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

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San Gimignano

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85 Holiday homes

(5) Excellent 

21

Holiday villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“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 Monterigg  …see more

from £128 / night

£848 - £1950 / week

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from £128 / night

(4) Excellent 

14

Castel San Gimignano holiday apartment rental

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 £85 / night

£467 - £721 / week

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from £85 / night

(21) Excellent 

43

Castel San Gimignano holiday apartment rental

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
“Brilliant location, fantastic views and the warmest of welcomes.” We have just returned from Casa Verbena having had a fabulous time. The accommodation is very spacious and exceptionally clean and well equipped. The pictures of the apartment do not il  …see more

from £85 / night

£467 - £721 / week

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from £85 / night

(33) Excellent 

32

Castel San Gimignano holiday apartment rental

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
“Fabulous holiday and accommodation” We stayed at this apartment in June this year. The apartment was really well fitted out and spotlessly clean, the oven looked like it had never been used !! The facilities were great and the location is lovely, it i  …see more

from £85 / night

£467 - £721 / week

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from £85 / night

(9) Excellent 

18

Holiday farmhouse with swimming pool in San Gimignano

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
“peaceful paradise” This villa met all our expectations. The view from the bedrooms and the terrace were spectacular. Location in small village was perfect. Villa had special arragements for food delivery from local restaurants. Vila was spotless an  …see more

from £84 / night

£560 - £1060 / week

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from £84 / night

(20) Excellent 

49

Holiday cottage in San Gimignano

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
Cottage view on San Gimignano country house countrysideThe cottage is provided with baby bed and bay chair.Pets: maximum 2 (small)  …see more

from £51 / night

£356 / week

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from £51 / night

(6) Excellent 

27

Apartment rental in San Gimignano

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 underst  …see more

from £85 / night

£509 / week

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from £85 / night

(45) Excellent 

25

Holiday home with shared pool in San Gimignano

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
“So good we came back in 2013 - Terrific Villa, Pool, Views & Airconditioning” A lovely traditional style Villa, extremely well appointed with the luxury of Airconditioned bedrooms - which meant a comfortable nights sleep for all. With two young childr  …see more

from £90 / night

£625 - £900 / week

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from £90 / night

(2) Very Good 

17

Holiday farmhouse rental

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
Self catering Farmhouse and 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence one hour .  …see more

from £56 / night

£339 - £933 / week

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from £56 / night

(11) Very Good 

31

Holiday farmhouse with shared pool in San Gimignano

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
“Fabulous holiday!” We had an absolutely great holiday in Tuscany. La Fontanella is ideally located to everything we wanted to do. 10 mins to beautiful San Giminiano, less than an hour to Florence, Siena and Chianti. Comfortable house, lovely terrace,  …see more

from £98 / night

£606 / week

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from £98 / night

(1) Very Good 

23

San Gimignano / Ulignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from £101 / night

£589 - £925 / week

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from £101 / night

(5) Excellent 

46

Holiday farmhouse rental

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
A typical stone barn immersed in the Tuscan countryside of San Gimignano. A large garden overlooks the hills and surrounding countryside. Up to 7 people in a both modern and rustic atmosphere.  …see more

from £197 / night

£1441 - £1950 / week

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from £197 / night

16

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

7 13 1 night min

  • 7 bedrooms
  • Sleeps 13
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
We are in a very good position, we are just 3,5 km from San Gimignano, 40 km from Firenze, 25 km from Siena, 25 km from Volterra, 15 km from Certaldo, 45 km from Pisa; you can visit a lots of thinghs and a lots of beautiful historical town.  …see more

from £119 / night

£526 / week

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from £119 / night

(1) Excellent 

19

Holiday farmhouse in San Gimignano

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
“Very good appartment, with great views” We stayed in Podere Le Monache 4 for one week in August. It was more then we expected from the pictures and the description. The appartment was very clean and spacious, with two large bedrooms and enough furnitu  …see more

from £68 / night

£467 - £975 / week

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from £68 / night

(9) 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 £93 / night

£589 - £765 / week

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from £93 / night

(2) Very Good 

10

San Gimignano holiday apartment rental

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
.This charming accommodation lies in the countryside enjoying the most marvellous views of the undulating landscape and the towers of the city of San Gimignano only 3km away. It is a lovely location for enjoying country walks and relaxingThe pool and the garden are not  …see more

from £136 / night

£933 - £1780 / week

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from £136 / night

(5) Excellent 

24

San Gimignano holiday apartment rental

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  …see more

from £60 / night

£416 - £975 / week

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from £60 / 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 £56 / night

£386 / week

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from £56 / night

25

Province of Siena / San Gimignano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £76 / night

£477 - £779 / week

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from £76 / night

(4) Excellent 

28

Holiday farmhouse with shared pool in San Gimignano

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 £68 / night

£467 - £585 / week

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from £68 / 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 £59 / night

