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94 Holiday homes

Filters applied: Non-Smoking property (94)

Travellers going to Gaiole in Chianti are booking October dates now. Secure your holiday home today and have the perfect trip.

(32) Excellent 

24

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS - Gaiole in Chianti apartment sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Ideal for couples looking for a relaxing romantic holiday, we provide everything you need in our fully equipped and tastefully decorated apartment, see our reviews. FREE WI-FI Walking distance to local restaurants. The large private garden for your exclusive use overlo  …see more

from £60 / night

£420 - £665 / week

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from £60 / night

(5) Very Good 

23

Spacious Chianti apartment with pool access, terrace and outdoor dining area - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
This is a spacious fully furnished 2 bedroom apartment in Borgo di Gaiole in the village of Gaiole in Chianti. Gaiole is in the heart of the Chianti Classico Region of Tuscany.The property has stunning views over the village and to the vineyards overlooking the village  …see more

from £100 / night

£600 - £850 / week

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from £100 / night

(13) Excellent 

23

Casacorvo Maggiore: *Eroica Weekend Available* - Gaiole in Chianti apartment sleeps 8

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A spacious well furnished three double bedroom, two bathroom apartment with an eight seating dining room and large lounge, just a few minutes stroll from the restaurants, cafes and wide range of services provided by Gaiole village. Outside, enjoy a game of boules in the  …see more

from £165 / night

£1000 - £1500 / week

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from £165 / night

(15) Excellent 

22

Casacorvo Minore *Late Booking Discounts* - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships.The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style with sol  …see more

from £85 / night

£525 - £725 / week

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from £85 / night

9

Gaiole Suites 8 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartmen  …see more

from £42 / night

£290 - £483 / week

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from £42 / night

(2) Excellent 

18

Province of Siena / Gaiole in Chianti

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £78 / night

£544 / week

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from £78 / night

12

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about pets

 …see more

from £60 / night

£518 - £733 / week

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from £60 / night

18

galassia 18 - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Air conditioning
appartamento, 2 - 3 persone, 2 vano/vani, 1 camera/e da letto, 1 bagno/bagni, ca. 44 m², 1 piano/piani, alloggio al piano terra. Accesso all'alloggio indipendente.TerrenoPorzione privata del terreno, giardino, lastre.Parcheggio: 1 x posto macchina in garage sotter  …see more

from £69 / night

£345 / week

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from £69 / night

(6) Excellent 

20

2 bedroom apartment in traditional Tuscan complex in village of Gaiole, sleeps 6, shared pool - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A fabulous place to relax, this apartment is at the edge of the Borgo furthest from the road. Designed in a traditional style incorporating a range of modern comforts and facilities, the apartment is the best of both worlds. Stone tiled floors with chestnut beams overhe  …see more

from £70 / night

£500 / week

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from £70 / night

15

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £62 / night

£432 / week

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from £62 / night

18

Villa Fontecaresino 1 - Montegrossi villa sleeps 9

Gaiole in Chianti / Montegrossi

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
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. Our close proximi  …see more

from £111 / night

£776 - £1983 / week

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from £111 / night

4

Province of Siena / Gaiole in Chianti

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £132 / night

£918 / week

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from £132 / night

(6) Excellent 

26

Just 5 minutes from the centre of the Gaiolie, wonderful apartment with pool and breathtaking terrace, sleeps 6 - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The apartment is just 5 minutes walk from the center of Gaiole, where you will find all the services you need. Like restaurants, bars, wineshops, banks, food shop, hairdressers etc.Gaiole is one of several traditional Chianti villages in the region. Others worth visitin  …see more

from £85 / night

£595 - £944 / week

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from £85 / night

7

Province of Siena / Gaiole in Chianti

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden

 …see more

from £87 / night

£544 / week

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from £87 / night

(1) Excellent 

20

Casa Giardino - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
A cosy and lovingly furnished 1 bedroom apartment located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful SienaT  …see more

from £45 / night

£311 - £535 / week

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from £45 / night

4

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £66 / night

£459 / week

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from £66 / night

4

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £66 / night

£459 / week

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from £66 / night

11

Gaiole Suites 7 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartmen  …see more

from £39 / night

£272 - £532 / week

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from £39 / night

(1) Very Good 

11

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from £69 / night

£414 - £647 / week

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from £69 / night

16

Galassia H - Gaiole in Chianti house sleeps 5

Province of Siena / Gaiole in Chianti

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Air conditioning
  • 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

from £87 / night

£432 / week

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from £87 / night

24

Casa Corte - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children age 5+
This beautiful and tastefully furnished 2 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the won  …see more

from £49 / night

£337 - £716 / week

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from £49 / night

8

Gaiole Suites 4 - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartmen  …see more

from £44 / night

£302 - £616 / week

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from £44 / night

22

Casa Borgo - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
This beautiful and tastefully furnished 1 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the won  …see more

from £45 / night

£311 - £595 / week

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from £45 / night

(1) Good 

33

Appartamento Gaiole 40 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Appartamento Gaiole 40 is a wonderful apartment in the heart of Chianti. This area is famous all over the world for its typical products and its superb wines. The apartment is located in Borgo di Gaiole, an ancient Borgo recently renovated that enjoys a magnificent view  …see more

from £92 / night

£640 - £981 / week

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from £92 / night

24

Casa Chianti - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
A cosy and lovingly furnished 1 bedroom apartment located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful SienaT  …see more

