50 Best San Gimignano Villas on Holiday Lettings - Apartments

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Pancole
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19 properties
Ulignano
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Castel San Gimignano
17 properties
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8 properties

San Gimignano

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5,376 Vacation rentals

5

Vacation home in San Gimignano

Province of Siena / San Gimignano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Rustic apartment in the green of the countryside for lovers of green and nature. Located on the ground floor has been renovated with handmade pieces respecting the characteristics of the house. E 'consists of a large living room with fireplace, double bedroom, bathroom, …see more

from $94 / night

$487 - $749 / week

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from $94 / 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 $55 / night

$367 / week

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from $55 / 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 $124 / night

$868 / week

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from $124 / 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 $81 / night

$564 / week

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Responds fast!
avg. 2 hours 33 minutes

from $81 / night

(2) Very Good 

28

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 $149 / night

$868 - $1,363 / week

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Responds fast!
avg. 2 hours 52 minutes

from $149 / night

(6) Excellent 

44

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 $298 / night

$2,107 / week

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Responds fast!
avg. 1 hour 20 minutes

from $298 / night

(1) Very Good 

39

Vacation townhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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 $149 / night

$868 / week

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Responds fast!
avg. 2 hours 52 minutes

from $149 / night

(2) Very Good 

13

Vacation villa rental

Province of Siena / San Gimignano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The sources of Santa Lucia is a beautiful farmhouse situated amidst olive groves and vineyards just outside the hamlet of ' Santa Lucia '. Immersed in silence and in a unique panoramic position, from here you can admire the wonderful towers of San Gimignano and space wi …see more

from $186 / night

$1,239 - $3,655 / week

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from $186 / night

(5) 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 $70 / night

$487 - $1,435 / week

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Responds fast!
avg. 2 hours 17 minutes

from $70 / night

15

Vacation farmhouse with shared pool in Ulignano

San Gimignano / Ulignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • 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 $104 / night

$736 - $1,213 / week

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from $104 / night

(16) 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
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
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 & kitch …see more

from $100 / night

$700 - $1,330 / week

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from $100 / night

23

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Nice property comprising 3 apartments situated near San Gimignano, only 300 meters away from the main entrance gate to the lovely historical city center. All of the 3 apartments offer a personal, furnished outdoor area. The property owners (nice and friendly people) liv …see more

from $77 / night

$496 - $1,115 / week

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from $77 / 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 $155 / night

$979 - $1,462 / week

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from $155 / night

(22) Excellent 

Certificate of Excellence

26

Vacation cottage in San Gimignano

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Nearest beach 75 mi
  • Child friendly
  • Pet friendly
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in a typical country-style using rustic furniture and bright terracotta floors, the airy hom …see more

Certificate of Excellence

from $75 / night

$521 / week

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Responds fast!
avg. 36 minutes

from $75 / night

16

Vacation apartment rental

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful country house situated just a stone's throw away from San Gimignano, an attractive medieval town with a unique collection of towers and winding lanes set in the heart of the Tuscan countryside. This farmhouse enjoys spectacular views over a picturesque rural l …see more

from $186 / night

$1,301 - $2,169 / week

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from $186 / 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 $87 / night

$521 - $694 / week

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Responds fast!
avg. 1 hour 37 minutes

from $87 / night

(1) Excellent 

30

San Gimignano Vacation home rental

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
A charming and new rustic house, 50 minutes from Florence and 35' from Siena, with large garden and spectacular views of the typical landscape of the Sienese hills of Chianti with the background the ancient city of San Gimignano. Brand new residence in country style ty …see more

from $100 / night

$657 - $1,190 / week

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Responds fast!
avg. 2 hours 47 minutes

from $100 / night

(12) Excellent 

27

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's toponym “Strada” attests to these places' historical value. Carefully restored, surrounded by centuries-old cypresses a …see more

from $180 / night

$1,053 - $1,462 / week

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Responds fast!
avg. 3 hours 43 minutes

from $180 / night

(2) Very Good 

12

Vacation farmhouse rental

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • 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 farmh …see more

from $112 / night

$744 / week

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from $112 / night

(1) Very Good 

39

Farmhouse rental in Castel San Gimignano with shared pool

San Gimignano / Castel San Gimignano

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • 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 $248 / night

