Long term rentals San Gimignano | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Siena
  • San Gimignano
  • All locations
  • Casaglia (9)
  • Castel San Gimignano (10)
  • Larniano (35)
  • Montauto (1)
  • Pancole (4)
  • San Donato in Siena (9)
  • Santa Maria, San Gimignano (3)
  • Ulignano (15)

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265 Holiday homes

Travellers going to San Gimignano are booking September dates now. Secure your holiday home today and have the perfect trip.

(9) Excellent 

1 / 18

3 bedroom farmhouse in the picturesque Tuscan hills boasting private pool, terrace and garden, sleeps 6 - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Child friendly ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £84 / night

£565 - £941 / week

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from £84 / night

(32) Excellent 

1 / 25

Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool - Castel San Gimignano apartment sleeps 6

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Child friendly ;
The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the oliv  …see more

from £86 / night

£471 - £727 / week

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from £86 / night

(1) Excellent 

1 / 16

Classic Tuscan farmhouse on a hilltop with brilliant views of the countryside, outdoor pool - San Gimignano farmhouse sleeps 13

Province of Siena / San Gimignano

7 13 1 night min stay

  • 7 bedrooms
  • Sleeps 13
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
Torreprima holidays house is 3 Km away from the historical center of San Gimignano, and is situated on top of a hill from where it is possible to delight the beautiful view over the surrounding valleys of olive groves and vineyards. It has availability of 5 apartments.  …see more

from £120 / night

£530 / week

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from £120 / night

1 / 29

Tuscan Feeling - Casa Ornella - San Gimignano villa sleeps 6

Province of Siena / San Gimignano

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Child friendly ; No pets allowed;
Located in the hills of the Val d'Elsa area, San Gimignano is famous mainly for its numerous noble towers that make this town, at the ancient atmosphere, one of the most striking and characteristic of Tuscany. A place where time has stopped, that has kept intact th  …see more

from £94 / night

£599 / week

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from £94 / night

(40) Excellent 

1 / 19

Stunning farmhouse apartment located between Tuscan cities of San Gimignano and Volterra, shared pool, private garden, sleeps 6 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

3 6 4 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Car essential;
Azzurra is an apartment in Poderra Torrichi, a gated community of three farm buildings, which is located between the medieval cities of San Gimignano and Volterra. Podera Torrichi is newly renovated and has retained the charm of the traditional Tuscan farm buildings, wi  …see more

from £184 / night

£993 - £1451 / week

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from £184 / night

1 / 26

Province of Siena / San Gimignano

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
 …see more

from £137 / night

£958 / week

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from £137 / night

1 / 31

San Gimignano / Castel San Gimignano

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £77 / night

£556 / week

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from £77 / night

(43) Excellent 

1 / 25

Lovingly restored stone-built Tuscan barn - San Gimignano house sleeps 4

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Child friendly ;
Podere Torricchi is a small collection of beautifully renovated 16th Century farm buildings converted into houses and apartments. Set on a hill the entire site has stunning views of the rolling Tuscan countryside. I'l Granario' is a house set on two floors, tastefully r  …see more

from £90 / night

£625 - £925 / week

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from £90 / night

(1) Good 

1 / 28

San Gimignano / Castel San Gimignano

1 3 3 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
 …see more

from £77 / night

£556 / week

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from £77 / night

1 / 27

San Gimignano / Castel San Gimignano

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £52 / night

£359 / week

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from £52 / night

1 / 20

Luxory Apartment San Gimignano - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
The recently renovated Villa is situated in a quiet location in a charming village, enhanced by a twelfth-century Romanesque church. and is overlooking the majestic landscape of Chianti, a few kilometres from important art cities of Tuscany (Siena, San Gimignano, Volter  …see more

from £92 / night

£641 - £832 / week

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from £92 / night

(8) Excellent 

1 / 20

Three bedroom apartment in stunning villa - San Gimignano villa sleeps 6

Province of Siena / San Gimignano

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Not suitable for children; Car advised;
Osservatorio is a stunning villa for up to 11guests divided into two independent units. Orione apartment for up to 6 guests.The property is extraordinarily cool and pleasant throughout the summer, thanks to its location on a higher altitude (about 500 AMSL) and the beau  …see more

from £183 / night

£1283 - £1453 / week

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from £183 / night

1 / 24

Podere la Marronaia Yellow 2p - San Gimignano farmhouse sleeps 2

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; No pets allowed;
Podere la Marronaia is a small and welcoming farmhouse situated on a small hill among vineyards and olive groves, close to the historical centre of San Gimignano (2km). The central part of this historical building is the watching tower built in 1200 ad as part of the c  …see more

Pricing unknown

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1 / 9

Apartment 406 - Santa Maria - San Gimignano apartment sleeps 2

San Gimignano / Santa Maria, San Gimignano

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
Consists of living room with kitchenette, double room with a double bed, bathroom. For 2 people. Heating. First floor. The apartment is characterized by the typical ceilings made of wooden beams.About 20 years ago our family decided to renovate an old farmhouse, pursuin  …see more

from £69 / night

£428 / week

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from £69 / night

(16) Excellent 

1 / 10

Sunny 1 bedroom apartment on the Podere Magione Holiday Farm in the San Gimignano region of Tuscany - San Gimignano apartment sleeps 2

