Home Vacation Rentals By Owner In San Gimignano, TOS

Showing 120 Of 194 Vacation Rentals
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$531.77

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Apartment

Zafferano Rooftop Terrace Tower House 4 pax

San Gimignano, Toscana, Italy

Zafferano is a luxurious apartment set in the very heart of San Gimignano, characterized by an elegant mixture of ancient and modern. brbrThe wide open spaces of this medieval tower are shaped by perfectly preserved squared stones dating back to the XIIth century and they are wisely combined with modern, comfortable furnishings. brbrA special mention is deserved by the breathtaking vistas over the wonderful Piazza della Cisterna and the Tuscan countryside enjoyable from Zafferano's windows.brbrThe apartment is developed on three levels, with 75 steps rising from the street level entrance to the rooftop terrace, but no worries: our welcoming staff will be at your disposal to help with the luggage!brbrWill find the two double bedrooms at second and third floor, both have private bathroom.brbrIn addition, the second floor features a fully equipped kitchen, two living rooms, one huge dining room and a toilet, while the third level is characterized by a comfortable studio and a furnished terrace where guests can relax and have alfresco meals while enjoying the exclusive view over the Tuscan hills and the famous towers of San Gimignano.brbrInternet wifi and air conditioning are available throughout the house and are at guests' free disposal.brbrThe apartment also comes with a laundry area with washer and dryer, located in a separate room on the first floor (right in front of the house entrance). brbrA free garage is also available, upon request, only 300 mt from the apartment.
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$833.14

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Villa

Villa Giorgia 10 pax

San Gimignano, Toscana, Italy

A place where unspoiled nature meets elegance and the luxury of simplicity to create a space in which to reconnect body, mind and soul. An enchanting retreat of peace and tranquility and absolute privacy.brbrThe villa was formerly used as a holiday home by a family of local artists who contributed to the decor with unique pieces of handmade ceramics and original paintings.brbrOn the ground floor, the courtyard leads to the main living room, furnished with antiques.brbrFrom the living room a corridor leads to the dining room, with a large solid wood table and antiques and the kitchen with everything you need, and from the glass door there is direct access to the pergola for al fresco dining.brbrStill on the ground floor, two of the five rooms are accessed from the living room, the first, located in the hallway to the kitchen and furnished in 19th-century style with a double bed, wardrobe, chest of drawers and its own ensuite bathroom with shower. The second, is located down a a small staircase. It is one of the most spacious and has direct access to the outside where you can enjoy a coffee or an aperitif. It includes a double bed, wardrobe, a small sitting area and an ensuite bathroom with shower.brbrFinally on the ground floor, you will also find a courtesy bathroom with toilet and sink.brbrA second living room welcomes you to the upper floor, with sofas, armchairs, a very large bookcase, and a piano, which can be accessed either from the outside staircase or from inside.brbrFrom here you can reach three double bedrooms each with an ensuite bathroom with shower. One of them also has a bathtub and access to a terrace overlooking the countryside.brbrThe outdoor spaces, which include the garden, pool lawn and a terrace overlooking the countryside, will allow you to find your own corner to relax, practice some yoga, morning meditation or simply enjoy a good book or a glass of wine.brbrThe pool for your exclusive use is complete with umbrellas and sunbeds.The private pool will be open from 1 Mabrbrbrbr-------------------------------------------------
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$642.31

