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from £143 / night

£1000 - £1500 / week

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(11) Excellent 5/5 

1 / 23

Holiday apartment with shared pool in Gaiole in Chianti

Apartment / 3 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £143 / night

£1000 - £1500 / week

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A bright roomy south facing 3 bed/2 bath apartment with panaramic views over Gaiole and the hills beyond. Enjoy al fresco dining on the terrace or doze in a wisteria shaded hammock. Relax by the pool, take a cycle ride or just stroll down to the village restuarants. Maggiore is ideally situated to enjoy the areas premier events including Siena Palio and Gaiole Eroica.  …see more

from £42 / night

£292 - £1278 / week

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(5) Very Good 4/5 

1 / 24

Radicondoli holiday cottage rental

Cottage / 2 Bedrooms / sleeps 5

  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4/5 

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from £42 / night

£292 - £1278 / week

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Tuscany cottage with stunning views over the Chianti hills. Private pool. Ideal for families and couples.  …see more

from £32 / night

£221 - £273 / week

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(10) Excellent 5/5 

1 / 10

Apartment rental in San Gimignano

Apartment / 1 Bedroom / sleeps 2

  • Nearest beach 72 km
  • Great for children of all ages
  • Car essential
  • No pets allowed

Excellent 5/5 

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from £32 / night

£221 - £273 / week

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The Podere Magione is immersed in the San Gimignano countryside, amidst hills covered with olive trees and vineyards. From its ideal position it is possible to quickly reach the most beautiful, historical and artistic towns of Tuscany. Podere Magione is a farm house; we produce Chianti wine, White wine and Olive oil, our Guests can test them.  …see more

Featured properties

from £122 / night

£850 - £1200 / week

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(4) Excellent 5/5 

1 / 12

Holiday villa in Val d'Orcia

Villa / 3 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning

Excellent 5/5 

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from £122 / night

£850 - £1200 / week

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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

from £163 / night

£1139 - £1851 / week

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(1) Excellent 5/5 

1 / 14

Rigomagno holiday villa rental

Villa / 5 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed

Excellent 5/5 

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from £163 / night

£1139 - £1851 / week

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Characteristic Tuscan country home in panoramic position, near the small town of Rigomagno between Cortona and Siena.  …see more

from £183 / night

£1278 - £2081 / week

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(6) Very Good 4.5/5 

1 / 24

Villa letting in Poggibonsi with swimming pool

Villa / 3 Bedrooms / sleeps 8

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4.5/5 

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from £183 / night

£1278 - £2081 / week

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Charming villa with private pool near San Gimignano. Magnificent views of the rolling Chianti hills. An oasis of peace and tranquillity.  …see more

from £42 / night

£289 - £530 / week

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(1) Excellent 5/5 

1 / 20

Gaiole in Chianti holiday apartment rental

Apartment / 1 Bedroom / sleeps 3

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £42 / night

£289 - £530 / week

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Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany. Gaiole is in the Chianti Classico area, ideal to taste and enjoy the best wines and olive oil in Italy.  …see more

from £58 / night

£405 / week

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(6) Excellent 5/5 

1 / 14

Holiday apartment in Monticchiello

Apartment / 1 Bedroom / sleeps 3

  • Nearest beach 100 km
  • Great for children of all ages
  • Car essential
  • Pets welcome

Excellent 5/5 

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from £58 / night

£405 / week

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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

from £258 / night

£1802 - £2795 / week

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(1) Excellent 5/5 

1 / 12

Castellina In Chianti holiday villa rental

Villa / 5 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed

Excellent 5/5 

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from £258 / night

£1802 - £2795 / week

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Beautiful independent restored villa (400 sqm) sleeping 10 with private pool, astro turf tennis court, gardens. Located in panoramic position on a Chianti Hillside only 5km from Castellini in Chianti. The property is surrounded by a well-maintained large garden.  …see more

from £472 / night

£3300 / week

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(1) Very Good 4/5 

1 / 24

Holiday home with shared pool in San Gimignano

House / 13 Bedrooms / sleeps 36

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages

Very Good 4/5 

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from £472 / night

£3300 / week

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On the sweet hills of the Chianti shire between vineyardand and olive groves, stands the "Podere il Pino". It offers a spectacular view on the beautiful medieval village of San Gimignano and it is very close to art cities as Florence, Siena, Pisa, Volterra and the sea.  …see more

from £249 / night

£1740 - £2285 / week

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(1) Excellent 5/5 

1 / 24

San Giovanni d'Asso holiday villa rental

Villa / 3 Bedrooms / sleeps 5

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning

Excellent 5/5 

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from £249 / night

£1740 - £2285 / week

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Italian village rental - This charming historic residence with private pool is located in the village of San Giovanni d'Asso, and it is just a short stroll from your door to the castle, the truffle museum and a nice restaurant.

