50 Best Vacation Rentals in San Polo in Chianti - Holiday Lettings - Cabins

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San Polo in Chianti

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54 Vacation rentals

(10) Excellent 

33

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
The IRIS apartment is on the ground floor of a characteristic barn on the farm estate of Podere Albereto, in the heart of the Tuscan countryside on the rolling hills above Florence, overlooking the San Polo in Chianti valley. The estate of 10 hectares of fields, olive  …see more

from $81 / night

$561 / week

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from $81 / night

(1) Excellent 

19

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful 13th century castle is located on the Chianti hills completely surrounded by hectares of olive groves, in an absolute quiet position. This exquisite holiday home consists in 7 spacious self-catering apartments, tastefully furnished, all restored in respec  …see more

from $155 / night

$684 - $1421 / week

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from $155 / night

(1) Very Good 

21

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful 13th century castle is located on the Chianti hills completely surrounded by hectares of olive groves, in an absolute quiet position. There 7 spacious self-catering apartments, tastefully furnished, all restored in respect of the traditional Tuscan style,  …see more

from $113 / night

$476 - $956 / week

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from $113 / night

23

San Polo in Chianti Vacation apartment rental

Greve in Chianti / San Polo in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This amazing villa is hidden in the green shades of the olive groves and vineyards of the hills, at just a few km from Greve in Chianti (15km), the heart of the wine production. The villa is a typical Tuscan 17th century manor house, totally renovated, which hosts 4 com  …see more

from $118 / night

$470 - $897 / week

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from $118 / night

42

Greve in Chianti / San Polo in Chianti

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from $235 / night

$1645 - $3236 / week

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from $235 / night

19

Vacation farmhouse in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Pet friendly
Villa il Cavato is one of the most ancient building in the area.The property has been fully restored to ensure confort and privacy to ower guests.The distance to Florence , the well know Art City in Italy, is only 18 km.The location is very convenient been, Villa il C  …see more

from $129 / night

$801 / week

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from $129 / night

31

Greve in Chianti / San Polo in Chianti

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from $486 / night

$3364 / week

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from $486 / night

(2) Excellent 

32

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful 13th century castle is located on the Chianti hills completely surrounded by hectares of olive groves, in an absolute quiet position. This exquisite holiday home consists in 7 spacious self-catering apartments, tastefully furnished, all restored in respec  …see more

from $230 / night

$1026 - $1923 / week

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from $230 / night

(1) Very Good 

19

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Nice romantic apartment for 2+1 people, 35sq.m, ground floor: It is composed of living room/kitchen (with an oven) with single sofabed, 1 double bedroom, and 1 bathroom with shower. Wooden beam ceilings and antique-style furnishings adorn this apartment. A private terra  …see more

from $77 / night

$289 - $673 / week

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from $77 / night

(6) Very Good 

33

Vacation apartment in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
The GIAGGIOLO apartment is on the first and top floor of this characteristic barn on the farm estate of Podere Albereto, in the heart of the Tuscan countryside on the rolling hills above Florence, overlooking the San Polo in Chianti valley. The estate of 10 hectares of  …see more

from $49 / night

$337 / week

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from $49 / night

(3) Excellent 

19

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
The 10 hectare estate of olive trees, fields and woodland is at 350 m above sea level. A spectacular view dominating the Florintine hills and even in the height of summer there is a gentle breeze in the evening so air-conditioning isn't necessary. The property  …see more

from $182 / night

$1271 / week

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from $182 / night

24

Apartment rental in San Polo in Chianti with shared pool

Greve in Chianti / San Polo in Chianti

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful 13th century castle is located on the Chianti hills completely surrounded by hectares of olive groves, in an absolute quiet position. This exquisite holiday home consists in 7 spacious self-catering apartments, tastefully furnished, all restored in respec  …see more

from $182 / night

$780 - $1709 / week

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from $182 / night

31

San Polo in Chianti Vacation apartment rental

Greve in Chianti / San Polo in Chianti

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful 13th century castle is located on the Chianti hills completely surrounded by hectares of olive groves, in an absolute quiet position. This exquisite holiday home consists in 7 spacious self-catering apartments, tastefully furnished, all restored in respec  …see more

