Villas in San Gimignano and Apartments - Holiday Lettings - Holiday Rentals San Gimignano

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90 Holiday homes

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

(10) 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

£622 / week

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from £100 / 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

(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 £86 / night

£574 - £1087 / week

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from £86 / 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

£292 - £422 / week

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from £48 / 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

£479 - £609 / week

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from £87 / night

(32) 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

£479 - £740 / week

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from £87 / 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 £156 / night

£1087 - £2861 / week

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from £156 / 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 £202 / night

£1479 - £2000 / week

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from £202 / 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

£348 - £957 / week

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from £57 / 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 £70 / night

£479 - £1000 / week

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from £70 / 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 £53 / night

£366 / week

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from £53 / 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

£479 - £653 / 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 £83 / night

£548 - £731 / week

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from £83 / night

23

San Gimignano / Ulignano

2 6 1 night min

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

 …see more

from £105 / night

£609 / week

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from £105 / night

47

Province of Siena / San Gimignano

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 50 km
  • Child friendly
  • Private garden

 …see more

from £60 / night

£340 / week

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from £60 / 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 £96 / night

£609 - £731 / week

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from £96 / 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 £122 / night

£540 / week

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from £122 / 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

£348 - £827 / week

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from £57 / 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

£287 / week

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from £41 / 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 £305 / night

£1348 - £2174 / week

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from £305 / night

10

la Stadera - Castel San Gimignano apartment sleeps 4

San Gimignano / Castel San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
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 £40 / night

£261 / week

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from £40 / night

16

Maccalli - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful country house situated just a stone's throw away from San Gimignano, an attractive medieval town with a unique collection of towers and winding lanes set in the heart of the Tuscan countryside. This farmhouse enjoys spectacular views over a picturesque rural l  …see more

from £128 / night

£895 - £1011 / week

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from £128 / 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

£522 / week

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from £87 / 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 £131 / night

£870 - £2000 / week

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from £131 / 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 £162 / night

£1131 / week

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from £162 / 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

£457 / week

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from £74 / night

7

Lovely countryside Podere San Luigi Apt Tramonto - Pancole farmhouse sleeps 2

San Gimignano / Pancole

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
You can enjoy a relaxing holiday in the center of Tuscany surrounded by nature and the countryside. Very close to San Gimignano, on the "VIA FRANCIGENA", the casale is the starting point for visiting the important Tuscan cities of Art, villages, and the famous  …see more

from £54 / night

£348 / week

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from £54 / 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 £140 / night

£957 - £1218 / week

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from £140 / 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 £104 / night

£725 - £968 / week

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from £104 / night

28

Province of Siena / San Gimignano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 70 km
  • Child friendly
  • Private garden

 …see more

from £105 / night

£609 / week

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from £105 / night

(1) Excellent 

30

San Gimignano / Santa Maria, San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £70 / night

£453 - £544 / week

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from £70 / night

(1) Good 

28

San Gimignano / Castel San Gimignano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

 …see more

from £79 / night

£566 / week

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from £79 / night

(7) Excellent 

35

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

 …see more

from £87 / night

£548 - £748 / week

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from £87 / 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 £161 / night

£1131 - £1305 / week

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from £161 / 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

£396 / week

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from £57 / 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

£453 - £676 / week

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from £74 / 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 £79 / night

£522 / week

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from £79 / night

34

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

 …see more

from £44 / night

£261 - £392 / week

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from £44 / night

27

Province of Siena / San Gimignano

1 2 Min stay varies

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

 …see more

from £58 / night

£400 - £548 / week

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from £58 / 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

£609 - £1696 / week

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from £87 / night

Top Destination reviews

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
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
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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