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Apartment

Zafferano Rooftop Terrace Tower House

San Gimignano, Toscana, Italy

Zafferano is a luxurious apartment set in the very heart of San Gimignano, characterized by an elegant mixture of ancient and modern.brbrThe wide open spaces of this medieval tower are shaped by perfectly preserved squared stones dating back to the XIIth century and they are wisely combined with modern, comfortable furnishings.brbrA special mention is deserved by the breathtaking vistas over the wonderful Piazza della Cisterna and the Tuscan countryside enjoyable from Zafferano's windows.brbrThe apartment is developed on three levels, with 75 steps rising from the street level entrance to the rooftop terrace, but no worries: our welcoming staff will be at your disposal to help with the luggage!brbrOn each level guests will find one double bedroom with private bathroom.brbrIn addition, the second floor features a fully equipped kitchen, two living rooms, one huge dining room and a toilet, while the third level is characterized by a comfortable studio.brbrthe apartment has a beautiful terrace overlooking the countryside and the rooftops of the city, in the furnished terrace where guests can relax and have alfresco meals while enjoying the exclusive view over the Tuscan hills and the famous towers of San Gimignano.brbrInternet wifi and air conditioning are available throughout the house and are at guests' free disposal.brbrThe apartment also comes with a laundry area with washer and dryer, located in a separate room on the first floor (right in front of the house entrance).brbrA free garage is also available, upon request, only 300 mt from the apartment.brbrA few kilometers away, at the village of Castelfalfi, splendid swimming pools surrounded by greenery await you for moments of relaxation. There are also Gofl courses at the Castelfalfi Golf Club.
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Exceptional(13)

$190.45

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Montegonfoli 3 Stunning San Gimignano Apartment with pool, Patio & Scenic Views

San Gimignano, san gimignano, Italy

Discover the Magic of Montegonfoli 3: Your Tuscan Dream AwaitsbrbrWelcome to Montegonfoli 3, a premium escape nestled in the heart of Tuscany, where every detail whispers relaxation and elegance. This ground-floor gem boasts two spacious double bedrooms, each with its own private bathroom, ensuring the utmost comfort and privacy. The living area, complete with two sofa beds and a fully equipped kitchenette, opens onto a private patio with breathtaking views of the iconic San Gimignano. Imagine savoring your morning coffee with the rolling hills as your backdrop or enjoying an alfresco dinner under the stars.brbrMontegonfoli 3 is more than just an apartment; it’s an experience. Part of the prestigious Agriturismo Montegonfoli, this exclusive retreat is housed within a lovingly restored 17th-century farmhouse. Perched atop one of the highest hills in the region, it offers panoramic 360-degree views that will leave you speechless. Whether it’s the sunrise or the golden hour, every moment here is framed by the timeless beauty of Tuscany.brbrExplore the best of both worlds with Montegonfoli’s unmatched location. While the tranquility of the countryside envelops you, the vibrant heart of San Gimignano is just a short 3.6 km drive away. Nearby, you’ll find charming restaurants, equestrian adventures, and the perfect spots for day trips to Tuscany’s most celebrated destinations, Siena, Florence, Volterra, Lucca, Pisa, and beyond.brbrStep inside Montegonfoli 3, and you’ll find 70 square meters of thoughtfully designed space. Each bedroom ensures privacy and comfort, while the living room connects the spaces with a welcoming warmth. A 32 LCD TV and WiFi provide modern conveniences, but it’s the outdoor patio with its mesmerizing view that truly steals the show. This is where you’ll spend your evenings, soaking in the magic of Tuscany with a glass of local wine in hand.brbrYour stay at Montegonfoli 3 comes with all the amenities you could wish for: a large, double-depth swimming pool, perfect for both kids and expert swimmers, a barbecue area for delightful outdoor meals, and a vast 23-hectare garden where you can lose yourself in nature. And when it’s time to explore, simply step outside, Montegonfoli’s own vineyards, olive groves, and forest trails await.brbrWhether you’re seeking a romantic getaway, a family retreat, or an adventure with friends, Montegonfoli 3 is designed to accommodate all your needs. Its thoughtful layout even includes accessible features, ensuring everyone can enjoy the beauty of this extraordinary place. And while the Tuscan summer might tempt you to stay inside, rest assured—the apartment’s design keeps it comfortably cool, even without air conditioning, thanks to its strategic use of fans and natural breezes.brbrAt Montegonfoli, you’re not just a guest; you’re part of our family. Our decades of experience in hospitality mean you’ll receive a warm, genuine welcome, complete with personalized recommendations to make the most of your stay. From discovering hidden gems in the surrounding countryside to enjoying the world-famous wines of the region, your Tuscan adventure begins here.brbrBring your heart to Montegonfoli 3, and let the beauty of San Gimignano and the Val d’Elsa captivate your soul. This is more than just a vacation, it’s a journey into the heart of Tuscany. Welcome home!br
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$365.37

