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90 Holiday homes in Gaiole in Chianti

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90 Results  |  
20 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £143 /night

£998 - £1205 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 5 persons, with swimming pool , in Siena  …see more

20 Photos

House | 4 Bedrooms | sleeps 7

1 night min stay

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from £550 /night

£3850 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Diora A is a splendid sixteenth-century two-story apartment that is part of a villa situated in the heart of the Tuscan countryside. It sleeps seven people. From Villa Diora A you will enjoy an enchanting view of the Chianti hills and of the vineyards  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £140 /night

£980 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Diora B is a characteristic and welcoming apartment that is part of a villa surrounded by vineyards and olive groves. It sleeps six people. From Villa Diora B you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

Featured properties

16 Photos

House | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £611 /night

£4273 - £6281 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Il Colombaio is a peaceful oasis in the heart of Chianti Classico, with expansive views on rolling hills and rows of vineyards. The location, near the village of Gaiole in Chianti, is perfect for visiting the several hilltop villages such as Radda, Castellina and Greve  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £129 /night

£900 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Diora D is a characteristic and welcoming independent house surrounded by vineyards and olive groves. It sleeps four people. From Villa Diora D you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £214 /night

£1494 - £1966 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Tuscan Sunandnbsp;is a holiday villa in Tuscany, in the municipality of Gaiole, in Siena. With an outdoor swimming pool and antique furnishing, the villa is ideal for an Italian vacation. Villa Tuscan Sun is situated on the green sloping hills of Siena, offering  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £123 /night

£861 - £1182 / week

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Key info:

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

16 Photos

House | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £551 /night

£3852 - £6604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

12 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £93 /night

£648 - £1507 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole -Apartment Yardandnbsp;is a rental holiday apartment inandnbsp;Gaiole, Chianti, in the province of Siena, Tuscany . The Chianti area is spread across the provinces of Florence and Siena and includes the municipalities ofandnbsp;Greve, Panzano, Radda, Gaiole and  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

5 Nights min stay

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from £189 /night

£1323 - £4744 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Il Giglio is a charming private villa located in the Chianti Senese area surrounded by a spacious 6000 sq mt parkland which is completely fenced in though giving access through an electronic gate. The villa has a lovely swimming pool ( 6 x 12 mts) with a  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £355 /night

£2480 - £3720 / week

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Key info:

  • Swimming pool
  • Suitable 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

8 Photos

B&B | 2 Bedrooms | sleeps 2

3 Nights min stay

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from £86 /night

£602 - £1339 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Archesandnbsp;is ideally located inandnbsp;Chianti countryside. It is on theandnbsp;ground floor, aboutandnbsp;80 m2, can comfortably sleepandnbsp;3andnbsp;people.andnbsp; There is aandnbsp;living roomandnbsp;with open fireplace,andnbsp;dining room,  …see more

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £142 /night

£992 - £2404 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • May take pets – please enquire
This beautiful, detached farmhouse has been carefully restored by the architect owner to the highest standards. He has maintained the original structure, while adding modern design ideas.  …see more

16 Photos

House | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £505 /night

£3529 - £5182 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Il Colombaio is a peaceful oasis in the heart of Chianti Classico, with expansive views on rolling hills and rows of vineyards. The location, near the village of Gaiole in Chianti, is perfect for visiting the several hilltop villages such as Radda, Castellina and Greve  …see more

9 Photos

B&B | 1 Bedroom | sleeps 2

3 Nights min stay

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from £86 /night

£602 - £1339 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartmentandnbsp;Barnandnbsp;is located in splendid Chianti country side on the ground floor, can comfortably accommodate andnbsp;twoandnbsp;people.andnbsp; There is aandnbsp;double bed roomandnbsp;with open fireplace,andnbsp;small kitchen, bath room with hydro  …see more

8 Photos

Apartment | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £120 /night

£834 - £2120 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Nestandnbsp;is a striking countryside apartment inandnbsp;Gaiole in Chianti, a municipality in Siena, Tuscany 'Forbes', a reputed American magazine, rates Gaiole in Chianti as "Europe's . Theandnbsp;Chianti Classico wineandnbsp;region is situated to  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 13

3 Nights min stay

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from £992 /night

£6943 - £8100 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This exclusive villa with private swimming pool and tennis court offers luxurious accommodation in Tuscany for 13 people. The apartments and farmhouse can be rented separately or combined with the villa to accommodate up to 35 guests.  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £70 /night

£488 - £1058 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This stunning villa located in Tuscany, Italy, has 3 bedrooms and 2 bathrooms, and can accommodate 6 people. The pet-friendly property is ideal for families.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £355 /night

£2480 - £3720 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Villa Gaiole features all the comforts and a wonderful panoramic Tuscan Villa in Chianti between Siena and Florence, with private pool, air conditioning, total privacy, and a lovely park.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £1 /night

