 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
From living room and kitchen you'll enjoy a wonderful sunset on the tusca hills  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 23

7 Nights min stay

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from £550 /night

£3847 - £5984 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

18 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £281 /night

£1967 - £3249 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • 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

22 Photos

Cottage | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £37 /night

£257 - £830 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • 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

18 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £202 /night

£1412 - £1734 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Unique villa with swimming pool.  …see more

18 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £58 /night

£404 - £565 / week

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Key info:

  • Nearest beach 106 km
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The apartment has two bedrooms one big bathroom and a service bath.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £220 /night

£1539 - £2650 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great 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

17 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

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from £46 /night

£317 - £385 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
holiday resort located in the middle of a vine yard, few minutes from Montepulciano. Excellent wine for tasting  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £274 /night

£1912 - £3218 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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 £98 /night

£684 - £4189 / week

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Key info:

  • Great for children of all ages
  • 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

16 Photos

Villa | 8 Bedrooms | sleeps 18

2 Nights min stay

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from £1179 /night

£8250 - £16250 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
The exquisite villa is located in Contignano surrounded by spectacular views of rolling clay hills and countryside. The villa sleeps up to 19 in 8 very spacious bedrooms, 2 twins, 5 doubles and a lofted bedroom containing a sofa bed, a twin and a double bed  …see more

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

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from £254 /night

£1775 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Moscatella is a characteristic three-story age-old farm house surrounded by vineyards and olive groves. It sleeps six people. From Casa Moscatella you will enjoy a fascinating view of Montepulciano and of the hills of Valdichiana  …see more

24 Photos

Farmhouse | 7 Bedrooms | sleeps 16

3 Nights min stay

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from £542 /night

£3791 - £5807 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Montepulciano with 7 bedrooms sleeps 16  …see more

15 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £156 /night

£1090 - £2140 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 10 persons, with swimming pool , in Cortona  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £69 /night

£477 - £825 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Montepulciano  …see more

13 Photos

Villa | 5 Bedrooms | sleeps 13

7 Nights min stay

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from £141 /night

£981 - £2083 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 13 persons, with swimming pool , in Cortona  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £572 /night

£4000 - £6775 / 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 Cortona with 8 bedrooms sleeps 16  …see more

20 Photos

Villa | 12 Bedrooms | sleeps 24

7 Nights min stay

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from £2178 /night

£15242 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
The villa is elegant and majestic in its eighteenth century form, the location is stunning with excellent furnishing and a beautiful garden, a welcoming and cozy atmosphere in a perfect Italian style Villa.  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 16

1 night min stay

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from £565 /night

£3952 - £4678 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Ciliegia is a charming three-story historical villa surrounded by a wonderful age-old park. It sleeps 16 people. It is appoximately 600 square meters (6460 square feet). It features a private swimming pool, a private garden and winter heating  …see more

11 Photos

Farmhouse | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £147 /night

£1028 - £2023 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Foiano Della Chiana with 5 bedrooms sleeps 10  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £231 /night

£1613 - £1718 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Montepulciano with 3 bedrooms sleeps 6  …see more

16 Photos

Villa | 9 Bedrooms | sleeps 18

2 Nights min stay

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from £1179 /night

£8250 - £16250 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annex. It is surrounded by breathtaking views over the Italian countryside  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £521 /night

£3641 - £6865 / week

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Key info:

  • Great for children of all ages
  • 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

22 Photos

Villa | 6 Bedrooms | sleeps 12

rentals_reviews_rating_2 

2 Nights min stay

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from £500 /night

£3495 - £5151 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Six bedroom historical villa in the countryside of Montepulciano, a vibrant city at the heart of the Siena region of Tuscany.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £595 /night

£4161 - £7698 / week

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Key info:

  • Great for children of all ages
  • 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

17 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £526 /night

£3678 - £4613 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
A stunning residence built into the ancient city walls of the medieval and atmospheric town of Castelmuzio, BORGO ANTICO is the epitome of style and grace. Situated in the tiny but charming Piazza San Bernardino in the town's historic center  …see more

10 Photos

Farmhouse | 5 Bedrooms | sleeps 13

7 Nights min stay

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from £133 /night

£925 - £1970 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 5 bedrooms sleeps 13  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £677 /night

£4734 - £5118 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Luxury holiday house for 16 persons, with swimming pool , in Chiusi - Chianciano  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £577 /night

£4033 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Montepulciano with 8 bedrooms sleeps 16  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £577 /night

£4033 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Montepulciano with 8 bedrooms sleeps 16  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £75 /night

£522 - £1075 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
1-room apartment 25 m2: living/dining room with 1 french bed and TV. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Recently renovated in full respect of Tuscan tradition, this old farmhouse situated in a panoramic position has managed to preserve its original  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £4 /night

£25 - £11358 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
2-room apartment 40 m2: living room with 1 double sofa bed and TV. 1 double bedroom. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Recently renovated in full respect of Tuscan tradition, this old farmhouse situated in a panoramic position has managed to prese  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

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from £109 /night

£761 - £1600 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
3-room apartment 45 m2: living/dining room with 1 sofa bed and TV. 1 double bedroom. 1 room with 2 beds. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Recently renovated in full respect of Tuscan tradition, this old farmhouse situated in a panoramic position  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £91 /night

£634 - £7814 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
2-room apartment: living/dining room with 1 double sofa bed, satellite-TV and air-conditioning. 1 room with 1 french bed. Kitchenette. Bath/bidet/WC. Farmhouse 'Poggio Olivo'. In the resort, in a quiet position. For shared use: swimming pool (12 x 6 m,  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

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from £109 /night

£761 - £1600 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
3-room apartment: living/dining room with 1 sofa bed, satellite-TV and air-conditioning. 1 room with 2 beds. Room with 1 french bed. Kitchenette. Bath/bidet/WC. Farmhouse 'Poggio Olivo'. In the resort, in a quiet position. For shared use: swimming pool  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £91 /night

£634 - £1339 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
2-room apartment 40 m2: living room with 1 double sofa bed and TV. 1 double bedroom. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Recently renovated in full respect of Tuscan tradition, this old farmhouse situated in a panoramic position has managed to prese  …see more