50 Best Vacation Rentals in Montaione - Holiday Lettings - Cabins

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Castelfalfi
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San Vivaldo
15 properties
Santo Stefano
11 properties
Alberi
10 properties

Montaione

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5,747 Vacation rentals

(2) Very Good 

8

Vacation townhouse with shared pool in Casicello

Montaione / Casicello

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Casa Vacanze Antica Pietra is a beautiful property in the green Tuscan hills. Our vacation home is in the small medieval village of Casicello, few kilometers from the most beautiful cities of Tuscany of art and culture , such as Montaione, Volterra, San Gimignano , Cer …see more

from $79 / night

$553 / week

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from $79 / night

(1) Excellent 

7

Casicello Vacation townhouse rental

Montaione / Casicello

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
Casa Vacanze Antica Pietra is a beautiful property in the green Tuscan hills. Our vacation home is in the small medieval village of Casicello, few kilometers from the most beautiful cities of Tuscany of art and culture , such as Montaione, Volterra, San Gimignano , Cer …see more

from $79 / night

$553 / week

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from $79 / night

13

Collegalli Vacation apartment rental

Montaione / Collegalli

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
The good rest is a cosy holiday house immersed in the enchanting scenery of the harmonious Tuscany countryside. Our House, a farm that grows in an area of about 100 hectares, lies in the harmonious scenery of the Tuscan countryside, where green hills occur degrading to …see more

from $103 / night

$801 - $1,202 / week

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from $103 / night

10

Vacation apartment rental

Province of Florence / Montaione

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Casavacanze Montericco si trova nella campagna Toscana a Montaione(FI) ed è il punto di partenza ideale per visitare Firenze, Pisa e Siena. La struttura ha 1 appartamento grande (8 posti)composto da: 4 camere, 2 bagni e una cucina All'esterno c'è un ampio giardino, i …see more

from $138 / night

$687 / week

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from $138 / night

(2) Very Good 

24

Villa rental in Montaione with shared pool

Province of Florence / Montaione

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Giardino is a self catering indipendent villa in the farmhouse Casa Vacanze Amarrante. It's located in the middle of Tuscany between the borders of the province of Firenze, Siena and Pisa: the perfect location to reach the great art cities with daily trip or just get re …see more

from $109 / night

$664 - $1,145 / week

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from $109 / night

(3) Excellent 

36

Vacation villa with swimming pool in Montaione

Province of Florence / Montaione

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
The villa is located right outside the picturesque hamlet of Iano, whose origins date back to the Etruscan times. This is the territory of Montaione which lies on the triangle of the provinces of Pisa, Florence and Siena, ideal starting point to visit S. Gimignano, Volt …see more

from $293 / night

$2,048 - $3,421 / week

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from $293 / night

27

Vacation apartment with shared pool in Alberi

Montaione / Alberi

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Sheltered in the middle of a valley of vineyards and olive groves, from which high quality olive oil and wine is made, these holiday homes in Tuscany are situated in a very quiet area, far from the noises of the towns and surrounded by an uncontaminated countryside. Thi …see more

from $195 / night

$630 - $1,476 / week

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Responds fast!
avg. 3 hours 5 minutes

from $195 / night

(2) Excellent 

14

Apartment rental in Alberi with shared pool

Montaione / Alberi

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Suitable for children age 5+
1 double bedroom + 1 bedroom with 2 single beds or double bed (of your choice). Also an additional single bed can be added. 1 bathroom with shower and bathtub, large livingroom and well-equipped kitchen with beautiful fireplace, great in autumn. The apartment has also …see more

from $113 / night

$790 / week

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from $113 / night

(2) Very Good 

16

Montaione Vacation home rental

Province of Florence / Montaione

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Purple House is a House free on three sides in support of a twin structure, which in turn, with other properties, is part of a vacation immersed in the Tuscan countryside and offering a wonderful swimming pool. The House is surrounded by a large private garden, with pan …see more

from $344 / night

$1,601 / week

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from $344 / night

(10) Excellent 

48

Villa rental in Collegalli with swimming pool

Montaione / Collegalli

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
A beautifully preserved Tuscan villa on the historic Collegalli estate in Montaione, situated on a peaceful hilltop with spectacular views of the countryside. Villa Strozzi offers complete privacy, including a private garden and swimming pool, surrounded by nature and w …see more

