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66 Holiday homes in Pienza

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66 Results  |  
12 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

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from £73 /night

£509 - £539 / week

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Key info:

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

14 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £165 /night

£1155 - £1582 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Pets welcome
In Podere Malabiccia all the rooms enjoy views of the surrounding landscape. Sunroom with west-facing arced windows. Kitchen with a large fireplace and antique wood burning oven. Living room and informal dining room with a fireplace. Antique Tuscan ceramics. Garden. The city of Pienza (UNESCO location) is 10 km away, Montepulciano 15, Siena 65, Arrezzo 40, Perugia 65.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

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from £233 /night

£1625 / week

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Key info:

  • Swimming pool
  • Great 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

Featured properties

19 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £153 /night

£1069 - £1838 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Beautiful independent country house near Pienza. This villa is located few minutes driving from Pienza, in a quiet and beautiful location in the middle of the country side. Private swimming pool. The villa is elegantly furnished, in a perfect combination between comfort and tradition  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £45 /night

£313 - £590 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa PoliFlora is a modern residence consists of two bedrooms and two bathrooms with a shared kitchen. The owners husband and wife Poli and Flora built the villa in 1988 and from there they guard with love the classic environment of the house surrounded by garden. Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site.  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £81 /night

£565 - £605 / week

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Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Enjoy Tuscany, in a unique village in a UNESCO world heritage site: access to art, good food and excellent wine.  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

1 night min stay

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from £58 /night

£404 - £444 / week

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Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
If you are looking for a romantic holiday, away from it all, in a perfect Tuscan village, to discover secret Tuscany this is the place: good food, wine , art and all set in an unique landscape.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £138 /night

£960 - £2057 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
It is the most photographed house in the area, a symbol of the Tuscany countryside, featured on many postcards and calendars simply because it has maintained the charm of the old farmhouse and the surrounding fields, without any new buildings as far as the eye can see.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £217 /night

£1513 - £2097 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Everybody who loves Tuscan tradition, excellent cuisine, biological food and, why not, horse riding and biking, besides a relaxing visit to thermal spas will be enchanted by this area.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £80 /night

£557 - £847 / week

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Key info:

  • Nearest beach 95 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This Tuscan 17th century farmhouse with 2 bedrooms, Villa Arpicella, is located very close to Pienza and it enjoys the stunning countryside setting with spectacular wide open views.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £145 /night

£1009 - £1492 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Casa Oriolo is an elegant apartment with 3 bedrooms and it is part of a small complex with 3 apartments total sharing a pool. Here you can enjoy a sojourn in contact with nature in a protected and uncontaminated oasis.  …see more

15 Photos

Townhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £101 /night

£706 - £908 / week

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Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
In the very center of a lovely ancient medieval village stands Casa Marelli. Recently carefully restored preserving all the traditional Tuscan characteristics of the building such as wooden beamed ceilings and brick work arches.  …see more

24 Photos

Lodge | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £198 /night

£1385 - £2522 / 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
Modern and tastefully decorated cottages with an infinity swimming pool where you can totally relaxed surrounded by the typical tuscany landscape: a fantastic view. Perfect for families, couples or groups of friends to enjoy cultural, art, good wine and italian food:  …see more

11 Photos

House | 6 Bedrooms | sleeps 12

Short stays welcome

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from £692 /night

£4839 - £6174 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
In this paradise, guests can enjoy deep blue skies, starry nights and silence, a unique and rare commodity nowadays. The property offers: - spacious, fully equipped family kitchen - living room with large fireplace  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

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from £87 /night

£607 - £642 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
The building includes four brand new completely independent flats, structured on two floors; they are very new and furnished in a modern manner, equipped with all comforts like a kitchen supplied with all of the tools and household appliances, colour TV-Set, autonomous  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

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from £87 /night

£607 - £642 / week

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Key info:

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

6 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

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from £73 /night

£509 - £539 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
“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

20 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £323 /night

£2259 - £2702 / week

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Key info:

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

20 Photos

Manor House | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £859 /night

£6009 - £7702 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Tenth century posting house which has kept its charm. Large garden with swimming pool.  …see more

20 Photos

Farmhouse | 6 Bedrooms | sleeps 13

7 Nights min stay

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from £530 /night

£3710 - £4275 / week

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Key info:

  • Nearest beach 44 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Wonderful Tuscan villa with pool.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £461 /night

£3226 - £3791 / 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
  • Private garden
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below.  …see more

15 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £657 /night

£4597 - £6170 / week

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Key info:

  • Nearest beach 44 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Situated between Monticchiello and Montepulciano in a secluded and extremely quiet position it is an attractive farmhouse surrounded by lavender and rosemary bushes. The large garden overlooks the valley like a terrace from where you can see one of the loveliest views.  …see more

18 Photos

Apartment | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £154 /night

£1078 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Farmhouse Agriturismo "Torrenieri" is at a short distance from the main tourist attractions of Siena and its surroundings. For instance, unique points of interest regarding art, culture and gastronomy are Pienza (4km far), Montepulciano (16km far), Montalcino (20km far) Free Internet Wireless Pets are welcome only with advance notice.  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £505 /night

£3529 - £5242 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
If a villa holiday in Tuscany is calling to you, take a closer look at Villa Magna. This property provides ample room for twelve guests, offering six beautiful bedrooms and a variety of other features you'll fall in love with on first sight.  …see more

