Vacation Rentals & Villas in San Gimignano

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1,808 Houses

CASA ALADINA: STUDIO RIGHT IN THE CITY S.GIMIGNANO

San Gimignano apartment

  • 1 bathroom
  • sleeps 3

Price per night from

$87

Barn Cafaggiola

San Gimignano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$301

Il Granaio 1 Bedroom Tuscan Farmhouse

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Peace and Tranquility in Tuscany” It was very easy to book online direct with the company in Italy. We were welcomed by the very friendly owners who were always available to offer help and assistance. Our apartment was clean and well equipped and overlooked the town of San Gimignano. The weather was unseasonally hot for October and we glad of the large pool.For touring around Tuscany you are perfectly placed with Florence, Pisa and Sienna less than an hour away. I have already recommended La Bella Tocana to my friends who are looking for a quiet holiday with the bustle of city life on the doorstep.

Price per night from

$63

One Bedroom Ground Floor Apartment San Gimignano

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“An idyllic escape” In the quaint, immaculate grounds of Le Volte, we had the most restful holiday of our lives. At Le Volte The Tuscan spirit of simplicity and comfort made this holiday an unforgettable experience, we are recommending the place to our friends and family, and we'll be back!!

Price per night from

$51

Badia

San Gimignano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$486

Villa Podere la Tesa

San Gimignano house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Great choice of location” We have visited Tuscany on many occasions and decided to introduce it to some of our friends. Eventually we chose Villa Il Podere and were thoroughly pleased. On arrival the villa was even more beautiful than we imagined. The location was perfect, we wanted to be in the countryside but close enough to the town of San Gimignano to be able to walk to it. This villa fitted the bill perfectly. The owners were wonderful, the grounds immaculate and the swimming pool in a lovely position. For friends travelling together it was perfect, being in two 'halves' as it were and a bathroom to every bedroom there was enough privacy, yet a there was plently of room for us all to get together. There were plenty of shady spots in the garden for just reading a book quietly for a bit of 'my time' if you wanted it. The interiors of the villa were very comfortable. What we most enjoyed was being able to wander into town on foot although some of us cheated a bit and went half way on the shuttle bus which ran nearby the property and took the effort out of the last uphill bit! Last but not least it's a good base from which to explore. Centrally placed in Tuscany so not too much long driving needed for sight seeing, We went to the nearby town by car and caught the bus to Florence and Siena so as to avoid parking difficulties and traffic. Definately a good idea. All in all its actually a place we would return to.

Price per night from

$283

Villa Arnilù

San Gimignano villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 20

Price per night from

$1,570

Vallebuia

San Gimignano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$1,244

Nido del Merlo

Ulignano house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$523

VILLA DEL GRILLO

Pancole cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$81

"La Rocca Romantica" apartment for two guest in the heart of San Gimignano!

San Gimignano apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Price per night from

$100

Bright and Spacious Apartment in the heart of town

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$125

Charming rooms with amazing view and breakfast.

San Gimignano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$162

Classic room with bathroom near San Gimignano

San Gimignano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$177

Tuscan-style apartment in spectacular surroundings, shared outdoor pool, sleeps up to 6

San Gimignano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 0 minutes

Price per night from

$178

Contessa Apt San Gimignano

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$131

Uliveta house,cosy Tuscan villa for friends or family

San Gimignano apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$374

Garden House

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$187

Deluxe vacation rental in Tuscany in San Gimignano

Castel San Gimignano farmhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Price per night from

$374

Le Fontanelle - rustic farm buildings with shared pool

San Gimignano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 23 minutes

Price per night from

$143

beautiful house in the heart of San Gimignano

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$187

' FIVE ', Farmhouse Apartment in San Gimignano

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$156

CHARMING FRESH APARTMENT with STUNNING VIEW of SAN GIMIGNANO, Olivo & Acacia 4p

San Gimignano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$175

CIPRESSO, CHARMING FRESH APARTMENT with STUNNING VIEW OF SAN GIMIGNANO, 2p

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$119

TULIP in San Gimignano Pool

Ulignano finca

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$199

Fantastic holiday accomodation on large Tuscan estate for party or family

Castel San Gimignano apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 22

Price per night from

$1,146

Apartment inside medioval wall with garden, at the ground floor

San Gimignano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$237

Casa maria guest house San Gimignano

San Gimignano house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Price per night from

