Think a quaint medieval town with towering buildings dominating its skyline, almost like a setting from a storybook come alive – that’s what San Gimignano is like. Dotted with ancient towers is this lovely little Italian hill town in the Siena province of Tuscany. It is a walled village, most famous for its 14 impressive medieval towers that are now UNESCO World Heritage Sites. Just about 40 km (25 miles) from both Florence and Siena, the town looks like an ancient renaissance painting paused in time. Hordes of enthusiastic travellers come to the city to experience its old-world charm and leave feeling wholly satisfied. Here are some the best Vrbo vacation rentals that capture the very beauty of San Gimignano, Italy and will enhance your Italian getaway, so get booking.
Tip from tour guide
Here's some useful information about San Gimignano that you should know before you book your stay in the town. The medieval town is full of art and beauty. You can purchase a San Gimignano pass with all the attractions included online before your stay or on the spot after you reach. Some must-visit attractions include the main church or Duomo with incredible frescoes and the Renaissance Chapel of Santa Fina; Palazzo Civico with Dante's hall, the chamber of Podestà, and the collection of paintings, including the ones by Filippino Lippi, Pinturicchio, Benozzo Gozzoli, and local painters; the highest tower in town, Torre Grossa, which offers an amazing view; and the church of San Lorenzo in Ponte with the very suggestive frescoes depicting hell. Other places included in the ticket are the Archeological Museum, the Apothecary of Santa Fina, and the Gallery of Modern and Contemporary Art.
In this town, you can also purchase leather goods, ceramic, lavender, saffron, olive oil, wine such as Vernaccia di San Gimignano, cheese, ham, pasta, sweets, and local sauces. Don't forget to try the delicious ice cream at Gelateria Dondoli. Overall, the town is a perfect place to spend all day and enjoy the slow life of Tuscany. I suggest visiting San Gimignano during the week to avoid crowds.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.
1. Romantic accommodation ideal for couples (from USD 110)
Pick this quintessential Italian apartment and add a dash of romance to your getaway. You’ll be treated with a complimentary bottle of Tuscan wine upon arrival and a tour of the property by the hosts. Sitting on the ground floor of the building, you’ll not only be able to enjoy a private garden but also befriend a turtle who calls the garden his home and the beautiful flowers that grow there. Inside, the apartment has been beautifully done up, ensuring that it makes for a great space for retreat after a long day of activities. Ideally meant for two, but the place can also accommodate a third young one. It is about 100 meters (330 feet) from the city’s historic districts such as Piazza della Cisterna and Piazza Duomo. Several art galleries, shops, museums, and markets are also within walking distance.
Top guest reviews
Amenities & Room:
The bed is super comfortableThe bed is very comfortableThe bed was quite comfortable and the bathroom was modern with a good sized showerThe apartment is very conveniently located inside the wall Mario helped get our car to our parking space outside the wallYou also are given a free parking space just outside the wallsCleanliness:
Mario and his daughter were very easy to work withWe had the most incredible stay here in San Gimignano Cristina and Mario were fantastic hosts and the apartment was everything we hoped for(it was rainy most of the week) and loved itThe apartment and yard were beyond beautifulHost:
She also gave great restaurant recommendationsWarm welcome and very helpfulMario communicated with us with all the needed information ahead of time and arranged for us to check in earlyso We encourage you to consider doing the same because Cristina and her husband Marco are delightful and we thoroughly enjoyed a great meal conversation and wineWe could not have been more pleased with our choiceRead more reviewsLocation:
It is only a 2 minute walk to the center squareIt is in a great locationOld stone archways a quaint garden and a bedrock wine cellar add to the enchantment of your stayIt's a lovely clean safe city to stay atThe Garden House in San Gimignano is a truly special place in a beautiful city hosted by the loveliest family
2. Apartment with panoramic views (from USD 127)
Large outdoor seating, stunning views of the city’s skyline, a sprawling garden, a swimming pool, and lovely weather – all these make for a fabulous accommodation. This apartment for two, it is located about 300 meters (985 feet) from the city’s main centre and offers gorgeous 360-degree views of the Italian landscape. It has been recently redecorated with top-of-the-line facilities. All the rooms are air-conditioned as well. Although one bedroom can accommodate only two, if you require another bedding for an extra guest, the hosts can arrange for that as well. However, additional charges are levied. The hosts also live on site and are really friendly and accommodating. If you’re a dog lover, you’ll find their two German shepherds (who also live on the property) an absolute delight!