Province of Siena / San Gimignano

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 72 km; Child friendly ; Car essential;
The Podere Magione Holiday Farm is capable of offering various possibilities for your stay in Tuscany, also maintaining an intimate, family atmosphere, considering its modest size.CIPRESSO APARTMENT has one bedroom with twins beds(or the possibility to have a big bed as  …see more

from £43 / night

£257 - £317 / week

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from £43 / night

1 / 15

Contessa Apt San Gimignano - Larniano apartment sleeps 4

San Gimignano / Larniano

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Suitable for children age 5+; Car not necessary; Air conditioning;
Lovely Two-roomed apartment (55 mq) with a comfortable terrace for outdoor dinners (10 mq). It is finely furnished with "arte povera toscana" furniture. Living room, separate kitchen corner, bathroom with shower, bedroom with a charming mezzanin floor from whi  …see more

from £76 / night

£530 / week

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from £76 / night

1 / 20

Podere la Marronaia Blue 2p - San Gimignano farmhouse sleeps 2

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Podere la Marronaia is a small and welcoming farmhouse situated on a small hill among vineyards and olive groves, close to the historical centre of San Gimignano (2km). The central part of this historical building is the watching tower built in 1200 ad as part of the c  …see more

Pricing unknown

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(20) Excellent 

1 / 49

3 bedroom holiday apartment near Tuscan cities, staffed property with outdoor pool - Castel San Gimignano apartment sleeps 6

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Child friendly ;
The apartment is placed in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the olive  …see more

from £86 / night

£471 - £727 / week

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from £86 / night

(6) Very Good 

1 / 15

2 bedroom holiday apartment in San Gimignano surrounded by stunning Tuscan landscape - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 72 km; Child friendly ; Car essential;
This apartment is for 2/4 people and is made up of two spacious rooms with double bed, two bathrooms with shower, a large and fully equipped kitchen/dining room and an outdoor area paved with terracotta tiles like the yards of old country farmhouses, offering a fabulous  …see more

from £89 / night

£496 - £556 / week

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from £89 / night

1 / 5

Province of Siena / San Gimignano

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Swimming pool; Ask owner if suitable for children; No pets allowed;
 …see more

from £135 / night

£941 / week

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from £135 / night

(5) Excellent 

1 / 6

Province of Siena / San Gimignano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; Pet friendly;
 …see more

from £69 / night

£479 / week

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from £69 / night

1 / 28

San Gimignano / Castel San Gimignano

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £86 / night

£642 / week

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from £86 / night

1 / 10

Province of Siena / San Gimignano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
 …see more

from £77 / night

£471 / week

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from £77 / night

1 / 7

Lovely countryside Podere San Luigi Apt Tramonto - Pancole farmhouse sleeps 2

San Gimignano / Pancole

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
You can enjoy a relaxing holiday in the center of Tuscany surrounded by nature and the countryside. Very close to San Gimignano, on the "VIA FRANCIGENA", the casale is the starting point for visiting the important Tuscan cities of Art, villages, and the famous  …see more

from £53 / night

£342 / week

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from £53 / night

(1) Very Good 

1 / 11

La Capanna di Sovestro - San Gimignano apartment sleeps 3

Province of Siena / San Gimignano

2 3 2 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min stay
Key info: Suitable for children age 5+; Car advised; Air conditioning;
The apartment is composed of a large double room with the possibility of additional sofa bed, a small double room , a private bathroom, fully equipped kitchen, private parking and a large terrace where you can play barbecue, solarium or reading.Free WiFi available every  …see more

from £60 / night

£359 / week

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from £60 / night

(19) Excellent 

1 / 49

Lovely detached cottage with view of San Gimignano - San Gimignano cottage sleeps 5

Province of Siena / San Gimignano

2 5 6 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min stay
Key info: Nearest beach 75 km; Child friendly ; Car essential;
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in a typical country-style using rustic furniture and bright terracotta floors, the airy hom  …see more

from £52 / night

£359 / week

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from £52 / night

(14) Excellent 

1 / 24

Charming 2 bedroom Tuscan villa with private pool - San Gimignano villa sleeps 5

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
Charming stone-built house located in a peaceful and panoramic position on the green, rolling hills near San Gimignano.The villa is the result of a recent renovation which has transformed this ancient barn into a beautiful and comfortable detached villa, ideal for spend  …see more

from £171 / night

£471 - £1539 / week

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from £171 / night

1 / 6

Province of Siena / San Gimignano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £73 / night

£509 / week

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from £73 / night

(14) Excellent 

1 / 17

Fabio Apartments San Gimignano - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 65 km; Child friendly ; Car advised;
Apartment "Il Duca" (2-6 beds)Bright three-roomed apartment (85 mq). With its twelve windows it offers a beautiful panoramic view of the surrounding Chianti countryside, the nearby gardens, the ancient buildings and the legendary Torre del Diavolo. It is finel  …see more

from £88 / night

£616 / week

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from £88 / night

1 / 5

Province of Siena / San Gimignano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £73 / night

