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555 Holiday homes in Province of Siena

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555 Results  |  
6 Photos

Villa | 2 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £70 /night

£484 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Una vacanza all'insegna del riposo con l'alternativa di poter viaggiare e visitare i luoghi che furono di Dante, dei Medici e di quanti hanno sete di cultura. Gaiole in Chianti cittadina divenuta famosa per "L'EROICA" si trova al centro della Toscana.  …see more

13 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

3 Nights min stay

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from £73 /night

£509 - £573 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
In open countryside, but near just few minutes drive to Siena, is the ideal location for visiting Tuscany. Historic farmhouse, nestled in a unique setting, a large park reserved for guests, ideal for families, groups of friends who love the tranquility and beauty.  …see more

17 Photos

Farmhouse | 8 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £208 /night

£1452 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Pets welcome
  • Private garden
il casale Roccone è immerso nel verde del monte Amiata, con oltre cento ettari di parco naturale privato all'interno della riserva del Pigelleto. 12 posti letto, possibilità di avere un servizio di cuochi, visite guidate nella miniera, passeggiate nella foresta. Il Roccone ha anche una sala multimediale, adatta per corsi yoga, pilates, proiezioni, conferenze.  …see more

Featured properties

23 Photos

Villa | 6 Bedrooms | sleeps 11

Excellent 5/5 

1 night min stay

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from £58 /night

£404 - £3307 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Villa in Chianti/Siena, Tuscany, Italy On top of a Hill with Private Pool and Large Terrace A Haven of Peace and Quietness, 20 Minutes from Siena Sleeps 11 (6 Bedrooms with en suite bathrooms) For parties of 2 or 4 people the villa will be shared , unless the guests are willing to pay an exta  …see more

24 Photos

Townhouse | 5 Bedrooms | sleeps 12

Excellent 5/5 

2 Nights min stay

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from £75 /night

£525 - £1976 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
SERVIZI Inclusi nel prezzo: televisione in soggiorno e in ogni camera, biancheria da bagno e da letto con cambio settimanale, stoviglie cucina, acqua, luce, gas, utilizzo lavatrice, utilizzo barbecue, parcheggio auto, utilizzo piscina da metà giugno a metà settembre. Prima Colazione Mezza pensione nel nostro ristorante a Sinalunga (3 km) Animali domestici ammessi  …see more

24 Photos

B&B | 4 Bedrooms | sleeps 10

Excellent 5/5 

1 night min stay

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from £139 /night

£968 - £2017 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Agriturismo termale convenzionato con stabilimento Fonteverde spa, prodotti agricoli, natura piscina, relax holiday, laghi e montagne, wine testing e percorsi enogastronomici.  …see more

11 Photos

B&B | 6 Bedrooms | sleeps 12

1 night min stay

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from £57 /night

£396 / 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
Situato nel piccolo borgo di Iesa, frazione di Monticiano, il casale mette subito a proprio agio, la gestione è a conduzione familiare e il clima che vi si respira fa sentire l'ospite a casa.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 16

Excellent 5/5 

1 night min stay

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from £75 /night

£524 - £1210 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Exclusive estate on top of a green hill, the image that you have is to be completely isolated from the world, from the pool and terrace overlooking a panoramic view of Siena and unique, just 4 km away and do at your disposal all the civilizations that you want!  …see more

6 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £172 /night

£1202 - £2998 / 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
Beautiful stone-built farmhouse that has been perfectly restored and equipped with all of the modern conveniences, situated in the heart of the Chianti Classico close to the typical tuscan town of Radda.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 13

7 Nights min stay

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from £456 /night

£3186 - £5242 / 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
Luxury Villa near Pienza, ideal for large families or friend's group.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £655 /night

£4581 - £7601 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa in San Casciano Dei Bagni with 5 bedrooms sleeps 10  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £185 /night

£1291 - £1775 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Colletalli is an ideal location to recharge ones energy away from the humdrum of daily life conveniently located within 1 hour motoring of Florence, Siena, Sangimignano, Volterra, sandy beaches  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £225 /night

£1573 - £3670 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This superb villa with pool in Tuscany is located at 8 km from the pretty medieval village of Asciano, 30 km east of Siena. Surrounded by a private garden full of olive trees, this holiday home has been renovated to an extremely high standard  …see more

