50 Best San Gimignano Villas on Holiday Lettings - Apartments

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Castel San Gimignano
27 properties
Pancole
25 properties
Larniano
23 properties
Ulignano
19 properties
Casaglia
8 properties

San Gimignano

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439 Vacation rentals

(45) 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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Responds fast!
avg. 2 hours 5 minutes

from $240 / night

(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 farmers o …see more

from $175 / night

$1161 - $2670 / week

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Responds fast!
avg. 49 minutes

from $175 / night

(4) 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 Gimignan …see more

from $47 / night

$325 - $1115 / week

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Responds fast!
avg. 1 hour 7 minutes

from $47 / night

(8) Excellent 

35

San Gimignano Vacation farmhouse rental

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
Less than 1km away from the Via Francigena, La Proda is part of a little rural hamlet, whose ancient nucleus dates back to the Middle Ages. The area toponym “Strada” attests to these places' historical value. Carefully restored, surrounded by centuries-old cypresses an …see more

from $151 / night

$951 - $1219 / week

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from $151 / night

34

San Gimignano Vacation apartment rental

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
Girasole (2 + 2) The “Girasole” apartment on the ground floor with independent access has a roomy kitchen with a large original century fireplace. One double bedroom and one double sofa- bed in the small living room make it suitable for a couple or a young family. It …see more

from $82 / night

$492 - $949 / week

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from $82 / night

(1) Excellent 

99

Vacation villa with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa with pool and large garden with fruit trees, halfway between the famous towers of San Gimignano and the charming medieval town of Certaldo Alto. Private entrance with living/dining room with double sofa bed, a kitchen, a bedroom and a bathroom with shower. Entirel …see more

from $146 / night

$894 - $1335 / week

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from $146 / 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 from Pisa, Florenc …see more

from $82 / night

$616 - $1097 / week

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avg. 2 hours 5 minutes

from $82 / night

(4) 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 San …see more

from $49 / night

$337 - $1150 / week

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Responds fast!
avg. 1 hour 7 minutes

from $49 / night

(10) Excellent 

Certificate of Excellence

18

Vacation 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 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

Certificate of Excellence

from $105 / night

$709 - $1393 / week

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Responds fast!
avg. 2 hours 18 minutes

from $105 / night

(47) Excellent 

Certificate of Excellence

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, tastefully r …see more

Certificate of Excellence

from $117 / night

$813 - $1170 / week

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Responds fast!
avg. 3 hours 48 minutes

from $117 / night

(5) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $140 / night

$755 - $987 / week

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Responds fast!
avg. 1 hour 16 minutes

from $140 / 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 $256 / night

$1625 - $2554 / week

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from $256 / night

(33) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $140 / night

$755 - $987 / week

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Responds fast!
avg. 1 hour 16 minutes

from $140 / night

(4) Excellent 

28

Vacation farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • 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 $134 / night

$929 - $1103 / week

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from $134 / night

(22) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $140 / night

$755 - $987 / week

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Responds fast!
avg. 1 hour 16 minutes

from $140 / 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 $82 / night

$569 - $1335 / week

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Responds fast!
avg. 3 hours 34 minutes

from $82 / 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 $233 / night

$1625 - $2438 / week

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from $233 / 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 Collinella …see more

from $105 / night

$709 - $801 / week

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from $105 / night

(24) Excellent 

Certificate of Excellence

60

Cottage rental in Pancole

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 mi
  • Child friendly
  • Air conditioning
The farm VillinodelGrillo born from an old barn of a small farm family, the center of a 4-hectare country estate. The attention to detail and cleanliness are the main features of the cottage. It consists of a single independent small house, set among vineyards and olive …see more

Certificate of Excellence

from $64 / night

$389 - $523 / week

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Responds fast!
avg. 53 minutes

from $64 / night

20

Vacation farmhouse rental

Province of Siena / San Gimignano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about pets
This lovely property is located only 5 Kms from the centre of San Gimignano, famous for its beautiful towers. This is the place for those who look for peace and quiet, who like nature with just the sound of birds. Situated at less than two miles from San Gimignano, bet …see more

from $428 / night

$2995 - $4632 / week

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from $428 / night

(6) 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 house i …see more

from $283 / night

$1974 / week

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Responds fast!
avg. 1 hour 27 minutes

from $283 / night

(2) Very Good 

10

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
Our apartments are located in the northern part of the country to 150 meters from the walls of the old town, in a very quiet area, where you can easily find place for the machine without having to pay. In about 5 minutes on foot you can reach the historic center. The ap …see more

