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74 Holiday homes in Gaiole in Chianti

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74 Results  |  
18 Photos

Villa | 4 Bedrooms | sleeps 8

Short stays welcome

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from £98 /night

£684 - £1967 / week

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Key info:

  • Swimming pool
  • Suitable for children over
  • 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

17 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

Short stays welcome

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from £98 /night

£684 - £1967 / 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
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

24 Photos

Apartment | 3 Bedrooms | sleeps 5

4 Nights min stay

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from £98 /night

£684 - £761 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
L'appartamento " RICASOLI " è l'ideale per un unico nucleo familiare con bambini Max.6 px. L'Appartamento è composto da tre camere. L'appartamento dispone di un bagno con doccia, lavabo  …see more

Featured properties

13 Photos

House | 3 Bedrooms | sleeps 5

4 Nights min stay

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from £88 /night

£616 - £766 / week

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Key info:

  • Swimming pool
  • Suitable for children over
  • Some pets are welcome - please contact the owner
maison toscane, appartement, piscine, chianti, gaiole in chianti, Sienne, visites de producters de vin, dégustations de vin, outlet shopping, siteseeing, marcher, villes d'art Distances airport 60km gare 16km emplettes 10 km hopital 16 km  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £38 /night

£265 - £658 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
With beautiful views over the village, this ground floor, comfortable apartment is the perfect spot! Modern facilities including a Swimming pool a gym, and table tennis. The apartment has 2 bedrooms, a well equipped kitchen, a dining terrace, and underground parking. The multinational users are generally quiet and friendly, respectful of the natural ambience of the Borgo.  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £98 /night

£684 - £727 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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. Fontecaresino 2 when rented without Fontecaresino 1 does not have access to the swimming pool.  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 2

4 Nights min stay

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from £66 /night

£462 / week

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Key info:

  • Swimming pool
  • Suitable for children over
  • Pets welcome
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

22 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £70 /night

£490 - £725 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious 1 bed apartment with garden and bbq terrace, in a picturesque setting, only a short walk to local services. Enjoy free use of cycles & gym or just relax by the pool. Launderette & internet services add home comforts and a glass of wine greets you on arrival. Minore is ideally situated to enjoy the areas premier events including Siena Palio & Gaiole Eroica.  …see more

23 Photos

Apartment | 3 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £143 /night

£1000 - £1500 / week

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Key info:

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

24 Photos

Apartment | 4 Bedrooms | sleeps 12

Excellent 5/5 

4 Nights min stay

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from £229 /night

£1600 - £2100 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
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

16 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

Short stays welcome

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from £220 /night

£1539 - £1753 / 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
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

24 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

4 Nights min stay

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from £98 /night

£684 - £761 / 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
L'appartamento " Brunello " è l'ideale per un unico nucleo familiare con bambini Max.6 px. L'Appartamento è composto da tre camere che sono disposte in sequenza e perciò comunicanti e di passo una dopo l'altra. L'appartamento dispone di un bagno con vasca/doccia, lavabo  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

1 night min stay

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from £168 /night

£1172 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
You can upgrade your stay to include 2 Vespa 125cc Scooters for a daily cost of Euro 60 per day per scooter plus IVA tax. Ask when booking about the scooters!  …see more

20 Photos

Villa | 1 Bedroom | sleeps 2

5 Nights min stay

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from £145 /night

£1009 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
You can upgrade your stay to include 2 Vespa 125cc Scooters for a daily cost of Euro 60 per day per scooter plus IVA tax. Ask when booking about the scooters!  …see more

11 Photos

House | 2 Bedrooms | sleeps 5

1 night min stay

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from £62 /night

£428 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. Details and the architecture are carefully planned.  …see more

19 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £147 /night

£1026 / week

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Key info:

  • Suitable for children over
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Experience Tuscany cooking class, Italian dining and Tuscany tours to Siena, Cortona, San Giminiano and the wine regions of Montalcino and Montepulciano, Pienza, Volterra. Villa Oliviera is a really ' A Taste of Tuscany ' in an authentic, unique, Tuscany Villa Breakfast with home made specialities is served in a charming patio in the stunning Chianti wines view.  …see more

6 Photos

Villa | 2 Bedrooms | sleeps 6

1 night min stay

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from £74 /night

£513 / 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

15 Photos

Apartment | 1 Bedroom | sleeps 3

4 Nights min stay

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from £49 /night

£342 - £471 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
La naturale estensione del paese di Gaiole in Chianti. Il concetto del “villaggio - nel - villaggio” unico nel suo genere. Il concetto del borgo che diventa parte integrante del villaggio. Una cura maniacale dell' architettura e dei materiali. Disponibilità di appartame  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £218 /night