from $278 / night

$1196 - $2670 / week

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from $278 / night

(1) Excellent 

19

Apartment rental in San Polo in Chianti with shared pool

Greve in Chianti / San Polo in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful 13th century castle is located on the Chianti hills completely surrounded by hectares of olive groves, in an absolute quiet position. This exquisite holiday home consists in 7 spacious self-catering apartments, tastefully furnished, all restored in respec  …see more

from $171 / night

$732 - $1656 / week

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from $171 / night

22

Vacation apartment rental

Greve in Chianti / San Polo in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful 13th century castle is located on the Chianti hills completely surrounded by hectares of olive groves, in an absolute quiet position. This exquisite holiday home consists in 7 spacious self-catering apartments, tastefully furnished, all restored in respec  …see more

from $182 / night

$769 - $1762 / week

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from $182 / night

18

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Large apartment of 90sq.m for max 9 people: On ground floor: living room with fire place, kitchen corner (fridge with freezer, 4 gas fire, oven, washing machine) 3 double bedrooms, 1 double with extra beds, 2 bathrooms with shower. Private furnished terrace. This holid  …see more

from $182 / night

$769 - $1549 / week

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from $182 / night

18

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment for 8 people of 80 sqm on two floors (ground + upper) composed of living room with fireplace, kitchenette (complete with an oven and a dishwasher), 4 double bedrooms (one with an extra bed for a child), and 2 bathrooms with shower. Wooden beam ceilings and ant  …see more

from $182 / night

$801 - $1570 / week

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from $182 / night

21

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Big apartment for 10 people, of 120 sq.m, ground floor + upper floor. The apartment is composed of a large living area with a fireplace, a dining room, a kitchen (equipped with an oven and a dishwasher), and a bathroom with shower on the ground floor. On the first floor  …see more

from $235 / night

$908 - $1869 / week

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from $235 / night

22

Farmhouse rental in San Polo in Chianti with swimming pool

Greve in Chianti / San Polo in Chianti

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
It is a very nice stone farmhouse located on the hills of Chiantishire 20 km far from the centre of Florerence. The house is completely immersed in nature. It was recently restored, leaving unchanged its original architectural features and was transformed into a comfor  …see more

Pricing unknown

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Pricing unknown

(1) Very Good 

17

Vacation apartment with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This amazing villa is hidden in the green shades of the olive groves and vineyards of the hills, at just a few km from Greve in Chianti (15km), the heart of the wine production. The villa is a typical Tuscan 17th century manor house, totally renovated, which hosts 4 com  …see more

from $118 / night

$433 - $887 / week

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from $118 / night

(1) Excellent 

25

Greve in Chianti / San Polo in Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 127 mi
  • Child friendly
  • Ask about pets

 …see more

from $214 / night

$1346 / week

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from $214 / night

20

Vacation farmhouse in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This villa in the Chianti hills is dating back to 1700. It's surrounded by olive groves, vineyards, cypresses and woods. There are 6 lovely apartments, all restored into comfortable holiday homes. A very peaceful place for relaxing and yet very near to art centres such  …see more

from $235 / night

$1015 - $2018 / week

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from $235 / night

18

Vacation villa rental

Greve in Chianti / San Polo in Chianti

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Holiday rental Castello Pandolfini is a nice property (1000 sq m) that includes WiFi internet, air conditioning and private pool. The property can sleep up to 18 people comfortably in nine bedrooms with seven bathrooms. Conveniently located 3 km (2 mi) from San Polo In  …see more

from $1602 / night

$11212 - $14950 / week

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from $1602 / night

13

Vacation farmhouse with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful villa dating back to the 13th century, situated in a panoramic spot among the verdant Chianti hills. The villa has been restored respecting the original architecture and divided into 7 comfortable apartments, all furnished in typical Tuscan style, matching t  …see more

from $176 / night

$845 - $1777 / week

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from $176 / night

14

Vacation farmhouse with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful villa dating back to the 13th century, situated in a panoramic spot among the verdant Chianti hills. The villa has been restored respecting the original architecture and divided into 7 comfortable apartments, all furnished in typical Tuscan style, matching t  …see more

from $219 / night

$962 - $1869 / week

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from $219 / night

14

Vacation farmhouse with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful villa dating back to the 13th century, situated in a panoramic spot among the verdant Chianti hills. The villa has been restored respecting the original architecture and divided into 7 comfortable apartments, all furnished in typical Tuscan style, matching t  …see more

