San Casciano in Val di Pesa Vacation Rentals, Apartments, & More

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1-37 of 37 San Casciano in Val di Pesa Rentals

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San Casciano in Val di Pesa Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$134

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$134 - $168
Per week:$938 - $1,170
Pets allowed:No
Internet:No

This estate stretches out over a hillside covered with vineyards, olive trees and woodland. It is set in the very heart of Chianti near the main road from Florence to Siena, only 16 km south of Florence. The lovely estate on the western fringe of Chianti is owned by one of Italy's...

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Private pool
1 / 23

San Casciano in Val di Pesa Castle
11 Bedrooms / 9 Bathrooms / Sleeps 20
Castle / 11 Bedrooms / Sleeps 20

Bedrooms:11
Bathrooms:9
Sleeps:20
Type:Castle
Per night:$1,167 - $1,372
Per month:$35,010 - $41,160
Pets allowed:No
Internet:No

This is a fabulous Tuscan villa sleeping between 15 and 20 people. Originally a Medieval feudal castle, the property was converted to a villa between 1450 and 1500. As you would expect, it is steeped in history and is a fascinating place to spend a holiday in this wonderful part...

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1 / 12

San Casciano in Val di Pesa Villa
6 Bedrooms / 4 Bathrooms / Sleeps 12
Villa / 6 Bedrooms / Sleeps 12

from

$398

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Villa
Per night:$398 - $723
Per month:$11,940 - $21,690
Pets allowed:Yes
Internet:No

Characteristic Tuscan- style Chianti villa, independent and secluded, located in the heart of Tuscany, in the Chianti Classico region, a few kilometers from San Casciano Val di Pesa. The villa rental is surrounded by the Tuscan hills, olive groves and vineyards, in a quiet area...

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1 / 36

San Casciano in Val di Pesa Villa
3 Bedrooms / 2 Bathrooms / Sleeps 8
Villa / 3 Bedrooms / Sleeps 8

(7)“ Excellent ”7 Reviews

from

$119

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Villa
Per night:$119 - $223
Per week:$828 - $1,556
Pets allowed:No
Internet:No

Villa Gentile is an age- old 300- square- meter (about 3, 229 square feet) countryside house in stone which sleeps eight people. It features a private garden and swimming- pool. It overlooks the valley. The house is located amidst the hills where the famous Chianti wine is produced....

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1 / 41

San Casciano in Val di Pesa Villa
4 Bedrooms / 3 Bathrooms / Sleeps 12
Villa / 4 Bedrooms / Sleeps 12

from

$225

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:12
Type:Villa
Per night:$225 - $420
Per week:$1,572 - $2,935
Pets allowed:No
Internet:Yes

Villa Lacustre is a characteristic and welcoming two- story villa in the characteristic style of the Tuscan countryside. It sleeps 12 people. From Villa Lacustre you will enjoy a charming view of the greenery. Villa Lacustre is 185 square meters (1990 square feet). It features a private...

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1 / 27

San Casciano in Val di Pesa Home
1 Bedroom / 1 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$68

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$68 - $90
Per week:$473 - $629
Pets allowed:No
Internet:Yes

Appartamento Edmondo B is a romantic and welcoming cottage surrounded by the vegetation. It sleeps two people. From Appartamento Edmondo B you will enjoy an enchanting view of the Chianti hills and of the surrounding countryside. Appartamento Edmondo B is 55 square meters (590 square...

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1 / 31

San Casciano in Val di Pesa Villa
8 Bedrooms / 7 Bathrooms / Sleeps 15
Villa / 8 Bedrooms / Sleeps 15

Bedrooms:8
Bathrooms:7
Sleeps:15
Type:Villa
Per night:$1,199 - $1,403
Per week:$8,387 - $9,815
Pets allowed:Yes
Internet:No

A typical example of a Tuscan medieval castle, dating to the 12th century, built by the architect Buondelmonti as a fortification to defend the feudal possessions. Transformed into a country villa in 1520, with large decorated rooms and elegant arcades, the castle is perched on...

