50 Best Vacation Rentals in Montaione - Holiday Lettings - Cabins

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6,273 Vacation rentals

47

Vacation apartment in Santo Stefano

Montaione / Santo Stefano

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • 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 $114 / night

$680 - $1,360 / week

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from $114 / night

(1) Excellent 

12

Vacation apartment rental

Montaione / Alberi

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The LEBBIO is situated in the heart of Tuscany, on the hills of Chianti, famous for its woods and poplars, grapevines and olive trees, where history has its mark in the little hamlets, stone farmhouses, castles and villas standing near "via francigena".The Lebbio, tucke …see more

from $165 / night

$1,021 / week

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from $165 / night

(2) Very Good 

8

Vacation townhouse with shared pool in Casicello

Montaione / Casicello

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • 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 $102 / night

$710 / week

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from $102 / night

(1) Excellent 

24

Vacation villa with swimming pool in Alberi

Montaione / Alberi

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • 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 $366 / night

$2,196 / week

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from $366 / night

(4) Excellent 

59

Vacation farmhouse in Montaione

Province of Florence / Montaione

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
Podere Settefrati an Impressive 17th Century Stone farmhouse originally a convent, spacious with many of its original features preserved. Its white washed walls, exposed beams, fireplaces and terracotta floors take you back to a nostalgic and romantic past. Set in …see more

from $136 / night

$947 - $2,480 / week

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Responds fast!
avg. 2 hours 58 minutes

from $136 / night

38

Apartment rental in Santo Stefano

Montaione / Santo Stefano

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • 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 $102 / night

$567 - $1,077 / week

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from $102 / night

(6) 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 $79 / night

$552 / week

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Responds fast!
avg. 2 hours 55 minutes

from $79 / night

21

Montaione Vacation villa rental

Province of Florence / Montaione

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Casale Bianchi is a luxury property with private swimming pool in the heart of the picturesque Tuscan countryside, a few kilometres from Montaione, between the well-known historical towns of Florence, Pisa and Siena. The house is one of several prestigious properties on …see more

from $1,512 / night

$10,583 - $15,649 / week

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from $1,512 / night

(9) Very Good 

18

Vacation apartment with shared pool in Montaione

Province of Florence / Montaione

2 7 3 nights min

  • 2 bedrooms
  • sleeps 7
  • 3 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Belmonte Vacanze is a residence for farm holidays in Tuscany. It is located inside a property of 200 hectares in the countryside of Montaione between San Gimignano and Volterra.The flats for holidays are furnished in Tuscan style and are equipped with air conditioning/h …see more

from $147 / night

$1,026 / week

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from $147 / 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 $111 / night

$778 / week

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from $111 / night

9

Montaione Vacation apartment rental

Province of Florence / Montaione

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • 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 $116 / night

$811 / week

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from $116 / night

13

Collegalli Vacation apartment rental

Montaione / Collegalli

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • 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 $102 / night

$1,184 / week

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from $102 / 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 $1,649 / night

$11,538 / week

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from $1,649 / night

13

Apartment accommodation in Sughera with shared pool

Montaione / Sughera

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Casa Ilaria: 70 sqm apartment with terrace, located in family-run farmhouse, immersed in the Green Tuscan hills. The apartment consists of a large kitchen with a living room with a sofa bed and a sofa bed, a bedroom and a bathroom. Can indoor parking. The farm is locat …see more

from $97 / night

$678 / week

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from $97 / 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 $586 / night

$1,759 - $3,663 / week

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from $586 / 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 $91 / night

$635 / week

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from $91 / night

12

Montaione Vacation apartment rental

Province of Florence / Montaione

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • 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 $97 / night

$676 / week

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from $97 / night

36

Apartment rental in Santo Stefano

Montaione / Santo Stefano

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • 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 $91 / night

$508 - $970 / week

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from $91 / night

22

Vacation farmhouse 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
The La Valle complex is comprised of seven comfortable apartments situated just a kilometre from the town of Montaione and roughly 45 kilometres from Florence. Each apartment has its own private and furnished outdoor area, perfect for dining alfresco. The complex has …see more

from $131 / night

$913 - $1,348 / week

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Responds fast!
avg. 3 hours 57 minutes

from $131 / night

(2) Excellent 

13

Vacation apartment rental

Montaione / Alberi

4 9 3 nights min

  • 4 bedrooms
  • sleeps 9
  • 3 nights min
  • 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 $203 / night

