Certaldo Vacation Rentals, Homes, & More

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1-39 of 39 Certaldo Rentals

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Certaldo Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$340

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$340
Per week:$2,377
Pets allowed:No
Internet:No

This villa near San Gimignano offers a pristine swimming pool, covered terraces and three bedrooms, two bathrooms, a kitchen, dining room and sitting room. Additional amenities include: pets considered, heating....

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1 / 50

Certaldo Home
5 Bedrooms / 5 Bathrooms / Sleeps 9
Home / 5 Bedrooms / Sleeps 9

from

$647

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:9
Type:Home
Per night:$647 - $848
Per week:$4,527 - $5,931
Pets allowed:No
Internet:Yes

Il Podere is a beautiful farmhouse located halfway between Florence and Siena, in the heart of the Chianti Hills. This is one of the most popular regions in central Tuscany, and the scenery around this house is of incredible beauty. Vineyards, olive groves and fields form a paradise-...

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1 / 26

Certaldo Home
3 Bedrooms / 4 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(6)“ Excellent ”6 Reviews

from

$446

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$446 - $493
Per week:$3,122 - $3,447
Pets allowed:No
Internet:Yes

This elegant farmstead is located in the most coveted region of central Tuscany. Strategically positioned in the middle of the Golden Triangle - Florence, Siena and Pisa - it sits on top of a hill. Capanna Olivo takes its name from the vast groves of olive trees that surround it...

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1 / 54

Certaldo Home
6 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:6
Sleeps:12
Type:Home
Per night:$1,204 - $1,760
Per week:$8,427 - $12,316
Pets allowed:No
Internet:No

Atop a hill with sweeping views over its vast estate of vineyards, olive groves and farmland in the beautiful Chianti country, this grand villa with pool and chapel is the ideal setting for a special wedding or luxury holiday. Additional amenities include: pets considered, heating....

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1 / 14

Certaldo Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

La Grande Terrazza is a very large section of a stately 18th century villa. It comprises the entire Piano Nobile (elegant upper floor) of this ancient villa with tower dating back to around the year 1000. (See picture below: the upper level with five windows four of which open). The...

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1 / 27

Certaldo Home
7 Bedrooms / 4 Bathrooms / Sleeps 13
Home / 7 Bedrooms / Sleeps 13

(41)“ Excellent ”41 Reviews

from

$460

/ night

Email Owner
Bedrooms:7
Bathrooms:4
Sleeps:13
Type:Home
Per night:$460 - $921
Per week:$3,214 - $6,444
Pets allowed:No
Internet:Yes

Immerse yourself in the Victorian- era atmosphere of this gorgeous Tuscany vacation rental, an excellent choice for a family holiday, full of period furniture and elegant decor. Surrounded by olive trees, rolling hills, and the vineyards of Tuscany, you will be at your leisure...

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1 / 39

Certaldo Home
2 Bedrooms / 22 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$193

/ night

Email Owner
Bedrooms:2
Bathrooms:22
Sleeps:4
Type:Home
Per night:$193 - $211
Per week:$1,347 - $1,476
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

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1 / 37

Certaldo Home
2 Bedrooms / 12 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$193

/ night

Email Owner
Bedrooms:2
Bathrooms:12
Sleeps:4
Type:Home
Per night:$193 - $211
Per week:$1,347 - $1,476
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

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Certaldo Italy Vacation Rentals - Home
1 / 34

Certaldo Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$167

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$167 - $193
Per week:$1,164 - $1,347
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

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Certaldo Italy Vacation Rentals - Home
1 / 27

Certaldo Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$199

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$199 - $214
Per week:$1,390 - $1,498
Pets allowed:No
Internet:Yes

The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany. Strategically positioned in the middle of the Golden Triangle - Florence, Siena and Pisa - it sits on top of a hill looking out onto the panoramic valley to south- west. Surrounded by vast...