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1 / 44

San Casciano in Val di Pesa Villa
4 Bedrooms / 4 Bathrooms / Sleeps 12
Villa / 4 Bedrooms / Sleeps 12

from

$505

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:12
Type:Villa
Per night:$505 - $773
Per week:$3,529 - $5,406
Pets allowed:Yes
Internet:Yes

Ancient farmhouse surrounded by olive groves and terraced areas and situated inside the Castello di Bibbione estate in the Chianti area. The castle dates back to the early 11th century, whereas the stone- built houses of the hamlet date back to the early 13th century. The villa rental...

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1 / 42

San Casciano in Val di Pesa Villa
5 Bedrooms / 4 Bathrooms / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$495

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Villa
Per night:$495 - $828
Per week:$3,460 - $5,792
Pets allowed:No
Internet:Yes

Splendid and characteristic Chianti villa (400 m2) that dates back to the early 15th century. Once belonging to the Medici family, it is situated in a small valley amid the Chianti hills and has been skilfully restored and transformed into a cosy country house. The villa rental is...

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1 / 27

San Casciano in Val di Pesa Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 7
Apartment / 2 Bedrooms / Sleeps 7

from

$166

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:7
Type:Apartment
Per night:$166 - $213
Per week:$1,159 - $1,491
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 30

San Casciano in Val di Pesa Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

from

$166

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$166 - $213
Per week:$1,159 - $1,491
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Home
1 / 14

San Casciano in Val di Pesa Home
3 Bedrooms / 1 Bathroom / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$133

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:6
Type:Home
Per night:$133 - $183
Per week:$929 - $1,277
Pets allowed:Yes
Internet:Yes

The historic Casa Gina, acquired from the Machiavelli family, together with the other farm houses on the property, has been restored with great care to its original form.  Casa Gina is positioned in a pristine location amid cypresses, olive groves and vineyards, with views ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 33

San Casciano in Val di Pesa Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

from

$166

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$166 - $213
Per week:$1,159 - $1,491
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 28

San Casciano in Val di Pesa Apartment
1 Bedroom / 1 Bathroom / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

from

$136

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$136 - $173
Per week:$950 - $1,205
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 26

San Casciano in Val di Pesa Apartment
1 Bedroom / 2 Bathrooms / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

from

$117

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$117 - $144
Per week:$819 - $1,004
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 29

San Casciano in Val di Pesa Apartment
1 Bedroom / 1 Bathroom / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

from

$136

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$136 - $173
Per week:$950 - $1,205
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 26

San Casciano in Val di Pesa Apartment
1 Bedroom / 1 Bathroom / Sleeps 3
Apartment / 1 Bedroom / Sleeps 3

from

$92

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Apartment
Per night:$92 - $112
Per week:$641 - $780
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 22

San Casciano in Val di Pesa Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

from

$92

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$92 - $112
Per week:$641 - $780
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 28

San Casciano in Val di Pesa Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

from

$92

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$92 - $112
Per week:$641 - $780
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 26

San Casciano in Val di Pesa Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

from

$92

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$92 - $112
Per week:$641 - $780
Pets allowed:No
Internet:Yes

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Home
1 / 80

San Casciano in Val di Pesa Home
18 Bedrooms / 17 Bathrooms / Sleeps 65
Home / 18 Bedrooms / Sleeps 65

Bedrooms:18
Bathrooms:17
Sleeps:65
Type:Home
Per night:$1,990 - $2,650
Per week:$13,924 - $18,545
Pets allowed:No
Internet:Yes

Castello Tenuta is a fabulous Tuscan estate combining a total of 12 apartments and houses, all situated in a private estate with a splendid view of the Chianti hills extending lazily to the horizon. The property has been restored with all due respect necessary to fully utilise the...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 26

San Casciano in Val di Pesa Apartment
1 Bedroom / 1 Bathroom / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

from

$136

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$136 - $173
Per week:$950 - $1,205
Pets allowed:No
Internet:No

In the ancient hamlet that surrounds the Bibbione Castle , 12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills ...

