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64 Holiday homes

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

(41) Excellent 

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

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
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 £185 / night

£1000 - £1462 / week

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from £185 / night

(3) Excellent 

20

Granaio 7 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 - £828 / week

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from £35 / night

(11) Very Good 

31

Le Fontanelle - rustic farm buildings with pool - San Gimignano farmhouse sleeps 5

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Nestled in a centuries-old complex of farm-house buildings, just 10 minutes drive from the medieval "skyscraper" fortress town of San Gimignano...Le Fontanelle is the perfect place to soak in Tuscany's sunshine, culture, food and fun.An easy drive from Pi  …see more

from £100 / night

£617 / week

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from £100 / night

(4) Excellent 

21

La Chiesina - Casaglia villa sleeps 6

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

(43) Excellent 

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
  • 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 - £900 / week

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from £90 / night

(5) Excellent 

46

Villa Sangimignano - Montauto farmhouse sleeps 5

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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 £200 / night

£1466 - £1983 / week

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from £200 / night

(3) Excellent 

22

Granaio 6 - San Gimignano apartment sleeps 7

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 7 (5+2) people in total. The apartment is next to Granaio nr 7 (advert nr 277234 ) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San  …see more

from £36 / night

£250 - £854 / week

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from £36 / night

(19) Excellent 

49

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

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Nearest beach 75 km
  • Child friendly
  • Pet friendly
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

£363 / week

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from £52 / night

(5) Excellent 

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
  • Swimming pool
  • Child friendly
  • Private garden
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 £61 / night

£423 - £992 / week

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from £61 / night

(4) Very Good 

21

Province of Siena / San Gimignano

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Nearest beach 77 km
  • Swimming pool
  • Child friendly

 …see more

from £108 / night

£630 - £811 / week

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from £108 / night

(11) Very Good 

17

Restored stone built villa near San Gimignano - San Gimignano villa sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Podera collinella is ideally situated in a beautiful rural location with fabulous panoramic 360 degree views. The villa is a newly renovated 16th century converted farmhouse with a light & open feel. It has all 21st century amenities with well equipped bathrooms & kitch  …see more

from £93 / night

£650 - £950 / week

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from £93 / night

(1) Very Good 

24

Beautiful detached Tuscan villa in Chianti hills featuring private outdoor pool, terrace and garden - San Gimignano cottage sleeps 8

Province of Siena / San Gimignano

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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

(14) Excellent 

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
  • 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

(1) Excellent 

19

La Fonte San Gimignano, Prov. Siena - San Gimignano apartment sleeps 2

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
Gelsomino: is one of four, very comfortable, quiet self catering apartments in a traditional Tuscan country villa. It comands fabulous views over the rolling hills, vineyards and olive groves. It has been completely refurbished yet retains all the original features  …see more

from £103 / night

£719 - £960 / week

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from £103 / night

(15) Very Good 

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 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • 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 - £625 / week

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from £71 / night

(1) Excellent 

99

Province of Siena / San Gimignano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £104 / night

£647 - £690 / week

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from £104 / night

(4) Excellent 

28

Apartment near San Gimignano - San Gimignano farmhouse sleeps 4

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
'Podere Collinella' has been re-built to a high standard, retaining the charm of a Tuscan farmhouse.The walls are of the old stone, chestnut beams support the ceiling, and positioned on a slight hill has wonderful views of the surrounding countryside. Podere C  …see more

from £61 / night

£311 - £423 / week

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from £61 / night

(2) Very Good 

12

Podere Remignoli Apt Luna - San Gimignano farmhouse sleeps 2

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • 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

(1) Excellent 

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
  • 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) Good 

