50 Best Vacation Rentals in Certaldo - Holiday Lettings - Cabins

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8,784 Vacation rentals

(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 $91 / night

$638 - $719 / week

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from $91 / night

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 $232 / night

$1,391 - $2,666 / week

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avg. 2 hours 5 minutes

from $232 / 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 $93 / night

$650 / week

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avg. 2 hours 55 minutes

from $93 / night

(1) Very Good 

80

Vacation apartment in Certaldo Alto

Certaldo / Certaldo Alto

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
The well House, in the medieval village of Certaldo Alto, is characterized by the typical Tuscan style with terracotta floors and beamed ceilings, and has its entrance in the main street, Via Boccaccio. The well House is located on the first floor and offers its guests …see more

from $70 / night

$499 - $765 / week

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from $70 / 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 $79 / night

$522 - $1,020 / week

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from $79 / 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 $72 / night

$481 / week

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from $72 / 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 $76 / night

$522 - $927 / week

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avg. 2 hours 5 minutes

from $76 / 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 $116 / night

$812 / week

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from $116 / 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 $66 / night

$463 / week

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avg. 1 hour 43 minutes

from $66 / night

(9) 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 $82 / night

$487 - $754 / week

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from $82 / 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 $70 / night

$464 - $869 / week

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Responds fast!
avg. 2 hours 5 minutes

from $70 / night

(2) Very Good 

34

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 $78 / night

$510 - $754 / week

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from $78 / 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 $93 / night

$649 / week

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Responds fast!
avg. 2 hours 55 minutes

from $93 / 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 $68 / night

$471 / week

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Responds fast!
avg. 1 hour 43 minutes

from $68 / 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 $75 / night

$522 - $696 / week

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from $75 / 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 $87 / night

$568 - $812 / week

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from $87 / night

(16) Excellent 

15

Vacation farmhouse with swimming pool in Certaldo

Province of Florence / Certaldo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Organic farm producing extra virgin olive oil. Located atop a hill on the ruins of the ancient city of Semifonte, it offers an apartment of 150 sqm on the first floor, equipped with all comforts and a private 15m infinity pool. Half way from Florence, Siena and S. Gimi …see more

from $250 / night

$1,739 - $1,860 / week

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Responds fast!
avg. 3 hours 22 minutes

from $250 / 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 $68 / night

$985 - $1,107 / week

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Responds fast!
avg. 1 hour 43 minutes

from $68 / night

(18) Excellent 

13

Vacation apartment with shared pool in Certaldo

Province of Florence / Certaldo

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
A rustic 1st floor apartment in a villa set amongst vineyards and olive groves in one of the most beautiful corners of the Chianti region. Use of shared garden and pool and allocated outside eating area. Located halfway between Florence and Siena, not only it pro …see more

from $99 / night

$660 / week

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from $99 / 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 $130 / night

$904 / week

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from $130 / 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 $87 / night

$603 - $777 / week

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from $87 / 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 $290 / night

$1,739 - $3,291 / week

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Responds fast!
avg. 2 hours 5 minutes

from $290 / 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 $151 / night

$1,057 / week

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from $151 / 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 $99 / night

$586 - $1,294 / week

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from $99 / night

(2) Excellent 

34

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 $78 / night

$510 - $754 / week

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from $78 / 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 $85 / night

$510 / week

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from $85 / night

(1) Very Good 

45

Apartment rental in Certaldo with shared pool

Province of Florence / Certaldo

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
La Certaldina is an holiday vacation rental independent apartment on the top of Chianti's hill at 6 Km from Certaldo. A place for a relaxing holiday with a panoramic swimming pool overlooking vineyards and olives threes.. The position is perfect as starting point, f …see more

from $70 / night

$487 / week

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Responds fast!
avg. 1 hour 43 minutes

from $70 / night

(2) Very Good 

97

Il Pino Vacation townhouse rental

Certaldo / Il Pino

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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 "B" is located on the ground floor and consists of liv …see more

from $87 / night

$603 - $777 / week

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from $87 / 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 $99 / night

$586 - $1,131 / week

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from $99 / 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 $105 / night

$731 / 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 $72 / night

$481 / week

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from $72 / 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 $67 / night

$464 - $696 / week

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from $67 / night

24

Vacation apartment rental

Province of Florence / Certaldo

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Pet friendly
Casa Alba is a typical apartment in a Tuscan farmhouse, not far from the beautiful medieval town of Certaldo Alto and the beautiful hills of Canonica Park. The apartment has beamed ceilings, terracotta floors and wooden floors, big fireplace. The house has a fully equip …see more

from $53 / night

$336 - $499 / week

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from $53 / night

10

Vacation apartment accommodation

Province of Florence / Certaldo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Nestling in the green heart of Tuscany, an Area of Outstanding Natural Beauty, The house is a self-contained self-catering apartment. Step outside your door and you have unparalleled access in every direction of footpaths that crisscross their wineyards and oliveyards …see more

from $116 / night

$696 / week

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from $116 / 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 $65 / night

$812 - $893 / week

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Responds fast!
avg. 1 hour 43 minutes

from $65 / 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 $66 / night

$463 / week

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Responds fast!
avg. 1 hour 43 minutes

from $66 / night

51

Vacation villa in Certaldo

Province of Florence / Certaldo

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 75 mi
  • Swimming pool
  • Child friendly
If you require superior accommodation with an unmistakable touch of class, this fully refurbished, early 19th century, two-storey villa will not disappoint you. It is furnished with valuable antiques dating back to the 1700’s, complemented by elegant, Venetian-design mi …see more

from $497 / night

$3,477 - $7,532 / week

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from $497 / 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 $240 / night

$1,679 / week

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from $240 / 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 $228 / night

$1,595 / week

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from $228 / night

(2) Excellent 

21

Vacation b&b in Certaldo

Province of Florence / Certaldo

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 70 mi
  • Suitable for children age 5+
  • Air conditioning
Mirtillo is a luxury apartment on the first floor of a classic 18th century Tuscan manor house in an old park amongst vineyards and olive groves. It is located in the heart of Tuscany, midway between Florence and Siena in the most characteristic Chianti landscape. The …see more

from $105 / night

$730 / week

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from $105 / night