50 Best San Gimignano Villas on Holiday Lettings - Apartments

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Larniano
30 properties
Castel San Gimignano
24 properties
Ulignano
18 properties
Pancole
16 properties
Casaglia
9 properties

San Gimignano

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432 Vacation rentals

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(5) Excellent 

21

Vacation villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 mi
  • 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 $162 / night

$1078 - $2479 / week

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from $162 / night

(4) Excellent 

14

Castel San Gimignano Vacation apartment rental

San Gimignano / Castel San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 55 mi
  • 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 $108 / night

$593 - $916 / week

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from $108 / night

(7) Excellent 

35

Province of Siena / San Gimignano

2 4 Min stay varies

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

 …see more

from $108 / night

$679 - $1132 / week

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from $108 / night

28

Vacation cottage in Castel San Gimignano

San Gimignano / Castel San Gimignano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
The Glicine is a studio apt,45 mq large, with complete bathroom with shower cubicle ,basin,wc There is a fully equipped area with fridge,hob. Old furniture.The Glicine was an old barn and old oven. The ceiling is wood Autside there is a private pergola, that is idealfor  …see more

from $76 / night

$485 - $809 / week

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from $76 / night

(11) Very Good 

32

Vacation 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 mi
  • 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 fro  …see more

from $76 / night

$572 - $1019 / week

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from $76 / night

(9) Excellent 

42

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 70 mi
  • Child friendly
  • Air conditioning

 …see more

from $94 / night

$657 - $981 / week

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from $94 / night

(3) Excellent 

28

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 mi
  • 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  …see more

from $45 / night

$313 - $1067 / week

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from $45 / night

(3) Excellent 

28

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 mi
  • 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 Gim  …see more

from $44 / night

$302 - $1035 / week

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from $44 / 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 $130 / night

$755 - $1186 / week

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from $130 / night

(1) Very Good 

35

Province of Siena / San Gimignano

7 10 Min stay varies

  • 7 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $232 / night

$1617 - $2587 / week

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from $232 / 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 $135 / night

$830 - $1240 / week

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from $135 / night

(42) Excellent 

19

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
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 $240 / night

$1300 - $1900 / week

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from $240 / night

(22) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

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

 …see more

from $60 / night

$361 - $523 / week

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from $60 / night

(33) Excellent 

32

Castel San Gimignano Vacation apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 mi
  • 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 $108 / night

$593 - $916 / week

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from $108 / night

(46) Excellent 

25

Vacation 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 mi
  • 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, ta  …see more

from $113 / night

$782 - $1125 / week

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from $113 / night

34

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly

 …see more

from $76 / night

$453 - $873 / week

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from $76 / night

(21) Excellent 

43

Castel San Gimignano Vacation apartment rental

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 mi
  • 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 $108 / night

$593 - $916 / week

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from $108 / 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 $108 / night

$647 / week

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from $108 / night

(5) Excellent 

46

Vacation farmhouse rental

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 mi
  • 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 ho  …see more

from $262 / night

$1832 / week

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from $262 / night

(14) Excellent 

24

San Gimignano Vacation villa rental

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 mi
  • 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 spe  …see more

from $87 / night

$593 - $1940 / week

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from $87 / night

(4) Excellent 

28

Vacation 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 mi
  • 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 $87 / night

$593 - $744 / week

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from $87 / 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 mi
  • Swimming pool
  • Child friendly

 …see more

from $130 / night

$755 - $943 / week

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from $130 / night

(1) Excellent 

19

Vacation farmhouse in San Gimignano

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 mi
  • 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 $81 / night

$539 - $1186 / week

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from $81 / night

(15) Very Good 

16

Vacation 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 mi
  • Swimming pool
Casa Florio' is a 2 bedroom apartment (upstairs 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 a  …see more

from $103 / night

$718 / week

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from $103 / night

25

Province of Siena / San Gimignano

1 3 Min stay varies

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

 …see more

from $96 / night

$606 - $991 / week

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from $96 / night

(1) Very Good 

20

Province of Siena / San Gimignano

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from $249 / night

$1309 / week

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from $249 / night

(5) Very Good 

21

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 77 mi
  • Swimming pool
  • Child friendly

 …see more

from $135 / night

$787 - $1197 / week

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from $135 / night

(5) Excellent 

24

San Gimignano Vacation 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 $76 / night

$529 - $1240 / week

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from $76 / night

(2) Very Good 

29

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Splendid three bedroom , 3 bathroom in suite 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 tra  …see more

from $216 / night

$1509 - $2263 / week

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from $216 / night

80

Farmhouse rental in Castel San Gimignano with shared pool, golf nearby

San Gimignano / Castel San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 70 mi
  • 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 $232 / night

$1455 - $2371 / week

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from $232 / night

(2) Very Good 

21

Apartment rental in San Gimignano

Province of Siena / San Gimignano

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 72 mi
  • 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 $184 / night

$1013 / week

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from $184 / night

(9) Excellent 

16

Vacation farmhouse in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 90 mi
  • 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 dinin  …see more

from $79 / night

$539 - $981 / week

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from $79 / night

(1) Good 

8

Apartment rental in San Gimignano

Province of Siena / San Gimignano

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Beautiful hilltop 2 story farmhouse apartment by owner Situated in the heart of tuscany (hills, between volterra, famous etruscan and medieval city and san gimignano, famous all over the world for its characteristic towers. You can easily visit florence, siena and pisa  …see more

from $12 / night

$27 - $430 / week

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from $12 / night

(1) Very Good 

39

Farmhouse rental in Castel San Gimignano with shared pool

San Gimignano / Castel San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
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 $216 / night

$1455 - $2371 / week

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from $216 / night

(9) Excellent 

20

San Gimignano Vacation villa rental

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $231 / night

$1401 - $2587 / week

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from $231 / night

47

Province of Siena / San Gimignano

2 3 1 night min

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

 …see more

from $75 / night

$421 / week

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from $75 / night

(12) Very Good 

17

San Gimignano Vacation villa accommodation

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 &am  …see more

from $89 / night

$625 - $1188 / week

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from $89 / night

(17) Excellent 

10

Apartment rental in San Gimignano

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 72 mi
  • 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 bi  …see more

from $62 / night

$361 / week

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from $62 / night

100

Villa rental in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
Exteriors       This sophisticated historic villa‘s location lets guests have a fabulous view of the typical Tuscan country landscape. It affords a terrace with commanding views and a swimming pool (5 x 12m) providing the best way for  …see more

from $570 / night

$3988 - $5173 / week

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from $570 / night

100

Larniano Vacation villa rental

San Gimignano / Larniano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Characteristic stone villa created from a carefully-renovated barn, just 5 km from the captivating medieval village of San Gimignano, and just 6 km from the charming town of Certaldo. The property is independent and offers a large, completely enclosed garden (2000 m2) a  …see more

from $433 / night

$2498 - $4163 / week

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from $433 / night

1