8

San Gimignano: Tuscan farmhouse apartment - San Gimignano apartment sleeps 5

Province of Siena / San Gimignano

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Beautiful hilltop 2 story farmhouse apartment by owner Situated in the heart of tuscany (hills, between volterra, famous etruscan and medieval city and san gimignano, famous all over the world for its characteristic towers. You can easily visit florence, siena and pisa  …see more

from £10 / night

£22 - £344 / week

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from £10 / night

(14) Excellent 

24

Renovated 5 bedroom villa surrounded by Tuscan vineyards, fetures private pool, log fire and terrace - San Gimignano villa sleeps 12

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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 - £2069 / week

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from £345 / night

22

Medieval Tower experience - San Gimignano tower sleeps 6

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
This lovely accommodation near San Gimignano (10 km) is set in a beautiful medieval complex renovated in 2002. This amazing luxury apartment, which is set in a tower, a wing of the ancient council hall of the Hospitaller Knights of Jerusalem on the via Francigena, dates  …see more

from £124 / night

£863 - £2113 / week

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from £124 / night

100

I Pini - San Gimignano villa sleeps 14

Province of Siena / San Gimignano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Exteriors       This sophisticated historic villa‘s location lets guests have a fabulous view of the typical Tuscan country landscape. It affords a terrace with commanding views and a swimming pool (5 x 12m) providing the best way for  …see more

from £456 / night

£3190 / week

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from £456 / night

(3) Very Good 

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

  • 6 bedrooms
  • Sleeps 17
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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) Excellent 

24

I Cipressi - San Gimignano cottage sleeps 7

Province of Siena / San Gimignano

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 97 km
  • Swimming pool
  • Child friendly
A charming villa set in a cypress-tree-lined garden with a lovely pool at just 4 km from the historic town of San Gimignano famous for its medieval towers, historical sights and craft shops, as well as having an excellent selection of restaurants and local amenities. T  …see more

from £124 / night

£819 - £1940 / week

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from £124 / night

(1) Excellent 

100

Magda - San Gimignano villa sleeps 12

Province of Siena / San Gimignano

6 12 5 nights min

  • 6 bedrooms
  • Sleeps 12
  • 5 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Exterior:Perched on top on a hill, in the heart of Chianti countryside, Villa Magda boasts what must be one of the most enviable views of Tuscany: rolling Chianti hills decked with vines and olives, crowned by the incredible profile of San Gimignano's towers (located on  …see more

from £880 / night

£5604 / week

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from £880 / night

100

San Gimignano 80249 - Larniano villa sleeps 10

San Gimignano / Larniano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Characteristic stone villa created from a carefully-renovated barn, just 5 km from the captivating medieval village of San Gimignano, and just 6 km from the charming town of Certaldo. The property is independent and offers a large, completely enclosed garden (2000 m2) a  …see more

from £339 / night

£1959 - £3265 / week

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from £339 / night

20

San Gimignano / Ulignano

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • 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

(18) Excellent 

24

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

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • 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 - £1983 / week

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from £345 / night

100

San Gimignano 69066 - San Gimignano villa sleeps 5

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful independent villa with private (above-ground) pool created from the restoration of an ancient barn dating back to the beginning of the 20th century. This property, nestling deep among green hills, is situated a short distance away from the lovely medieval town  …see more

from £169 / night

£993 - £1656 / week

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from £169 / night

100

Sacra - San Gimignano villa sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
ExteriorsLocation in San Gimignano can only mean one thing: endless options to explore natural sceneries and traditional, ancient villas and cities. Siena, Florence, Pisa, Volterra and even the Chianti Classico and its vineyards are less than 30km away from the property  …see more

from £130 / night

£863 - £1983 / week

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from £130 / night

(12) Excellent 

70

VILLA IRIS, LUXURY VILLA IN SAN GIMIGNANO - San Gimignano villa sleeps 12

Province of Siena / San Gimignano

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 71 km
  • Swimming pool
  • Child friendly
This superb villa, obtained from the careful restoration of an old brick kiln of 1737, is situated in a unique position on a hill opposite the towers of San Gimignano. The villa has been lovingly restored with materials of the highest quality and finished after long and  …see more