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San Casciano in Val di Pesa Italy Vacation Rentals - Apartment
1 / 11

San Casciano in Val di Pesa Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 3
Apartment / 2 Bedrooms / Sleeps 3

from

$151

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:3
Type:Apartment
Per night:$151 - $272
Per week:$1,051 - $1,904
Pets allowed:No
Internet:Yes

(Minimum of one week rental required) This country estate is composed of several buildings of historical and artistic importance; among them, the most beautiful is the main house with its typical Tuscan architecture. The villa faces a little private chapel, built in the 17th century,...

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San Casciano in Val di Pesa Italy Vacation Rentals - Villa
1 / 43

San Casciano in Val di Pesa Villa
6 Bedrooms / 6 Bathrooms / Sleeps 17
Villa / 6 Bedrooms / Sleeps 17

Bedrooms:6
Bathrooms:6
Sleeps:17
Type:Villa
Per night:$1,093 - $1,682
Per week:$7,648 - $11,769
Pets allowed:No
Internet:No

Located in the heart of Tuscany's Chianti region, Casa Matteo is an outstanding villa with stunning views over characteristic olive groves, vineyards, forests and country estates.   This spacious independent country house, originally a small monastery, has five bedrooms with...

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1 / 14

San Casciano in Val di Pesa Apartment
3 Bedrooms / 3 Bathrooms / Sleeps 6
Apartment / 3 Bedrooms / Sleeps 6

from

$244

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$244 - $323
Per month:$7,320 - $9,690
Pets allowed:No
Internet:No

Entry to this large 1st floor apartment is from the front terracotta- tiled piazza, to the side of which is a pergola furnished for outdoor meals. The stairs lead up to the living area with comfortable sofas and a dining table for six and the nearby kitchen has both the modern convenience...

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San Casciano in Val di Pesa Home
8 Bedrooms / 9 Bathrooms / Sleeps 12
Home / 8 Bedrooms / Sleeps 12

(5)“ Excellent ”5 Reviews

from

$717

/ night

Email Owner
Bedrooms:8
Bathrooms:9
Sleeps:12
Type:Home
Per night:$717 - $902
Per week:$5,015 - $6,311
Pets allowed:No
Internet:Yes

The La Corte estate stretches out over a hillside covered with vineyards, olive trees and woodland. It is set in the very heart of Chianti near the main road from Florence to Siena, only 16 km south of Florence. This lovely estate on the western fringe of Chianti is owned by one...

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1 / 29

San Casciano in Val di Pesa Apartment
3 Bedrooms / 3 Bathrooms / Sleeps 8
Apartment / 3 Bedrooms / Sleeps 8

(85)“ Excellent ”85 Reviews

from

$257

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Apartment
Per night:$257 - $441
Per week:$1,797 - $3,081
Pets allowed:No
Internet:Yes

Looking to explore the Chianti region of Tuscany with all the comforts of home and more? This accommodation in a Tuscany villa has it all, from a huge swimming pool to sprawling grounds and all the amenities indoors. One of the owners, who lives on the estate in the family villa,...

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San Casciano in Val di Pesa Italy Vacation Rentals - Home
1 / 31

San Casciano in Val di Pesa Home
1 Bedroom / 1 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$61

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$61 - $83
Per week:$423 - $581
Pets allowed:No
Internet:No

Appartamento Marvena B is a characteristic ancient house surrounded by the vegetation. It sleeps two people. From Appartamento Marvena B you will enjoy an enchanting view of the Chianti hills and of the surrounding countryside. Appartamento Marvena B is 45 square meters (485 square...

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San Casciano in Val di Pesa Home
11 Bedrooms / 10 Bathrooms / Sleeps 22
Home / 11 Bedrooms / Sleeps 22

Bedrooms:11
Bathrooms:10
Sleeps:22
Type:Home
Per night:$1,560 - $2,000
Per week:$10,920 - $14,000
Pets allowed:No
Internet:Yes

(Minimum of one week rental required) Unit 1 sleeps six guests and is located in the large building, (the former oil mill). The ground floor consists of a large, fully equipped kitchen (stove, oven, fridge/freezer, microwave, toaster, coffee maker), living room with open fireplace,...