22 Photos

Cottage | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £194 /night

£1355 - £1775 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This holiday home in Tuscany is immersed in the green countryside of the Sienese hills, between the Chianti area and the Val d'Orcia. Located 40 km east of Siena, this charming old farmhouse is quite near to the medieval villages of Lucignano and Sinalunga,  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 21

3 Nights min stay

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from £260 /night

£1815 - £3392 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This beautiful holiday home in the Val d'Orcia, surrounded by gently rolling hills, is near Castiglione d'Orcia (12km), just a few kilometres from the famous spa waters at Bagno Vignoni (10km) and Bagni San Filippo (7km). Surrounded by peace and quiet  …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

24 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £461 /night

£3226 - £3670 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
A delightful Villa in Siena overlooking a small lake between woods and rolling hills. A beautiful spot for a large family.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 13

7 Nights min stay

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from £836 /night

£5847 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Independent farmhouse that sleeps 13 people. The main house sleeps 6. On the ground floor there are a large living room with fireplace, library, hi-fi, TV, DVD, small kitchen, a double bedroom with a separate entrance from the outside with an en-suite bathroom  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £1479 /night

£10348 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
This large farmhouse was famous as far back as the 10th century as a post-house for changing coaches and horses along the Via Francigena and the architecture of the house shows this origin.  …see more

19 Photos

Apartment | 10 Bedrooms | sleeps 22

3 Nights min stay

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from £404 /night

£2823 - £5807 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
The whole property Sassi Bianchi is ideal for large groups, because there are four farmhouses, each family live in its farmhouse and you can be together for dinner or to another at Lilium farmhouse Also swimming pool, tennis court, booling green is only for you  …see more

22 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

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from £521 /night

£3642 - £5815 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Enchanting typical Villa located in the very heart of Chianti between Siena and Firenze.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 12

Short stays welcome

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from £231 /night

£1613 - £2420 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Molino la Senna is a beautiful house for families and groups - a pool set in the landscape, a great pizza oven and fantastic wysteria.  …see more

9 Photos

Villa | 10 Bedrooms | sleeps 20

1 night min stay

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from £611 /night

£4275 - £5081 / 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
Typical Tuscan villa, ancient and charming. Large Dining room with huge fireplace (15 century). Frescoed ballroom. Some of the bedrooms are frescoed too. Extensive gardens with table to have dinners outside. Panoramic pool area overlooking Siena, the Chianti area.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £283 /night

£1976 - £3605 / 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
Nearby there are others agreeable towns like Pienza, Cortona, San Quirico d'Orcia, making it an ideal destination from which to savor the full essence of Tuscany. All around the villa an enchanting garden equipped with gazebo, table and chairs, the swimming pool  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £1048 /night

£7334 - £9789 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Born from the careful restoration of an ancient manor's dwelling, this enchanting property comprises two restored historic farmhouses: the manor's farmhouse and the independent guest house. Surrounded by 20 hectares of ground, it comprises woods, an olive grove  …see more

12 Photos

Villa | 8 Bedrooms | sleeps 25

7 Nights min stay

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from £93 /night

£646 - £2823 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany, Toscana, Casale, Piscina, Vigneto, Corsi cucina, Caccia al tartufo, Villa, Casa Vacanze, Italia, Equitazione, Matrimonio, matrimoni, eventi, lusso, Catering ;Tastings and Wine Tour's; Truffle Hunting ;Cooking Classes; Excursions; Horse Riding  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £553 /night

£3871 / 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
Cosoli is located in Chianti Classico, conveniently half way from Florence and Siena. The villa overlooks a massive olive grove but yet surrounded by a great view of surrounding vineyards and small cities in the distance. 3 hours weekly housekeeping is included as well as the complete house cleaning after leaving.  …see more

21 Photos

House | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £384 /night

£2688 - £3648 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Walk to the local restaurants & grocery store or drive a short distance to numerous historical towns, but still enjoy the privacy & beautiful scenery of Tuscany. Dine 'al-fresco' under the vine-draped pergola & swim in the pool that looks out upon a timeless landscape. If you desire privacy with convenience; scenic views without isolation, Casa Oliveto is for you!  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £416 /night

£2908 - £4065 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden
Is a typical Tuscan “farm” from the 1800's located in the heart of Tuscany, in the municipality of Pienza in the province of Siena, and in the Val d'Orcia Natural Park nominated by UNESCO as a human patrimony. At 500mt above sea level it has a unique view  …see more

