10 Best Vrbo Vacation Rentals In San Gimignano, Italy - Updated 2021

vrbo san gimignano italy

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.

1. Romantic accommodation ideal for couples (from USD 133)

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.

'....A flowered oasis inside the medieval walls....
15 reviews
Apartment 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The bed is super comfortable
The bed is very comfortable
The bed was quite comfortable and the bathroom was modern with a good sized shower
The apartment is very conveniently located inside the wall Mario helped get our car to our parking space outside the wall
You also are given a free parking space just outside the walls
Mario and his daughter were very easy to work with
We 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 it
The apartment and yard were beyond beautiful
She also gave great restaurant recommendations
Warm welcome and very helpful
Mario communicated with us with all the needed information ahead of time and arranged for us to check in early
so 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 wine
We could not have been more pleased with our choice
It is only a 2 minute walk to the center square
It is in a great location
Old stone archways a quaint garden and a bedrock wine cellar add to the enchantment of your stay
It's a lovely clean safe city to stay at
The Garden House in San Gimignano is a truly special place in a beautiful city hosted by the loveliest family
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2. Apartment with panoramic views (from USD 204)

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!

Cosy apartment for 2 guests with pool, A/C, WIFI, TV, panoramic view and parking
San Gimignano, Tuscany, IT
7 reviews
Apartment 1 Bedroom 2 Bathrooms
Top guest reviews
Amenities & Room:
The accommodation and facilities were excellent only surpassed by the friendliness of the owners
Great position great views and great property
The location allows you to thoroughly relax and enjoy the stunning views as well as having the option to simply walk into San Gimignano
We had a fantastic two weeks
God combination between closed to San Gimignano and slence of a village 300m far from the SG gate
Wonderful apartment in a fantastic setting Great access to the town of San Giminano Car parking but can walk into San Gimignano
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3. Centrally located property for large groups (from USD 201)

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!

Apartment San Girolamo in San Gimignano - 6 persons, 3 bedrooms
9 reviews
Apartment 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The apartment had lots of room tons of HOT water
The town itself was gorgeous and the apartment was very large
Four friends (two couples) shared the apartment for a week With 3 bedrooms and 2 bathrooms there was plenty of space
a 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 charm
We cooked together in the kitchen ate lunch on the terrace and dinner in the dining room and explored Tuscany from this very central position
comfortable and beautiful Claudia was patient very helpful and easy to work with My husband
We were warm and dry
However the property is definitely starting to show its age and could use a slight refurbishing
the welcome from our host was charming and our stay was perfect
Our only "American hardship" was that the american coffee pot did not work and another was not available
We had restaurants and Pizzerias plus the market Bakery and wine shop at our fingertips
I was mesmerized by the location in the walled city - could not have been more perfect
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4. Park-view property, great for a twosome (from USD 93)

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.

"The apartment you were looking for in the heart of San Gimignano" .... book it now!
8 reviews
Apartment 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The bed was comfortable and the apartment was plenty big enough
The town was crowded with tourists during the day but the night and early mornings were amazingly quiet
The most enjoyable part of our stay was the central location of La Rocca and the friendliness and helpfulness of the owners
The village is beautiful with breathtaking views of the surrounding countryside
very welcoming and wonderful hosts
Renata was always quick to reply to messages
The hosts were very kind and helpful with accommodations
The decor is very well done
Unfortunately we didn't get to meet her :(
This is a beautiful little village that takes you back to an amazing time period
This small one bedroom flat on a quiet street in San Gimignano is perfect
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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.

San Gimignano apartment 9, full center, fast free wifi, lovely courtyard
7 reviews
Apartment 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
you will not be disappointed
Just 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 know
We enjoyed our say in the palace
The room was magical and overlooking a courtyard only for guests
The breakfast was wonderful and fresh -
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 out
The breakfast was excellent and the owner and staff were very friendly and helpful with suggesting things to do and see as well as dining recommendations
While booking I made sure all our places had it
The palace is in a great location with major attractions near by
it's a jewel in the city
The owners were wonderful easy to talk to recommendations for place to visit good restaurants
The parking is a bit far
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6. Recently renovated, plush cottage (from USD 238)

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.

BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
20 reviews
cottage 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
the views are stunning there are comfortable loungers and chairs and the pool area is
This beautiful little villa is on a hillside with a priceless view of the valley covered in grape vines and olive trees
A 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...
The property was spotlessly clean and ideally situated for exploring the region
comfortable well equipped and well maintained
The pool is absolutely private and spotless The owner and agent could not have been more helpful and available Terrific folksLooking forward to booking againHighly
The owner did not bother us at all during the stay
We also enjoyed the warm welcome from Brunello and Ilaria when we arrived
The owner is very generous providing all of the necessities when arriving (including wine and his own olive oil )
The location is great - just ten minutes to San Gimignano and 25 minutes to Siena
This 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 restaurants
If you want peace and quite in a lovely area then this is the place for you
The views from the garden are excellent
The location of the cottage is very peaceful and quiet and has a beutiful garden with hundreds of flowers and a private pool
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7. Best of both worlds - a peaceful neighbourhood and a bustling main district (from USD 140)

Here’s another place you must consider if you’re travelling in a pack of five. Located within walking distance from the town’s main districts, it makes for a top choice for people with packed itineraries. Staying here will not only keep you close to the main parts of the city but also let you enjoy the peace of a quiet neighbourhood. The apartment overlooks a lovely park, strewn with cypress and pine trees where kids can easily go and spend their day playing. Indoors, the place is well lit, airy, spacious, and carefully done up. Although, please note that there’s air conditioning only in one of the two bedrooms.

Apartment/ flat inan historical house of San Gimignano
15 reviews
Apartment 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
The kitchen is well equipped to cook light meals for 5
the beds were comfortable and the space was plenty for two couples
Great apartment for up to 4 people
However the reasons for giving the apartment a 3 5 are: the kitchen had plenty of pots and pans but few usable dishes
but it should be in the posting All in all
The apartment was clean and quiet
The two bedrooms are very similar to each other in size and furnishings which is particularly helpful when two couples are traveling together as there is no "master bedroom" per se
Maar wij waren toch niet veel in het huisje
Summers can get hot in Tuscany and the shutters are working well to keep the apartment cool
Everyone was super helpful and we loved it
The owners were very nice people helpful and accommodating
We of course understood the cost
Communication was first class and we were made to feel very welcome
The owner greeted us nicely and efficiently upon our arrival and made sure we found free street parking for our car while staying there
that are 5 min away by foot
Location is great for exploring San Gimignano but also as a base for exploring Tuscany as a whole Siena was only a 35 minute drive away Overall a very good place to stay
The place was comfortable and clean and an easy walk to everything from tourist sites to food shops
We were told on arrival we had to park in the 10min walk away public lot for 10 Euro which turned out to be 13 Euro
not a bad stay for one night but not for more than two days
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8. Superb space for art lovers (from USD 132)

Fond of art and architecture yourself? Pick this home that once belonged to the renowned architect Francesco Ridolfi and that has been retained to emanate his character in its decor, furnishings, and vibe. It can easily sleep up to three guests who’ll be able to marvel at the panoramic views of this charming little town and the Chianti Hills from its balcony. Not only will you be amply pleased with the amenities offered inside the house, but also with the fact that it offers free garage parking for vehicles. It is located in San Gimignano’s Piazza della Cisterna so all noteworthy sites in town will be within easy reach for you.

Panoramic terrace in the Piazza della cisterna
2 reviews
Apartment 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
Cozy apartment with wonderful views of the countryside Conveniently located within the walls of San Gimignano Great apartment for exploring the city especially after the crowds have left for the...
The apartment was very clean and nicely stocked
The host has great communication throughout the rental process
The available garage parking is very convenient
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9. Apartment for four, packed with amenities (from USD 105)

Head to San Gimignano with your family of four and stay in the comfort of this two-bedroom apartment. Furnished with artistic Tuscan furniture, this place is a superb combination of modern amenities and old-world charm. The master bedroom climbs into a mezzanine that makes for an exciting space for the kids. WiFi access is available across the house and there’s also a satellite-enabled television in the living room. Else, you can also enjoy lovely outdoor meals on their large terrace. Trust us when we say that you’ll not be bored while indoors. As for its location, the local market, pharmacy, bank, and main tourist attractions of the town are all within walking distance. Book this rental and make it a memorable holiday for your family.

Panoramic Apartment with a Wonderful View On Towers
1 review
Apartment 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
the balcony does not have this view
The apartment was centrally located and secure and access to off
Our stay commenced with a very warm welcome from Fabio and Sara including lots of welcome advice and suggestions of touring the region
Nevertheless we were very happy with everything about our stay here
The village of San Gimignano has everything you need and all within an easy walk Eating breakfast on the balcony was great but the view on the picture is not accurate
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10. Located in the heart of the historic district

located in the heart of the historic district
Source: www.vrbo.com

Great for a family of five, this place is a fantastic option for those who want to stay close to the historic sights of the city. It has been furnished in a slightly distressed manner to give it the “rustic” feel that San Gimignano resonates with. However, no aspect of comfort and convenience has been overlooked. You can look out the window and see crowds of happy people exploring their way through the town, or step out and leave yourself to be swept away by the mystique that abounds the airs. Although, do note that the apartment is on the second floor of the building and can only be accessed via stairs.

In the historic center: immersed in the medieval city of San Gimignano.
2 Bedrooms 2 Bathrooms

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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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