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367 Holiday homes in Siena Province

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367 Results  |  
20 Photos

House | 1 Bedroom | sleeps 2

1 night min stay

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from £136 /night

£950 - £1195 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Emide A is a graceful apartment in a history-rich eighteenth-century estate. It sleeps two people. From Casa Emide A you will enjoy a marvelous view of the greenery. Casa Emide A is 55 square meters (590 square feet)  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

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from £114 /night

£798 - £1109 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Appartamento Reginaldo A is a pleasant and spacious villa in the characteristic style of the Tuscan countryside. It sleeps six people. From Appartamento Reginaldo A you will enjoy a view of the surrounding countryside and of the towers of San Gimignano  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Short stays welcome

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from £70 /night

£486 - £1807 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Impressive villa with private pool fantastically located in the heart of Tuscany. 6 bedrooms, huge indoor and outdoor spaces, air-conditioning, high quality traditional finishing, walking distance to shops. Unbeatable value for money.  …see more

Featured properties

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £182 /night

£1270 - £1550 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Emide B is a graceful apartment in a history-rich eighteenth-century estate. It sleeps four people. From Casa Emide B you will enjoy a marvelous view of the greenery. Casa Emide B is 70 square meters (750 square feet)  …see more

24 Photos

Villa | 18 Bedrooms | sleeps 35

7 Nights min stay

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from £3725 /night

£26075 - £46140 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden

Total Luxury - Italy special occasion villa with services - this magnificent 14th century estate is situated in the heart of rural Tuscany between San Gimignano and Siena. The villa's hilltop position offers wonderful 360 degree views of the surrounding countryside

 …see more

20 Photos

House | 1 Bedroom | sleeps 2

1 night min stay

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from £136 /night

£950 - £1195 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Emide C is a graceful apartment in a history-rich eighteenth-century estate. It sleeps two people. From Casa Emide C you will enjoy a marvelous view of the greenery. Casa Emide C is 50 square meters (540 square feet)  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £104 /night

£726 - £807 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Leopoldo C is a romantic 65-square-meter (about 700 square feet) apartment which sleeps two people. It features a view to the hills famous as 'Crete Senesi '. There is also a shared swimming pool and shared gardens  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £60 /night

£416 - £755 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children over
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
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

20 Photos

Villa | 6 Bedrooms | sleeps 18

7 Nights min stay

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from £1072 /night

£7500 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Its independent location surveys a luminous valley in the heart of Tuscany, where you will have the chance to enjoy the beauty of a new discovered nature also through the taste of its cuisine.  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £180 /night

£1260 - £1450 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Appartamento Cecco C is an elegant and welcoming apartment. It sleeps six people. It is appoximately 90 square meters (970 square feet)  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 5

1 night min stay

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from £111 /night

£776 - £1066 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Appartamento Reginaldo G is a charming villa in the characteristic style of the Tuscan countryside. It sleeps five people. From Appartamento Reginaldo G you will enjoy an enchanting view of the surrounding countryside and of the towers of San Gimignano  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

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from £58 /night

£404 - £589 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Prospero E is a graceful apartment surrounded by the vegetation. It sleeps four people. From Casa Prospero E you will have a view of the swimming pool and of the garden and of the surrounding countryside. Casa Prospero E is 100 square meters (1076 square feet)  …see more

16 Photos

Villa | 9 Bedrooms | sleeps 18

2 Nights min stay

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from £1179 /night

£8250 - £11250 / 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

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £104 /night

£726 - £807 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Leopoldo D is a romantic 60-square-meter (about 646 square feet) apartment which sleeps two people. It features shared swimming pool and garden  …see more

19 Photos

Villa | 6 Bedrooms | sleeps 11

2 Nights min stay

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from £774 /night

£5412 - £7576 / 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
Lovely Villa situated in the Chianti area between the provinces of Florence and Siena. The location, in the heart of Tuscany, is rich in history with many Renaissance cities and towns nearby, including Florence, Siena, San Gimignano, and Volterra.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £58 /night

£404 - £589 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Prospero F is a characteristic apartment surrounded by the vegetation. It sleeps four people. It is appoximately 100 square meters (1076 square feet)  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £124 /night

£868 - £1735 / week

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Key info:

  • Nearest beach 65 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Attractive holiday house for 5 persons, with swimming pool , in San Gimignano  …see more

9 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £104 /night

£726 - £1679 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Holiday house for 4 persons, with swimming pool , in San Gimignano  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

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from £82 /night

£573 - £1307 / week

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Key info:

  • Nearest beach 107 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Located within walking distance of the village of Gaiole in Chianti, the villa offers the perfect setting to explore the Chianti Classico region, enjoy the breathtaking views of the vineyards and olive groves, and experience the charming Tuscan lifestyle. Beautiful villa located within walking distance of the village of Gaiole in Chianti, near Siena, Tuscany  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £346 /night

£2420 - £3630 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Eracle is a bright and elegant three-story villa surrounded by vineyards and olive groves. It sleeps eight people. From Villa Eracle you will enjoy a fascinating view of the Chianti hills and of the vineyards  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £46 /night

£319 - £609 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
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 wine and food in Italy.  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £353 /night

£2470 - £3250 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Calpurnia is a charming two-story historical villa situated in the heart of the Tuscan countryside. It sleeps eight people. From Villa Calpurnia you will enjoy a spellbinding view of the Chianti hills and of the vineyards  …see more

16 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £689 /night

£4823 - £6283 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
La Maccinaia is a beautiful property located in a very quiet location, in the heart of the Chianti region, between Gaiole and Castelnuovo Berardenga. The main villa dates to the 17th century, and has been immaculately restored by its Belgian owner who combined modern  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £83 /night

