35 Best Vacation Rentals in San Gusme - Holiday Lettings - Cabins

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4,238 Vacation rentals

(2) Very Good 

27

San Gusme Vacation villa rental

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Private garden
San Donato is an exquisite gem set in rolling Chianti vineyards with views that stretch 360 degrees past a nearby 13th century hill town to Siena and into infinity. Part of the original estate of Villa Arceno, San Donato has a history that goes back many 100's of years …see more

from $266 / night

$1,860 - $2,483 / week

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from $266 / night

30

San Gusme Vacation villa rental

Castelnuovo Berardenga / San Gusme

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly
Colonica Gigli is a portion of a typical Tuscan farmhouse immersed in the green Chianti hills covered with vineyards and olive groves. Recently restored the original stone building stands in a well tended green lawn. The large private garden is totally fenced ensuring …see more

from $217 / night

$1,518 - $2,094 / week

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from $217 / night

8

San Gusme Vacation apartment rental

Castelnuovo Berardenga / San Gusme

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
intimate studio for 2 people with a small kitchen, ideal for couples who want tranquility and comfort. Large bathroom with shower and even a jacuzzi corner. The apartment is reached after traveling a dirt road from the Roman period, and therefore protected by Unesco. Ar …see more

from $73 / night

$512 / week

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from $73 / night

16

Vacation farmhouse with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Splendid and ancient mansion situated in the heart of Chianti region, among vineyards and woods, owned from 15th century by the Medici family, who considered this property as one of their most prestigious estates. This property is surrounded by a gorgeous 80-hectare pa …see more

from $298 / night

$1,697 - $2,427 / week

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from $298 / night

14

Farmhouse rental in San Gusme with shared pool

Castelnuovo Berardenga / San Gusme

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 bedrooms with ten bathrooms. Villa Di S …see more

from $279 / night

$1,846 / week

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from $279 / night

12

Farmhouse rental in San Gusme with shared pool

Castelnuovo Berardenga / San Gusme

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 bedrooms with ten bathrooms. Villa Di S …see more

from $195 / night

$1,215 / week

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from $195 / night

12

Farmhouse rental in San Gusme with shared pool

Castelnuovo Berardenga / San Gusme

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 bedrooms with ten bathrooms. Villa Di S …see more

from $195 / night

$1,215 / week

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from $195 / night

14

Farmhouse rental in San Gusme with shared pool

Castelnuovo Berardenga / San Gusme

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 bedrooms with ten bathrooms. Villa Di S …see more

from $261 / night

$1,648 / week

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from $261 / night

15

Farmhouse rental in San Gusme with shared pool

Castelnuovo Berardenga / San Gusme

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 bedrooms with ten bathrooms. Villa Di S …see more

from $275 / night

$1,797 / week

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from $275 / night

12

Farmhouse rental in San Gusme with shared pool

Castelnuovo Berardenga / San Gusme

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 bedrooms with ten bathrooms. Villa Di S …see more

from $174 / night

$992 / week

Inquire View

from $174 / night

14

Farmhouse rental in San Gusme with shared pool

Castelnuovo Berardenga / San Gusme

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 bedrooms with ten bathrooms. Villa Di S …see more

from $174 / night

$992 / week

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from $174 / night

28

Home rental in San Gusme

Castelnuovo Berardenga / San Gusme

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Fantastic hillside villa and infinity pool overlooking the Chianti countryside and the medieval walled village of San Gusmè. A large Villa, Chiusarella is set on the slopes of a small hill within the 'Villa D'Arceno' Estate, a one thousand hectare nature reserve. Once …see more

from $682 / night

$4,770 - $6,567 / week

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from $682 / night

23

Vacation home with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Among the oak forest in the Villa Arceno Estate sits Villa Casanova, a 'bijou' house set over two floors. It was once a hayloft and barn. Restored to high standards with all the conveniences and comfort of today, Villa Casanova oozes charm and tranquility, and being sec …see more

from $205 / night

$1,425 - $1,673 / week

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from $205 / night

20

Farmhouse rental in San Gusme with swimming pool

Castelnuovo Berardenga / San Gusme

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful villa with private pool dating back to the 16 century, situated in quiet and panoramic location, on a large farming estate producing excellent olive oil and wine. This villa provides elegant and refined interiors furnished with antiques. Outside guests can e …see more