from $76 / night

$529 / week

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Responds fast!
avg. 2 hours 53 minutes

from $76 / night

15

Vacation apartment in Larniano

San Gimignano / Larniano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 which it is p …see more

from $103 / night

$720 / week

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Responds fast!
avg. 2 hours 7 minutes

from $103 / night

18

Vacation farmhouse in Ulignano

San Gimignano / Ulignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful house dating back to the end of the 18th century comprising 6 welcoming apartments. This property is situated on the hills surrounding Volterra and enjoys amazing views of the Tuscan landscape. All of the 6 units have been recently restored and are furnished i …see more

from $266 / night

$1860 - $2193 / week

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from $266 / night

17

Vacation apartment in Castel San Gimignano

San Gimignano / Castel San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 mi
  • 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 $53 / night

$352 / week

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from $53 / night

(1) Excellent 

20

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 $88 / night

$581 - $1196 / week

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Responds fast!
avg. 2 hours 18 minutes

from $88 / night

(1) Excellent 

7

San Gimignano Vacation 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 th …see more

from $111 / night

$697 - $975 / week

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from $111 / 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 $233 / night

$1625 - $2554 / week

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from $233 / night

26

Vacation apartment accommodation

San Gimignano / Castel San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
Casa La Rondine is a nice apartment located midway between the beautiful cities of the towers of San Gimignano and the beautiful medieval town of Certaldo Alto. Casa La Rondine is situated on the first and second floor of a stone house completely renovated, part of a sm …see more

from $64 / night

$395 - $720 / week

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from $64 / night

(1) Very Good 

35

Villa accommodation in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 10 Min stay varies

  • 7 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Large country house, luxury and historic with a breathtaking and unique view on San Gimignano and its medieval towers. 'Podere Vedi Torre' was renovated in 2009, surrounded by cypresses and pines, olive trees and vineyards. In the House: central heating, washing machine …see more

from $250 / night

$1742 - $2786 / week

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from $250 / night

(1) Excellent 

20

Vacation 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 mi
  • 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 $216 / night

$1509 - $2380 / week

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from $216 / night

(13) Excellent 

Certificate of Excellence

42

Vacation apartment rental

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
"Garden house" ......a flowering oasis inside the medieval walls .. The owners Mario and Donella would like to offer you an unforgettable holiday in San Gimignano. The accommodation This unique and luxurious apartment is situated on the ground floor of a medieval buil …see more

Certificate of Excellence

from $128 / night

$813 / week

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Responds fast!
avg. 25 minutes

from $128 / night

(5) Very Good 

Certificate of Excellence

21

Vacation townhouse rental

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
Beautiful apartment situated in an ancient hamlet on the ground floor of a two-storied House with an enchanting view on the heart of the Tuscan Countryside, 3 km from the centre of San Gimignano, Worlwide Heritage Town of UNESCO. The apartment is composed of 1 double be …see more

Certificate of Excellence

from $146 / night

$848 - $1289 / week

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from $146 / night

7

Pancole Vacation farmhouse rental

San Gimignano / Pancole

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 hills of …see more

from $79 / night

$523 - $639 / week

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from $79 / night

(5) Very Good 

33

Vacation apartment with swimming pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $62 / night

$465 - $987 / week

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from $62 / night

21

Vacation apartment with shared pool in Pancole

San Gimignano / Pancole

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The apartment, part of a complex consisting of 10 apartments of various sizes, is made up of: living room / kitchen with double sofa bed, 1 double bedroom and 2 terraces. The apartment offers satellite TV, telephone, Internet WI-FI, air conditioning, heating, laundry se …see more

from $163 / night

$1138 / week

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from $163 / night

(18) 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 big bed …see more

from $72 / night

$418 - $516 / week

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from $72 / night

(2) Very Good 

20

Vacation apartment rental

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
On San Gimignano main square (Piazza Della Cisterna square), in the middle of the most fascinating medieval places in Tuscany, "Becci San Gimignano Palace Suite" is a unique property. Build around 1 of the main San Gimignano Towers, the property is conserving the charm …see more

from $271 / night

$1422 - $1768 / week

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from $271 / night

(3) Very Good 

7

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
Our apartment is located in the North of the country to 150 meters from the walls of the old town, in a very quiet area, where you can easily find place for the machine without having to pay. In about 5 minutes on foot you can reach the historic center. The apartment is …see more

from $70 / night

$488 / week

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Responds fast!
avg. 2 hours 53 minutes

from $70 / night

21

San Gimignano Vacation farmhouse rental

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 kitche …see more

from $111 / night

$755 - $906 / week

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from $111 / night