23 Photos

Apartment | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £113 /night

£787 - £1437 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Terrace - pool - Wine - Brunello - spa - restaurants - shops - great standard - wine tours - cycling - walking - big jacuzzi on roof terrace - wifi - AC - Sky TV - SMEG Jacuzzi on the roof terrace with beautiful views over Montalcino - home of the famous Brunello wine. Truly a luxorius flat with stunning views from the roof terrace  …see more

9 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £283 /night

£1976 - £2682 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Situated in a prominent position overlooking the Val d'Orcia, this villa for rent in Tuscany offers incredible views and is in a peaceful and natural setting.  …see more

12 Photos

Farmhouse | 6 Bedrooms | sleeps 14

7 Nights min stay

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from £317 /night

£2217 - £5992 / 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
Villa / Farmhouse / Home in Pienza with 6 bedrooms sleeps 14  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £86 /night

£597 - £974 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 6 persons, with swimming pool , in Pienza - Montalcino  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £56 /night

£388 - £684 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Attractive apartment for 4 persons, with swimming pool , in Pienza - Montalcino  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

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from £366 /night

£2559 - £6139 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury holiday house for 14 persons, with swimming pool , in Pienza - Montalcino  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 16

2 Nights min stay

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from £704 /night

£4928 - £7665 / 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
Just six kilometres from the Renaissance masterpiece town of Pienza, yet light years away from the stresses of modern living, this luxury 8-bedroom farm conversion has the cosiest of interiors, the most luxurious of finishes and the warmest of welcomes awaiting.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £67 /night

£469 - £817 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Attractive apartment for 5 persons, with swimming pool , in Pienza - Montalcino  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 14

7 Nights min stay

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from £346 /night

£2420 - £6777 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Pienza with 8 bedrooms sleeps 14  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £80 /night

£557 - £908 / 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
Villa / Farmhouse / Home in Pienza with 3 bedrooms sleeps 6  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £52 /night

£363 - £636 / 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
Villa / Farmhouse / Home in Pienza with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £331 /night

£2311 - £3163 / week

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Key info:

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

20 Photos

Villa | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £384 /night

£2687 - £5606 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Hidden at the end of a long drive through never ending fields of wheat, you will find this enchanting farmhouse surrounded by a typical Mediterranean garden with rosemary, lavender, sage and flowers in every season.  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

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from £482 /night

£3368 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
We're excited to introduce this wonderful typical Tuscan villa, it ticks all the boxes, it's incredibly old with heaps of character, yet has just been renovated to the highest spec, in a breathtaking location just a short drive from one of our favourite towns, Pienza  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £353 /night

£2469 - £3379 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Holiday house for 10 persons, with swimming pool , in Montepulciano  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £63 /night

£436 - £763 / 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
Villa / Farmhouse / Home in Pienza with 2 bedrooms sleeps 5  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 14

7 Nights min stay

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from £346 /night

£2420 - £6777 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
stunning villa, located in Tuscany Italy, has a max. capacity of 14 people. This stunning villa is perfect for families and friends  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £922 /night

£6452 - £8065 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This exclusive villa works as the perfect starting point to explore the countryside and all the art cities in Tuscany and their surroundings. It is spacious, airy, welcoming and fully equipped and accommodates up to 16 people.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

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from £317 /night

£2217 - £5992 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Set in Tuscany Italy, this charming villa is the ideal place for your holidays. The villa offers: a swimming Pool, air Conditioning, an internet Connection .  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £331 /night

£2311 - £3163 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Set in Tuscany Italy, this grand villa is the perfect place for your holidays. The villa features: a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £195 /night

£1363 - £1928 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Elegant and affordable villa in Val d'Orcia, near Pienza (Siena). Riding stable, tennis club and thermal baths within a few kilometres. Wide garden, swimming pool, Internet connection, hydromassage.  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 14

3 Nights min stay

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from £152 /night

£1063 - £1932 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Self-catering farmhouse for groups of 10 or 14 at different prices near Pienza, in Val d'Orcia. Swimming pool, children's playground, barbecue, table-tennis table, mountain bikes. Partly accessible to people with disabilities.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £880 /night

£6159 - £8161 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Dongiovanni is a Premier Villa located in Pienza near Siena, Tuscany, central Italy. Recently renovated to the highest standard, the property is a deluxe country house in the beautiful Val DOrcia in the south eastern part of the Siena province in Tuscany. This is a r  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £41 /night

£283 - £308 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Delizioso appartamento in un angolo di paradiso per una vacanza all'insegna del relax  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £74 /night

£513 / 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
Quattro appartamenti indipendenti - Ristorante di ottimo livello - Colazione a buffet - Piscina esterna - Piscina esterna idromassaggio non riscaldata - Internet wi fi free - Giardino e spazi esterni attrezzati - Parcheggio coperto riservato - Tv satellitare - Appartamento Pagliaio, pianterreno, è composto da una camera matrimoniale, una cucina e un bagno con doccia  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £107 /night

£744 / 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
Quattro appartamenti indipendenti - Ristorante di ottimo livello - Colazione a buffet - Piscina esterna - Piscina esterna idromassaggio non riscaldata - Internet wi fi free - Giardino e spazi esterni attrezzati - Parcheggio coperto riservato - Tv satellitare - Granaio, su due piani, camera matrimoniale + camera due letti singoli, una cucina, due bagni, uno con doccia  …see more