Certaldo Vacation Rentals, Homes, & More

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1-32 of 32 Certaldo Rentals

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1 / 14

Certaldo Home
9 Bedrooms / 10 Bathrooms / Sleeps 189 BR / 10 BA / Sleeps 18
Home / 9 Bedrooms / Sleeps 18

from

$17

/ night

Email Owner
Bedrooms:9
Bathrooms:10
Sleeps:18
Type:Home
Per night:$17 - $1,042
Per week:$113 - $7,292
Pets allowed:No
Internet:No

Nine Bedroom Independent Villa Chianti Villa Pucci is a splendid 19th Century independent villa with private swimming pool, surrounded by gardens. The villa is in a perfect position enjoying fabulous unspoilt views of the unique rolling countryside of the famous Chianti region for...

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1 / 15

Certaldo Home
6 Bedrooms / 7 Bathrooms / Sleeps 126 BR / 7 BA / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

from

$17

/ night

Email Owner
Bedrooms:6
Bathrooms:7
Sleeps:12
Type:Home
Per night:$17 - $1,904
Per week:$113 - $13,322
Pets allowed:No
Internet:Yes

Six Bedroom Independent Villa Chianti Villa Il Castello, whose origins date back to 13th Century, is an elegant country villa in a perfect position enjoying fabulous unspoilt views over the sweeping Chianti countryside. Surrounded by gardens with lawns and terraces, the villa...

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1 / 27

Certaldo Home
7 Bedrooms / 4 Bathrooms / Sleeps 137 BR / 4 BA / Sleeps 13
Home / 7 Bedrooms / Sleeps 13
(44) Excellent 44 Reviews

from

$407

/ night

Email Owner
Bedrooms:7
Bathrooms:4
Sleeps:13
Type:Home
Per night:$407 - $832
Per week:$2,847 - $5,819
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 / 46

Certaldo Home
6 Bedrooms / 6 Bathrooms / Sleeps 106 BR / 6 BA / Sleeps 10
Home / 6 Bedrooms / Sleeps 10

from

$341

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:10
Type:Home
Per night:$341 - $681
Per week:$2,382 - $4,765
Pets allowed:No
Internet:No

A holiday at Villa Elsa is a unique experience. Guests will spend their stay in a traditional Florentine residence surrounded by the stunning Tuscan countryside and truly immerse themselves in Italian life. The property consists of four large and well- lit apartments to provide...

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1 / 50

Certaldo Home
5 Bedrooms / 5 Bathrooms / Sleeps 95 BR / 5 BA / Sleeps 9
Home / 5 Bedrooms / Sleeps 9

from

$686

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:9
Type:Home
Per night:$686 - $895
Per week:$4,797 - $6,265
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 / 14

Certaldo Home
3 Bedrooms / 3 Bathrooms / Sleeps 63 BR / 3 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$436

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$436 - $492
Per week:$3,048 - $3,443
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 / 26

Certaldo Home
3 Bedrooms / 4 Bathrooms / Sleeps 63 BR / 4 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6
(6) Excellent 6 Reviews

from

$466

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$466 - $515
Per week:$3,262 - $3,601
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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Certaldo Italy Vacation Rentals - Home
1 / 37

Certaldo Home
2 Bedrooms / 12 Bathrooms / Sleeps 42 BR / 12 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$202

/ night

Email Owner
Bedrooms:2
Bathrooms:12
Sleeps:4
Type:Home
Per night:$202 - $221
Per week:$1,411 - $1,547
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 42 BR / 1 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$175 - $202
Per week:$1,219 - $1,411
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 / 39

Certaldo Home
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$208

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$208 - $225
Per week:$1,456 - $1,569
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 / 38

Certaldo Home
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$208

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$208 - $225
Per week:$1,456 - $1,569
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 / 38

Certaldo Home
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$208

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$208 - $225
Per week:$1,456 - $1,569
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 - Farmhouse / Barn
1 / 23

Certaldo Farmhouse / Barn
2 Bedrooms / 1 Bathroom / Sleeps 42 BR / 1 BA / Sleeps 4
Farmhouse / Barn / 2 Bedrooms / Sleeps 4

from

$70

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Farmhouse / Barn
Per night:$70 - $117
Per month:$2,100 - $3,510
Pets allowed:No
Internet:No

This group of apartments can be found near Certaldo, a renowned central Tuscan town, just a short hop from Florence, Siena, San Gimignano and the Chianti wine region. The property is made up of five apartments in total (one of which is lived in permanently) and a communal area...