£509 / week

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from £73 / night

1 / 9

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Not suitable for children; No pets allowed;
 …see more

Pricing unknown

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(4) Excellent 

1 / 23

Podere Lo Spadino - San Gimignano villa sleeps 9

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
The villa, on two floors, is just 5 km from the historic center of San Gimignano, in a secluded location is surrounded by large well kept garden and green, with lawn, where you can spend time and relax. The garden also features a gazebo with garden furniture, barbecue.  …see more

from £300 / night

£1325 - £2137 / week

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from £300 / night

1 / 9

APARTMENT " IL PICCOLO GUFO" - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Suitable for children age 5+; Ask about pets;
The little owl" is a lovely apartment ideal for enjoying a relaxing holiday in the wonderful Tuscan countryside.   It is located on a hill, surrounded by vineyards, in front of San Gimignano, a medieval town famous for its 7 towers. It's in an excellent posi  …see more

Pricing unknown

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Pricing unknown

1 / 12

Agriturismo B&B I Pini - San Gimignano guest house sleeps 2

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Not suitable for children;
Our romantic Agriturismo I Pini, whose roots date back to the 17th Century, represents an alternative to the typical Hotel accommodation: Here nature meets culture, design tradition and harmony lifestyle. The Guesthouse I Pini awaits you with familiar atmosphere and off  …see more

from £95 / night

£599 - £677 / week

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from £95 / night

(6) Excellent 

1 / 27

Bright and Spacious Apartment in the heart of town - San Gimignano apartment sleeps 5

Province of Siena / San Gimignano

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Child friendly ; Ask about pets;
Holiday in San Gimignano ... a journey into the heart of Tuscany.Dear Guests, we are the sisters Stefania and Margherita and we are the owners of Appartamento Margherita. We decided to rent the apartment where we were born about 15 years ago, when we understood that it  …see more

from £86 / night

£513 / week

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from £86 / night

(2) Excellent 

1 / 14

New Casa Titta apt 3 bedrooms , amazing view - Castel San Gimignano apartment sleeps 5

San Gimignano / Castel San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 55 km; Child friendly ; Car advised;
C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has  …see more

from £86 / night

£471 - £727 / week

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from £86 / night

(1) Excellent 

1 / 21

Podere Magione - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Nearest beach 72 km; Child friendly ; Car essential;
The holiday farm is immersed in the San Gimignano countryside, amidst hills covered with olive trees and vineyards, between the Val d'Elsa and Chianti. From its ideal position it is possible to quickly reach the most beautiful, historical and artistic towns of Tusc  …see more

from £134 / night

£753 - £804 / week

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from £134 / night

(21) Excellent 

1 / 60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 90 km; Child friendly ; Car essential;
 …see more

from £48 / night

£287 - £415 / week

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from £48 / night

(2) Very Good 

1 / 12

Podere Remignoli Apt Luna - San Gimignano farmhouse sleeps 2

Province of Siena / San Gimignano

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 80 km; Swimming pool;
The farm Podere Remignoli is set halfway between Florence and Siena on top of a hill overlooking the unique scenery of San Gimignano, from where you can admire the Chianti hills on the east, the Elsa valley on the north and the Montagnola Senese on the south. The farmho  …see more

from £77 / night

£513 / week

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from £77 / night

1 / 11

Volterra - 15681001 - Ulignano farmhouse sleeps 6

San Gimignano / Ulignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Nice farming villa in Tuscany, Italy, comprising 2 small independent stone farmhouses, which were skilfully restored and turned into 3 nice apartments, all of which offering comfortably interiors decorated in a rustic style. This villa in Tuscany, Italy, if quietly situ  …see more

from £53 / night

£445 - £846 / week

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from £53 / night

Top Destination reviews

Podere Lo Spadino
What a wonderful place in Italy

We stayed now the second time in Podere Lo Spadino, we are a Group with 8 peoples, and everything in this house is amazing. The whole house, the garden, the pool and of course Barbara with her Family, they are helpful and very friendly and nice. We … see more
6 bedroom villa Tuscany (BFY13480)
excellent place, very ingoibale holliday

we stay in the villa for 5 nights. 5 couples 3 infants. everything was like it describe in the site. very large rooms with all the facilities you need. wifi works perfect, the pool was very clean. the kitchen was well equipped, the dining room ver … see more
Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool
What a great place to stay

My wife and I, along with our friends from Edinburgh, rented for a week at the end of June. What great accommodation, well presented, and the gardens, pool etc was a wonderful environment to relax in. Easy travelling to all the major Tuscan sights, … see more
La Chiesina
An awesome villa in the Tuscan hills

A wonderfully restored church with plenty of character. Privacy with trees and hedges. Fab and accessible pool. Well equipped kitchen. An amazing welcome pack. We cycled from here to San Gimignano and to Monteriggioni. The location is superb and we d … see more
Very clean and pleasant apartment

The apartment is very clean, the kitchen equipment is brand new. Even the owner changed both the TV's, so we could watch the European Football Championship. Veronica very kindly meet us late in the evening and drove us from the parking lot to the a … see more

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