Vacation Rentals & Villas in San Gimignano

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2,264 Houses

Holiday home Il Corbezzolo with Infinity pool

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$624

CASA ALADINA: STUDIO RIGHT IN THE CITY S.GIMIGNANO

San Gimignano apartment

  • 1 bathroom
  • sleeps 3

Price per night from

$88

Casa Bartoli at Borgo Mummialla-your Tuscan home !

San Gimignano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“A jewel in the heart of Tuscany.” Booking very easy helped by the owner. Apartment exceptionally comfortable with all the facilities we required. There was no problem moving in thanks to being met by Fabio when we arrived. A beautiful location with amazing views of Tuscany. An ideal spot for touring and visiting the many medieval towns in this area.

Price per night from

$187

Tuscan countryhouse apartment in San Gimignano

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$106

Apartment Borgo Antico

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“superbe apartment at a suberbe place” We stayed at the lovely old town of San Gimignano a year ago. Everything was perfect. We received a warm welcome by a nice old lady. The apartment is just next to the central square in the pedestrian area. In summer you can even enjoy opera, theatre and music performances from one window of the apartment. Inside everything worked fine including a free washing machine. Payment and organisation worked smoothly, strongly reommended!

Price per night from

$131

CHARME B&B * CAPANNA1826 * San Gimignano Tuscany

Ulignano b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 2

Price per night from

$137

Tuscany Villas La Casetta del Borgo San Gimignano

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Perfect base to see all that Tuscany has to offer” La Casetta del Borgo was the perfect location for my recent trip to Tuscany with my wife. The unit is located in a resort with plenty of amenities including two pools and a very nice tennis court with faux grass that can be used for a small fee. It is a 10 minute drive to Montaione where one can go for dinner or buy groceries to cook in the unit's kitchen. All the necessary utensils are available to do some home cooking and I enjoyed a number of home cooked dinners and a delicious breakfast every morning thanks to my lovely wife. The main resort building has a restaurant that serves breakfast, lunch and dinner, however I didn't try it out so I can't say anything about it. Paolo, the owner, was a pleasure to deal with. I was having trouble finding the location with my GPS so Paolo had me meet him at his home which is just off the highway from Florence and very easy to find. To ensure that I found it with no problem Paolo drove to the resort while I followed . Once at the resort he had the keys, a nice bottle of wine, and plenty of info about the local area ready for me. Since he knew that I had the flu he even had some flu medication for me in case I needed it! The weather was unseasonably cold when we arrived and the bedding wasn't sufficient, but Paolo came to the rescue and drove over in the rain with more blankets for us. You'll be hard pressed to find a better host at this type of vacation rental. The location was perfect for us as it was very quiet, yet was within easy driving distance of many towns and cities in Tuscany. Smaller towns like Montaione and San Gimignon were within a 10-20 minute drive and Florence, Pisa, Lucca and Sienna were all within an hours scenic drive. If driving into Florence remember that free parking can be found at the Piazzale Michelangelo which is located outside of the ZTL and is a short walk to the Ponte Vecchio, Uffizi and other old city sites. The views are also magnificent! I wouldn't hesitate to recommend this property!

Price per night from

$86

San Gimignano villa rental

San Gimignano house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$810

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

“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.

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

il pozzo

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$125

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

$1,496

Vallebuia

San Gimignano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$1,247

Nido del Merlo

Ulignano house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$524

Podere La Marronaia

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$100

Restored stone built villa near San Gimignano

San Gimignano villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$146

VILLA DEL GRILLO

Pancole cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$81

Ollie House, Room Antica

San Gimignano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$100

"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

Casa Gelsomino, ground floor, 2 bedrooms, private garden and shared pool

Castel San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$187

Podere La Proda - apartment La Corte

San Gimignano farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$162

Podere La Proda - apartment Il Gallo

San Gimignano farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$144

Bright and Spacious Apartment in the heart of town

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 51 minutes

Price per night from

$106

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. 2 hours 46 minutes

Price per night from

$179

VILLA ROSANNA

San Gimignano townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$147

Casa Verbena, 3 bedrooms apartment, first floor, terrace

Castel San Gimignano apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$187

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

Giovanna apartment 100 m from the walls of San Gimignano

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 42 minutes

Price per night from

$100

Le Fontanelle - rustic farm buildings with pool

San Gimignano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 11 minutes

Price per night from

$144

beautiful house in the heart of San Gimignano

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$187

Viewing 38 of 2,264
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
Tuscany at its best!