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Montagnana Country House - Relax and stunning view

San Gimignano, Siena, Italy

Montagnana Country House is located in a tiny rural hamlet, a handful of stone houses nestled in the silence of the hills surrounding San Gimignano.brbrThe soul of this home dates back to the 17th century: within these massive walls and in the surrounding fields, my ancestors lived and worked for generations. Here, life followed the rhythm of the land; my grandparents and their fathers before them spent their days among olive groves and vineyards, dedicatedly tending to every inch of this generous soil that has sustained us for centuries.brbrIn the 1990s, the entire hamlet underwent a careful restoration that preserved its architectural charm, safeguarding the original stones and the atmosphere of yesteryear.brbrThe apartment is located on the upper floor, accessible via a driveway with stairs, and has 2 bedrooms, 1 bathroom, a private fenced garden, parking, a shared swimming pool (open from May 15th to September 29th included), Wi-Fi, and can accommodate up to 5 people.brbrBEDROOM 1 located on the upper floorbrbr-Double bed (160cm x 200cm)br-Bedside tablesbr-Large wardrobebr-Desk and chairbr-AC/HeatingbrbrBEDROOM 2 located on the upper floorbrbr-2 single beds (80cm x 190 cm each)br-Bedside tablesbr-Dresserbr-Coat rackbr-AC/HeatingbrbrBATHROOM located on the upper floorbrbr-Shower stallbr-Sinkbr-Bidetbr-WCbr-Hair dryerbr-Heatingbrbr LIVING ROOMbrbr-Sofa bed (130cm x 190cm) br-Coffee tablebr-Armchairsbr-Smart TVbr-AC/Heatingbrbr KITCHENbrbr-Dining table and chairsbr-Fridge/Freezerbr-Dishwasherbr-Hob, microwave, electic ovenbr-Coffee machinebr-Toasterbr-Kettlebr-Cookware, crockery, cutlery, glassware, utensil setsbr-AC/HeatingbrbrUTILITY ROOMbrbr-Washing machinebr-Drying rackbr-Iron and ironing boardbrbrPRIVATE FENCED OUTDOOR GARDENbrbr-Dining table and chairsbr-Garden chairsbrbrUNHEATED SHARED SWIMMING POOL (open from May 15th to September 29th included)brPrivate area for guests with:brbr-Parasolbr-Sun bedsbr-ChairsbrbrGUEST ACCESSbrbrMontagnana Country House is not accessible to people with reduced mobility as there are stairs to access both the apartment and its interior.brbrThe apartment is located in a small residential village consisting of 10 privately owned units, therefore the swimming pool and common areas are shared with other people.brbrADDITIONAL INFORMATIONbrbrPlease note that the tourist tax is an additional fee of EUR 2.50 per person, per day, with a maximum of 5 days. This tax does not apply to children under 14 years old. Payment for the tourist tax is required upon check-in and must be made in cash.brbrCIN IT052028B4IFD39QKI
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Exceptional(3)

$117.52

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La Casa dei Ricordi - Car/motorcycle garage 650 m away