£1525 - £3347 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
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

41 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £672 /night

£4702 - £5557 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
VILLA DEL SOLE is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. This wonderful villa comprises of the main house which is spread over three floors and a separate ground floor villa which is aproximately 50 metres away.  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £349 /night

£2438 / 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
Podere Scopeto, a former hill farm on sunset-facing slopes of the Chianti in the heart of the wine-region. Main House sleeps 10 and separately available self-contained studio for 2 in its own 30 acres of woodland. 15m saltwater pool on terraces with spectacular views.  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £596 /night

£4170 - £6130 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £67 /night

£463 / week

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Key info:

  • Swimming pool
  • Great 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

24 Photos

House | 1 Bedroom | sleeps 3

2 Nights min stay

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from £49 /night

£342 - £616 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to enjoy the calm, the beauty and all the pleasures our region has to offer. Our apartments have been renovated with respect for tradition.  …see more

10 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £68 /night

£471 - £847 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
The Chianti As You Always Dreamed It. A charming Medieval borgo in the heart of Chianti Classico, 15 km far from Siena. Relax and discovery hour incredible landes. The charme of an ancient Medieval borgo in the heart of Chianti Classico  …see more

24 Photos

Apartment | 5 Bedrooms | sleeps 4

1 night min stay

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from £74 /night

£513 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti.  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 3

1 night min stay

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from £57 /night

£396 - £509 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
These holiday apartments in Tuscany are part of an estate situated in the Chianti Classico area, just 13 km from Siena, surrounded by vineyards and olive groves, in a peaceful place far from the traffic and bustle.  …see more

24 Photos

Apartment | 4 Bedrooms | sleeps 5

1 night min stay

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from £79 /night

£550 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti  …see more

22 Photos

Apartment | 4 Bedrooms | sleeps 6

3 Nights min stay

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from £89 /night

£621 - £734 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
These holiday apartments in Tuscany are part of an estate situated in the Chianti Classico area, just 13 km from Siena, surrounded by vineyards and olive groves, in a peaceful place far from the traffic and bustle.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £77 /night

£537 - £678 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
These holiday apartments in Tuscany are part of an estate situated in the Chianti Classico area, just 13 km from Siena, surrounded by vineyards and olive groves, in a peaceful place far from the traffic and bustle.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £49 /night

£339 - £452 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
These holiday apartments in Tuscany are part of an estate situated in the Chianti Classico area, just 13 km from Siena, surrounded by vineyards and olive groves, in a peaceful place far from the traffic and bustle.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1367 - £1968 / week

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Key info:

  • Swimming pool
  • Great 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

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £155 /night

£1079 - £1540 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …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

20 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £111 /night

£771 - £1079 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

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from £84 /night

£588 - £1307 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Wavesandnbsp;is provided withandnbsp;private terrace, air conditioning, panoramic living roomandnbsp;with open fireplace, aandnbsp;fully furnished kitchen and dining room, a double bedroomandnbsp;withandnbsp;queen size bed, beautifully tiled bathroom with  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

5 Nights min stay

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from £185 /night

£1291 - £4630 / 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

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £351 /night

£2457 - £3685 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 8  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £78 /night

£545 - £692 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £70 /night

£484 - £626 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £216 /night

£1508 - £1996 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Lecchi with 5 bedrooms sleeps 10  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £344 /night

£2404 - £2952 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
This particular and fascinating farmhouse is located in the heart of Chianti, a region renowned worldwide for its wine production. The property has a great and particular charm and although maintaining the rural character of the structure and the classic style typical  …see more

22 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £118 /night

£822 - £1130 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

7 Nights min stay

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from £46 /night

£319 - £585 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
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

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£517 - £656 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £104 /night

£727 - £888 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 2 bedrooms sleeps 4  …see more

20 Photos

House | 4 Bedrooms | sleeps 7

1 night min stay

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from £426 /night

£2980 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora F is a splendid sixteenth-century apartment that is part of a villa in the characteristic style of the Tuscan countryside. It sleeps seven people. From Villa Diora F you will enjoy an enchanting view of the Chianti hills and of the vineyards  …see more

16 Photos

House | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £492 /night

£3444 - £3565 / week

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Key info:

  • Great for children of all ages
  • 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

16 Photos

House | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £596 /night

£4170 - £4275 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £118 /night

£822 - £1130 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more