50 Best San Gimignano Villas on Holiday Lettings - Apartments

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Larniano
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27 properties
Castel San Gimignano
27 properties
Ulignano
19 properties
Casaglia
9 properties

San Gimignano

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443 Vacation rentals

(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 San …see more

from $47 / night

$326 - $1111 / week

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from $47 / 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

(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 $79 / night

$594 - $1060 / week

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from $79 / 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 $141 / night

$864 - $1290 / week

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from $141 / 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 $167 / night

$1114 - $2560 / week

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from $167 / night

(7) 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 $146 / night

$919 - $1178 / week

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from $146 / 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 Gimignan …see more

from $45 / night

$315 - $1077 / week

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from $45 / 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 $135 / night

$730 - $954 / week

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from $135 / 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 $135 / night

$730 - $954 / week

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from $135 / 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 $101 / night

$685 - $774 / week

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from $101 / night

10

Vacation condo in San Gimignano

Province of Siena / San Gimignano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 80 mi
  • Car not necessary
  • Air conditioning
Characteristic apartment in historical building of 1300, located on main street just 100 metres from Piazza Duomo. Surrounded by shops and restaurants to taste the life of our very special town., convenient for visits to the major art cities of Tuscany and the Chianti a …see more

from $90 / night

$629 / week

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from $90 / night

(1) Very Good 

23

Vacation apartment with shared pool in Ulignano

San Gimignano / Ulignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
The ONE is the premium apartment of our Montegonfoli Farmhouse. What makes this apartment special and all the property is its position, on the highest hill of the surroundings, that provides wonderful views at 360°, including San Gimignano towers and Tuscany hills. The …see more

from $135 / night

$786 - $1234 / week

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from $135 / night

(2) Excellent 

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 $68 / night

$471 / week

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from $68 / 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 $247 / night

$1571 - $2468 / week

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from $247 / night

(15) Very Good 

17

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 and sp …see more

from $106 / night

$741 / week

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from $106 / 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 $209 / night

$1459 - $2300 / week

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from $209 / night

(4) Excellent 

19

Vacation apartment in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
Apartment Viola, in the historical centre of the beautiful San Gimignano, located on the top floor of a historical building and enjoys this spectacular views over the towers. The apartment, recently renovated, has maintained the typical Tuscan style, with wooden ceiling …see more

from $79 / night

$472 - $629 / week

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from $79 / night

(14) Excellent 

17

Vacation apartment in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 65 mi
  • 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 finely furn …see more

from $116 / night

$808 / week

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from $116 / 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 $107 / night

$730 - $875 / week

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from $107 / night

(2) Excellent 

20

Ulignano Vacation apartment rental

San Gimignano / Ulignano

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
The apartment is located at the first floor of a residential complex, and it feature a large double bedroom with view, modern bathroom with shower, an open-plane with living-dining room and separate kitchen. An additional mezzanine open onto the kitchen and dining room …see more

from $90 / night

$624 / week

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from $90 / night

(4) Very Good 

8

Condo rental in San Gimignano

Province of Siena / San Gimignano

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 80 mi
  • Car not necessary
Apartment in Historical Palace Notified overlooking Via San Matteo the main road linking Porta San Matteo Piazza Duomo. The apartment consists of two double rooms, each of which has a bathroom with sink, bidet, toilet and shower, and a small kitchen / dining room with a …see more

from $146 / night

$1021 / week

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from $146 / 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 $273 / night

$1907 / week

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from $273 / night

(10) 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 $124 / night

$786 - $1021 / week

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from $124 / 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 Tuscany Holiday 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 $82 / night

$561 - $1021 / week

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from $82 / 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 $79 / night

$550 - $1290 / week

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from $79 / 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, tastefully r …see more

from $117 / night

$813 - $1170 / week

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from $117 / night

(1) Very Good 

39

Vacation townhouse with shared pool in San Gimignano

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
The Montegonfoli Farmhouse is placed on top of an hill with an amazing view on San Giminano and on Tuscany hills. The farmouse is made of some ancient buildings of the Seventeen century, and it's featured by about 1000 olive trees, has 2.6 of vineyard (Vernaccia di San …see more

from $135 / night

$786 - $982 / week

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from $135 / 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 $135 / night

$730 - $954 / week

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from $135 / 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 $225 / night

$1571 - $2356 / week

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from $225 / 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 $107 / night

$674 - $943 / week

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from $107 / 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 $68 / night

$449 - $909 / week

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from $68 / night

10

Vacation finca with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
Housed in a 17th century farmhouse, immersed in the Tuscan countryside, Agriturismo Natura E Salute is a family-run establishment that offers an outdoor swimming pool, a relaxing garden, a traditional restaurant and rustic-style rooms. The rooms include TV, wood-beamed …see more

from $101 / night

$617 / week

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from $101 / night

19

Vacation farmhouse with shared pool in Ulignano

San Gimignano / Ulignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Nice farming villa in Tuscany, Italy, comprising 2 small independent stone farmhouses, which were skilfully restored and turned into 3 nice apartments, all of which offering comfortably interiors decorated in a rustic style. This villa in Tuscany, Italy, if quietly situ …see more

from $82 / night

$573 - $932 / week

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from $82 / 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 $414 / night

$2895 - $4476 / week

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from $414 / night

24

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about pets
  • Private garden
Nice accommodations created from the restoration of an ancient tower (48 meters tall) dating back to the year 1200 and built b the Salvucci family. In the town of San Gimignano there are 14 towers and this tower is the only one where you can live in. The 2 units "Tower …see more

from $241 / night

$1480 - $2589 / week

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from $241 / 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 big bed …see more

from $70 / night

$404 - $499 / week

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from $70 / 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 $79 / night

$505 - $841 / week

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from $79 / night

12

Vacation farmhouse rental

San Gimignano / Ulignano

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 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 $168 / night

$1170 - $1381 / week

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from $168 / night

(3) Very Good 

16

Vacation farmhouse rental

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 $76 / night

$499 - $1177 / week

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from $76 / night

(1) Good 

13

Vacation farmhouse in San Gimignano

Province of Siena / San Gimignano

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The House is in a dominant position compared to the surrounding countryside, you can enjoy a beautiful panorama. Rests well because immersed in silence. Guests have access to the entire first floor of the House, which has an area of 350 square meters, and the garden. Th …see more

from $107 / night

$730 - $1319 / week

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from $107 / night

1