Certaldo Vacation Rentals, Homes, & More

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1-34 of 34 Certaldo Rentals

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Certaldo Home
7 Bedrooms / 4 Bathrooms / 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 / 16

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

from

$345

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$345
Per week:$2,415
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. This villa near San Gimignano offers a pristine swimming pool, covered terraces and three bedrooms, two bathrooms, a kitchen,...

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1 / 60

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

from

$113

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$113 - $178
Per week:$791 - $1,241
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

$113

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$113 - $178
Per week:$791 - $1,241
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

$113

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$113 - $178
Per week:$791 - $1,241
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 2
Home / 1 Bedroom / Sleeps 2

from

$91

/ night

Email Owner
Bedrooms:1
Sleeps:2
Type:Home
Per night:$91 - $134
Per week:$637 - $934
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 / 26

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

(6)“ Excellent ”6 Reviews

from

$454

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$454 - $501
Per week:$3,173 - $3,502
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 / 50

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

from

$658

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:9
Type:Home
Per night:$658 - $861
Per week:$4,600 - $6,027
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 / 39

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

from

$203

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$203 - $218
Per week:$1,417 - $1,526
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
1 Bedroom / 0 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$87

/ night

Email Owner
Bedrooms:1
Sleeps:2
Type:Home
Per night:$87 - $123
Per week:$604 - $857
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 / 54

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

Bedrooms:6
Bathrooms:6
Sleeps:12
Type:Home
Per night:$1,020 - $1,788
Per week:$7,136 - $12,514
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. Atop a hill with sweeping views over its vast estate...

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Certaldo Italy Vacation Rentals - Farmhouse / Barn
1 / 23

Certaldo Farmhouse / Barn
1 Bedroom / 1 Bathroom / Sleeps 3
Farmhouse / Barn / 1 Bedroom / Sleeps 3

from

$58

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Farmhouse / Barn
Per night:$58 - $94
Per month:$1,740 - $2,820
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 / 46

Certaldo Home
6 Bedrooms / 6 Bathrooms / Sleeps 10
Home / 6 Bedrooms / Sleeps 10

from

$331

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:10
Type:Home
Per night:$331 - $662
Per week:$2,317 - $4,634
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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Certaldo Italy Vacation Rentals - Home
1 / 34

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

from

$170

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$170 - $197
Per week:$1,186 - $1,373
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 / 38

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

from

$203

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$203 - $218
Per week:$1,417 - $1,526
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 - Home
1 / 38

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

from

$203

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$203 - $218
Per week:$1,417 - $1,526
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 - Home
1 / 37

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

from

$197

/ night

Email Owner
Bedrooms:2
Bathrooms:12
Sleeps:4
Type:Home
Per night:$197 - $215
Per week:$1,373 - $1,504
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 / 22 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$197

/ night

Email Owner
Bedrooms:2
Bathrooms:22
Sleeps:4
Type:Home
Per night:$197 - $215
Per week:$1,373 - $1,504
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 / 61

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

from

$113

/ night

Email Owner
Bedrooms:1
Sleeps:4
Type:Home
Per night:$113 - $178
Per week:$791 - $1,241
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 / 36

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

from

$170

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$170 - $197
Per week:$1,186 - $1,373
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 2
Home / 1 Bedroom / Sleeps 2

from

$124

/ night

Email Owner
Bedrooms:1
Bathrooms:9
Sleeps:2
Type:Home
Per night:$124 - $143
Per week:$868 - $999
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

$187

/ night

Email Owner
Bedrooms:-1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$187 - $203
Per week:$1,307 - $1,417
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

$124

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$124 - $143
Per week:$868 - $999
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

$124

/ night

Email Owner
Bedrooms:-1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$124 - $143
Per week:$868 - $999
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 / 37

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

from

$124

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$124 - $143
Per week:$868 - $999
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

$124

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$124 - $143
Per week:$868 - $999
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 - Home
1 / 60

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

from

$118

/ night

Email Owner
Bedrooms:2
Sleeps:4
Type:Home
Per night:$118 - $186
Per week:$824 - $1,296
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 - Farmhouse / Barn
1 / 23

Certaldo Farmhouse / Barn
2 Bedrooms / 1 Bathroom / Sleeps 4
Farmhouse / Barn / 2 Bedrooms / Sleeps 4

from

$69

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Farmhouse / Barn
Per night:$69 - $114
Per month:$2,070 - $3,420
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 / 25

Certaldo Farmhouse / Barn
1 Bedroom / 1 Bathroom / Sleeps 3
Farmhouse / Barn / 1 Bedroom / Sleeps 3

from

$58

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Farmhouse / Barn
Per night:$58 - $94
Per month:$1,740 - $2,820
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...

See more

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Certaldo Italy Vacation Rentals - Farmhouse / Barn
1 / 24

Certaldo Farmhouse / Barn
1 Bedroom / 1 Bathroom / Sleeps 2
Farmhouse / Barn / 1 Bedroom / Sleeps 2

from

$52

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Farmhouse / Barn
Per night:$52 - $85
Per month:$1,560 - $2,550
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...

See more

Close x

Certaldo Italy Vacation Rentals - Home
1 / 14

Certaldo Home
9 Bedrooms / 10 Bathrooms / Sleeps 18
Home / 9 Bedrooms / Sleeps 18

from

$393

/ night

Email Owner
Bedrooms:9
Bathrooms:10
Sleeps:18
Type:Home
Per night:$393 - $1,020
Per week:$2,745 - $7,136
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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Certaldo Italy Vacation Rentals - Home
1 / 15

Certaldo Home
6 Bedrooms / 7 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:7
Sleeps:12
Type:Home
Per night:$1,275 - $1,863
Per week:$8,919 - $13,036
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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Certaldo Italy Vacation Rentals - Home
1 / 14

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

from

$424

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$424 - $479
Per week:$2,964 - $3,348
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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Certaldo Italy Vacation Rentals - Home
1 / 38

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

(1)“ Excellent ”1 Review

from

$148

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$148 - $164
Per week:$1,032 - $1,142
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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