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Certaldo Italy Vacation Rentals - Home
1 / 27

Certaldo Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$199

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$199 - $214
Per week:$1,390 - $1,498
Pets allowed:No
Internet:Yes

The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany. Strategically positioned in the middle of the Golden Triangle - Florence, Siena and Pisa - it sits on top of a hill looking out onto the panoramic valley to south- west. Surrounded by vast...

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1 / 60

Certaldo Home
2 Bedrooms / 0 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$111

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$111 - $174
Per week:$776 - $1,218
Pets allowed:No
Internet:Yes

Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached. It is only a 15 minutes' drive to the jewel of San Gimignano, and within an hour you can reach both Florence and Siena. Closer...

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1 / 56

Certaldo Home
2 Bedrooms / 0 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(1)“ Excellent ”1 Review

from

$111

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$111 - $174
Per week:$776 - $1,218
Pets allowed:No
Internet:Yes

Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached. It is only a 15 minutes' drive to the jewel of San Gimignano, and within an hour you can reach both Florence and Siena. Closer...

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1 / 61

Certaldo Home
1 Bedroom / 0 Bathroom / Sleeps 4
Home / 1 Bedroom / Sleeps 4

from

$111

/ night

Email Owner
Bedrooms:1
Sleeps:4
Type:Home
Per night:$111 - $174
Per week:$776 - $1,218
Pets allowed:No
Internet:Yes

Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached. It is only a 15 minutes' drive to the jewel of San Gimignano, and within an hour you can reach both Florence and Siena. Closer...

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1 / 61

Certaldo Home
2 Bedrooms / 0 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(1)“ Excellent ”1 Review

from

$111

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$111 - $174
Per week:$776 - $1,218
Pets allowed:No
Internet:Yes

Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached. It is only a 15 minutes' drive to the jewel of San Gimignano, and within an hour you can reach both Florence and Siena. Closer...

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Certaldo Italy Vacation Rentals - Home
1 / 27

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

(1)“ Excellent ”1 Review

from

$145

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$145 - $161
Per week:$1,013 - $1,121
Pets allowed:No
Internet:Yes

The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany. Strategically positioned in the middle of the Golden Triangle - Florence, Siena and Pisa - it sits on top of a hill looking out onto the panoramic valley to south- west. Surrounded by vast...

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Certaldo Italy Vacation Rentals - Home
1 / 61

Certaldo Home
1 Bedroom / 0 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$85

/ night

Email Owner
Bedrooms:1
Sleeps:2
Type:Home
Per night:$85 - $101
Per week:$593 - $701
Pets allowed:No
Internet:Yes

Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached. It is only a 15 minutes' drive to the jewel of San Gimignano, and within an hour you can reach both Florence and Siena. Closer...

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1 / 36

Certaldo Home
1 Bedroom / 9 Bathrooms / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$122

/ night

Email Owner
Bedrooms:1
Bathrooms:9
Sleeps:2
Type:Home
Per night:$122 - $141
Per week:$852 - $981
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

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Certaldo Italy Vacation Rentals - Home
1 / 34

Certaldo Home
-1 Bedroom / 2 Bathrooms / Sleeps 2
Home / -1 Bedroom / Sleeps 2

from

$184

/ night

Email Owner
Bedrooms:-1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$184 - $199
Per week:$1,283 - $1,390
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

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Certaldo Italy Vacation Rentals - Home
1 / 33

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$122

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$122 - $141
Per week:$852 - $981
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

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Certaldo Italy Vacation Rentals - Home
1 / 37

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$122

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$122 - $141
Per week:$852 - $981
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

See more

Close x

Certaldo Italy Vacation Rentals - Home
1 / 36

Certaldo Home
1 Bedroom / 2 Bathrooms / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$122

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$122 - $141
Per week:$852 - $981
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

See more

Close x

Certaldo Italy Vacation Rentals - Home
1 / 36

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$167

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$167 - $193
Per week:$1,164 - $1,347
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

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Certaldo Italy Vacation Rentals - Home
1 / 34

Certaldo Home
-1 Bedroom / 2 Bathrooms / Sleeps 2
Home / -1 Bedroom / Sleeps 2

from

$122

/ night

Email Owner
Bedrooms:-1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$122 - $141
Per week:$852 - $981
Pets allowed:No
Internet:Yes

Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees...