San Gimignano, Provincia di Siena, Italy

La Casa dei Ricordi is located in the heart of San Gimignano, in a very quiet and charming area, a few steps away from the famous squares of the village.brThis first-floor apartment, which you can reach by stairs, is perfect for up to 4 guests. It comes with a bedroom, bathroom, living room, kitchen, Wi-Fi, heating, and stunning views.brbrBEDROOM located on a mezzaninebrbr-Double bed (160cm x 200cm) or 2 single beds upon requestbr-Night standsbr-Clothes rackbr-Dresserbr-Heatingbrbr LIVING ROOMbrbr-Sofa bed (140cm x 210cm) which sleeps 1 adult or 2 kidsbr-Closetbr-Coffee tablebr-Armchairbr-Smart TVbr-Small balcony br-Heatingbrbr BATHROOMbrbr-Showerbr-Sinkbr-Bidetbr-WCbr-Hair dryerbr-Heatingbrbr KITCHEN located on a mezzaninebrbr-Dining table and chairsbr-Fridge/Freezerbr-Washing machinebr-Hob, microwave, electric oven br-Coffee machinebr-Toasterbr-Cookware, crockery, cutlery, glassware, utensil sets br-HeatingbrbrGUEST ACCESSbrbrLa Casa dei Ricordi is located in the historic center, within a restricted traffic zone (ZTL), therefore, it is not possible to park directly at the apartment. However, you may reach the property by car or motorcycle to load and unload your luggage, using a dedicated permit.brbrFor guests arriving with a car or a motorcycle, a privately covered garage, located outside the restricted traffic zone (ZTL) and approximately 650 meters from the apartment, is available. The garage is accessible 24/7.brbrCovered garage costs (to be paid upon arrival):brbrHigh season (June, July, August, September, New Year)br- Euro 9.00 per day (stays up to 3 nights)br- Euro 7.00 per day (stays longer than 3 nights)brbrMid season (April, May, October)br- Euro 7.00 per day (stays up to 3 nights)br- Euro 5.00 per day (stays longer than 3 nights)brbrLow season (November, December, January, February, March)br- Euro 5.00 per daybrbrFurthermore, the apartment is not accessible to people with reduced mobility as there are stairs both to access the apartment and inside.brbrOTHER THINGS TO KEEP IN MINDbrbrThe tourist tax is not included in the price of the stay and amounts to 2.50 EUR per day/per person, over 14 years of age.The tax must be paid for a maximum of 5 days and payment is due in cash upon check-in.brbrbrCIN IT052028B4I4YOQDI5
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Exceptional(5)

$331.63

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Private Vacation Home

Le Rose di Montagnana

San Gimignano, Toscana, Italy

Le Rose di Montagnana is an independent cottage set in the property of Montagnana, developed on two floors.brbrThe entrance is on the ground floor, where only a few steps need to be climbed.brbrThe bright living room is the first thing that welcomes our guests.brbrCozy and colorful, it features a vintage Bang & Olufsen tv and stereo enjoyable from the couch or the sofa while looking at the medieval towers through the window.brbrAn old charming stove is also part of the room furnishings.brbrIn the same area, there is also a well-equipped kitchen with dishwasher, regular and small electric oven, fridge with freezer, induction hobs and all the necessary to cook.brbrAn old wooden table with chairs is also at guests' disposal.brbrRight above the kitchen, there is a perfect place for smart working: it's a mezzanine where a small studio is set, with bookshelves, a desk and a chair.brbrAt the ground floor you can find a small bath furnished with sink, toilet and shower and closet with a washing machine and drying rack.brbrOn the upper floor, there are two double bedrooms with two separate bathrooms, complete with sink, toilet, bidet and shower.brbrOutside the house, guests will find a patio furnished with a large table, a stone bench and some chairs where to have al fresco meals.brbrAnother exclusive feature of the house is the garden, where there is another small table with chairs and another bench.brbrThe only shared space is the swimming pool, which is the condominium. There, Le Rose di Montagnana's guests will have a table, two sunbeds, two chairs and a parasol at their exclusive disposal.brbrFree fenced parking and free internet are available.brbrPool opening 2025: May 15 through September 30 - barring adverse weather conditions
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Private Vacation Home

