Villas with a pool San Gimignano | Apartments to rent with swimming facilities | Holiday Lettings

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320 Holiday homes

Filters applied: Swimming pool (320)

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

(13) Excellent 

1 / 24

Charming 2 bedroom Tuscan villa with private pool

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 £173 / night

£475 - £1552 / week

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from £173 / night

(40) Excellent 

1 / 25

Lovingly restored stone-built Tuscan barn

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) Excellent 

1 / 16

Classic Tuscan farmhouse on a hilltop with brilliant views of the countryside, outdoor pool

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 £121 / night

£535 / week

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from £121 / night

(16) Excellent 

1 / 24

Attractive stone-built villa in extraordinary Tuscan locale, private terrace and swimming pool, incredible views, sleeps up to 9

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
Villa La Porticciola take its charm from the extroardinary position in front of the silhouette of San Gimignano towers. Everywhere it is possible to admire the unforgettable panoramic view of the town or the hilly landscape of the Chianti region. Ideal position for excu  …see more

from £345 / night

£1466 - £2500 / week

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from £345 / night

(1) Very Good 

1 / 24

Beautiful detached Tuscan villa in Chianti hills featuring private outdoor pool, terrace and garden

Province of Siena / San Gimignano

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
Tameriggio is a beautiful detached villa converted from a lovely, old hay store situated in the Chianti hills half way (35 km) between Florence and Siena.In the well kept garden there is an inviting swimming pool (8 x 5 m) available from May to October for exclusive use  …see more

from £87 / night

£604 - £1682 / week

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from £87 / 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 / 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 £78 / night

£561 / week

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from £78 / night

(18) Excellent 

1 / 49

3 bedroom holiday apartment near Tuscan cities, staffed property with outdoor pool

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 £87 / night

£475 - £733 / week

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from £87 / 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 £78 / night

£475 / week

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from £78 / night

(13) Excellent 

1 / 24

Renovated 5 bedroom villa surrounded by Tuscan vineyards, fetures private pool, log fire and terrace

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
The completely renovated property occupies a panoramic position within an estate of olive groves and vineyards, boasting an entrancing view of the famous towers of San Gimignano 4 km away. The characteristic architecture enables guests to experience a specifically Tusc  …see more

from £345 / night

£1552 - £2759 / week

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from £345 / night

(30) Excellent 

1 / 25

Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool

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 £87 / night

£475 - £733 / week

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from £87 / night

(40) Excellent 

1 / 19

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

(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 £78 / night

£518 / week

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from £78 / night

(7) Excellent 

1 / 18

3 bedroom farmhouse in the picturesque Tuscan hills boasting private pool, terrace and garden, 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 £85 / night

£569 - £949 / week

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from £85 / 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 £93 / night

£646 - £839 / week

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from £93 / night

(6) Very Good 

1 / 18

Holiday apartment in restored Tuscan farmhouse, sleeps 4, features private garden and shared pool

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 renovated 16th Century farm buildings converted into luxury houses and apartments. 'Torricchi 6' is a beautiful spacious ground floor house and is located on a hill with stunning views of the Tuscan hills. The renovation has r  …see more

from £75 / night

£525 - £800 / week

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from £75 / 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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Pricing unknown

1 / 19

APARTMENT IRIS 2206 - Casaglia apartment sleeps 2

San Gimignano / Casaglia

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
Located in the elegantly renovated barn, Iris is particularly spacious and filled with natural light. It has a large kitchen which can also be used as a cosy dining room, a living room, a double bedroom (with king size bed ) and a twin bedroom (the twin beds for child u  …see more

from £129 / night

£830 - £1139 / week

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from £129 / night

1 / 15

Province of Siena / San Gimignano

9 21 1 night min stay

  • 9 bedrooms
  • Sleeps 21
  • 1 night min stay
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
 …see more

from £91 / night

£634 / week

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from £91 / 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 £87 / night

