50 Best Vacation Rentals in Certaldo - Holiday Lettings - Cabins

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8,375 Vacation rentals

13

Vacation apartment in Certaldo

Province of Florence / Certaldo

5 12 4 nights min

  • 5 bedrooms
  • Sleeps 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
On an estate of 200 hectares. of forests, fields, vineyards and olive groves lies the ancient complex of Villa Taddei, comprising the traditional country manor house, the typical Tuscan barn, about 100 meters, other 4 apartments obtained from rural schools specification …see more

from $247 / night

$1,480 - $2,836 / week

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Responds fast!
avg. 2 hours 5 minutes

from $247 / night

(2) Excellent 

31

Certaldo Vacation apartment rental

Province of Florence / Certaldo

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary
"The Bifora", in the center of Certaldo, is a characteristic apartment in a Tuscan style, completely renovated. It is located on the second floor of a small nineteenth-century building in the center, just steps from the train station and cable car that takes in the medi …see more

from $83 / night

$544 - $803 / week

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from $83 / night

21

Apartment rental in Marcialla with swimming pool

Certaldo / Marcialla

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Small medieval village nestled in the Chianti countryside a short distance from Certaldo, a few kilometers from Florence, Siena and San Gimignano. Wine and oil production, panoramica.Luogo pool ideal for living and relaxing in contact with nature and animals sharing the …see more

from $74 / night

$519 / week

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Responds fast!
avg. 2 hours 38 minutes

from $74 / night

(7) Very Good 

11

Vacation home in Certaldo Alto

Certaldo / Certaldo Alto

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 50 mi
  • Child friendly
  • Private garden
Casa situata nel centro storico di Certaldo Alto, borgo medievale ancora intatto, nella centrale Via Boccaccio a pochi passi dalla casa del grande poeta del 1300 e dal Palazzo Pretorio. La casa offre un grande giardino panoramico con alberi da frutto, olivi e orci in te …see more

from $93 / night

$642 - $766 / week

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from $93 / night

20

Marcialla Vacation apartment rental

Certaldo / Marcialla

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Small medieval village nestled in the Chianti countryside a short distance from Certaldo (birthplace of Boccaccio), a few kilometers from Florence, Siena and San Gimignano. Wine and oil production, panoramica.Luogo pool ideal for living and relaxing in contact with natu …see more

from $74 / night

$519 / week

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Responds fast!
avg. 2 hours 38 minutes

from $74 / night

(6) Excellent 

20

Certaldo Vacation apartment rental

Province of Florence / Certaldo

6 14 4 nights min

  • 6 bedrooms
  • Sleeps 14
  • 4 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
All'interno di una tenuta di 200 ha. di boschi, campi, vigneti e oliveti si trova l'antico complesso di Villa Avanella, comprendente la tradizionale villa signorile di campagna composta da due grandi appartamenti, il caratteristico Fienile e, a circa 100 mt ci sono altr …see more

from $309 / night

$1,853 - $3,507 / week

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Responds fast!
avg. 2 hours 5 minutes

from $309 / night

(5) Excellent 

18

Vacation b&b rental

Province of Florence / Certaldo

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 mi
  • Suitable for children age 5+
  • Air conditioning
Albicocca is a luxury apartment on the first floor of a classic Tuscan manor house in an old park among vineyard and olive groves. Guests have at disposal spacious and bright rooms, furnished with antique Tuscan furniture, creating a romantic atmosphere. Building arti …see more

from $112 / night

$778 / week

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from $112 / night

4

Vacation apartment in Certaldo Alto

Certaldo / Certaldo Alto

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Car not necessary
  • Air conditioning
Located in the ancient and well-preserved medieval village of Certaldo Alto, our apartments offer a holiday of relaxation and culture that the Valdelsa area presents us with ease to reach the most beautiful Tuscan cities like Florence, Siena, Pisa , Lucca. The apartment …see more

from $124 / night

$865 / week

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from $124 / night

(3) Very Good 

23

Vacation apartment in Certaldo

Province of Florence / Certaldo

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
On an estate of 200 hectares. of forests, fields, vineyards and olive groves lies the ancient complex of Villa Taddei, comprising the traditional country manor house, the typical Tuscan barn, about 100 meters, 4 apartments created by the features of Tuscan rural schools …see more