from $288 / night

$1268 - $2716 / week

Inquire View

from $288 / night

16

San Polo in Chianti Vacation farmhouse rental

Greve in Chianti / San Polo in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful villa dating back to the 13th century, situated in a panoramic spot among the verdant Chianti hills. The villa has been restored respecting the original architecture and divided into 7 comfortable apartments, all furnished in typical Tuscan style, matching t  …see more

from $153 / night

$801 - $1524 / week

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from $153 / night

17

Vacation farmhouse with swimming pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse which has been recently restored preserving its original architectural features and its ancient materials such as the charming terracotta-tiled floors. This property comprising 3 welcoming units (connected via an internal staircase) that are rented tog  …see more

from $272 / night

$1580 - $3417 / week

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from $272 / night

15

Vacation farmhouse with swimming pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Experience Chianti: dive in the pool, swimming and enjoying our villa. Beautiful stone farmhouse peacefully situated in the heart of the Chianti Classico area. The villa has been skilfully restored with its original architectural features and its ancient charm preserved  …see more

from $275 / night

$1923 - $3532 / week

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from $275 / night

15

San Polo in Chianti Vacation farmhouse rental

Greve in Chianti / San Polo in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This villa in the Chianti hills is dating back to 1700. It's surrounded by olive groves, vineyards, cypresses and woods. There are 6 lovely apartments, all restored into comfortable holiday homes. A very peaceful place for relaxing and yet very near to art centres such  …see more

from $74 / night

$321 - $1015 / week

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from $74 / night

15

San Polo in Chianti Vacation farmhouse accommodation

Greve in Chianti / San Polo in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This villa in the Chianti hills is dating back to 1700. It's surrounded by olive groves, vineyards, cypresses and woods. There are 6 lovely apartments, all restored into comfortable holiday homes. A very peaceful place for relaxing and yet very near to art centres such  …see more

from $176 / night

$861 - $1671 / week

Inquire View

from $176 / night

19

Vacation farmhouse in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This villa in the Chianti hills is dating back to 1700. It's surrounded by olive groves, vineyards, cypresses and woods. There are 6 lovely apartments, all restored into comfortable holiday homes. A very peaceful place for relaxing and yet very near to art centres such  …see more

from $118 / night

$485 - $967 / week

Inquire View

from $118 / night

13

Vacation farmhouse with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful villa dating back to the 13th century, situated in a panoramic spot among the verdant Chianti hills. The villa has been restored respecting the original architecture and divided into 7 comfortable apartments, all furnished in typical Tuscan style, matching t  …see more

from $185 / night

$903 - $1748 / week

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from $185 / night

19

San Polo in Chianti Vacation farmhouse rental

Greve in Chianti / San Polo in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This villa in the Chianti hills is dating back to 1700. It's surrounded by olive groves, vineyards, cypresses and woods. There are 6 lovely apartments, all restored into comfortable holiday homes. A very peaceful place for relaxing and yet very near to art centres such  …see more

from $176 / night

$888 - $1730 / week

Inquire View

from $176 / night

9

Vacation farmhouse with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful villa dating back to the 13th century, situated in a panoramic spot among the verdant Chianti hills. The villa has been restored respecting the original architecture and divided into 7 comfortable apartments, all furnished in typical Tuscan style, matching t  …see more

from $120 / night

$538 - $1044 / week

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from $120 / night

10

Vacation farmhouse in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This villa in the Chianti hills is dating back to 1700. It's surrounded by olive groves, vineyards, cypresses and woods. There are 6 lovely apartments, all restored into comfortable holiday homes. A very peaceful place for relaxing and yet very near to art centres such  …see more

from $118 / night

$485 - $967 / week

Inquire View

from $118 / night

10

Vacation farmhouse with shared pool in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

4 5 Min stay varies

  • 4 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful villa dating back to the 13th century, situated in a panoramic spot among the verdant Chianti hills. The villa has been restored respecting the original architecture and divided into 7 comfortable apartments, all furnished in typical Tuscan style, matching t  …see more

from $176 / night

$903 - $1720 / week

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from $176 / night

11

Greve in Chianti / San Polo in Chianti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $182 / night

$1271 - $2452 / week

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from $182 / night

29

Greve in Chianti / San Polo in Chianti

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Suitable for children age 5+

 …see more

from $898 / night

$6291 - $12281 / week

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from $898 / night

13

Greve in Chianti / San Polo in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly

 …see more

from $129 / night

$855 / week

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from $129 / night