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50 Holiday homes

Filters applied: City breaks (51)

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

(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

(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

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

(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

(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

(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

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

(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

(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

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

£337 / week

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from £60 / 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

(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

(3) Very Good 

13

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary

 …see more

from £113 / night

£785 / week

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from £113 / 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

22

Province of Siena / San Gimignano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Ask about pets

 …see more

from £188 / night

£1311 - £1753 / week

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from £188 / 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

(6) Very Good 

15

2 bedroom holiday apartment in San Gimignano surrounded by stunning Tuscan landscape - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 72 km
  • Child friendly
  • Private garden
This apartment is for 2/4 people and is made up of two spacious rooms with double bed, two bathrooms with shower, a large and fully equipped kitchen/dining room and an outdoor area paved with terracotta tiles like the yards of old country farmhouses, offering a fabulous  …see more

from £90 / night

£500 - £561 / week

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from £90 / night

26

San Gimignano / Castel San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £44 / night

£294 - £388 / week

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from £44 / night

22

Apartment Corbezzolo - Castel San Gimignano apartment sleeps 5

San Gimignano / Castel San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
IMPORTANT: This holiday house is registered and has the licence number 19814 - San Gimignano. Welcome to San Gimignano in Tuscany."LE FONTANELLE", a completely restored rural hamlet, is located eight km from the medieval town of San Gimignano. San Gimignano was a st  …see more

from £67 / night

£432 - £819 / week

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from £67 / night

(1) Very Good 

11

La Capanna di Sovestro - San Gimignano apartment sleeps 3

Province of Siena / San Gimignano

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets
The apartment is composed of a large double room with the possibility of additional sofa bed, a small double room , a private bathroom, fully equipped kitchen, private parking and a large terrace where you can play barbecue, solarium or reading.Free WiFi available every  …see more

from £61 / night

£363 / week

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from £61 / night

(1) Very Good 

8

Province of Siena / San Gimignano

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Air conditioning

 …see more

from £119 / night

£664 / week

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from £119 / night

20

Aquario - San Gimignano apartment sleeps 5

Province of Siena / San Gimignano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Aquario apartment for up to 5 guests. The property is extraordinarily cool and pleasant throughout the summer, thanks to its location on a higher altitude (about 500 AMSL) and the beautiful structure in heavy stones. This magnificent country home offers no compromise in  …see more

from £185 / night

£1294 - £1466 / week

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from £185 / night

(8) Excellent 

20

Three bedroom apartment in stunning villa - San Gimignano villa sleeps 6

Province of Siena / San Gimignano

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
Osservatorio is a stunning villa for up to 11guests divided into two independent units. Orione apartment for up to 6 guests.The property is extraordinarily cool and pleasant throughout the summer, thanks to its location on a higher altitude (about 500 AMSL) and the beau  …see more

from £185 / night

£1294 - £1466 / week

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from £185 / night

(1) Excellent 

17

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 109 km
  • Swimming pool
  • Child friendly

 …see more

from £95 / night

£647 / week

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from £95 / night

(1) Good 

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 £104 / night

£604 / week

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from £104 / 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

£259 - £388 / week

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from £44 / night

(2) Very Good 

31

San Gimignano / Larniano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 69 km
  • Swimming pool
  • Child friendly

 …see more

from £78 / night

£518 - £832 / week

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from £78 / night

(1) Excellent 

21

Podere Magione - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 72 km
  • Child friendly
  • Ask about pets
The holiday farm is immersed in the San Gimignano countryside, amidst hills covered with olive trees and vineyards, between the Val d'Elsa and Chianti. From its ideal position it is possible to quickly reach the most beautiful, historical and artistic towns of Tusc  …see more

from £135 / night

£759 - £811 / week

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from £135 / night

13

Agriturismo I Pini San Gimignano - San Gimignano farmhouse sleeps 24

Province of Siena / San Gimignano

11 24 Min stay varies

  • 11 bedrooms
  • Sleeps 24
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Pet friendly
Enjoy an unforgettable holiday experience in the heart of Tuscany and discover the beauty of the medieval town San Gimignano. Our guesthouse with panoramic swimming pool is situated on a charming hill in the midst of nature just 1 km away from the UNESCO World Heritage  …see more

from £1037 / night

£7254 / week

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from £1037 / night

(14) Excellent 

17

Fabio Apartments San Gimignano - San Gimignano apartment sleeps 4

Province of Siena / San Gimignano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 65 km
  • Child friendly
  • Air conditioning
Apartment "Il Duca" (2-6 beds)Bright three-roomed apartment (85 mq). With its twelve windows it offers a beautiful panoramic view of the surrounding Chianti countryside, the nearby gardens, the ancient buildings and the legendary Torre del Diavolo. It is finel  …see more

from £89 / night

£621 / week

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from £89 / night

11

Focolare - San Gimignano apartment sleeps 5

Province of Siena / San Gimignano

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
Living room with french windows on to balcony, fully equipped kitchen area with fridge, hob (3 gas rings), dining area with table and chairs, lounge area with settee and armchairs and large traditional fireplace, one bedroom with double bed; one bedroom with double bed  …see more

from £100 / night

£690 - £776 / week

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from £100 / night

5

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £74 / night

£513 / week

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from £74 / night

6

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £74 / night

£513 / week

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from £74 / night

23

Romantic apartment in the heart of San Gimignano! - San Gimignano apartment sleeps 2

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 68 km
  • Child friendly
  • Car not necessary
In the historic centre of San Gimignano, right in front of “La Rocca” (the Fortress) and only about 80 metres away from the famous Dome Square, you will find this charming small flat in absolute quiet position. La Rocca Apartment fully renovated and restored by Marc  …see more

from £65 / night

£432 - £483 / week

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from £65 / night

16

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from £78 / night

£518 / week

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from £78 / 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 £78 / night

£561 / week

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from £78 / 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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