from $81 / night

$556 - $988 / week

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Responds fast!
avg. 2 hours 5 minutes

from $81 / night

21

Vacation apartment in Certaldo

Province of Florence / Certaldo

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Car not necessary
The Camino is a small but nice apartment located in the center of Certaldo, a few steps from the train station and cable car leading to the medieval village of Certaldo Alto. The apartment, completely restored and is on the second floor of a small nineteenth century bui …see more

from $44 / night

$284 - $457 / week

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from $44 / night

(2) Excellent 

32

Vacation apartment with shared pool in Certaldo

Province of Florence / Certaldo

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
La Certaldina Holiday villa is on the top of a hill in the Chianti country side, Ideal place for a relaxing holiday and as starting point for visiting the most Tuscan cities. Pisa, Florence, Siena, San Gimignano and Volterra are reachable in 15 to 50 minutes drivi …see more

from $71 / night

$493 / week

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from $71 / night

(1) Excellent 

99

Vacation apartment in Certaldo Alto

Certaldo / Certaldo Alto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
The apartment "The rooms of Boccaccio" is located along the main street of Certaldo Alto, medieval town in the province of Florence which was the birthplace of Giovanni Boccaccio, famous author of the Decameron. The apartment is on the first floor of a historic building …see more

from $84 / night

$556 - $1,087 / week

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from $84 / night

(4) Excellent 

24

Vacation apartment in Certaldo Alto

Certaldo / Certaldo Alto

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 85 mi
  • Child friendly
The apartment has two entrances and a large courtyard where you can park your car. Certaldo High is a medieval village still intact, is ideal for a holiday of peace, art and history. Here you can visit the house, the tower and the church with the tomb of Giovann …see more

from $80 / night

$556 - $741 / week

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from $80 / night

45

Vacation apartment with shared pool in Certaldo

Province of Florence / Certaldo

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
La Certaldina is a vacation rental between Florence and Siena, with self catering apartments restored in an ancient Villa , overlooking the Chianti countryside. An ideal place for a relaxing and peaceful holiday, with the swimming pool surrounded by olive trees and …see more

from $72 / night

$1,050 - $1,180 / week

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from $72 / night

(2) Very Good 

31

Vacation apartment in Certaldo

Province of Florence / Certaldo

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary
"The Arch", in the center of Certaldo, is a characteristic apartment in a Tuscan style, completely renovated. It is located on the second floor of a small nineteenth-century building in the center, just steps from the train station and cable car that takes in the mediev …see more

from $83 / night

$544 - $803 / week

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from $83 / night

(1) Excellent 

27

Villa rental in Certaldo

Province of Florence / Certaldo

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
La casa vacanze "Poggio ai Venti" dispone di due ampi monolocali di circa 40 mq. ciascuno, con ingresso indipendente, finemente arredati in stile toscano e dotati di ogni confort e comodità. Gli appartamenti (Girasole e Papavero), dispongono di una zona pranzo composta …see more

from $139 / night

$964 / week

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from $139 / night

15

Vacation apartment with shared pool in Certaldo

Province of Florence / Certaldo

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
On an estate of 200 hectares. of forests, fields, vineyards and olive groves lies the ancient complex of Villa Taddei, comprising the traditional country manor house, the typical Tuscan barn, about 100 meters, # 4 apartments created by the features of Tuscan Rural Schoo …see more

from $74 / night

$494 - $926 / week

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Responds fast!
avg. 2 hours 5 minutes

from $74 / night

34

Vacation home in Certaldo

Province of Florence / Certaldo

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Car not necessary
Beautiful flat completely Restructured, well furnished and equipped of all the linen being Necessary for kitchen, bath and bedrooms, in typical Tuscan house with independent entrance in a noiseless central area. Free private parking in the garage at mt. 50 from the flat …see more

from $71 / night

$494 - $741 / week

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from $71 / night

32

Vacation apartment in Certaldo

Province of Florence / Certaldo

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
The Casale del Vacanziere was created by restructuring a farmhouse, making the beautiful view and peacefulness of the area. Casale del Vacanziere, surrounded by the green Tuscan hills, is perfect to accommodate those who love nature, the typical and historical tours fla …see more