£647 / week

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from £87 / night

(1) Excellent 

1 / 11

Podere Remignoli Apt Selva - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
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 £87 / night

£604 - £776 / week

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from £87 / night

1 / 20

San Gimignano / Ulignano

4 9 7 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Nearest beach 90 km; Swimming pool; Suitable for children age 5+;
 …see more

from £364 / night

£2544 / week

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from £364 / night

(3) Excellent 

1 / 20

Granaio 7 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 6 people (4+2) in total. The apartment is next to Granaio nr 6 (nr 277512) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San Gimignan  …see more

from £35 / night

£242 - £906 / week

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from £35 / 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 £74 / night

£513 / week

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from £74 / night

1 / 12

Province of Siena / San Gimignano

2 4 30 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £130 / night

£863 / week

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from £130 / night

(1) Excellent 

1 / 17

Tuscan hillside farmhouse with private pool, terrace and garden, great for family holidays

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 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 £57 / night

£345 - £819 / week

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from £57 / night

(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 £302 / night

£1337 - £2156 / week

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from £302 / 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 £138 / night

£966 / week

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from £138 / 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 £74 / night

£513 / week

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from £74 / 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

£363 / week

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from £52 / 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 £78 / night

£561 / week

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from £78 / 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 / 21

La Chiesina - Casaglia villa sleeps 6

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 75 km; Swimming pool; Child friendly ;
The villa was an ancient historical structure going back to before the year 1200, originally the chapel "Santa Maria Church", near the burg of Casaglia. Over the centuries, the chapel was deconsecrated to become, first a watchtower, and then a place where the  …see more

from £130 / night

£863 - £1983 / week

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from £130 / night

1 / 14

Apt. Sole - San Gimignano farmhouse sleeps 4

Province of Siena / San Gimignano

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Originally the stable of the farm it has been restored according to the most modern standards and comfortably furnished. Ideal for 4 people. The entrance is through the spacious kitchen, equipped with a fireplace. There are 2 bedrooms and a modern bathroom. The kitchen  …see more

from £74 / night

£453 / week

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from £74 / night

(3) Very Good 

1 / 24

Splendid period farmhouse in the Tuscan countryside with 6 bedrooms, swimming pool and private garden

Province of Siena / San Gimignano

6 17 7 nights min stay

  • 6 bedrooms
  • Sleeps 17
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Splendid period farmhouse dating back many centuries which was once a water tower and mill. Expertly converted offering accommodation of large proportions and only 4 kms from San Gimignano and close for excursions for both Florence and Siena. The property stands in seve  …see more

from £154 / night

£1078 - £2837 / week

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from £154 / night

1 / 12

Volterra - 57931005 - Ulignano farmhouse sleeps 2

San Gimignano / Ulignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Beautiful house dating back to the end of the 18th century comprising 6 welcoming apartments. This property is situated on the hills surrounding Volterra and enjoys amazing views of the Tuscan landscape. All of the 6 units have been recently restored and are furnished i  …see more

from £70 / night

£447 - £1073 / week

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from £70 / night

(1) Excellent 

1 / 20

Podere le Monache 1 - San Gimignano farmhouse sleeps 4

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • 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 £57 / night

£345 - £750 / week

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from £57 / night

(8) Excellent 

1 / 20

Three bedroom apartment in stunning villa

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
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 £185 / night

£1294 - £1983 / week

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from £185 / night

1 / 7

Charming rooms with amazing view and breakfast.

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;
Conveniently placed between world famous hilltop towns of San Gimignano Florence and Siena. We offer 360° views from the top of a hill surrounded by vines and olive trees. Abundant buffet breakfast and home cooked evening meals are avaialble for our guests, relax by t  …see more

from £82 / night

£544 - £725 / week

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from £82 / night

1 / 34

Province of Siena / San Gimignano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
 …see more

from £61 / night

£388 / week

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from £61 / 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
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
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
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
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

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