from $378 / night

$2,632 - $3,662 / week

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from $378 / night

25

Vacation apartment with shared pool in Montaione

Province of Florence / Montaione

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Sheltered in the middle of a valley of vineyards and olive groves, from which high quality olive oil and wine is made, these holiday homes in Tuscany are situated in a very quiet area, far from the noises of the towns and surrounded by an uncontaminated countryside. Thi …see more

from $115 / night

$435 - $1,019 / week

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Responds fast!
avg. 3 hours 5 minutes

from $115 / night

(1) Excellent 

24

Vacation villa with swimming pool in Alberi

Montaione / Alberi

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villino Santo Stefano is a beautiful private Villa in the Florentine Chianti area. It has been recently restored and it is fully equipped. It overlooks the gently Tuscan rolling hills and it is surrounded by a typical Tuscan landscape: hills, olive trees and vineyards. …see more

from $258 / night

$1,659 - $2,231 / week

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from $258 / night

12

Montaione Vacation apartment rental

Province of Florence / Montaione

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 40 mi
  • Swimming pool
  • Private garden
Fully furnished and equipped house. Approximately 55 m2. Beds 4 . Lounge with dining room, table and fireplace. Cooking area with equipped kitchen. Double bedroom. Room with two single beds. Bathroom with shower box, bidet, wc and wash basin. Outdoor area featuring a t …see more

from $103 / night

$653 - $1,007 / week

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from $103 / night

(2) Excellent 

12

Vacation apartment in Alberi

Montaione / Alberi

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The Lebbio farmhouse is a touristic ensemble composed by several ancient stone made buildings, situated among Tuscany hills, plunged into the silence and shaded by old-age trees Ground Floor 130 sqm Private garden (2,000 sqmt) Private parking Furnished loggia (32 sqmt) …see more

from $218 / night

$1,419 - $2,128 / week

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from $218 / night

11

Vacation apartment in Sughera

Montaione / Sughera

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
Matteo House: Apartment of 65 m2 with terrace, located in family-run farmhouse, immersed in the Green Tuscan hills. The apartment consists of a large kitchen with living room, bedroom, bedroom with bunk beds and bathroom. Can indoor parking. The farm is located a few ki …see more

from $99 / night

$689 / week

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from $99 / night

7

Vacation home with shared pool in Montaione

Province of Florence / Montaione

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
CASAVACANZE MONTERICCO IS IN TUSCANY MONTAIONE (FI). FLAT 2 + 2 PLACES CONSISTS OF: 1 DOUBLE, 1 BATHROOM AND KITCHEN AND SOFA BED 1 X2. LARGE GARDEN, BARBECUE, POOL AND PRIVATE PARKING. IDEAL STARTING POINT TO VISIT Florence, Siena and Pisa. THE THERMAL CENTER OF GAMBAS …see more

from $172 / night

$401 / week

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from $172 / night

9

Montaione Vacation apartment rental

Province of Florence / Montaione

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fully furnished and equipped house. Approximately 50 m2 on the first floor. 4 Beds. Large lounge with dining room table divan-bed and fireplace - cooking area with well-equipped kitchen. Double bedroom. Bathroom with box shower, bidet, wc and washbasin. Outdoor area fea …see more

from $92 / night

$515 - $824 / week

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from $92 / night

(1) Excellent 

42

Santo Stefano Vacation villa rental

Montaione / Santo Stefano

17 29 7 nights min

  • 17 bedrooms
  • sleeps 29
  • 7 nights min
  • Nearest beach 65 mi
  • Swimming pool
  • Child friendly
!!!EARLY BOOKING DISCOUNT!!! FOR STAYS IN HSS1 & HS (2018): 10% discount for bookings confirmed within 45 days before the arrival date. FOR STAYS IN MS and HSS Seasons (2018): 15% discount for bookings confirmed within 30 days before the arrival date. FOR STAYS IN LS a …see more

from $1,037 / night

$7,254 - $11,727 / week

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from $1,037 / night

25

Montaione Vacation villa rental

Province of Florence / Montaione

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 75 mi
  • Swimming pool
  • Child friendly
Relax on one of the large private terraces and at sunrise and sunset, when all is calm, you may glimpse the deer, rabbits and pheasants that populate the extensive grounds. Tre Querce is independent, finely restructured and comfortably furnished: everything is at the di …see more

from $205 / night

$1,431 - $2,432 / week

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from $205 / night

(1) Excellent 

24

Vacation villa in Montaione

Province of Florence / Montaione

5 14 7 nights min

  • 5 bedrooms
  • sleeps 14
  • 7 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Surrounded by five hectares of olive groves and vineyards, situated in an elevated position, this enchanting property overlooks the surrounding countryside, offering a beautiful view of the hills in the distance. San Gimignano, Certaldo and Volterra, musts on every tour …see more