from $105 / night

$621 - $1,371 / week

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from $105 / night

65

Vacation apartment in Certaldo

Province of Florence / Certaldo

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
La casa vacanze "Poggio ai Venti" si trova nel cuore della Toscana, a soli 5 Km dall'antico borgo medievale di Certaldo Alto e a pochi Km di distanza da altri luoghi d'arte come San Gimignano, Firenze, Siena, Volterra ecc..."Poggio ai Venti" è adagiato su una collina co …see more

from $77 / night

$513 / week

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from $77 / night

27

Vacation villa in Certaldo

Province of Florence / Certaldo

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Belsole Villa is a villa in Tuscany with swimming pool, located in one of the hills that characterize the landscape, a few steps from Certaldo, an ancient town located halfway between Siena and Florence, suitable to spend holidays in Tuscany for groups. Beautiful and un …see more

from $529 / night

$3,705 - $8,026 / week

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from $529 / night

(1) Excellent 

97

Vacation townhouse with shared pool in Il Pino

Certaldo / Il Pino

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The guest house "Petriccio" is located a few kilometers from the center of Certaldo and from most cities of Tuscany. The house consists of the main house (Apartment "A" and Apartment "B") and an annex. The apartment "A" is on the first floor and has living room / kitche …see more

from $93 / night

$642 - $828 / week

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from $93 / night

19

Vacation apartment in Certaldo

Province of Florence / Certaldo

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Pet friendly
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, gue …see more

from $62 / night

$440 - $507 / week

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from $62 / night

33

Certaldo Vacation apartment rental

Province of Florence / Certaldo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 109 mi
  • Swimming pool
  • Child friendly
Stillo House is located in a historic 15th century building restored in 2010 conserving its original structure and design. It features a living room with a fireplace, a large kitchen, 2 double bedrooms one of them with a loft with a single bed, 2 bathrooms, private gard …see more

from $256 / night

$1,790 / week

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from $256 / night

23

Vacation townhouse rental

Province of Florence / Certaldo

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 80 mi
  • Child friendly
  • Pet friendly
House with independent entrance with first floor large living room with kitchen, double bedroom with bathroom 2 beds single bedroom; the ground floor lounge and garden with possibility to eat outside private parking. The House is equipped with accessories for cooking, s …see more

from $91 / night

$544 / week

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from $91 / night

31

Vacation apartment in Certaldo

Province of Florence / Certaldo

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
Casale del Vacanziere, surrounded by the green Tuscan hills, is perfect to accommodate those who love nature, the typical and historical tours flavors. Casale was born from the renovation of a farmhouse, making the beautiful view and peacefulness of the area. Casale wer …see more

from $105 / night

$621 - $1,199 / week

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from $105 / night

67

Vacation townhouse rental

Province of Florence / Certaldo

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
La casa vacanze "Poggio ai Venti" si trova nel cuore della Toscana, a soli 5 Km dall'antico borgo medievale di Certaldo Alto e a pochi Km di distanza da altri luoghi d'arte come San Gimignano, Firenze, Siena, Volterra ecc... "Poggio ai Venti" è adagiato su una collina c …see more

from $77 / night

$513 / week

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from $77 / night

17

Villa rental in Certaldo

Province of Florence / Certaldo

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
The villa enjoys a blissful isolation in the Tuscan countryside, unique views over the surrounding hills, the views ranging up to catch a glimpse in the distance the towers of San Gimignano. The house is located at the crossroads of many centers of historical and artist …see more

from $161 / night

$1,124 / week

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from $161 / night

(1) Excellent 

34

Certaldo Vacation apartment rental

Province of Florence / Certaldo

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
Apartment in the Chianti area between Florence and Siena with a pool surrounding of olive grove . Ideal for a relaxing holiday and as starting point for visiting the Tuscan important cities. The bright and tastefully furnished independent apartment is at the firs …see more

from $71 / night

$493 / week

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from $71 / night

(8) Excellent 

88

Vacation apartment rental

Certaldo / Certaldo Alto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
Pretty and comfortable apartment located in the medieval town of Certaldo Alto, in the heart of Tuscany, a few kilometres from Florence, Siena, Pisa, San Gimignano and Volterra. The apartment on the ground floor with independent entrance, kitchen/living room with sofa b …see more

