50 Best San Gimignano Villas on Holiday Lettings - Apartments

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Pancole
53 properties
Ulignano
19 properties
Larniano
18 properties
Castel San Gimignano
17 properties
Casaglia
8 properties

San Gimignano

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5,829 Vacation rentals

(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 $185 / night

$1,228 - $2,825 / week

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avg. 1 hour 12 minutes

from $185 / 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 $86 / night

$553 - $762 / week

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from $86 / night

(14) Excellent 

Certificate of Excellence

25

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 $121 / night

$811 - $1,413 / week

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avg. 2 hours 35 minutes

from $121 / 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

$479 - $1,413 / week

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avg. 2 hours 33 minutes

from $69 / 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 $80 / night

$516 - $944 / week

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from $80 / 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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avg. 2 hours 39 minutes

from $230 / 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 $128 / night

$888 - $1,278 / week

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from $128 / 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 $74 / night

$516 / week

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avg. 35 minutes

from $74 / night

(25) 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 $123 / night

$676 - $921 / week

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Responds fast!
avg. 1 hour 10 minutes

from $123 / 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 $69 / night

$479 - $1,413 / week

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avg. 2 hours 33 minutes

from $69 / night

19

Apartment rental in San Gimignano with shared pool

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
Soarzio apartment, located within the medieval home of Fulignano, ancient fortification dating back to the tenth century, in the heart of the green Tuscan hills, overlooks a breathtaking view of one of the most famous villages of Tuscany: San Gimignano and its famous to …see more

from $123 / night

$983 - $1,437 / week

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from $123 / 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 $178 / night

$1,044 - $1,450 / week

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avg. 2 hours 8 minutes

from $178 / 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 $111 / night

$676 / week

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from $111 / night

(2) Excellent 

25

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The apartment is located in the historic center of San Gimignano and is derived from the recent restructuring of a medieval building. The facility is equipped with all comforts such as air conditioning, heating, outdoor spaces and wi-fi, that will make your stay unforge …see more

from $124 / night

$865 - $988 / week

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from $124 / 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 $148 / night

$860 - $1,351 / week

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avg. 3 hours 48 minutes

from $148 / night

(1) Very Good 

16

Vacation villa with swimming pool, golf nearby in Larniano

San Gimignano / Larniano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful Villa in the middle of a nature reserve near San Gimignano. Includes 6 bedrooms, 3 bathrooms, a large party room, a kitchen, a dining room for about 280 square meters, a large terrace and a garden with olive grove for about 2000 square meters. The garden …see more

from $439 / night

$3,071 / week

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from $439 / 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 $119 / night

$833 / week

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Responds fast!
avg. 2 hours 46 minutes

from $119 / 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 $297 / night

$2,853 / week

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Responds fast!
avg. 1 hour 30 minutes

from $297 / night

15

Vacation villa with shared pool in San Gimignano

Province of Siena / San Gimignano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
Located between the beautiful vineyards and olive groves in the rolling hills of Chianti dominates "Podere il Pino". This privileged location offers a spectacular view over the charming medieval town of San Gimignano and the entire Elsa Valley. The farmhouse is situated …see more

from $185 / night

$1,290 - $1,849 / week

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from $185 / 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 $99 / night

$676 - $1,290 / week

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avg. 2 hours 35 minutes

from $99 / 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 $246 / night

$4,667 - $9,150 / week

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from $246 / 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 $154 / night

$971 - $1,450 / week

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from $154 / night

(16) Very Good 

16

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 $111 / night

$770 - $1,330 / week

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from $111 / night

(1) Excellent 

24

Vacation farmhouse rental

San Gimignano / Larniano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Nice complex situated in quiet and panoramic location on a farming estate 8 km from San Gimignano away. This property, surrounded by olive groves and vineyards, comprises a small, independent barn and 2 units set on the first floor of the owners' house. The property ow …see more

from $113 / night

$793 - $1,382 / week

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from $113 / 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 $148 / night

$921 - $1,130 / week

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Responds fast!
avg. 2 hours 8 minutes

from $148 / night

(1) Excellent 

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 $221 / night

$1,474 - $2,825 / week

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from $221 / night

(1) Very Good 

57

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 80 mi
  • Swimming pool
  • Child friendly
Thefarmhouse, located in the hillside dominating the tennis court, is an unusual building: originally it was a lookout tower for Castelvecchio, subsequently transformed into a furnace. The house has two independent entrances: the main entrance opens on to a paved court …see more

from $203 / night

$1,351 - $2,702 / week

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from $203 / night

(1) Excellent 

21

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
Beautiful newly renovated .On 2 levels with 1 double, 1 double room with twin beds (can also join us to get a double bed), sofa bed, 2 bathrooms, fitted kitchen, TV, free wi-fi, iron iron, kettle, toaster, outdoor space for dining, swimming pool 14 meters X 7 meters wit …see more

from $135 / night

$946 / week

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Responds fast!
avg. 2 hours 21 minutes

from $135 / night

(16) Very Good 

32

Vacation farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • 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 $142 / night

$989 / week

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Responds fast!
avg. 3 hours 44 minutes

from $142 / night

15

Vacation apartment in San Gimignano

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • 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 $117 / night

$817 / week

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from $117 / 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 $123 / night

$676 - $921 / week

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Responds fast!
avg. 1 hour 10 minutes

from $123 / night

(8) 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 $123 / night

$676 - $921 / week

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Responds fast!
avg. 1 hour 10 minutes

from $123 / night

(1)  

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 $80 / night

$492 - $921 / week

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from $80 / 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 $185 / night

$1,290 - $2,150 / week

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from $185 / night

17

Vacation apartment in San Gimignano

Province of Siena / San Gimignano

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Child friendly
Beautiful apartment, centrally located, 100 meters from the cathedral, with bars, restaurants and shops within 100 meters. It can accommodate up to 6 people. The apartment is 120 square meters, on three levels, in an ancient building, is composed of a room, a room with …see more

from $185 / night

$1,290 / week

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from $185 / night

(19) Excellent 

19

Apartment rental in San Gimignano

Province of Siena / San Gimignano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 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 $77 / night

$443 - $547 / week

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from $77 / 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 $185 / night

$1,228 - $3,623 / week

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from $185 / night

20

Ulignano Vacation villa rental

San Gimignano / Ulignano

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Suitable for children age 5+
Old barn located across the street from Poggibonsi to San Gimignano. The property is part of a typical Tuscan Hamlet of houses, but is completely independent of the complex and has a lovely view over the countryside and the towers of San Gimignano. Great care has been u …see more

from $521 / night

$3,643 / week

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from $521 / 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

$31 - $430 / week

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from $14 / night

(2) Excellent 

18

San Gimignano Vacation farmhouse rental

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $83 / night

$1,020 / week

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from $83 / night