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Certaldo Italy Vacation Rentals - Home
1 / 60

Certaldo Home
2 Bedrooms / 0 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$116

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$116 - $182
Per week:$809 - $1,272
Pets allowed:No
Internet:Yes

Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached. It is only a 15 minutes' drive to the jewel of San Gimignano, and within an hour you can reach both Florence and Siena. Closer...

See more

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Certaldo Italy Vacation Rentals - Home
1 / 28

Certaldo Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$199

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$199 - $214
Per week:$1,390 - $1,498
Pets allowed:No
Internet:Yes

The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany. Strategically positioned in the middle of the Golden Triangle - Florence, Siena and Pisa - it sits on top of a hill looking out onto the panoramic valley to south- west. Surrounded by vast...

See more

Close x

Certaldo Italy Vacation Rentals -
1 / 26

Certaldo
3 Bedrooms / 2 Bathrooms / Sleeps 8
/ 3 Bedrooms / Sleeps 8

from

$104

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Per night:$104 - $186
Per week:$722 - $1,297
Pets allowed:No
Internet:No

Nice complex in Chianti, with pool, for rent. A villa comprising 3 buildings recently restored preserving its original architectural features and turned into 6 apartments and a small independent villa. The property for rent is situated in panoramic location on the hills of the Chianti...

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Certaldo Italy Vacation Rentals -
1 / 25

Certaldo
2 Bedrooms / 2 Bathrooms / Sleeps 6
/ 2 Bedrooms / Sleeps 6

from

$95

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Per night:$95 - $169
Per week:$659 - $1,180
Pets allowed:No
Internet:No

Nice complex in Chianti, with pool, for rent. A villa comprising 3 buildings recently restored preserving its original architectural features and turned into 6 apartments and a small independent villa. The property for rent is situated in panoramic location on the hills of the Chianti...

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Certaldo Italy Vacation Rentals -
1 / 25

Certaldo
1 Bedroom / 1 Bathroom / Sleeps 4
/ 1 Bedroom / Sleeps 4

from

$72

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Per night:$72 - $111
Per week:$498 - $776
Pets allowed:No
Internet:No

Nice complex in Chianti, with pool, for rent. A villa comprising 3 buildings recently restored preserving its original architectural features and turned into 6 apartments and a small independent villa. The property for rent is situated in panoramic location on the hills of the Chianti...

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Certaldo Italy Vacation Rentals - Home
1 / 15

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 3
Home / 1 Bedroom / Sleeps 3

from

$65

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Home
Per night:$65 - $70
Per month:$1,950 - $2,100
Pets allowed:No
Internet:No

Ancient building comprising 4 apartments (one is occupied by the property owners) situated in the historical centre of the medieval town of Certaldo Alto. All of the 3 units have been recently restored and offer nicely furnished and cozy interiors. At their arrival, guests staying...

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Certaldo Italy Vacation Rentals - Home
1 / 60

Certaldo Home
1 Bedroom / 0 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$85

/ night

Email Owner
Bedrooms:1
Sleeps:2
Type:Home
Per night:$85 - $121
Per week:$593 - $841
Pets allowed:No
Internet:Yes

Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached. It is only a 15 minutes' drive to the jewel of San Gimignano, and within an hour you can reach both Florence and Siena. Closer...

See more

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Certaldo Italy Vacation Rentals -
1 / 27

Certaldo
3 Bedrooms / 3 Bathrooms / Sleeps 8
/ 3 Bedrooms / Sleeps 8

from

$104

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Per night:$104 - $186
Per week:$722 - $1,297
Pets allowed:No
Internet:No

Nice complex in Chianti, with pool, for rent. A villa comprising 3 buildings recently restored preserving its original architectural features and turned into 6 apartments and a small independent villa. The property for rent is situated in panoramic location on the hills of the Chianti...