£1 - £2720 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This property in Tuscany Italy is a elegant house that sleeps 8 people, so it is ideal for a large group of friends. The accommodation offers: a swimming Pool .  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £886 /night

£6199 - £7852 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This exclusive and luxurious villa in Chianti affords 5 bedrooms, dining room, 2 sitting rooms, kitchen, gym, games room and a fabulous infinity swimming pool.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 7

4 Nights min stay

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from £1 /night

£1 - £1984 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
wonderful house, located in Tuscany Italy, has a max. capacity of 7 people. This wonderful house is ideal for families and friends  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £106 /night

£736 - £1586 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This gorgeous house located in Tuscany, Italy, sleeps 8 people and is ideal for large families. The villa features a swimming pool and an Internet connection .  …see more

11 Photos

House | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £51 /night

£351 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Located in an excellent position to visit the typical villages of the Chianti Classico and Chianti Fiorentino Chainti ... Paved road to the village Montegrossi  …see more

9 Photos

Apartment | 3 Bedrooms | sleeps 8

1 night min stay

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from £57 /night

£399 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
Just a few minutes far from the small village of Montegrossi where you are staying in our home holiday, you can discover the architectural, natural and gourmet marvels of Classic Chianti, Florentine Chianti and Sienese Chianti…  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £71 /night

£492 - £823 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
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

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £201 /night

£1401 - £3104 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This comfortably furnished country style Tuscan villa sleeps up to ten persons. Set amongst a mature well tended garden with its own private swimming pool. The property is in a great location only five minutes away from Gaiole.  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

Very Good 4/5 

7 Nights min stay

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from £74 /night

£513 - £939 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
This well positioned house has gardens to the South and East and enjoys a sunny aspect from sun rise to sun set, the house has a high quality finish in the old Tuscan style and has superb views all around of pine forest, vineyards and olive groves.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4/5 

7 Nights min stay

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from £152 /night

£1058 - £1769 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
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

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £369 /night

£2581 - £4562 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
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

20 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £195 /night

£1364 - £2273 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
La Fontanella is fantastically located in the heart of the Chianti, just on the edge of a quaint stone village filled with Tuscan character and charm. Several of the main Chianti vineyards can easily be reached for wine tastings, these include Brolio, Dievole and Meleto  …see more

15 Photos

Villa | 6 Bedrooms | sleeps 14

Short stays welcome

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from £220 /night

£1534 - £2629 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The "Molino della Carpinese" is located in the municipality of Gaiole in Chianti. The peace and silence characterize the environment that makes it particularly suitable for a relaxing vacation that helps you to forget the stress of those who live in big cities. The Mill of Carpinese is located in the municipality of Gaiole in Chianti, Province of Siena. The peace and  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 2

4 Nights min stay

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from £68 /night

£474 - £579 / week

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Key info:

  • Swimming pool
  • Suitable for over 5s only
  • Car not necessary
  • Pets welcome
  • Private garden
Siena (Km30), Monteriggioni, Colle Val d'Elsa, Firenze (Km60), San Gimigniano, Volterra, Arezzo to reache into an hour APT. 1) 4 LOCATAIRES APT. 7) 2 " APT.8) 6 " APT.4) 8 " APT.5) 6 "  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £101 /night

£701 - £2191 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, and 55 km from Florence. EXCLUSIVE USE of the Swimming Pool! The swimming pool is available from April 1 to October 15, it may varies depending on weather conditions.  …see more

10 Photos

Villa | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £51 /night

£351 - £1052 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence.  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £151 /night

£1052 - £3242 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
2 Villas in the heart of Chianti with the exclusive use of a swimming pool! Beautiful, isolated property with breathtaking views of the hills of Tuscany. The villas are located close by to Gaiole in Chianti and all the cultural and artistic activities of the region.  …see more

12 Photos

House | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £76 /night

£526 - £745 / week

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Key info:

  • Not suitable for children
  • Car essential
  • May take pets – please enquire
Casa colonica chiantigiana di grande charme, comoda e arredata con gusto e attenzione al dettaglio.  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £68 /night

£474 - £744 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This is a quiet and peaceful corner of the property idea for relaxing after sighseeing or for cooling off after the warm Tuscan day. Pool fenced - a 16x6 mtr pool open from mid-May to mid-September (weather permitting)  …see more

13 Photos

Condo | 3 Bedrooms | sleeps 5

2 Nights min stay

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from £44 /night

£307 - £614 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Nel periodo invernale l'uso del riscaldamento AUTONOMO è a pagamnento euro 4,00 a metro cubo. Tassa di soggiorno dal 6 Aprile al 31 Ottobre da pagare all'arrivo, euro 1,50 a notte per persona per un massimo di sette pernottamenti esclusi i minori fino a 14 anni.  …see more

15 Photos

Villa | 6 Bedrooms | sleeps 12

1 night min stay

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from £188 /night

£1315 - £2015 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tranquilla Confortevole Cibo Cucina Salumi Vino Olio Piscina Palestra Panorama Chianti Castello  …see more