£581 - £775 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Sole is an apartment of 50 square meters (about 538 square feet), for four people. It is part of an historic stone house, and has a patio, it also shares a pool and a 4000 square meter (about 1 acre) park  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £300 /night

£2100 - £3990 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Toiano is a quaint, lovingly decorated property. The stones and the old ceiling beams have been incorporated into a beautifully-finished new country home that oozes personality and charm.  …see more

20 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £503 /night

£3516 - £5680 / 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
This beautifully restored 14th century farmhouse sits within a farming estate on a hilltop with magnificent views over the soft hills of the Arbia river valley.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £69 /night

£480 - £686 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Monia D is a welcoming cottage made of stone. It sleeps four people. From Casa Monia D you will have a pleasant view of the Tuscan hills. Casa Monia D is 50 square meters (540 square feet)  …see more

20 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £957 /night

£6694 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Relais Chianti is a typical Tuscan homestead from the early 1800s located in the unmistakable Chianti Classico countryside, in the renowned vine-growing and wine-making region.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £650 /night

£4550 - £5850 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden

Centred around a pretty garden, Casa Vittorio is a notable, historic residence set over several levels and elegantly furnished. It is in a village location, just a short stroll from a restaurant, the castle and the truffle museum.

 …see more

15 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £100 /night

£699 - £1034 / 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
Apartment for 4 persons, with swimming pool , in Montepulciano  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £119 /night

£830 - £1906 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Attractive holiday house for 4 persons, with swimming pool , in San Gimignano  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £67 /night

£464 - £553 / week

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Key info:

  • Nearest beach 72 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
This charming farmhouse complex is the result of a recent and elegant restoration of a typical Tuscan country complex, near the town of Casole d'Elsa, in the province of Siena.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £1508 /night

£10550 - £14675 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Large air conditioned villa near Siena - Villa Santa Caterina is an imposing fully restored 13th-century monastery, subsequently used as a farmhouse, which has been transformed into an elegant country holiday house.  …see more

6 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £74 /night

£512 - £911 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Apartment for 4 persons, with swimming pool , in San Gimignano  …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

24 Photos

Villa | 3 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

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from £249 /night

£1740 - £2285 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden

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

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £511 /night

£3573 - £5073 / 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
This Italian vacation rentals Villa has its independent location surveys a luminous valley in the heart of Tuscany, where you will have the chance to enjoy the beauty of a new discovered nature also through the taste of its wine and Italian cuisine  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £612 /night

£4280 - £4790 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden

This charming Italian property has been carefully restored by the owner as a fine example of Tuscan rural 18th century style.

 …see more

20 Photos

Villa | 1 Bedroom | sleeps 2

1 night min stay

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from £73 /night

£509 - £565 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Beata E is a characteristic apartment made of stone. It sleeps two people. From Villa Beata E you will enjoy a pleasant view of the Tuscan countryside  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 6

1 night min stay

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from £64 /night

£444 - £847 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Villa Davide F is an elegant apartment surrounded by the vegetation. It sleeps six people. From Villa Davide F you will enjoy a pleasant view of the Tuscan countryside. Villa Davide F is 80 square meters (860 square feet)  …see more

20 Photos

Cottage | 2 Bedrooms | sleeps 6

1 night min stay

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from £96 /night

£670 - £960 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Casa Porzia is a gracious cottage of 80 square meters (about 860 square feet) for six people, with garden and access to a pool of 7 X 14 meters (23 X 46 feet)  …see more

24 Photos

Villa | 1 Bedroom | sleeps 4

7 Nights min stay

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from £76 /night

£530 - £663 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Holiday house for 4 persons, with swimming pool , in Siena  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £478 /night

£3343 - £4382 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Cottage in the tuscan countryside close to Siena and Florence, in the Chianti shire. Typical tuscan style and very comfortable place. Swimming pool and huge garden.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £81 /night

£561 - £803 / week

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Key info:

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

23 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

5 Nights min stay

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from £83 /night

£575 - £900 / week

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Key info:

  • Nearest beach 55 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautifully restored 16th century Granary building; stunning views of the Tuscan hills. Perfect for a romantic holiday; explore the best Tuscany has to offer or a family getaway. Gorgeous pool area and large private garden. Easy access to Florence, Pisa and Siena. The house has been tastefully renovated and is equipped to a very high standard throughout.  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £116 /night

£808 - £1119 / week

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Key info:

  • Swimming pool
  • Suitable for children over
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Sleeps 6. 3 bedroom apartment with two private covered terraces and shared pool. Central heating. Peaceful location with panoramic views of the countryside. 20 minutes drive to San Gimignano. 50km to beaches. 20 min drive to golf course.  …see more

12 Photos

Hotel apartment | 10 Bedrooms | sleeps 20

Short stays welcome

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from £122 /night

£854 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Dimora Storica di lusso con migliori viste della Toscana. Vicino a Chianti, Monteriggioni, Siena, San Gimignano, Volterra, Firenze, Pienza e Montepulciano. Sperimentate la magia di un luogo senza tempo dove la storia incontra la natura e la tranquillità avvolge l'anima Appartamenti di Lusso, Spa,Piscina, Sauna, Bagno turco, ristorante, vista su Siena,relax, Tuscan Experience.  …see more

15 Photos

Villa | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £115 /night

£803 - £1206 / week

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Key info:

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

24 Photos

Villa | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £623 /night

£4355 - £6291 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Villa Magda is a luxurious villa in San Gimignano, and is perfect for a large group of family or friends that appreciate tranquility, privacy, and beautiful natural surroundings.  …see more

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Cottage | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £35 /night

£242 - £783 / 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