$4,708 - $9,230 / week

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from $248 / night

(6) Excellent 

28

Vacation farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • 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 $112 / night

$781 / week

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from $112 / night

21

Vacation 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
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in modern-style using and bright terracotta floors, the airy home contains 1 double bedroom. …see more

from $59 / night

$408 / week

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Responds fast!
avg. 36 minutes

from $59 / night

(35) 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 $124 / night

$620 - $930 / week

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Responds fast!
avg. 49 minutes

from $124 / night

(7) 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 $69 / night

$484 - $1,425 / week

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Responds fast!
avg. 2 hours 17 minutes

from $69 / night

18

Ulignano Vacation finca rental

San Gimignano / Ulignano

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Spacious holiday apartment of 70 m2. composed of a double bedroom, a twin bedroom, a kitchen and a living/dining room with table for 6 persons. Located on the ground floor of the farmhouse IL POGGETTO with separate entrance, is equipped with a spacious veranda with tab …see more

from $161 / night

$1,103 / week

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from $161 / night

13

Vacation b&b rental

Province of Siena / San Gimignano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ask about children
A 3 km dal centro di San Gimignano (5' in bus o auto, oppure una passeggiata panoramica di circa 30'), trovate un angolo accogliente dove potete rilassarvi all'ombra degli olivi, fare un barbecue, una passeggiata sulla via Francigena o partecipare a un laboratorio sul b …see more

from $106 / night

$738 / week

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from $106 / night

9

Vacation home in San Gimignano

Province of Siena / San Gimignano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The apartment is part of a house dating back to 1300. And 'furnished with antique pieces of craftsmanship. The floors and ceilings are original, like the fireplace, typical of country homes of times.  Atmosphere and intimacy characterize simple environments and not arti …see more

from $125 / night

$549 / week

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from $125 / night

29

Vacation apartment in San Gimignano

Province of Siena / San Gimignano

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 mi
  • Child friendly
  • Car not necessary
Entrance hall with small sitting area and antique well, staircase leading to first floor gallery with two large windows opening on to the side of the cathedral ; spacious living room with lounge area with traditional woodburning fireplace and armchairs, divided by an …see more

from $130 / night

$868 - $930 / week

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from $130 / night

(6) 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 $155 / night

$806 - $1,239 / week

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from $155 / night

26

Vacation apartment accommodation

San Gimignano / Castel San Gimignano

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • 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 $87 / night

$558 - $769 / week

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from $87 / 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

$524 - $749 / week

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from $82 / night

(5) Very Good 

33

Vacation 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 $66 / night

$496 / week

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Responds fast!
avg. 2 hours 47 minutes

from $66 / 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 $14 / night

$32 - $437 / week

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from $14 / 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 $186 / night

$1,239 - $2,850 / week

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Responds fast!
avg. 1 hour 6 minutes

from $186 / night

(19) Very Good 

Certificate of Excellence

17

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night 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

Certificate of Excellence

from $120 / night

$839 / week

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Responds fast!
avg. 3 hours 52 minutes

from $120 / night

(14) 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 $122 / night

$818 - $1,549 / week

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from $122 / night

(1) Excellent 

23

Vacation farmhouse with shared pool in San Gimignano

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
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's toponym “Strada” attests to these places' historical value. Carefully restored, surrounded by centuries-old cypresses a …see more

from $149 / night

$930 - $1,140 / week

Book View

Responds fast!
avg. 3 hours 43 minutes

from $149 / night

(50) 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 $126 / night

$875 - $1,260 / week

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from $126 / night

(48) 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 $230 / night

$1,200 - $1,900 / week

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Responds fast!
avg. 2 hours 8 minutes

from $230 / 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 $112 / night

$682 / week

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from $112 / night