$1,318 / week

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from $203 / 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 $113 / night

$429 - $1,003 / week

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from $113 / night

(2) Excellent 

7

Casicello Vacation townhouse rental

Montaione / Casicello

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • 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 $102 / night

$710 / week

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from $102 / night

(10) Excellent 

48

Villa rental in Collegalli with swimming pool

Montaione / Collegalli

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • 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 $510 / night

$3,571 / week

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from $510 / night

24

Vacation apartment in Montaione

Province of Florence / Montaione

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
3-Bedrooms apartment of 90sqm on the ground floor with private terrace. One double bedroom, 2 single bedrooms, living room, kitchen and 2 bathrooms with shower. These holiday apartments in Chianti are located near the medieval village of Montaione, right within the hea …see more

from $105 / night

$677 - $1,127 / week

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from $105 / night

13

Apartment rental in Montaione with shared pool

Province of Florence / Montaione

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Fully furnished and equipped house. Approximately 80 m2. Beds 4 + 2. Lounge with dining room, table and fireplace. Cooking area with equipped kitchen. Upstair double bedroom. Room with two single beds. Bathroom with shower box, bidet, wc and wash basin. Outdoor area fea …see more

from $153 / night

$1,070 / week

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from $153 / night

(1) Excellent 

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 $192 / night

$620 - $1,453 / week

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from $192 / night

(4) Very Good 

18

Vacation farmhouse rental

Montaione / Sughera

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Tuscany, the heart of the Renaissance, great wines, great food, great scenery, the real Tuscany are here in this campaign where Woods and vineyards alternate in a poem punctuated by cypress trees. Fantastic sunsets that slide over rolling hills like an Impressionist pai …see more

from $169 / night

$1,184 / week

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from $169 / 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 $85 / night

$591 / week

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from $85 / 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 $288 / night

$2,016 - $3,366 / week

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from $288 / 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 $481 / night

$3,366 / week

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from $481 / night

(4) Excellent 

25

Vacation apartment rental

Province of Florence / Montaione

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Bouganville is a self catering apartment 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 relaxed …see more

from $96 / night

$558 - $896 / week

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from $96 / night

(1) Excellent 

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 65sqm with private terrace. Living room with kitchen corner and double sofa bed, double bedroom, one bedroom with twin beds, 2 bathrooms with shower. Tv-sat, Internet wi-fi connection. This beautiful holiday accommodation in Chianti is located …see more

from $159 / night

$522 - $1,247 / week

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from $159 / night

6

Vacation apartment in Montaione

Province of Florence / Montaione

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Located on the marvellous Chianti Hills, in the heart of Tuscany, surrounded by a splendid natural scenary at 350 a.s.l, Vecchia Sassa overlooks the valley once known as “ETRUSCAN BARNâ which still preserves the antique beauty. Vecchia Sassa is located below the a …see more

from $181 / night

$1,263 / week

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from $181 / night

(10) Very Good 

18

Vacation apartment with shared pool in Mura,Italy

Montaione / Mura,Italy

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • 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 $51 / night

$355 / week

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Responds fast!
avg. 46 minutes

from $51 / 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 $107 / night

$654 - $1,127 / week

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from $107 / night

(1) Excellent 

12

Vacation apartment in Alberi

Montaione / Alberi

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • 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 $147 / night

$879 / week

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from $147 / 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 $97 / night

$679 / week

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from $97 / night

(2) Excellent 

12

Vacation apartment in Alberi

Montaione / Alberi

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • 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 $214 / night

$1,396 / week

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from $214 / night

(2) Very Good 

29

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
One bedroom apartment of 45sqm with private terrace. Living room with kitchen corner and double sofa bed, double bedroom, bathroom with shower. Sat-Tv, Internet wi-fi connectionThis beautiful holiday accommodation in Chianti is located near the medieval village of Monta …see more

from $124 / night

$384 - $902 / week

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from $124 / night

(3) Excellent 

22

Vacation apartment rental

Province of Florence / Montaione

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 53 mi
  • Swimming pool
  • Child friendly
In via Matteotti in Montaione is the Villa Bonsignori that for old montaionesi still is the "Via della Villa". The villa we see today dates from the seventeenth century and is on two levels. It was restored in 2015 retaining the charm and the original integrity. Many ro …see more

from $112 / night

$781 / week

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Responds fast!
avg. 1 hour 48 minutes

from $112 / night