Top guest reviews
Amenities & Room:
The accommodation and facilities were excellent only surpassed by the friendliness of the ownersHost:
Great position great views and great propertyThe location allows you to thoroughly relax and enjoy the stunning views as well as having the option to simply walk into San GimignanoWe had a fantastic two weeksRead more reviewsLocation:
God combination between closed to San Gimignano and slence of a village 300m far from the SG gateWonderful apartment in a fantastic setting Great access to the town of San Giminano Car parking but can walk into San Gimignano
3. Centrally located property for large groups (from USD 141)
Is it likely that you’ll be travelling with a slightly large group? Don’t worry, we’ve got you covered. Here’s one Vrbo vacation rental that can easily sleep up to six across its three bedrooms on a twin-sharing basis. Think a couple more people will join? Request the host for extra bedding and you can accommodate two more guests in the living room at an additional charge. There’s not much traffic in the neighbourhood so you can expect plenty of peace while you rest. Else, it is just about 100 meters (330 feet) from several utility stores, souvenir shops, bars, and restaurants. Zero down on this great option and have a gala time with the group!
Top guest reviews
Amenities & Room:
The apartment had lots of room tons of HOT waterThe town itself was gorgeous and the apartment was very largeFour friends (two couples) shared the apartment for a week With 3 bedrooms and 2 bathrooms there was plenty of spacea nice stocked kitchen and the outside patio was a wonderful plus Would highly recommend it if you would enjoy staying in an apartment that is hundreds of years old with history and charmWe cooked together in the kitchen ate lunch on the terrace and dinner in the dining room and explored Tuscany from this very central positionHost:
comfortable and beautiful Claudia was patient very helpful and easy to work with My husbandWe were warm and dryHowever the property is definitely starting to show its age and could use a slight refurbishingthe welcome from our host was charming and our stay was perfectOur only "American hardship" was that the american coffee pot did not work and another was not availableRead more reviewsLocation:
We had restaurants and Pizzerias plus the market Bakery and wine shop at our fingertipsI was mesmerized by the location in the walled city - could not have been more perfect
4. Park-view property, great for a twosome (from USD 77)
A super choice for couples, this Vrbo vacation rental captures the essence of San Gimignano in its atmosphere, furnishings, and decor. It has been recently renovated and is equipped with all the modern fittings and amenities that you’d require for a comfortable stay. Peek out the windows and you’ll see camera-toting tourists and relaxed sojourners soaking in the Italian sun at the Rocca Park right out front. You can even head there for a hearty picnic if you feel like. The place is just about 80 meters (260 feet) from the famous Piazza del Duomo.
Top guest reviews
Amenities & Room:
The bed was comfortable and the apartment was plenty big enoughThe town was crowded with tourists during the day but the night and early mornings were amazingly quietThe most enjoyable part of our stay was the central location of La Rocca and the friendliness and helpfulness of the ownersThe village is beautiful with breathtaking views of the surrounding countrysideHost:
very welcoming and wonderful hostsRenata was always quick to reply to messagesThe hosts were very kind and helpful with accommodationsThe decor is very well doneUnfortunately we didn't get to meet her :(Read more reviewsLocation:
This is a beautiful little village that takes you back to an amazing time periodThis small one bedroom flat on a quiet street in San Gimignano is perfect
5. Super place for three guests (from USD 85)
Sitting at a distance of about 50 meters (165 feet) from the northern entrance of San Gimignano, this rental’s doors open bang in the middle of the town’s main street. Indoors, it is immaculate, thoughtfully designed, and utterly pleasing in its atmosphere. You can access its patio and soak in lovely views of the Italian streets and the many people they host. The living area is split across two floors, with each floor equally pleasing. If you’re not too sure of where to go, what to do, and where to eat, the hosts offer some super helpful tips and suggestions. Take them up on their recommendations and you’ll not be disappointed. Other than that with its free parking, unlimited WiFi access, and convenient location, here’s one place that ticks all the boxes.
