50 Best Vacation Rentals in Gaiole in Chianti - Holiday Lettings - Cabins

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Gaiole in Chianti

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191 Vacation rentals

(15) Excellent 

22

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 80 mi
  • 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 solid …see more

from $130 / night

$728 - $988 / week

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from $130 / night

(12) Excellent 

69

Vacation villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Ciao from Petra & Alexa! We warmly welcome you in our unbeatable location, discover more ... THE VILLA: Villa LisiDor has been fully renovated beginning of 2016 with all new amenities, with a habitable area of 300 square meters. On GROUND FLOOR, which is at garden l …see more

from $555 / night

$3883 - $5973 / week

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from $555 / night

(2) Excellent 

18

Vacation apartment with shared pool in Gaiole in Chianti

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
The old farm of the Aquila (Eagle in French) is an atypical Tuscan country house, situated on the hills of the Chianti Classico region, near Gaiole Chianti. The panoramic position gives you the opportunity to enjoy a view of breathtaking on the surrounding woods, hills …see more

from $106 / night

$738 / week

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Responds fast!
avg. 2 hours 47 minutes

from $106 / night

(6) Very Good 

Certificate of Excellence

43

Montefienali Vacation home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na …see more

Certificate of Excellence

from $64 / night

$366 - $820 / week

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Responds fast!
avg. 1 hour 43 minutes

from $64 / night

(6) Very Good 

23

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 mi
  • 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 $195 / night

$780 / week

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Responds fast!
avg. 2 hours 12 minutes

from $195 / night

(13) Excellent 

23

Vacation apartment with shared pool in Gaiole in Chianti

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 boule …see more

from $228 / night

$1430 - $2080 / week

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from $228 / night

22

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 105 mi
  • 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 $66 / night

$457 - $961 / week

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from $66 / night

24

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 mi
  • 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 Siena< …see more

from $66 / night

$457 - $862 / week

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from $66 / night

(1) Excellent 

20

Gaiole in Chianti Vacation apartment rental

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 mi
  • 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 Siena< …see more

from $66 / night

$457 - $862 / week

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from $66 / night

(1) Very Good 

15

Gaiole in Chianti Vacation home rental

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
The House, with its own entrance, has been lovingly restored while maintaining the charm of the typical Chianti House: terracotta, wooden beams, fireplaces and stone stairs. First floor: living room with fireplace, tv and a sofa bed, kitchen with dishwasher, second floo …see more

from $88 / night

$563 - $1043 / week

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from $88 / night

18

Gaiole in Chianti Vacation condo rental

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Casa del Cirica is a pretty and comfortable apartment in a small building of only three families, ideal holiday for families and for couples or groups of friends. It is 500 metres from situatoa small and picturesque village of Castagnoli, near the village of Gaiole in C …see more

from $65 / night

$422 - $504 / week

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from $65 / night

(1) Excellent 

12

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
, The plant L'Aquila can accommodate 30 people and has six apartments, a studio and three double bedrooms, each with bath, shower and toilet. Fireplaces in some of the apartments and the rustic spread a cozy atmosphere with a good dose of atmosphere. All apartments and …see more

from $94 / night

$656 - $762 / week

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from $94 / night

(6) Excellent 

20

Apartment accommodation in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Casa Felice is 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 chestn …see more

from $91 / night

$650 - $1040 / week

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from $91 / night

(4) Excellent 

17

Vacation villa rental

Province of Siena / Gaiole in Chianti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
The structure surrounded by nature, situated on the beautiful hills of Chianti Senese, welcomes you in an apartment, and immersed in a phenomenal panorama, at 2 steps from a small town. The apartment (about 110mq – 2/6 pax) in private villa, consists of living room, 2 …see more

from $141 / night

$703 / week

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Responds fast!
avg. 3 hours 3 minutes

from $141 / night

18

Villa rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • 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 $227 / night

$1874 - $3286 / week

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Responds fast!
avg. 2 hours 52 minutes

from $227 / night

24

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 105 mi
  • 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 $82 / night

$574 - $1190 / week

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from $82 / night

38

Vacation home in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • 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 10 km from Radda in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from …see more

from $163 / night

$1300 - $2044 / week

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Responds fast!
avg. 2 hours 52 minutes

from $163 / night

(13) Very Good 

26

Vacation villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Ciao from Petra &Alexa and thank you for stopping by! AUGUST PROMOTION: 25% off!! 19 - 26 August and 26-August - 2 September: 1.800 Euro instead of 2.400 Euro Here is what our villa offers you for a memorable stay: Villa PetrAlexa is a renovated barn, with natural st …see more

from $241 / night

$1687 - $2811 / week

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from $241 / night

(3) Very Good 

24

Vacation villa with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 107 mi
  • 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 $104 / night

$727 - $2073 / week

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from $104 / night

42

Vacation home in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

6 13 3 nights min

  • 6 bedrooms
  • Sleeps 13
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Nestled in the lush nature of the Chianti region, this charming manor built in the early 1900s lovingly embraces and preserves the romance of bygone times. It is an ideal place for relaxing in the surrounding nature while enjoying the area’s superb foods and wines. The …see more

from $387 / night

$2437 - $3754 / week

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from $387 / night

100

Gaiole in Chianti Vacation villa rental

Province of Siena / Gaiole in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 130 mi
  • 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 all gu …see more

from $539 / night

$3748 - $5505 / week

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from $539 / night

17

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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. Availabil …see more

from $153 / night

$926 / week

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from $153 / night

44

Vacation home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This Cottage is one of 15 of Hamlet Motefiorile. It is situated on a hillside with stunning views across the Castello di Ama vineyards and olive groves, in the heart of Chianti Classico, offering maximum appreciation of the magnificent surrounding countryside. It's a s …see more

