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

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Gaiole in Chianti

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4,920 Vacation rentals

(2) Good 

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 $106 / night

$737 / week

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from $106 / 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 $139 / night

$974 - $1,722 / week

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from $139 / night

18

Gaiole in Chianti Vacation condo rental

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • 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 $69 / night

$446 / week

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from $69 / night

(16) Excellent 

22

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 stone …see more

from $140 / night

$784 - $1,064 / week

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from $140 / night

(1) Good 

25

Lecchi Vacation apartment rental

Gaiole in Chianti / Lecchi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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 $137 / night

$781 - $992 / week

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avg. 1 hour 53 minutes

from $137 / 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 $199 / night

$1,388 / week

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from $199 / 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 $275 / night

$1,686 / week

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from $275 / 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 $69 / night

$484 - $912 / week

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from $69 / night

(13) Excellent 

23

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 t …see more

from $245 / night

$1,540 - $2,240 / week

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from $245 / night

(7) Very Good 

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

$560 - $980 / week

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from $91 / night

6

Gaiole in Chianti Vacation farmhouse rental

Province of Siena / Gaiole in Chianti

2 2 3 nights min

  • 2 bedrooms
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Great 104 mt², can accommodate up to 5 people. Reached by external staircase and separate entrance on the first floor. It has: kitchen, large kitchen floor, 4 induction stove, a wood stove, water boiler, mocha coffee, fridge with freezer compartment and a large table. d …see more

from $69 / night

$434 / week

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from $69 / night

(2) Good 

23

Lecchi Vacation apartment rental

Gaiole in Chianti / Lecchi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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 $124 / night

$707 - $905 / week

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Responds fast!
avg. 1 hour 53 minutes

from $124 / 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 $149 / night

$744 / week

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avg. 1 hour 56 minutes

from $149 / night

(1) Excellent 

4

Vacation b&b in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
The dell'Ortolano room consists of a double bedroom and a bathroom. The structure for use Bed & Breakfast is located within a farm. Nestled in the green hills of Chianti, it can offer a comfortable point of reference for your travel in Tuscany or a place to spend the ti …see more

from $95 / night

$664 / week

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from $95 / night

16

Gaiole in Chianti Vacation farmhouse rental

Province of Siena / Gaiole in Chianti

9 22 1 night min

  • 9 bedrooms
  • Sleeps 22
  • 1 night min
  • Child friendly
  • Private garden
Reggioli è una grande casa colonica in vero stile toscano dell'800. Finemente ristrutturata secondo le regole della bio-edilizia, si appoggia su una verde collina con vista panoramica sulla bellissima Val D'Orcia fino a scorgere il monte Amiata all'orizzonte. Qui è poss …see more

from $93 / night

$651 / week

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from $93 / 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 $88 / night

$612 - $1,268 / week

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from $88 / night

(1) Excellent 

24

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $420 / night

$2,100 - $2,800 / week

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from $420 / 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 $123 / night

$855 - $1,357 / week

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Responds fast!
avg. 1 hour 41 minutes

from $123 / 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 $90 / night

$632 - $1,289 / week

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from $90 / 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 $205 / night

$1,431 / week

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from $205 / night

(7) 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 $67 / night

$387 - $930 / week

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Responds fast!
avg. 1 hour 26 minutes

from $67 / 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 $73 / night

$508 - $1,089 / week

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from $73 / 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 $70 / night

$487 - $919 / week

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from $70 / night

47

Gaiole in Chianti Vacation apartment rental

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Private garden
The Dudda is a farmhouse 300 years old and was part of Brolio Farm. On the ground floor the apartment La Loggia has been recently renovated and refurbished with great attention to detail. The apartment (about 67 sqm) has 2 bedrooms (4 beds), one double and one room with …see more

from $174 / night

$1,215 / week

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from $174 / night

16

Vacation b&b rental

Gaiole in Chianti / Lecchi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 95 mi
  • 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 $137 / night

$744 / week

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from $137 / 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 $210 / night

$840 / week

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Responds fast!
avg. 2 hours 36 minutes

from $210 / 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 $93 / night

$595 - $803 / week

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from $93 / 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 $186 / night

$4,956 / week

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Responds fast!
avg. 2 hours 8 minutes

from $186 / night

20

Gaiole in Chianti Vacation apartment rental

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 is ideally located in the hamlet and develops on one level on the first floor. There is independent access via an external staircase and views over the village and countryside. It avails of a private terraced garden outside …see more

from $87 / night

$607 - $1,138 / week

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from $87 / 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 $69 / night

$484 - $1,016 / week

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from $69 / night

(38) Excellent 

24

Gaiole in Chianti Vacation apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • 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 $126 / night

$882 / week

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Responds fast!
avg. 1 hour 55 minutes

from $126 / 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 $124 / night

$781 / week

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from $124 / night

100

Gaiole in Chianti Vacation villa rental

Province of Siena / Gaiole in Chianti

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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 $567 / night

$3,965 - $5,823 / week

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from $567 / night

(2) Very Good 

13

Vacation apartment with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside. Outside a portion of an equipped courtyard is available for t …see more

from $62 / night

$434 - $781 / week

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from $62 / night

(2) Excellent 

45

Vacation farmhouse with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 75 mi
  • Swimming pool
  • Child friendly
THE BUILDING. The building is located in a mountainous area of the classic chianti and is built entirely with local stones. It is surrounded by an olive grove from which high quality oil is obtained. The mountainous landscape with its views full of green is an invitatio …see more

from $266 / night

$1,853 - $2,850 / week

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Responds fast!
avg. 3 hours 23 minutes

from $266 / night

4

Vacation townhouse in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
In the small village of Vertine, a fortified medieval town made of stone walls, narrow streets and typical Tuscan views never conquered over the centuries and this remained perfectly intact. An elegant apartment for guests who want to discover the Chianti and enjoy the …see more

from $250 / night

$1,747 / week

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from $250 / night

21

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Large and comfortable apartment of 80 sqm for 5 people, located in the building near the swimming pool, at 200 meters from the restaurant and the reception. It is on the ground floor and consists of a living room with stone fireplace, a single sofa bed, Sat TV, a dining …see more

from $149 / night

$992 - $1,103 / week

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Responds fast!
avg. 1 hour 53 minutes

from $149 / night

29

Gaiole in Chianti Vacation apartment rental

Province of Siena / Gaiole in Chianti

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Stunning, large apartment of 140 sqm for 8 people, located in the medieval castle, near the restaurant and the reception, at 200 meters from the swimming pool. It is on two floors. Entrance on the ground floor, large kitchen (oven, two fridges, toaster, kettle) with a l …see more

from $223 / night

$1,425 - $1,698 / week

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avg. 1 hour 53 minutes

from $223 / 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 $587 / night

$4,107 - $6,319 / week

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from $587 / night

21

Vacation guest house in Montefienali

Gaiole in Chianti / Montefienali

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
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 …see more

from $67 / night

$434 - $930 / week

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Responds fast!
avg. 1 hour 26 minutes

from $67 / night