from $326 / night

$2,278 - $4,402 / week

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from $326 / night

12

Mura,Italy Vacation b&b rental

Montaione / Mura,Italy

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Deep in the Tuscan landscape stillness our farm offers four rooms, all finely furnished according to the traditional Tuscan style. Our rooms provide all modern comforts. Our guest will have the possibility to leave their cars in our private park place and borrow a bike …see more

from $86 / night

$601 / week

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from $86 / night

(5) Excellent 

37

Vacation apartment in Montaione

Province of Florence / Montaione

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Air conditioning
Located in the historical village centre of Montaione (Florence region), the apartment has been restored to a high standard with 2 bedroom, 2 bathroom. It is conveniently located in the main pedestrian street of town surrounded by restaurants, shops, local markets and …see more

from $80 / night

$561 / week

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Responds fast!
avg. 2 hours 54 minutes

from $80 / night

32

Vacation apartment with shared pool in Montaione

Province of Florence / Montaione

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Two bedroom apartment of 60sqm with private terrace. Living room with kitchen corner and double sofa bed, double bedroom, one bedroom with twin beds, bathroom with shower. Tv-sat, Internet wi-fi connection. This beautiful holiday accommodation in Chianti is located nea …see more

from $149 / night

$460 - $1,133 / week

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Responds fast!
avg. 3 hours 5 minutes

from $149 / night

38

Vacation villa with swimming pool in Montaione

Province of Florence / Montaione

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely villa in Chianti is located in Iano, a peaceful, little hamlet near Volterra and San Gimignano (at 20 km), right in the heart of Tuscany. The area has a picturesque landscape, full of fine views, with the typical colours of the Tuscan countryside. Recently r …see more

from $595 / night

$1,785 - $3,719 / week

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Responds fast!
avg. 3 hours 5 minutes

from $595 / night

(1) Excellent 

87

Vacation apartment in Montaione

Province of Florence / Montaione

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 73 mi
  • Child friendly
  • Pet friendly
Borgo La Casaccia, renovated 01/2011, born from a medieval village, It is composed of 12 apartments which retain the original architecture of the 17th century, with the ceiling consists of wooden beams and florentine terra-cotta floors. All apartments are equipped with …see more

from $93 / night

$561 / week

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Responds fast!
avg. 2 hours 35 minutes

from $93 / night

25

Vacation villa with swimming pool in Mura,Italy

Montaione / Mura,Italy

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Five bedrooms and five bathrooms for ten guests, two hundred and twenty squared meters of comfort and elegance, two hectars of private park with swimming pool and hydromassage corner for living a really exclusive Tuscan experience. Villa Lionella is a big independent h …see more

from $550 / night

$3,833 - $4,806 / week

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from $550 / night

(2) Excellent 

13

Vacation apartment rental

Montaione / Alberi

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The Lebbio farmhouse is a touristic ensemble composed by several ancient stone made buildings, situated among Tuscany hills, plunged into the silence and shaded by old-age trees. For all its characteristics, The Lebbio is the perfect place for a quiet and relaxing stay. …see more

from $206 / night

$1,339 - $2,060 / week

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from $206 / night

27

Vacation apartment with shared pool in Montaione

Province of Florence / Montaione

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Sheltered in the middle of a valley of vineyards and olive groves, from which high quality olive oil and wine is made, these holiday homes in Tuscany are situated in a very quiet area, far from the noises of the towns and surrounded by an uncontaminated countryside. Thi …see more

from $138 / night

$492 - $1,202 / week

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Responds fast!
avg. 3 hours 5 minutes

from $138 / night

(2) Excellent 

24

Vacation villa with tennis court in Collegalli

Montaione / Collegalli

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 50 mi
  • Child friendly
  • Air conditioning
San Paolo di Collegalli: in the middle of the green Tuscany countryside, amidst rolling hills, cypresses and olive trees 50 Km from Florence, 50 Km from Pisa and 50 Km from Siena We offer a villa and an annexed guest house , a private half Olympic pool (25x12,5 m) wit …see more

from $489 / night

$3,421 / week

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from $489 / night

36

Apartment rental in Santo Stefano

Montaione / Santo Stefano

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
Relaxation and comfort characterize this complex in the heart of Toscana, it is made up of a villa in the centre and three groups of independent apartments. They are carefully restored, respecting the environment, so friendly, functional and fully equipped. They have t …see more

