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

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308 Holiday homes

Filters applied: Swimming pool (309)

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

(33) Excellent 

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
  • 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

(9) Excellent 

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
  • 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 - £1078 / week

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from £85 / night

(20) Excellent 

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
  • 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 - £604 / week

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from £87 / night

(1) Excellent 

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
  • 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

£475 - £992 / week

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from £69 / night

(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

(2) Very Good 

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
  • 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 - £949 / week

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from £57 / night

(7) Excellent 

15

Holiday farmhouse apartment rental in Tuscany, property features beautiful garden and private fishing lake - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats inside an old barn that were recently restructured.Both the apartments can accommodate up to 4 people and are composed of a bedroom with bathroom, a small bedroom and a dining room/k  …see more

from £61 / night

£414 - £785 / week

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from £61 / 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

7

Charming rooms with amazing view and breakfast. - San Gimignano b&b sleeps 2

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
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) Excellent 

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
  • 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

13

Province of Siena / San Gimignano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £173 / night

£992 - £2845 / week

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from £173 / night

(2) Very Good 

10

Cosy Tuscan villa for friends or family - San Gimignano apartment sleeps 7

Province of Siena / San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Splendid three bedroom two bathroom villa located right outside of San Gimignano. Absolut privacy and quiet location !! Incredible private pool with a panoramic position over the Tuscan landscape Three double bedrooms - perfect for couples or friends travelling to  …see more

from £138 / night

£949 / week

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from £138 / 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

(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

29

Il Granaio - San Gimignano villa sleeps 2

Province of Siena / San Gimignano

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Private garden
<br>Il Granaio – San Gimignano – Tuscany<br>1 Double Bedroom – Shared Pool<br>This quaint cottage dates back to the 1400's when it was a granary, part of the farmers houses in a tiny village just 6 km from the center of San Gimignano. The &q  …see more

from £148 / night

£1035 - £1250 / week

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from £148 / 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

(1) Excellent 

20

Villa Cafaggiola 3 bedroom villa with private pool - San Gimignano villa sleeps 6

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
The Villa has been completely renovated from an old barn and materials have been used for its original restructuring terracotta floors and exposed beams on the ceilings. It 'a great place to spend a quiet holiday without sacrificing the various excursions just a short d  …see more

from £161 / night

£1121 / week

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from £161 / night

23

San Gimignano / Ulignano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly

 …see more

from £104 / night

£604 / week

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from £104 / night

(5) Excellent 

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
  • Swimming pool
  • Child friendly
  • Ask about pets
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

10

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly

 …see more

from £78 / night

£475 / week

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from £78 / 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

(1) Very Good 

7

Sassi Bianchi - Ginestra - Larniano farmhouse sleeps 7

San Gimignano / Larniano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Ginestra [200 sqm] This House is a restored barn and it was restored in 2008. Ginestra farmhouse 6/7 persons The main entrance is at ground floor up 2 steps from the gardenThe entrance is directly into the dining room. Through an open door passage and down 1 step t  …see more

from £138 / night

£949 - £1207 / week

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from £138 / 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

9

Deluxe vacation rental in Tuscany in San Gimignano - Larniano farmhouse sleeps 7

San Gimignano / Larniano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Luxury and charm located on the outskirts of San Gimignano, tennis court and large garden areaDeluxe vacation rental in Tuscany near the wonderful cities of San Gimignano and Siena.Three large and charming bedrooms each with an en suite bathroomFully equipped kitchen in  …see more

from £160 / night

£1121 - £1294 / week

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from £160 / night

25

Province of Siena / San Gimignano

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £74 / night

£449 - £595 / week

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from £74 / 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

(1) Very Good 

39

Province of Siena / San Gimignano

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £104 / night

£604 / week

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from £104 / night

(1) Very Good 

15

Sassi Bianchi Acacia - Larniano farmhouse sleeps 7

San Gimignano / Larniano

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Thefarmhouse, located in the hillside dominating the tennis court, is an unusual building: originally it was a lookout tower for Castelvecchio, subsequently transformed into a furnace. The house has two independent entrances: the main entrance opens on to a paved c  …see more

from £138 / night

£949 - £1207 / week

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from £138 / night

(3) Very Good 

33

Via Vecchia apartment - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Just 1800 mt from the historical centre of San Gimignano, along the Francigena road, you will find a place where you can spend beautiful Tuscany holidays. The apartment is located in the countryside of the medieval town, in the centre of Tuscany. The house is surround  …see more

from £46 / night

£337 - £423 / week

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from £46 / night

100

San Gimignano - 2+2 pax - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
2+2 paxThis ground floor country apartment of 90 sq-m is a lovely haven to spend holidays in Tuscany. The apartment features a spacious living room with dining area and kitchenette provided with all comforts. It can host 2+2 guests as it features a double bedroom and tw  …see more

from £108 / night

£630 - £746 / week

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from £108 / 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 

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

  • 7 bedrooms
  • Sleeps 13
  • 1 night min
  • 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

(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

14

Apt. Sole - San Gimignano farmhouse sleeps 4

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
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

(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

Top Destination reviews

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
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
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
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
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
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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