from $87 / night

$519 - $803 / week

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from $87 / night

36

Vacation apartment in Certaldo

Province of Florence / Certaldo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 109 mi
  • Swimming pool
  • Child friendly
Torre house was built around the medieval tower of Paluffo is the most ancient part of the estate. This house has three levels with a marvelous view of the Chianti hills and San Gimignano. It features a wide private garden with chairs, table and sun umbrella. - Ground-f …see more

from $299 / night

$2,092 / week

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from $299 / night

17

Apartment rental in Marcialla with shared pool

Certaldo / Marcialla

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
La Certaldina Vacation rental is located on the top of a Chianti hill at 6 km from the village of Certaldo. The position is ideal place for a relaxing and peaceful holiday, with the swimming pool surrounded by olive trees and it is perfect as starting point, for vis …see more

from $70 / night

$865 - $951 / week

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from $70 / night

29

Vacation apartment with shared pool in Certaldo

Province of Florence / Certaldo

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 109 mi
  • Swimming pool
  • Child friendly
Frantoio House is located in a historic 15th century building restored in 2010 conserving its original structure and design. It features a large living room, a loft with a single bed overlooking the living room, kitchen, 3 double bedrooms, 2 bathrooms, private garden wi …see more

from $281 / night

$1,962 / week

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from $281 / night

15

Certaldo Vacation guest house rental

Province of Florence / Certaldo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
La Certaldina is an Vacation rental self catering apartment located on the top Chianti's hill at 6 km from the village of Certaldo. The position is perfect for visiting the most important Tuscan cities; Florence, Siena, Pisa, Lucca, Volterra, San Gimignano are at 20 …see more

from $105 / night

$735 / week

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from $105 / night

5

Vacation apartment in Certaldo

Province of Florence / Certaldo

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
In the pinewood, close to Villa Bacìo, a finely furnished first floor apartment consisting of a wide living-room with kitchenette, 4 bedrooms, 2 bathrooms, and a little storage room. The surrounding pinewood gives the guests the opportunity of living in a peaceful area …see more

from $244 / night

$1,704 / week

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from $244 / night

(1) Good 

14

Vacation apartment accommodation

Province of Florence / Certaldo

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Our farmhouse in the beautiful Tuscan countryside between Florence, Siena and San Gimignano, is composed of 6 apartments and a double room. Ideal for families and children, has a swimming pool and riding school with opportunity for excursion! The apartment is of 80 mq f …see more

from $99 / night

$556 / week

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from $99 / night

(2) Excellent 

6

Castle rental in Certaldo with swimming pool

Province of Florence / Certaldo

19 40 2 nights min

  • 19 bedrooms
  • Sleeps 40
  • 2 nights min
  • Swimming pool
  • Private garden
Medieval castle in the middle of Tuscany on the highest Hill between Florence and Siena dominating the Val d'Elsa to the via Francigena, surrounded by his farm, the first example of a fortified farm in 1300, where today the greenness of nature with its products (wine, o …see more

from $4,940 / night

$30,870 / week

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Responds fast!
avg. 3 hours 17 minutes

from $4,940 / night

(5) Very Good 

104

Vacation apartment in Certaldo Alto

Certaldo / Certaldo Alto

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
Casa Chiara is a characteristic apartment with vaulted ceilings, and recently completely renovated, which has its particularity in the contrast between the original structure of the House and modern décor. Casa Chiara is situated along the famous Via del Castello, road …see more

from $93 / night

$605 - $865 / week

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from $93 / night

(3) Very Good 

21

Vacation apartment with shared pool in Certaldo

Province of Florence / Certaldo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
On an estate of 200 hectares. of forests, fields, vineyards and olive groves lies the ancient complex of Villa Taddei, comprising the traditional country manor house, the typical Tuscan barn, about 100 meters, other 4 apartments created by the features of Tuscan rural s …see more

from $99 / night

$617 - $1,480 / week

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Responds fast!
avg. 2 hours 5 minutes

from $99 / night

(1) Very Good 

40

Vacation apartment with shared pool in Certaldo

Province of Florence / Certaldo

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
La Certaldina Holidays House is a few steps from Florence and Siena, with self catering apartment overlooking the wonderful Chianti countryside. The Villa is sourrended of gardens and a pool overlooking vineyards and olive groves and the position is perfect for visit …see more

from $72 / night

$502 / week

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from $72 / night