from $1,884 / night

$9,886 - $11,894 / week

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from $1,884 / night

(3) Excellent 

16

Vacation villa with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 185 mi
  • Swimming pool
  • Private garden
San Donato is an exquisite gem set in rolling Chianti vineyards with views that stretch 360 degrees past a nearby 13th century hill town to Siena and into infinity. Part of the original estate of Villa Arceno, San Donato has a history that goes back many 100's of years …see more

from $264 / night

$1,846 - $2,466 / week

Inquire View

from $264 / night

(1) Excellent 

22

Vacation villa with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly
Colonica Gigli is a portion of a typical Tuscan farmhouse immersed in the green Chianti hills covered with vineyards and olive groves. Recently restored the original stone building stands in a well tended green lawn. The large private garden is totally fenced ensuring …see more

from $217 / night

$1,518 - $2,094 / week

Inquire View

from $217 / night

19

Villa rental in San Gusme

Castelnuovo Berardenga / San Gusme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
Owner's description:Main Description : Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 …see more

from $160 / night

$1,120 / week

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from $160 / night

26

Vacation home with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 113 mi
  • Swimming pool
  • Child friendly
Casina di Arceno is located in one of Tuscany most charming wine estates known as Tenuta di Arceno, in the Chianti Classico area. The property sits central to the estate with olive groves and vineyards streching out in all directions. This farmhouse is part of a …see more

from $310 / night

$2,045 / week

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from $310 / night

23

Vacation villa with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Owner's description:This property is a welcoming apartment in the characteristic style of the Tuscan countryside. It sleeps two people. From this property you will enjoy an enchanting view of the Tuscan hills and of the surrounding countryside. this property is 50 squar …see more

from $160 / night

$1,120 / week

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from $160 / night

19

Vacation villa with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Owner's description:This property is a welcoming apartment in the characteristic style of the Tuscan countryside. It sleeps two people. From this property you will enjoy an enchanting view of the Tuscan hills and of the surrounding countryside. this property is 30 squar …see more

from $160 / night

$1,120 / week

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from $160 / night

23

Vacation villa in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Owner's description:This property is a welcoming two-story apartment in the characteristic style of the Tuscan countryside. It sleeps four people. From this property you will enjoy an enchanting view of the Tuscan hills and of the surrounding countryside. this property …see more

from $297 / night

$2,086 / week

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from $297 / night

17

Vacation villa in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Owner's description:This property is a welcoming two-story apartment in the characteristic style of the Tuscan countryside. It sleeps four people. From this property you will enjoy an enchanting view of the Tuscan hills and of the surrounding countryside. this property …see more

from $196 / night

$1,372 / week

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from $196 / night

17

Vacation villa rental

Castelnuovo Berardenga / San Gusme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Owner's description:Main Description : Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 …see more

from $160 / night

$1,120 / week

Inquire View

from $160 / night

17

Vacation villa in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Owner's description:Main Description : Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 …see more

from $196 / night

$1,372 / week

Inquire View

from $196 / night

22

San Gusme Vacation villa rental

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Owner's description:This property is a welcoming apartment in the characteristic style of the Tuscan countryside. It sleeps four people. From this property you will enjoy an enchanting view of the Tuscan hills and of the surrounding countryside. this property is 55 squa …see more

from $290 / night

$2,030 / week

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from $290 / night

19

San Gusme Vacation villa rental

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Owner's description:Main Description : Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 …see more

from $297 / night

$2,086 / week

Inquire View

from $297 / night

23

Vacation villa in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Owner's description:This property is a welcoming apartment in the characteristic style of the Tuscan countryside. It sleeps four people. From this property you will enjoy an enchanting view of the Tuscan hills and of the surrounding countryside. this property is 50 squa …see more

from $266 / night

$1,862 / week

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from $266 / night

31

Vacation apartment rental

Castelnuovo Berardenga / San Gusme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Owner's description:Farmhouse with 7 individual apartments with 2 big pools close to Siena, Tuscany. There is a beautiful panoramic view. Location: The farmhouse is located in the hills of Tuscany, in Castelnuovo Berardenga, only 20 km from Siena. From there you have a …see more