Top guest reviews
Amenities & Room:
you will not be disappointedJust as described the apartment is clean with everything you need Located on the second floor with two windows that can be open overlooking the patio which gives you a sense of privacy while a...cooking classes and anything else we wanted to knowWe enjoyed our say in the palaceThe room was magical and overlooking a courtyard only for guestsCleanliness:
The breakfast was wonderful and fresh -Host:
Host was informative and sent information and a map about how to best access the site Friendly and warm reception with information about parking and best restaurants in the area Would definitely ...Home is historic and well kept Host allowed us to store luggage for free while we visited the town on the day of check outThe breakfast was excellent and the owner and staff were very friendly and helpful with suggesting things to do and see as well as dining recommendationsWhile booking I made sure all our places had itRead more reviewsLocation:
The palace is in a great location with major attractions near byit's a jewel in the cityThe owners were wonderful easy to talk to recommendations for place to visit good restaurantsThe parking is a bit far
6. Recently renovated, plush cottage (from USD 189)
Picturesque, comfortable, and packed with facilities, this rental is hard to miss. Large enough to sleep up to five guests, the cottage is a barn transformed into a living space, with many luxurious additions. Not only are the rooms cosy, but unlimited WiFi accessibility, laundry services, central cooling/heating, swimming pool, and the large open space makes it quite a package. It is set in an olive grove and provides a stunning vista of the region’s landscape from its lawn out front. There’s also a fully furnished terrace for you to make use of. There are grocery stores, supermarkets, restaurants, banks, and also a railway station within a close distance from the property.
Top guest reviews
Amenities & Room:
the views are stunning there are comfortable loungers and chairs and the pool area isThis beautiful little villa is on a hillside with a priceless view of the valley covered in grape vines and olive treesA short car ride down the road and there was a lovely little pub serving pizza and bbq food with friendly ownersGreat location for exploring nearby towns and san Gimignano was around 20mins by carF...Cleanliness:
The property was spotlessly clean and ideally situated for exploring the regionHost:
comfortable well equipped and well maintainedThe pool is absolutely private and spotless The owner and agent could not have been more helpful and available Terrific folksLooking forward to booking againHighlyThe owner did not bother us at all during the stayWe also enjoyed the warm welcome from Brunello and Ilaria when we arrivedThe owner is very generous providing all of the necessities when arriving (including wine and his own olive oil )Read more reviewsLocation:
The location is great - just ten minutes to San Gimignano and 25 minutes to SienaThis charming cottage is a perfect located property in the Tuscan countryside with a stunning view San Gimignano and Certaldo are both 9km from the location and has good restaurantsIf you want peace and quite in a lovely area then this is the place for youThe views from the garden are excellentThe location of the cottage is very peaceful and quiet and has a beutiful garden with hundreds of flowers and a private pool
Visit picturesque San Gimignano
Tall stone towers circled by 13th-century walls enchant many a pilgrim, residents, and travellers here. Among the best preserved medieval Italian towns, burgeoning with art, culture, history, and thorough satisfaction is what a trip to San Gimignano ensures. Gothic frescoes, Romanesque cathedrals, medieval stone skyscrapers, delicious white wine, pungent saffron, and Tuscan magic – you’ll find it all in this little town. Pick one of these Vrbo vacation rentals and marvel at the city’s beauty.
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