£331 / week

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from £59 / night

(2) 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 £51 / night

£356 / week

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from £51 / 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 £47 / night

£282 - £408 / week

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from £47 / night

9

Farmhouse rental in Larniano with shared pool, golf nearby

San Gimignano / Larniano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Silence, nice countryside, good food.Relax  …see more

from £157 / night

£1102 - £1865 / week

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from £157 / night

(2) Very Good 

12

Holiday farmhouse letting

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 fa  …see more

from £77 / night

£509 / week

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from £77 / night

(1) Excellent 

20

Holiday villa with swimming pool in San Gimignano

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
Offers a unique view of the surrounding valley typical of the Sienese hills (olives and grapes) and is located a short distance (3 km) from the town of San Gimignano famous for its medieval towers.  …see more

from £158 / night

£1102 / week

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from £158 / night

(1) Excellent 

20

Farmhouse rental in San Gimignano with swimming pool

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
Self catering Farmhouse with 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence, Siena and Pisa one hour from the house.  …see more

from £56 / night

£339 - £806 / week

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from £56 / night

13

Holiday cottage in San Gimignano

Province of Siena / San Gimignano

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Cottage country house countryside  …see more

from £40 / night

£279 / week

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from £40 / night

(6) Excellent 

23

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
“What a wonderful place in Italy” We stayed now the second time in Podere Lo Spadino, we are a Group with 8 peoples, and everything in this house is amazing. The whole house, the garden, the pool and of course Barbara with her Family, they are helpful  …see more

from £297 / night

£1314 - £2119 / week

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from £297 / night

(1) Excellent 

19

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from £101 / night

£706 - £944 / week

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from £101 / night

(7) Excellent 

35

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £85 / night

£534 - £890 / week

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from £85 / night

(15) Very Good 

16

Holiday apartment with shared pool in San Gimignano

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
“Beautiful apartment in stunning Tuscan landscape” If you want a base in Tuscany that seems in the middle of nowhere, but is less than an hour from all of the famous Tuscan towns/villages, and a lovely apartment that is in the middle of stunning countr  …see more

from £82 / night

£574 / week

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from £82 / night

19

Holiday apartment in Casaglia

San Gimignano / Casaglia

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the elegantly renovated barn, Iris is particularly spacious and filled with natural light.Baby bed on request is free  …see more

from £127 / night

£816 - £1120 / week

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from £127 / night

10

Holiday apartment in Casaglia

San Gimignano / Casaglia

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Consists of a small entrance hall, living room with kitchenette, 2 double rooms with a double bed, bathroom. For 4 people, independent entrance. Heating. First floor.  …see more

from £81 / night

£551 / week

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from £81 / night

7

San Gimignano holiday b&b rental

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 £81 / night

£534 - £712 / week

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from £81 / night

(1) Very Good 

39

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £102 / night

£594 - £742 / week

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from £102 / night

(1) Excellent 

99

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £106 / night

£653 - £975 / week

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from £106 / 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 £68 / night

£437 - £526 / week

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from £68 / night

(3) Very Good 

33

Holiday apartment with swimming pool in San Gimignano

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 £45 / night

£339 / week

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from £45 / night

(14) Excellent 

17

Holiday apartment in San Gimignano

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
“Great Tuscan apartment... but not for summer heat.” My husband and I had originally hoped to stay in Il Duca for 2 months, but because of the heat in Tuscany this summer, we had to seek other accommodations with air conditioning. Pros: The apartme  …see more

from £88 / night

£611 / week

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from £88 / night

Top Destination reviews

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
La Chiesina
An awesome villa in the Tuscan hills

A wonderfully restored church with plenty of character. Privacy with trees and hedges. Fab and accessible pool. Well equipped kitchen. An amazing welcome pack. We cycled from here to San Gimignano and to Monteriggioni. The location is superb and we d … see more
6 bedroom villa Tuscany (BFY13480)
excellent place, very ingoibale holliday

we stay in the villa for 5 nights. 5 couples 3 infants. everything was like it describe in the site. very large rooms with all the facilities you need. wifi works perfect, the pool was very clean. the kitchen was well equipped, the dining room ver … see more
Restored stone built villa near San Gimignano
Fantastic

We had such a wonderful holiday in your beautiful villa. It was great having the baby things already there for our son. Lovely and peaceful with fantastic views. Really relaxing. … see more
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
3 bedroom holiday apartment near Tuscan cities, staffed property with outdoor pool
Perfect location with delightful owners

This is such a beautiful spot and ideal for exploring as very close to everything we wanted to see: Siena, San Gimignano, Volterra and many other less well known medieval towns and villages. The pool has a stunning view and is a perfect place to sun … see more