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1 / 46

San Casciano in Val di Pesa Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(97)“ Excellent ”97 Reviews

from

$244

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$244 - $421
Per week:$1,702 - $2,941
Pets allowed:No
Internet:Yes

Looking to explore the Chianti region of Tuscany with all the comforts of home and more? This accommodation in a Tuscany villa has it all, from a swimming pool to sprawling grounds and all the amenities indoors. One of the owners, who lives on the estate in the family villa, is...

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1 / 20

San Casciano in Val di Pesa Villa
5 Bedrooms / 3 Bathrooms / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$562

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:10
Type:Villa
Per night:$562 - $665
Per month:$16,860 - $19,950
Pets allowed:No
Internet:Yes

Villa Il Turco is an elegant, aristocratic, sixteenth- century country estate which once belonged to a noble family named Rosselli Del Turco. Enjoy noble splendour in this gracious antique villa which is both close to Florence and immersed in tranquillity. Complete with vaulted ...

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1 / 37

San Casciano in Val di Pesa Home
6 Bedrooms / 7 Bathrooms / Sleeps 15
Home / 6 Bedrooms / Sleeps 15

(5)“ Excellent ”5 Reviews

from

$463

/ night

Email Owner
Bedrooms:6
Bathrooms:7
Sleeps:15
Type:Home
Per night:$463 - $798
Per week:$3,240 - $5,582
Pets allowed:No
Internet:Yes

Looking to explore the Chianti region of Tuscany with all the comforts of home—and more? This estate features two private villas for rent in Tuscany, two swimming pools, sprawling grounds and all the amenities indoors. How is this possible? One of the owners of this accommodation...

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San Casciano in Val di Pesa Italy Vacation Rentals - Villa
1 / 24

San Casciano in Val di Pesa Villa
3 Bedrooms / 3 Bathrooms / Sleeps 6
Villa / 3 Bedrooms / Sleeps 6

from

$232

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Villa
Per night:$232 - $403
Per week:$1,624 - $2,821
Pets allowed:No
Internet:Yes

Unwind after climbing through hilltop villages with a dip in the private pool, enjoy the spoils of your wine tasting excursion in this villa’s lush private garden, or just snuggle up next to the fireplace with family or friends. Set in a tranquil location in Tuscany’s Chianti...

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1 / 23

San Casciano in Val di Pesa Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$294

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$294 - $437
Per week:$2,055 - $3,055
Pets allowed:No
Internet:Yes

This is a 4 bedroom villa located in the Chianti Classico region of Tuscany, just 20 minutes from Central Florence. It is a perfect base for larger families or groups of friends who are looking for the privacy that a villa offers. The property enjoys use of a circular swimming pool,...

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San Casciano in Val di Pesa Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$537

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$537 - $823
Per week:$3,759 - $5,756
Pets allowed:Yes
Internet:Yes

Casa Poggio is a farmhouse located in a beautiful estate, 100 m from a charming medieval village. Guests can enjoy outstanding views of the Chianti hills and olive groves from all its rooms. The house is friendly, luminous and decorated with antique furniture, kilim carpets and...

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San Casciano in Val di Pesa Home
6 Bedrooms / 7 Bathrooms / Sleeps 11
Home / 6 Bedrooms / Sleeps 11

from

$672

/ night

Email Owner
Bedrooms:6
Bathrooms:7
Sleeps:11
Type:Home
Per night:$672 - $1,008
Per week:$4,700 - $7,050
Pets allowed:No
Internet:Yes

(Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. This country estate is composed of several buildings of historical and artistic importance, and the most beautiful is the main house with its typical Tuscan architecture....

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San Casciano in Val di Pesa Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$83

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$83 - $114
Per week:$581 - $792
Pets allowed:No
Internet:No

Appartamento Marvena A is a cozy ancient house in the characteristic style of the Tuscan countryside. It sleeps four people. From Appartamento Marvena A you will enjoy a broad view of the Chianti hills and of the surrounding countryside. Appartamento Marvena A is 80 square meters ...

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