 …see more

from £199 / night

£1390 - £3052 / week

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(1) Very Good 4/5 

1 / 17

Villa rental in Gaiole in Chianti with swimming pool

Villa / 6 Bedrooms / sleeps 12

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4/5 

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from £199 / night

£1390 - £3052 / week

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The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa.  …see more

from £494 / night

£3456 - £5809 / week

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(1) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in Val d'Orcia

Villa / 7 Bedrooms / sleeps 14

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

Excellent 5/5 

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from £494 / night

£3456 - £5809 / week

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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

from £75 / night

£523 - £1744 / week

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(1) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in Radicondoli

Villa / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Excellent 5/5 

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from £75 / night

£523 - £1744 / week

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Holiday house for 6 persons, with swimming pool , in Siena  …see more

from £157 / night

£1096 - £1464 / week

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(1) Very Good 4/5 

1 / 16

San Gusme holiday villa rental

Villa / 2 Bedrooms / sleeps 4

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

Very Good 4/5 

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from £157 / night

£1096 - £1464 / week

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San Donato is an exquisite gem set in rolling Chianti vineyards with views that stretch 360 degrees past a nearby 13th century hill town to Siena and into infinity.  …see more

from £53 / night

£365 - £2154 / week

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(4) Very Good 4.5/5 

1 / 24

Radicondoli holiday farmhouse rental

Farmhouse / 6 Bedrooms / sleeps 13

  • Nearest beach 55 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4.5/5 

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from £53 / night

£365 - £2154 / week

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Typical Tuscany stone farmhouse with private pool in the heart of Tuscany. Convenient position for visiting the most important historical centres in Tuscany.  …see more

from £109 / night

£758 - £1262 / week

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(1) Excellent 5/5 

1 / 25

Holiday farmhouse with shared pool in Val d'Orcia

Farmhouse / 2 Bedrooms / sleeps 4

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £109 / night

£758 - £1262 / week

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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

from £90 / night

£625 - £898 / week

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(1) Excellent 5/5 

1 / 21

Holiday villa with swimming pool in Montisi

Villa / 2 Bedrooms / sleeps 5

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary

Excellent 5/5 

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from £90 / night

£625 - £898 / week

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Villino Montisi is a splendid two-story ancient farmhouse surrounded by meadows with breathtaking views over the sweet hills of Tuscany. Recently restored following the architectural Tuscan style with the pale Tuscan stone of the façade.  …see more

from £53 / night

£365 - £1241 / week

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(2) Excellent 5/5 

1 / 24

Farmhouse rental in Casole d'Elsa with swimming pool

Farmhouse / 3 Bedrooms / sleeps 6

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £53 / night

£365 - £1241 / week

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Self-catering Tuscany farmhouse with private pool and garden for al fresco dining. Ideal for families and couples seeking relaxation.  …see more

from £200 / night

£1398 - £1692 / week

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(8) Excellent 5/5 

1 / 20

San Gimignano holiday villa rental

Villa / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

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from £200 / night

£1398 - £1692 / week

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Naturally cool stone villa for 11 persons with large private pool & gardens in San Gimignano area  …see more

from £165 / night

£1155 - £1923 / week

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(1) Very Good 4/5 

1 / 24

Holiday villa with swimming pool in Radda in Chianti

Villa / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed

Very Good 4/5 

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from £165 / night

£1155 - £1923 / week

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Adine is a fantastic, private villa situated in a typical Tuscan hamlet of private homes. It is a few minutes drive from the quaint village of Lecchi in Chianti . There are breathtaking views from the windows, terraces and pool area.  …see more

from £71 / night

£493 - £727 / week

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(1) Excellent 5/5 

1 / 24

Holiday apartment with shared pool in Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning

Excellent 5/5 

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from £71 / night

£493 - £727 / week

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A fantastic apartment, 2 bedrooms, 2 bathrooms and livingroom/kitchen. The apartment is one of the towers in beautiful Borgo Gaoile. From the livingroom/kitchen there is a wonderful view over Gaiole and the valley. The wall in the living/kitchen is a glasfoldingdoor. You can open the whole wall in the livingroom/kitchen and make an "out side room" - and what a view.  …see more

from £169 / night

£1177 - £2170 / week

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(3) Excellent 5/5 

1 / 24

Holiday villa in San Gimignano

Villa / 5 Bedrooms / sleeps 12

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £169 / night

£1177 - £2170 / week

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Self-catering Tuscan villa with private pool ideal for 8-12 persons. Each room with ensuite bathroom Private infinity swimming pool The skilful renovation of the premises has fully preserved the typical rustic Tuscan style.  …see more

from £73 / night

£511 - £1022 / week

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(3) Very Good 4.5/5 

1 / 24

Cottage rental in Casole d'Elsa with swimming pool

Cottage / 2 Bedrooms / sleeps 5

  • Nearest beach 65 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

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from £73 / night

£511 - £1022 / week

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Cottage Bel Sole is a comfortable 2 bedrooms Tuscan farmhouse with private swimming pool and sunny garden set in the beautiful countryside near Casole d'Elsa. This well furnished villa is located in a perfect position.  …see more

from £315 / night

£2203 - £4059 / week

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(7) Excellent 5/5 

1 / 24

Gaiole in Chianti holiday villa rental

Villa / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed

Excellent 5/5 

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from £315 / night

£2203 - £4059 / week

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Private Villa with pool in Gaiole in Chianti in Tuscany sleeping up to 12 people with 5 beds 5 baths in main house and a barn conversion with a separate one bedroomed apartment in the grounds. A great property for large families or groups travelling together.  …see more

from £215 / night

£1500 - £2650 / week

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(3) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in San Giovanni d'Asso

Villa / 4 Bedrooms / sleeps 8

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £215 / night

£1500 - £2650 / week

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Charming country house in idyllic setting, stunning views in unique landscape, real family home. Beautifully restored, lovely private pool in delightful gardens and olive groves, village 1 km, nearby Montalcino and Pienza  …see more

from £135 / night

£942 - £1574 / week

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(1) Very Good 4/5 

1 / 24

Holiday villa rental

Villa / 3 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed

Very Good 4/5 

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from £135 / night

£942 - £1574 / week

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Vignale is a small hamlet that has a total of 6 private homes. It is located on top of a Chianti hill that gives it the luxury of a stunning view all around. Within a short drive there are three of the five famous Chianti towns.  …see more

from £148 / night

£1030 - £1986 / week

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(4) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in San Gimignano

Villa / 4 Bedrooms / sleeps 9

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £148 / night

£1030 - £1986 / week

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Self-catering Tuscan villa with private pool ideal for 8-9 persons. Each room with ensuite bathroom Very close to the town  …see more

from £73 / night

£511 - £1424 / week

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(1) Very Good 4/5 

1 / 24

San Gimignano holiday cottage rental

Cottage / 3 Bedrooms / sleeps 8

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4/5 

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from £73 / night

£511 - £1424 / week

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Self-catering Tuscany cottage with stunning views over the Chianti hills, half way (35 km) between Florence and Siena.  …see more

from £229 / night

£1600 - £2100 / week

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(1) Excellent 5/5 

1 / 24

Holiday apartment with shared pool in Gaiole in Chianti

Apartment / 4 Bedrooms / sleeps 12

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £229 / night

£1600 - £2100 / week

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A spacious townhouse complex on two levels well suited to sharing families in easy strolling distance of restaurants, delicatessens, bars etc; large pool, gym, free bicycle hire and plenty of private outdoor space with lovely views offers something for all the family.  …see more

from £74 / night

£512 - £1100 / week

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(1) Very Good 4/5 

1 / 13

Montisi holiday villa rental

Villa / 5 Bedrooms / sleeps 10

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4/5 

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from £74 / night

£512 - £1100 / week

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Located on a hill overlooking the Val D'Orcia Tuscany's only Unesco heritage site is truly beautiful. A stay here will relax body and mind. We now offer excellent home cooked food within your house in the traditional tuscan style and cater for large or small groups.  …see more

from £172 / night

£1200 - £1950 / week

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(2) Excellent 5/5 

1 / 20

Holiday farmhouse in Castellina In Chianti

Farmhouse / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed

Excellent 5/5 

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from £172 / night

£1200 - £1950 / week

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Chianti - well situated farmhouse with beautiful views  …see more

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