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Certaldo Italy Vacation Rentals -
1 / 31

Certaldo
3 Bedrooms / 3 Bathrooms / Sleeps 8
/ 3 Bedrooms / Sleeps 8

from

$308

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Per night:$308 - $411
Per month:$9,240 - $12,330
Pets allowed:No
Internet:No

Beautiful former barn situated in quiet and panoramic location on the Chianti hills. This house has been recently and carefully restored and turned into a charming country house offering welcoming, tastefully furnished interiors. Outside guests can enjoy use of a beautiful, well-...

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1 / 34

Certaldo
3 Bedrooms / 3 Bathrooms / Sleeps 6
/ 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$174

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Per night:$174 - $303
Per week:$1,212 - $2,116
Pets allowed:No
Internet:No

Welcoming country house with private pool situated in quiet location on the Chianti hills, a short distance away from the charming medieval villages of Certaldo (5 km away) and San Gimignano (18 km away). This villa has been recently restored and provides nice, tastefully furnished...

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Certaldo Italy Vacation Rentals -
1 / 15

Certaldo
2 Bedrooms / 2 Bathrooms / Sleeps 6
/ 2 Bedrooms / Sleeps 6

from

$99

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Per night:$99 - $169
Per week:$690 - $1,180
Pets allowed:No
Internet:No

Welcoming, independent villa with private pool situated only 2 km from the charming village of Certaldo away, along the road connecting Certaldo to Castelfiorentino. This small villa has been recently restored and it is in easy reach of Tuscany’s most important places of interest....

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Certaldo Italy Vacation Rentals -
1 / 27

Certaldo
2 Bedrooms / 1 Bathroom / Sleeps 6
/ 2 Bedrooms / Sleeps 6

from

$106

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Per night:$106 - $177
Per week:$738 - $1,235
Pets allowed:No
Internet:No

Welcoming independent villa with private pool situated a short distance away from the charming, medieval town of Certaldo, on the Chianti hills. This property was restored in 2008 and turned into a nice, small villa providing comfortable interiors. Outside guests can enjoy use ...

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Certaldo Italy Vacation Rentals - Home
1 / 16

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 4
Home / 1 Bedroom / Sleeps 4

from

$70

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Home
Per night:$70 - $77
Per month:$2,100 - $2,310
Pets allowed:No
Internet:No

Ancient building comprising 4 apartments (one is occupied by the property owners) situated in the historical centre of the medieval town of Certaldo Alto. All of the 3 units have been recently restored and offer nicely furnished and cozy interiors. At their arrival, guests staying...

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Certaldo Italy Vacation Rentals - Home
1 / 16

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 3
Home / 1 Bedroom / Sleeps 3

from

$65

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Home
Per night:$65 - $71
Per month:$1,950 - $2,130
Pets allowed:No
Internet:No

Ancient building comprising 4 apartments (one is occupied by the property owners) situated in the historical centre of the medieval town of Certaldo Alto. All of the 3 units have been recently restored and offer nicely furnished and cozy interiors. At their arrival, guests staying...

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Certaldo Italy Vacation Rentals -
1 / 38

Certaldo
7 Bedrooms / 4 Bathrooms / Sleeps 13
/ 7 Bedrooms / Sleeps 13

from

$306

/ night

Email Owner
Bedrooms:7
Bathrooms:4
Sleeps:13
Per night:$306 - $615
Per week:$2,137 - $4,299
Pets allowed:No
Internet:No

If you want to spend your holidays in Chianti, living in a prestigious villa in Tuscany, choose Villa Orchidea. Splendid, ancient Tuscan villa dating back to the 17th century, owned by the Posarelli family, completely restored and set inside a large property of 90 hectares surrounded...

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