$86

Melograno San Gimignano Apartment Pool

San Gimignano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$150

Lovely countryside Podere San Luigi Apt Alba

Pancole farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$127

ILVECCHIOCIPRESSO

San Gimignano apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 3

Price per night from

$100

Camera Matrimoniale "Cinguettio"

San Gimignano private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$100

Romantic cottage Glicine

Castel San Gimignano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$137

"MARGHERITA", DOUBLE WITH TERRACE IN SAN GIMIGNANO

San Gimignano farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$87

PODERE MAGIONE, CHARMING FRESH FARM HOUSE with STUNNING VIEW of SAN GIMIGNANO 6p

San Gimignano farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$262

Sassi Bianchi Acacia beautiful ancient restored tower

Castel San Gimignano farmhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Price per night from

$374

Beautiful setting for the perfect Tuscan vacation

Castel San Gimignano farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$374

Spacious tuscan Family apartment at Il Rosolaccio

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$214

Viewing 38 of 1,808
rentals in San Gimignano

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About San Gimignano

Tuscany is home to many beautiful old towns and the historical town of San Gimignano is no exception. With its medieval architecture, vast vineyards, and hospitable locals, San Gimignano is an excellent introduction to the amazing country of Italy. Porto San Giovanni is considered to be the main street in town, but there are plenty of more hidden side streets that have unique restaurants and shopping options, so be sure to explore the entire downtown.

As you stroll, check out some of these top destinations:

  • Piazza del Duomo: This main square in the town is surrounded by towers which are over 1,000 years old.
  • Torre Grossa: At over 200 feet tall, this is the tallest tower in the city.
  • Rocca: This rock offers an amazing panorama of the Tuscan countryside from the top.
  • The Collegiata: The main cathedral in the city, this beautiful attraction has a series of frescoes on Old and New Testament subjects.
  • Piazza della Cisterna: This beautiful piazza is home to a market every Thursday.
  • San Gimignano 1300: Located right in the middle of the town, this museum features a large reconstruction of San Gimignano.

Despite being somewhat small, San Gimignano has an impressive number of events and festivals held year-round. Some of them include the San Gimignano Musica, a series of classical music concerts held in September and October; the Archaeological Summer Camp, excavations at Castelvecchio held every August; and the Medieval Harvest Festival, a series of events every March that include a blessing of the knights, historical parade, and medieval games.

A vacation rental is the preferred option for those staying in San Gimignano. With homes ranging from villas overlooking the beautiful architecture and vineyards in the area, to spacious and luxurious condos in the heart of town, there's sure to be a property available that's right for you.

Top Destination reviews

Villa Podere la Tesa
Wonderful Villa - Highly Recommended

An extremely well maintained villa (originally a Tuscan farm house - now separated into two: 2 bedroomed units each with own kitchen/dining and living areas) set in large private grounds, comprising olive groves and manicured lawns with a swimming pool and views of the surrounding Tuscan countryside. Extremely clean and fully equiped. San Gimignano was very conveniently located - a short walk away. The owners were truly delightful, genuine, friendly hosts and always available with local recommendations and advice. Would highly recommend this villa.see more
Il Granaio 1 Bedroom Tuscan Farmhouse
Heaven in Tuscany

Our stay at the cottage of Il Granaio was like a slice of heaven. Wonderful location in the most beautiful setting. The owner Rosina is the most delightful lady, we loved her instantly. The property is clean, well appointed and the owners are only too pleased to meet any requirement you may have. Thank you for this gorgeous happening in our life.see more
One Bedroom Ground Floor Apartment San Gimignano
When you really need to disconnect with the rest of the world...

A friendly and warm welcome from geniun tuscan people. The room was nice and clean and had all comfort, simple but that's all you need up there. The garden was well kept and the swimming pool clean. The longchairs could have been more comfortable and the umbrellas more stable and bigger as they fell over when there was to much wind. The location of "Le Volte" is perfect with a wonderfull view of San Gimignano as well during the day as at night. It is peacefull and you feel "at home". San Gimignano is amazing and lies not to far away from big cities like Sienna, Pizza and Firenze if you want to visit them. You have a supermarket just outside the city walls where you can buy almost everything. We fell in love with Tuscany and in particular with San Gimignano where you should go to "le vecchia mura" to have a wonderfull diner with a view to die for. Don't forget to make a reservation because it's very busy. "Le Volte" is a good "price-quality" vacation. Thank you!see more

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