12 Photos

Villa | 7 Bedrooms | sleeps 14

3 Nights min stay

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from £431 /night

£3013 - £3870 / 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
Villa with swimming-pool just five kilometers from Siena in the middle of Tuscany. Originally a 17th century chapel, Villa del Cielo has been tastefully converted into a charming and unique villa rental in Tuscany.  …see more

24 Photos

Castle | 6 Bedrooms | sleeps 14

Short stays welcome

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from £346 /night

£2420 - £3307 / 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
Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

18 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £265 /night

£1855 - £4597 / 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

24 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £196 /night

£1371 - £4275 / 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
Splendid villa with breathtaking view over the Castle of Strozzavolta, in the Chianti, between Florence and Siena.  …see more

4 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Short stays welcome

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from £223 /night

£1560 - £2760 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Farm Holiday for rent in Siena Toscany 6 bedrooms Farm Holiday for rent in Siena Firenze Toscany Italy  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

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from £208 /night

£1452 - £2823 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa in Siena with SPA room, exclusive use.  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £116 /night

£806 - £896 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Large, comfortably equipped and well furnished apartment, all the furniture is from the 19th century and has been recently restored, "La Fattoria" is situated at the centre of the ancient village and has got a private, fenced garden.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £194 /night

£1355 - £1896 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Beautiful house with private pool in one of the most interesting area of Tuscany. It also perfect for trekking, jogging and mountain biking among the forests of Monte Amiata.  …see more

15 Photos

Watermill | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £202 /night

£1412 - £2138 / 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
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

21 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £86 /night

£600 - £880 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
On the first floor of the villa, Camelia is the most elegant of our apartments.It has a living room with a large fresco, a large kitchen/dining room, double bedroom and bathroom. (with shower stall). Enfant bed  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £271 /night

£1892 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Independent Farm house. Childrens play ground with games. Air conditioned with seven bedrooms. Fenced swimming pool. Can sleep up to 18 people if required. Disabled friendly bathroom in one room.  …see more

14 Photos

Cottage | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £162 /night

£1130 - £2017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
The Romance Cottage represents a slice of Italian life that's not easily replicated. This lovely cottage is set in a residential neighborhood less than two miles or a 10 minute drive from Siena with easy access into the city.  …see more

8 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £185 /night

£1291 - £2017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Not far from Siena, for 5 minutes along the road from San Gimignano goes towards Gambassi, we find the gates of Villa Panorama. It is an old building of more than 5 centuries and tastefully decorated and with quality furniture and style typical of the villas in Tuscany  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 23

7 Nights min stay

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from £519 /night

£3630 - £5646 / 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

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £164 /night

£1148 - £1394 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
The old style restoerd flats can offer a perfect feeling of Tuscany. The large garen with view will grant you of unforgettable sunsets over the hills. A large garden with 6x12 mt swimming pool and a very nice barbeque area are at the guest's disposal. In summertime is absolutely nice to go by bike/walking/jogging, it's very easy to find people doing the same  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £150 /night

£1049 - £1775 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Offers a unique view of the surrounding valley typical of the Sienese hills (olives and grapes) and is located a short distance (3 km) from the town of San Gimignano famous for its medieval towers.  …see more

24 Photos

Apartment | 8 Bedrooms | sleeps 15

7 Nights min stay

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from £507 /night

£3549 - £5726 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
This lovely 18th century villa with swimming-pool in Val d'Orcia is located near Pienza, surrounded by the gently rolling hills of this magnificent countryside  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £93 /night

£646 - £1855 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Tuscany. Heart of Chiant.iExclusive use of private swimming pool. The Villa accommodates up to 8/9 people. Beautiful views of the country side. Only a few other farmhouses are visible in the distance. Outdoor dining area. Fontecaresino, located in the hills of Chianti, in the heart of Tuscany. Breathtaking views.  …see more

24 Photos

Apartment | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £1078 /night

£7541 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
An Independent farmhouse that sleeps 14 with designer furnishings yet with rustic flavour and style. Very nice swimming pool and is well positioned for touring Tuscany.  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £306 /night

£2138 - £2904 / 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

21 Photos

Tower | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £98 /night

£686 - £726 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Torre Romantic View Lake Vineyards Olive Grouth Swimming Pool Wine Relax Families Childrens Peacefull The Torre is 1,5 km from Radda enjoing all the facilities of a charming small village. Full of Activities!  …see more

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