from $156 / night

$1090 - $1623 / week

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from $156 / night

19

Vacation cottage with shared pool in Lecchi

Gaiole in Chianti / Lecchi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
Lemon Villa is a spacious two bedroomed cottage facing on to the main square of the village Montefiorile. From the piazza views over the Chianti countryside can be enjoyed. The front door is reached up a set of steps and terracotta opens straight into the living and din …see more

from $85 / night

$598 - $1219 / week

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from $85 / night

18

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 120 mi
  • 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.Terreno Porzione privata del terreno, giardino, lastre. Parcheggio: 1 x posto macchina in garage sott …see more

from $93 / night

$469 / week

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from $93 / night

(1) Excellent 

24

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Casacorvo Grande is a townhouse that sits on the edge of the unique development of Borgo di Gaiole overlooking the Chianti Hills. It is a perfect location for a holiday. The accommodation comprises of two apartments, one 1bed/1bath and one 3bed/2bath, that can be combi …see more

from $390 / night

$1950 - $2600 / week

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from $390 / night

(1) Good 

25

Lecchi Vacation apartment rental

Gaiole in Chianti / Lecchi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday ap …see more

from $118 / night

$528 - $785 / week

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from $118 / night

11

Gaiole in Chianti Vacation apartment rental

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Badia a Coltibuono welcomes travelers who want a unique experience in a magical place, surrounded by nature and silence. Ancient abbey of Vallombrosa 'XI century, converted into wine resort, Badia a Coltibuono has retained its original features, the structure and the at …see more

from $258 / night

$1583 - $1878 / week

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from $258 / night

(1) Good 

23

Lecchi Vacation apartment rental

Gaiole in Chianti / Lecchi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly
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. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday ap …see more

from $118 / night

$539 - $795 / week

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from $118 / night

(1) Excellent 

12

Vacation farmhouse rental

Province of Siena / Gaiole in Chianti

5 16 7 nights min

  • 5 bedrooms
  • Sleeps 16
  • 7 nights min
  • 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 $586 / night

$4100 - $6325 / week

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from $586 / night

27

Montegrossi Vacation home rental

Gaiole in Chianti / Montegrossi

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
2 Villas (1 FONTECARESINO and 2 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 10 km from Radda in Chianti, 35 km from Siena, …see more

from $422 / night

$3174 - $5452 / week

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Responds fast!
avg. 2 hours 52 minutes

from $422 / night

(12) Excellent 

60

Vacation villa with indoor pool, golf nearby in Montefienali

Gaiole in Chianti / Montefienali

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
NEW MANAGEMENT from Summer 2015 Villa Albizi Tuscany life and more….for groups of friends or large families Villa Albizi is normally rented on a villa-only weekly basis and are ideal for those seeking independence and privacy. We have created a formula designed to o …see more

from $1945 / night

$13610 / week

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Responds fast!
avg. 2 hours 23 minutes

from $1945 / night

22

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 107 mi
  • Swimming pool
  • Child friendly
A charming stone staircase leads up to the entrance of this first-floor apartment which opens directly in to the large kitchen/living room. The living area consists of a wooden table and chairs which seats up to 3 people, a Satellite TV and side unit, comfortable sofa t …see more

from $66 / night

$457 - $862 / week

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from $66 / night

24

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly
Casa Lecchi is a spacious two bedroom apartment facing on to the main piazza of Montefiorile which is a small hamlet of 14 villas situated in a quiet position in the heart of the Chianti Classico wine producing area. The hamlet is on a hillside and the houses enjoy st …see more

from $99 / night

$691 - $1312 / week

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from $99 / night

21

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 107 mi
  • Swimming pool
  • Child friendly
This cosy and comfortable first floor 1-bedroom apartment sits nestled within the hamlet of Giaole. The main entrance leads into the open plan kitchen/living room. The living area consists of a wooden table and chairs which seats up to 3 people, a Satellite TV and side …see more

from $66 / night

$457 - $862 / week

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from $66 / night

25

Apartment rental in Gaiole in Chianti with shared pool, golf nearby

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 107 mi
  • Swimming pool
  • Child friendly
This cosy and comfortable 2-bedroom apartment sits nestled within the hamlet of Giaole. An open plan kitchen/living room allows for easy preparation of meals and the dining area with table and chairs hosts up to 5 people, a Satellite TV and side unit finish this room. A …see more

from $82 / night

$574 - $1076 / week

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from $82 / night

7

Vacation apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The basket-maker of the apartment is included in a farmhouse built in 1800 completely restored. It has independent access, fully equipped kitchen and 6 beds with the possibility of adding the seventh on request. Our farm is nestled in the Chianti hills, completely surro …see more

from $118 / night

$738 / week

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from $118 / night

24

Vacation apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 107 mi
  • Swimming pool
  • Child friendly
This cosy and comfortable first-floor 2-bedroom apartment sits overlooking the rest of the hamlet, also with views over the pool. The entrance leads into the spacious living room where crisscrossed terracotta tiling runs seamlessly throughout the apartment, whilst Chest …see more

from $82 / night

$574 - $1076 / week

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from $82 / night

(1) Excellent 

22

Vacation farmhouse in Montegrossi

Gaiole in Chianti / Montegrossi

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 100 mi
  • 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 gr …see more

from $176 / night

$4685 / week

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Responds fast!
avg. 2 hours 8 minutes

from $176 / night

(6) Excellent 

26

Vacation apartment with shared pool in Gaiole in Chianti

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 vis …see more

from $116 / night

$809 - $1283 / week

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Responds fast!
avg. 1 hour 35 minutes

from $116 / night