from £432 / night

£3018 - £7156 / week

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from £432 / night

23

Fantastic 2 bedroom apartment in Traditional Tuscan villa with amazing views of the countryside and pool access, sleeps 4 - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Girasole is a very comfortable, quiet, self catering apartment on the first and second floor of a traditional Tuscan country villa commanding fabulous views over rolling hills, vineyards and olive groves. It has been totally refurbished but retains all its original f  …see more

from £108 / night

£755 - £1238 / week

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from £108 / night

(3) Good 

24

Casale - San Gimignano cottage sleeps 5

Province of Siena / San Gimignano

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 80 km
  • Child friendly
  • Ask about pets
Charming little house situated in the beautiful countryside just outside the town of San Gimignano, ideal place for couples and families wishing to visit Tuscany enjoying the freedom and privacy as well as the central position that this property has to offer.The cottage  …see more

from £74 / night

£518 - £733 / week

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from £74 / night

(1) Very Good 

5

Province of Siena / San Gimignano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Private garden

 …see more

from £136 / night

£949 / week

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from £136 / night

21

La Fonte San Gimignano Prov. of Siena - Pancole apartment sleeps 4

San Gimignano / Pancole

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Olivo is one of four self catering apartments at La Fonte. It is a spacious, two bed roomed apartment on the first floor of La Fonte. This apartment can be used for either 4 guests or 2 guests using one bedroom only. The apartment overlooks the garden and valley.  …see more

from £100 / night

£694 - £1165 / week

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from £100 / night

(2) Excellent 

23

San Gimignano Tuscany, Castelfalfi resort - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Il Cipresso is a luxurious and contemporary fully air conditioned 1 bedroom, open plan, 1 bathroom condo with designated parking space, private terrace and garden. Located in the newly restored, 800 year old hill town resort of Castelfalfi in Tuscany, 20 minutes driving  …see more

from £75 / night

£519 / week

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from £75 / night

(1) Excellent 

13

San Gimignano - 26417001 - Larniano farmhouse sleeps 4

San Gimignano / Larniano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Nice complex situated in quiet and panoramic location on a farming estate 8 km from San Gimignano away. This property, surrounded by olive groves and vineyards, comprises a small, independent barn and 2 units set on the first floor of the owners' house. The property ow  …see more

from £97 / night

£564 - £919 / week

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from £97 / night

20

San Gimignano - 10767001 - San Gimignano farmhouse sleeps 2

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
A typical rustic house built of stone situated in one of the most suggestive panoramas in Tuscany. The house is a charming and traditional Tuscan farmhouse with a lovely garden that encircle the house and enjoys a magnificent view of the medieval walled town with his fa  …see more

from £62 / night

£324 - £454 / week

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from £62 / night

22

San Gimignano - 69066001 - San Gimignano farmhouse sleeps 5

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful independent villa with private (above-ground) pool created from the restoration of an ancient barn dating back to the beginning of the 20th century. This property, nestling deep among green hills, is situated a short distance away from the lovely medieval town  …see more

from £171 / night

£997 - £1661 / week

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from £171 / night

Top Destination reviews

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
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
Restored stone built villa near San Gimignano
Fantastic

We had such a wonderful holiday in your beautiful villa. It was great having the baby things already there for our son. Lovely and peaceful with fantastic views. Really relaxing. … 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
Podere Lo Spadino
Absolutely wonderful and picturesque!

We rented this beautiful house with two other couples for two weeks and absolutely loved our stay. Barbara and her family are gracious and kind hosts, always going our of their way to make our stay comfortable and enjoyable. The view of San Gimigna … see more
Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool
Great apartment. Fantastic Tuscan hospitality.

My wife and I chose Casa Gelsomino because we were travelling with our 18-month old daughter and wanted to be in a location with amenities within walking distance. The hamlet of Castel San Gimignano itself is a sleepy one but offers a great little co … see more

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