Long term rentals San Gimignano | Holiday Lettings

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Location

  • Italy
  • Tuscany
  • Province of Siena
  • San Gimignano
  • All locations
  • Casaglia (9)
  • Castel San Gimignano (18)
  • Larniano (35)
  • Montauto (1)
  • Pancole (25)
  • San Donato in Siena (9)
  • Santa Maria, San Gimignano (3)
  • Ulignano (19)

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408 Holiday homes

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

(21) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

 …see more

from £48 / night

£289 - £419 / week

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from £48 / 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

(8) Excellent 

24

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Private garden

 …see more

from £95 / night

£604 - £725 / week

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from £95 / 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

13

Piccolo Cottage San Gimignano - San Gimignano cottage sleeps 4

Province of Siena / San Gimignano

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden
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 modern-style using and bright terracotta floors, the airy home contains 1 double bedroom.  …see more

from £41 / night

£284 / week

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from £41 / night

(3) Excellent 

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
  • Nearest beach 55 km
  • Child friendly
  • Ask about pets
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 £87 / night

£475 - £647 / week

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from £87 / 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

(6) Excellent 

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

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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 £87 / night

£518 / week

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from £87 / 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 - £1207 / 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

(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

(1) Excellent 

7

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £52 / night

£363 / week

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from £52 / night

13

15656-Holiday house San Gimign - San Gimignano villa sleeps 4

Province of Siena / San Gimignano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Two Bedroom Detached House San Gimignano Il Vecchio Fienile is a beautiful detached house with private swimming pool, surrounded by its own well kept garden with wonderful views over vineyards and cypress groves towards medieval San Gimignano visible in the distance. I  …see more

from £107 / night

£745 - £908 / week

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from £107 / 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

20

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £151 / night

£793 - £1301 / week

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from £151 / night

(4) Excellent 

19

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £61 / night

£363 - £483 / week

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from £61 / 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

(16) Excellent 

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

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 72 km
  • Child friendly
  • Private garden
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 £44 / night

£259 - £319 / week

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from £44 / night

15

Contessa Apt San Gimignano - Larniano apartment sleeps 4

San Gimignano / Larniano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 £77 / night

£535 / week

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from £77 / 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

(1) Excellent 

10

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £57 / night

£393 / week

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from £57 / 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

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
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
La Chiesina
An awesome villa in the Tuscan hills

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

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