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Vacation Rentals & Villas in San Gimignano

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2,776 Houses

Holiday home Il Corbezzolo with Infinity pool

San Gimignano house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$550

CASA ALADINA: STUDIO RIGHT IN THE CITY S.GIMIGNANO

San Gimignano apartment

/ 1 bathroom / sleeps 3

Price per night from

$77

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

$165

Tuscan countryhouse apartment in San Gimignano

San Gimignano apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 51 minutes

Price per night from

$94

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!

Responds fast! avg. 8 minutes

Price per night from

$89

CHARME B&B * CAPANNA1826 * San Gimignano Tuscany

Ulignano b&b

3 bedrooms / 3 bathrooms / sleeps 2

Price per night from

$121

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

$76

Vernaccia

San Gimignano villa

8 bedrooms / 7 bathrooms / sleeps 16

Price per night from

$1,521

San Gimignano 6 bedroom villa with pool

San Gimignano house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$522

Tychehouse Holidays House in Tuscany San Gimignano

San Gimignano house

1 bedroom / 1 bathroom / sleeps 5

“Excellent apartment” Thank you for everything. We had a wonderful holiday in a quiet and nice. Excellent apartment

Price per night from

$78

Barn Cafaggiola

San Gimignano house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$236

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

$54

la Torretta Apartment

San Gimignano apartment

2 bedrooms / 2 bathrooms / sleeps 5

“great stay!” We stayed in La Torretta in October of 2013 for 5 nights! It is a wonderful apartment and a great location! The owners were always close by if we had a question or needed help. We can't wait to go back!

Responds fast! avg. 8 minutes

Price per night from

$89

Beautiful Hilltop 2-Story Farmhouse Apartment

San Gimignano apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$76

Hilltop Escape for Families & Double-Date Couples

San Gimignano apartment

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$79

One Bedroom Ground Floor Apartment San Gimignano

San Gimignano house

1 bedroom / 1 bathroom / sleeps 2

“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!

Price per night from

$43

Old Barn House

San Gimignano house

2 bedrooms / 3 bathrooms / sleeps 4

“Beautiful secluded villa in a quiet and peacefull location” This was our second visit to this villa it met all our requirments and expectations it stands in its own grounds with nice gardens and a well maintained swimming pool,the rooms are clean and comfortable and furnished to a high standard you will be looked after well by the owners who are nice friendly people we would definitly recomend it to our friends and anyone looking for a relaxing holiday.

Price per night from

$169

il pozzo

San Gimignano apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$110

Badia

San Gimignano house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$221

larks G

San Gimignano house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$87

Villa Podere la Tesa

San Gimignano house

4 bedrooms / 4 bathrooms / sleeps 8

“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.

Price per night from

$251

Villa Campiglia

Castel San Gimignano villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$194

Tolly 5

San Gimignano house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$151

The big terrace in a comfortable spacious apartment ideal for two persons

San Gimignano apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$149

Villa Arnilù

San Gimignano villa

7 bedrooms / 7 bathrooms / sleeps 14

Price per night from

$860

Vallebuia

San Gimignano villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,100

Nido del Merlo

Ulignano house

6 bedrooms / 4 bathrooms / sleeps 15

Price per night from

$415

Tolly 7

San Gimignano house

4 bedrooms / 4 bathrooms / sleeps 7

Price per night from

$201

Tolly 4

San Gimignano house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$90

Podere La Marronaia

San Gimignano apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$88

Restored stone built villa near San Gimignano

San Gimignano villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 10 minutes

Price per night from

$123

VILLA DEL GRILLO

Pancole cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$55

Ollie House, Room Antica

San Gimignano b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$88

Monache 4 Farmhouse holiday rental with private pool ,gardens near San Gimignano

San Gimignano farmhouse

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$105

"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

$89

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

Castel San Gimignano apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 59 minutes

Price per night from

$110

Podere La Proda - apartment La Corte

San Gimignano farmhouse

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$143

Podere La Proda - apartment Il Gallo

San Gimignano farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$127

Viewing 38 of 2,776
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

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
la Torretta Apartment
La Torretta, San Gimignano, it

Last year we were in appartment "Il Borgo antico" and spent wonderfull days in San Gimignano. That's why we turned back to the pearl of Tuscany - San Gimignano. Now we stayed in appartment "La Torretta" which is in the same building on the 3rd floor. The house is in the center of San Gimignano just to the cathedral. Pizzerias, gelatteria (ice creams), restaurants, museums - all is near by. The appartment is very clean, convenient, the kitchen is well equipped. It has 2 bedrooms and is ideal for a family with children or for 2 couples. It is offered also garrage near Parking P3 (the nearest point to the house). Short-time access with car is allowed for unloading/loading of baggage. San Gimignano is an ideal starting point for trips in Tuscany - not only for Siena and Florence, but also for a number of small picturesque towns - Monteriggioni, Volterra, Chianti valley, Montalcino, Pienza, Montepulciano etc. The owner - Mrs Giulianna Taddei is very very nice and helpfull! She met us near the garrage and showed us the way to the house, told us about the sightseeings and the events in San Gimignano, said us goodbye with nice presents and wine from San Gimignano. Thank you again, Giulianna! We'll be back again!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
Beautiful Hilltop 2-Story Farmhouse Apartment
Excellent Trip

Well what a trip. Something I will cherish forever. The owner was extremely helpful and location was perfect. The home had an old school charm and was nice and clean. Everything was as promised and our honeymoon was definitely something to remember. The Charm of Tuscany was definitely evident and we made many short trips to all the attractions (Florence, Pisa, Siena, San Gimignano ) I would definitely stay again without hesitation. Thanks for the wonderful memories.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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