from $80 / night

$481 - $572 / week

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from $80 / night

(9) Very Good 

18

Vacation apartment with shared pool in Mura,Italy

Montaione / Mura,Italy

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
Apartment ground floor in the old historic farmhouse; It renovated and furnished in every detail reflecting the Tuscan tradition. It consists of kitchen-living room, bedroom and bathroom with shower. Surrounded by a beautiful garden has a veranda where you can eat or re …see more

from $52 / night

$361 / week

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Responds fast!
avg. 47 minutes

from $52 / night

55

Farmhouse rental in Montaione with shared pool

Province of Florence / Montaione

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The Agritourism Le Capanne, immersed in the Tuscany countryside among Florence, Pisa and Siena, offers warm and family hospitality. Without sacrificing modern convenience, it maintains the tradition of the past, between the garden and farmyard animals. In the fa …see more

from $68 / night

$473 - $593 / week

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from $68 / night

18

Vacation home with shared pool in Montaione

Province of Florence / Montaione

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Beautiful holiday home in the heart of Tuscany. Ideal for a family vacation or couple. Two bedrooms, two bathrooms, kitchen and living room with fireplace. Patio on the terrace with breathtaking views. Wi Fi is free and available throughout the property. Frame the struc …see more

from $149 / night

$1,030 - $1,659 / week

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from $149 / night

47

Vacation apartment in Santo Stefano

Montaione / Santo Stefano

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
Relaxation and comfort characterize this complex in the heart of Toscana, it is made up of a villa in the centre and three groups of independent apartments. They are carefully restored, respecting the environment, so friendly, functional and fully equipped. They have t …see more

from $109 / night

$687 - $801 / week

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from $109 / night

(1) Very Good 

24

Vacation villa with swimming pool in Montaione

Province of Florence / Montaione

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Villa Montaione Hills has been recently renovated respecting his traditional Tuscan architecture, characterized by lining on the floor (the famous Tuscan cotto), kitchen in brickwork, soft coloured tiles of the bathrooms and beautiful tapestries. The Villa can comfort …see more

from $515 / night

$3,376 - $4,462 / week

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from $515 / night

23

Vacation apartment in Montaione

Province of Florence / Montaione

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Nearest beach 40 mi
  • Swimming pool
  • Suitable for children age 5+
Among the secular Woods of Val d'Elsa extends the estate of Castelfalfi on an area of 1200 hectares and the wonderful landscape turns to loss of eye and reworks the themes of the paintings of the great masters of the Renaissance. The apartments placed in the "Borgo", we …see more

from $115 / night

$687 / week

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from $115 / night

(2) Excellent 

17

Vacation apartment rental

Province of Florence / Montaione

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Le Case di San Vivaldo is situated in the countryside of Tuscany Region. Is 40 km away from Florence, 42 km from Siena, 45 km from Pisa and 17 km from San Gimignano. The houses for rent are equipped with all amenities (kitchen with dishwasher, private bathroom, TV). We …see more

from $138 / night

$858 / week

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Responds fast!
avg. 2 hours 50 minutes

from $138 / night

25

Vacation apartment with shared pool in Montaione

Province of Florence / Montaione

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
These holiday homes in Chianti are located near the medieval village of Montaione, right within the heart of the Tuscan triangle created by Florence, Pisa and Siena. Situated on the hills, the apartments enjoy a breathtaking view over the valleys, Val d'Elsa and Val d'E …see more

from $98 / night

$424 - $750 / week

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Responds fast!
avg. 3 hours 5 minutes

from $98 / night

12

Montaione Vacation apartment rental

Province of Florence / Montaione

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
81 House: 40 sqm apartment with terrace, located in family-run farmhouse, immersed in the Green Tuscan hills. The apartment consists of a large kitchen with living room, bedroom, bathroom and closet. Can indoor parking. The farm is located a few kilometres from the most …see more

from $92 / night

$641 / week

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from $92 / night

(1) Excellent 

12

Vacation apartment in Alberi

Montaione / Alberi

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
The Lebbio is a touristic ensemble composed by several ancient stone made buildings, situated among Tuscany hills, plunged into the silence and shaded by old-age trees. For all its characteristics, The Lebbio is the perfect place for a quiet and relaxing stay. Everythin …see more

from $149 / night

$893 - $1,453 / week

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from $149 / night