from £45 / night

£311 - £535 / week

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from £45 / night

100

Gaiole In Chianti 70247 - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful independent villa with private pool situated in the heart of the Chianti region, a short distance away from the town of Gaiole in Chianti. This villa, nestling deep in quiet position among vineyards and woods, offers full privacy and is the ideal place for tho  …see more

from £436 / night

£2625 - £3938 / week

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from £436 / night

9

Gaiole Suites 1 - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Borgo di Gaiole, is an ancient town in the heart of Chianti hills. This area is famous all over the world for the typical products and therefore known destination for wine tourism. Here, also, there are all finds of shops and restaurants. Siena, the wonderful city that  …see more

from £44 / night

£302 - £616 / week

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from £44 / night

19

Province of Siena / Gaiole in Chianti

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from £363 / night

£1294 / week

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from £363 / night

(3) Very Good 

24

Villa Gaiole - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly
Beautiful Family Villa in Borgo di Gaiole, surrounded by the Chianti hills covered in vineyards and olive groves, just a 100 meters walk from the quiet village of Gaiole in Chianti, a typical Tuscan hamlet with restaurants, shops and amenities, an ideally located betwee  …see more

from £84 / night

£587 - £1406 / week

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from £84 / night

100

Gaiole - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
ExteriorsVilla Gaiole is an authentic Sienese-style retreat with total privacy and comfort. Located in a natural environment of absolute privacy Villa Gaiole has recently  been remodeled and elegantly furnished. All rooms and bedrooms are air conditioned to allow a  …see more

from £397 / night

£2759 - £3880 / week

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from £397 / night

8

Gaiole Suites 3 - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartmen  …see more

from £44 / night

£302 - £616 / week

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from £44 / night

(1) Excellent 

22

Le Diacce - Montegrossi farmhouse sleeps 10

Gaiole in Chianti / Montegrossi

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Le Diacce villa, benefits of a total privacy and enjoys splendid sunsets and a beautiful pool. The living room and kitchen open onto spacious terraces fully equipped for outdoor dining and surrounded by lawns, gardens and ancient trees.Ideal for families or a group of f  …see more

from £130 / night

£3449 / week

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from £130 / night

(1) Excellent 

12

Il Mulinaccio - Gaiole in Chianti farmhouse sleeps 16

Province of Siena / Gaiole in Chianti

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
On entering the property, guests will find a welcoming living area, furnished with sofas around a traditional, focal fireplace. The kitchen is adjacent to this room. The kitchen is a typical Tuscan kitchen, well-equipped with plenty of pots and pans for those that enjoy  …see more

from £432 / night

£3018 - £4656 / week

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from £432 / night

20

Province of Siena / Gaiole in Chianti

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £81 / night

£561 / week

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from £81 / night

16

Il Borghetto, Gaiole-in-Chianti - Lecchi b&b sleeps 2

Gaiole in Chianti / Lecchi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 95 km
  • Swimming pool
  • Car not necessary
Adjacent apartment with terra-cotta floors and furnished with a double Chianti iron bed (subsequently with a madonna picture above), a large armadio and an en suite bathroom. Through French doors the room leads to a 55 square meter terrace with an antique iron sofa, a f  …see more

from £95 / night

£518 / week

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from £95 / night

24

Ancient castle in the heart of Tuscany, 6 bedrooms - Lecchi castle sleeps 14

Gaiole in Chianti / Lecchi

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A dive into an ancient culture in the heart of Tuscany, the Chianti Classico.Il Castello Medievale is situated in a medieval hamlet, constructed of white stone, built around 1000AD, surrounded by forests and olive groves, immersed in a magical atmosphere of tranquility.  …see more

from £414 / night

£2897 - £3345 / week

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from £414 / night

21

Gaiole in Chianti / Lecchi

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly

 …see more

from £61 / night

£388 - £660 / week

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from £61 / night

16

Holidayhome Casa Isa, Borgo San Vincenti,Tuscany - Gaiole in Chianti house sleeps 5

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
A dream home set in the heart of Chianti. Relax, landscapes, nature, good food, wine ... for a unique holiday! Borgo San Vincenti is composed not only from Casa Isabella: Casa Guia( 4guests);Casa Eolo( 4 guests); Casa Monte Cristo (4 guests) , Casa Maestrale (8 guests)  …see more

from £113 / night

£785 - £1121 / week

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from £113 / night

22

Holidayhome Casa Guia, Borgo San Vincenti,Tuscany - Gaiole in Chianti house sleeps 4

Province of Siena / Gaiole in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Homelidays "Casa Guia " is immersed in the most idyllic Chiantishire: surrounded by vineyards producing world-class red wine, overlooking the rolling hills of Tuscany and is located in the village of San Vincenti, with its stone houses and clay roof tiles. The village h  …see more

from £108 / night

£755 - £949 / week

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from £108 / night

(2) Excellent 

45

Province of Siena / Gaiole in Chianti

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

 …see more

from £197 / night

£1380 - £1897 / week

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from £197 / night

Top Destination reviews

A HOLIDAY IN THE HEART OF CHIANTI
Authentic unspoiled Italian charm!

My family and I stayed at this beautiful property and had a relaxed and wonderful holiday. Gaiole in Chianti is a small village totally unspoilt by tourism and the location of this property is ideal if you hire a car and travel to all the surrounding … see more
Villa Podere Earthly
Perfect, beautifil little place in tuscany

A beautiful place full of happines, were you can stay The time you want for a very very good price ,there's a beautiful view, is very relaxing and you can enjoy The animals and nature … see more
Villa PetrAlexa, Tuscany cottage in Chianti area
Villa PetrAlexa - excellent leisure facility

This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfectly prepared. The house was heated up and foo … see more

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