We stayed at the property Il Granaio for 1 week and added two days because we fell in love with it the moment we saw it. First of all, the booking was done very professionally right up to the point when we phoned from San Gimignano for directions and were guided right to the gate. The owners of the property Guiseppe and Rosina welcomed us warmly and showed us the cottage we had booked. We loved it the minute we set foot into it. The view over vineyards and olive groves to the towers of San Gimignano on the hill was breathtaking. The cottage itself was well appointed, clean and comfortable. The living room-kitchen was well appointed and had everything one would need. The bedroom was spacious and the bed very comfortable. The cottage was advertised for 2 to 4 people. I would say that it is perfect for a couple and maybe a couple with 1 child. I would find it to be too small for 4. The grounds were immaculately kept, the pool sparkled and the relaxed atmosphere made for a perfect Tuscan experience, especially because the towers of San Gimignano were always visible. The property is only minutes from the town of San Gimignano and a super market for grocery shopping. It is close enough to visit such Tuscan treasures like Siena, Pisa, Voltera, Greve di Chianti and more. I am mobility challenged so what made it even more special for me was the help of Guiseppe. Tthere were three steps to get into the cottage. Guiseppe, without having to ask, immediately brought boards and built a ramp which made it possible for me to enter the cottage with my scooter. This was far beyond the call of duty and very much appreciated. Rosina had offered a unit that had no steps but once I had seen the cottage I didn't want to give it up, so Guiseppe's ramp was a real gift. Because we loved our stay so much, we added 2 more days. While we had to vacate the cottage for the next guests, Rosina offered us the accessible unit, which we were able to enjoy for these last two days. It was a dream vacation and I can only recommend this lovely property to anybody who likes a peaceful, relaxed vacation near beautiful San Gimignano.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
Apartment Borgo Antico
Il Brogo antico - San Gimignano, it

Perfect appatrment in the heart of San Gimignano - just near to the cathedral. The owner - Mrs Giuliana Taddei is very, very cordial and helpfull woman. All was perfect! Thank you, Giuliana!" … see more
Tuscany Villas La Casetta del Borgo San Gimignano
Wonderful Tuscany villa - and hosts!!

We had a wonderful stay at Resort Borgo la Fornace in the apartment owned by Paolo and Tania in October, 2013. Paolo and Tania were very helpful, first meeting us at an intersection in a nearby town (after we got a bit lost), then guiding us to the resort. The resort is a lovely Italian designed villa setting, with a few pools and nice grounds. Our stay was after the season for the resort, and the on-site restaurant was closed. Paolo and Tania's apartment is very nicely furnished and decorated - very new and modern - and they make sure the unit is clean and completely stocked with all basic needs - dishes, pots & pans, paper products, linens etc. Wifi is somewhat limited - usually only available in the garden area, but not a real problem. From this location, a car is a must. We shopped for food in Montaione and Il Castagno (a short drive) and over a few days visited the beautiful hilltop towns of San Gimignano, Voltera, and Siena. Had a great winery tour and lunch at Sovestro in Poggio Winery near San Gimignano, and to celebrate a very special day, enjoyed a wonderful Italian dinner at Casa Masi near Montaione. The restaurant even helped make arrangements for a taxi to take us both ways, all making for a very special evening - again, a recommendation from Paolo and Tania. The apartment is centrally located in the beautiful Tuscany region, and made for a great spot for day trips and a restful place to come back to. We highly recommend this location and the excellent hosts, Paolo and Tania.see more
Casa Bartoli at Borgo Mummialla-your Tuscan home !
Fantastic!

This place surpassed all of our expectations. It was a little slice of heaven. The surroundings are beautiful, and the accomodations checked all of our boxes. By day we visited the surrounding towns and wineries and at night we dined at nearby restaurants. The kitchen was so well equipped we even cooked dinner twice! It was a true Tuscan experience and we can't wait to return.see more

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