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78 Holiday homes

Filters applied: Cycling holidays (78)

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

(7) 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

(30) 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

(18) 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

1 / 10

la Stadera - Castel San Gimignano apartment sleeps 4

San Gimignano / Castel San Gimignano

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 60 km; Child friendly ; Car essential;
The apartment (max 4 people) located on a beautiful hill overlooking San Gimignano, is situated in Castel San Gimignano at 375 m above sea level. The village of 400 inhabitants, offers a restaurant, a grocery store and tranquility. From there you can quickly reach the  …see more

from £39 / night

£257 / week

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from £39 / 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 / 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 £73 / night

£449 / week

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from £73 / 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 / 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) 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) 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

(40) 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

(3) Very Good 

1 / 24

Splendid period farmhouse in the Tuscan countryside with 6 bedrooms, swimming pool and private garden - San Gimignano villa sleeps 17

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 £153 / night

£1069 - £2812 / week

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from £153 / night

1 / 26

San Gimignano / Castel San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; Ask about pets;
 …see more

from £43 / night

£291 - £522 / week

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from £43 / night

1 / 16

Province of Siena / San Gimignano

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £77 / night

£513 / week

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from £77 / night

(6) Very Good 

1 / 18

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

(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) 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 / 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

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) Excellent 

1 / 17

Tuscan hillside farmhouse with private pool, terrace and garden, great for family holidays - San Gimignano farmhouse sleeps 6

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 £56 / night

£342 - £812 / week

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from £56 / night

1 / 22

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
 …see more

Pricing unknown

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Pricing unknown

(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 £56 / night

£342 - £744 / week

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from £56 / 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

£240 - £582 / week

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from £35 / 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 £60 / night

£385 / week

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from £60 / night

(14) Very Good 

1 / 16

Traditional Tuscan-style country house with beautiful pool area, lush gardens and great views, sleeps 4 - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 55 km; Swimming pool;
Casa Florio' is a 2 bedroom apartment incorporated into an ancient farm comprising 12 beautifully renovated stone buildings . Designed in traditional Tuscan country style with chestnut beamed ceilings and terraccota tiled floors. It is light and spacious with doors lea  …see more

from £71 / night

£500 - £750 / week

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from £71 / night

(14) 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

(4) Excellent 

1 / 24

Tuscan-style apartment in spectacular surroundings, shared outdoor pool, sleeps up to 6 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
Podere Torricchi is in a typical tuscan landscape characterised by hills with olive trees and mediterrenean bush. Podere Torricchi is a group of converted farm buildings. The apartment has been newly restored in a traditional Tuscan style.Gambassi Terme and San Gimignan  …see more

from £73 / night

£510 - £983 / week

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from £73 / night

(1) Excellent 

1 / 19

Farmhouse holiday rental with private pool and garden in San Gimignano - San Gimignano farmhouse sleeps 6

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 £69 / night

£471 - £855 / week

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from £69 / 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 £182 / night

£985 - £1440 / week

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from £182 / night

1 / 25

Fabulous farmhouse with gorgeous garden and incredible views of the Siena countryside boasts private pool and terrace - San Gimignano farmhouse sleeps 22

Province of Siena / San Gimignano

8 22 Min stay varies

  • 8 bedrooms
  • Sleeps 22
  • 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 £248 / night

£1667 - £3633 / week

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from £248 / 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

(5) Very Good 

1 / 30

Province of Siena / San Gimignano

2 3 1 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Nearest beach 100 km; Child friendly ; Car advised;
 …see more

from £60 / night

£419 / week

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from £60 / 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) 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 £86 / night

£599 - £770 / week

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from £86 / night

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

(5) Excellent 

1 / 46

Villa Sangimignano - Montauto farmhouse sleeps 5

San Gimignano / Montauto

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
The 200 sqm villa is a typical stone barn in an early '900 style, characterized by the tranquility of the Tuscan countryside of San Gimignano in which it is immersed.It can be accessed via a large private and completely fenced garden of 2,000 sqm.The house is the r  …see more

from £199 / night

£1453 - £1966 / week

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from £199 / night

(1) Excellent 

1 / 17

Province of Siena / San Gimignano

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 109 km; Swimming pool; Child friendly ;
 …see more

from £95 / night

£642 / 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

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
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

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