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Certaldo Italy Vacation Rentals - Home
1 / 39

Certaldo Home
2 Bedrooms / 22 Bathrooms / Sleeps 42 BR / 22 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$202

/ night

Email Owner
Bedrooms:2
Bathrooms:22
Sleeps:4
Type:Home
Per night:$202 - $221
Per week:$1,411 - $1,547
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 / 60

Certaldo Home
2 Bedrooms / 0 Bathroom / Sleeps 42 BR / 0 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$121

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$121 - $144
Per week:$847 - $1,005
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 / 60

Certaldo Home
2 Bedrooms / 0 Bathroom / Sleeps 42 BR / 0 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$117

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$117 - $134
Per week:$813 - $937
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 / 56

Certaldo Home
2 Bedrooms / 0 Bathroom / Sleeps 42 BR / 0 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4
(1) Excellent 1 Review

from

$117

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$117 - $134
Per week:$813 - $937
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 42 BR / 0 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4
(1) Excellent 1 Review

from

$117

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$117 - $134
Per week:$813 - $937
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 41 BR / 0 BA / Sleeps 4
Home / 1 Bedroom / Sleeps 4

from

$117

/ night

Email Owner
Bedrooms:1
Sleeps:4
Type:Home
Per night:$117 - $134
Per week:$813 - $937
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 - Farmhouse / Barn
1 / 25

Certaldo Farmhouse / Barn
1 Bedroom / 1 Bathroom / Sleeps 31 BR / 1 BA / Sleeps 3
Farmhouse / Barn / 1 Bedroom / Sleeps 3

from

$59

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Farmhouse / Barn
Per night:$59 - $96
Per month:$1,770 - $2,880
Pets allowed:No
Internet:No

This group of apartments can be found near Certaldo, a renowned central Tuscan town, just a short hop from Florence, Siena, San Gimignano and the Chianti wine region. The property is made up of five apartments in total (one of which is lived in permanently) and a communal area...

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Certaldo Italy Vacation Rentals - Farmhouse / Barn
1 / 23

Certaldo Farmhouse / Barn
1 Bedroom / 1 Bathroom / Sleeps 31 BR / 1 BA / Sleeps 3
Farmhouse / Barn / 1 Bedroom / Sleeps 3

from

$59

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Farmhouse / Barn
Per night:$59 - $96
Per month:$1,770 - $2,880
Pets allowed:No
Internet:No

This group of apartments can be found near Certaldo, a renowned central Tuscan town, just a short hop from Florence, Siena, San Gimignano and the Chianti wine region. The property is made up of five apartments in total (one of which is lived in permanently) and a communal area...

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Certaldo Italy Vacation Rentals - Home
1 / 61

Certaldo Home
1 Bedroom / 0 Bathroom / Sleeps 21 BR / 0 BA / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$94

/ night

Email Owner
Bedrooms:1
Sleeps:2
Type:Home
Per night:$94 - $100
Per week:$655 - $700
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 / 38

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 21 BR / 1 BA / Sleeps 2
Home / 1 Bedroom / Sleeps 2
(1) Excellent 1 Review

from

$152

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$152 - $168
Per week:$1,061 - $1,174
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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Close x

Certaldo Italy Vacation Rentals - Home
1 / 36

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 21 BR / 1 BA / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$175

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$175 - $202
Per week:$1,219 - $1,411
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 / 36

Certaldo Home
1 Bedroom / 9 Bathrooms / Sleeps 21 BR / 9 BA / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$128

/ night

Email Owner
Bedrooms:1
Bathrooms:9
Sleeps:2
Type:Home
Per night:$128 - $147
Per week:$892 - $1,028
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 2-1 BR / 2 BA / Sleeps 2
Home / -1 Bedroom / Sleeps 2

from

$192

/ night

Email Owner
Bedrooms:-1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$192 - $208
Per week:$1,344 - $1,456
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 21 BR / 1 BA / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$128

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$128 - $147
Per week:$892 - $1,028
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
1 Bedroom / 0 Bathroom / Sleeps 21 BR / 0 BA / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$89

/ night

Email Owner
Bedrooms:1
Sleeps:2
Type:Home
Per night:$89 - $96
Per week:$621 - $666
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

Close x

Certaldo Italy Vacation Rentals - Home
1 / 37

Certaldo Home
1 Bedroom / 1 Bathroom / Sleeps 21 BR / 1 BA / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$128

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$128 - $147
Per week:$892 - $1,028
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 / 36

Certaldo Home
1 Bedroom / 2 Bathrooms / Sleeps 21 BR / 2 BA / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$128

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$128 - $147
Per week:$892 - $1,028
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 2-1 BR / 2 BA / Sleeps 2
Home / -1 Bedroom / Sleeps 2

from

$128

/ night

Email Owner
Bedrooms:-1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$128 - $147
Per week:$892 - $1,028
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

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Certaldo Italy Vacation Rentals - Farmhouse / Barn
1 / 24

Certaldo Farmhouse / Barn
1 Bedroom / 1 Bathroom / Sleeps 21 BR / 1 BA / Sleeps 2
Farmhouse / Barn / 1 Bedroom / Sleeps 2

from

$53

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Farmhouse / Barn
Per night:$53 - $87
Per month:$1,590 - $2,610
Pets allowed:No
Internet:No

This group of apartments can be found near Certaldo, a renowned central Tuscan town, just a short hop from Florence, Siena, San Gimignano and the Chianti wine region. The property is made up of five apartments in total (one of which is lived in permanently) and a communal area...

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