from $167 / night

$1,167 / week

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from $167 / night

19

San Gusme Vacation villa rental

Castelnuovo Berardenga / San Gusme

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Owner's description:Main Description : Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 …see more

from $266 / night

$1,862 / week

Inquire View

from $266 / night

17

Vacation villa in San Gusme

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Owner's description:Main Description : Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 …see more

from $196 / night

$1,372 / week

Inquire View

from $196 / night

25

Vacation villa in San Gusme

Castelnuovo Berardenga / San Gusme

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Owner's description:This property is a welcoming apartment in the characteristic style of the Tuscan countryside. It sleeps six people. From this property you will enjoy an enchanting view of the Tuscan hills and of the surrounding countryside. this property is 80 squar …see more

from $266 / night

$1,862 / week

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from $266 / night

29

Vacation apartment rental

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Owner's description:Farmhouse with 7 individual apartments with 2 big pools close to Siena, Tuscany. There is a beautiful panoramic view. Location: The farmhouse is located in the hills of Tuscany, in Castelnuovo Berardenga, only 20 km from Siena. From there you have a …see more

from $203 / night

$1,430 / week

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from $203 / night

31

Vacation apartment with shared pool in San Gusme

Castelnuovo Berardenga / San Gusme

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Outside 7 km from Castelnuovo Berardenga: Former farmhouse built around the inner courtyard which is equipped with seating divided into private outdoor areas Simple, pleasant furnishings with washing machine, TV and own heating. For share 2 swimming pools (one of them i …see more

from $399 / night

$728 - $2,798 / week

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from $399 / night

30

Vacation villa in San Gusme

Castelnuovo Berardenga / San Gusme

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
Owner's description:Beautiful country house situated in the heart of the renowned Chianti Classico region, approx. 20 km from Siena away. The house interiors are tastefully furnished with a charming combination of old materials and refined details. Outside guests can en …see more

from $273 / night

$857 - $1,918 / week

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from $273 / night

29

Vacation apartment rental

Castelnuovo Berardenga / San Gusme

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Owner's description:Farmhouse with 7 individual apartments with 2 big pools close to Siena, Tuscany. There is a beautiful panoramic view. Location: The farmhouse is located in the hills of Tuscany, in Castelnuovo Berardenga, only 20 km from Siena. From there you have a …see more

from $203 / night

$1,430 / week

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from $203 / night

20

San Gusme Vacation villa rental

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Owner's description:Main Description : Villa Di Sotto is a beautiful holiday home with shared pool, air conditioning and WiFi internet. Villa Di Sotto is a country resort that has a total of seven separate units. The property can sleep up to 26 people comfortably in 13 …see more

from $290 / night

$2,030 / week

Inquire View

from $290 / night

34

Vacation apartment rental

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Owner's description:Farmhouse with 7 individual apartments with 2 big pools close to Siena, Tuscany. There is a beautiful panoramic view. Location: The farmhouse is located in the hills of Tuscany, in Castelnuovo Berardenga, only 20 km from Siena. From there you have a …see more

from $310 / night

$2,169 / week

Inquire View

from $310 / night

34

Vacation apartment rental

Castelnuovo Berardenga / San Gusme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Owner's description:Farmhouse with 7 individual apartments with 2 big pools close to Siena, Tuscany. There is a beautiful panoramic view. Location: The farmhouse is located in the hills of Tuscany, in Castelnuovo Berardenga, only 20 km from Siena. From there you have a …see more

from $167 / night

$1,167 / week

Inquire View

from $167 / night

34

Vacation apartment rental

Castelnuovo Berardenga / San Gusme

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Owner's description:Farmhouse with 7 individual apartments with 2 big pools close to Siena, Tuscany. There is a beautiful panoramic view. Location: The farmhouse is located in the hills of Tuscany, in Castelnuovo Berardenga, only 20 km from Siena. From there you have a …see more

from $310 / night

$2,169 / week

Inquire View

from $310 / night