Betulla C, San Gimignano, Italy

San Gimignano, San Gimignano, Italy

In the heart of central Tuscany, there is a semi-independent annexe to a newly-restored country residence that is perfect for a group of 3 guests. br brLocated on Tuscan hills and surrounded by olive groves and cypresses, this one-bedroom vacation rental with a shared pool and a private as well as a shared garden promises an authentic holiday experience. Guests can soak in the beauty of its natural landscape from the manicured garden area which also has a small set up for dining. The shared, outdoor pool is also equipped with salt filters, sunbeds and sun chairs. br brGuests are welcomed into the charming ambience of its living room with terracotta floor and exposed beam ceiling. This room features a single sofa bed, a wooden dining table and an open kitchenette. Guests will find an oven, a Mokka coffee machine, a dishwasher, a toaster, a cooker hob, an electric kettle and a fridge with a freezer in its kitchen-diner. br brSleepingbr brBedroom 1: The classical-style bedroom has a traditional double bed and a wooden wardrobe. br brGuests can also sleep on the single sofa bed in the living room.br brBathroombr brBathroom 1: The elegant bathroom has a bath with a shower, a WC and a bidet. br brThere is also a dressing room with washing machine. br brAdditionalbr br • Outdoor, shared swimming pool • Private Parking Space • Very Quiet Location • Suitable for all age groups • Central Heating • SAT-TV • Free Internetbr brLarger group of guests (up to 12 guests in total) can stay at adjoining holiday houses in the same complex. br brLocationbr brThe holiday house is located in a peaceful surrounding blessed with bounteous nature. It is a perfect retreat for those looking to unwind and de-stress or a romantic getaway in the typical Tuscan countryside. The nearest shop, restaurant and supermarket are about 5 kilometers’ drive from the house. There is a golf course about 13 kilometers away. br brSan Gimignano, which is the nearest town to the holiday house is well known for its tall towers that are often dubbed as medieval skyscrapers. The town also serves some of the best traditional Tuscan cuisine, wine and gelato. A lot of architectural and artistic gems, historical monuments and museums abound the place which has caught the attention of travelers. br brGuests can conveniently take day trips to all the major tourist destinations of Central Tuscany such as San Gimignano (10 kilometers), Poggibonsi (5 kilometers), Siena (31 kilometers) and Florence (42 kilometers). br brFlorence International Airport is about 62 kilometers and Pisa International Airport is about 87 kilometers from here.brbrIf necessary, GAS for heating between April 15th to November 1st, have to be paid on the spot basing on consumption. 
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$110.54

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Agritourism

Independent, cozy and private cottage, nestled in the Tuscan countryside

San Gimignano, Toscana, Italy

The Villino del Grillo farmhouse was born from an old barn of a small family-run farm, in the middle of a 4-hectare country estate. The attention to detail and cleanliness are the main features of the cottage. It is composed of a single small independent house, surrounded by the vineyards and olive groves of the hills of San Gimignano.brIn 2000 the Pierantozzi family decided to renovate a small barn; After years of work and sacrifice, taking care of every little detail, the small barn has been transformed into a small cozy house full of details, which bear witness to the love and passion with which all the members of the family took part in the work. .brThus, in 2004, the Villino del Grillo was born, which, in its small, with its characteristics, is completely different from other structures in its category. A place that makes guests feel at ease, surrounded by a unique atmosphere, full of intimacy, a nest where to take refuge to find peace and tranquility. At the same time it is a place where you can participate in the daily activities of a small farm, which, with its modest size, remains linked to ancient traditions, as evidenced by the phrases left in the guest book.brThe Villino del Grillo consists of a single apartment consisting of a double bedroom, a complete bathroom, a living room with kitchenette and a large garden, for the exclusive use of guests.brThe whole structure is equipped with independent heating system, air conditioning system and wi-fi internet connection.br It is furnished in a rustic Tuscan style, with the typical ceiling of Tuscan farmhouses, terracotta and wooden beams.brThe master bedroom with large bathroom, is equipped with satellite TV, armchair, air conditioning and wi-fi internet connection.brThe living room with kitchenette is equipped with sofa, fireplace, microwave, toaster, coffee machine, fridge, satellite TV, air conditioning, wi-fi internet, dishes and appliances for preparing meals.brThe bathroom with sink, toilet, bidet and shower, is equipped with washing machine and hair dryer.brOutside there is a large terrace with seating in a shaded area, a large garden exclusively for guests with chairs, deckchairs and parasol.brIt also provides free: iron, ironing board, clothesline, barbecue, deck chairs, tables and chairs for outdoor, mountain biking.brThe Villino del Grillo is the ideal place to spend a holiday in absolute rest, tranquility and privacy, even in winter.brbrTO KNOW:br- Please note that in the winter months heating comes at an additional cost, calculated according to consumption;br- From March to October the Tourist Tax will be applied - Tourist Tax, calculated only for the first 5 days (€ 1.50 per person per day).brbrThe Villino del Grillo farmhouse is located between San Gimignano and Certaldo, 3 km from the latter.brComing from the North: motorway A1 exit Impruneta, direction Siena, exit Poggibonsi Nord, follow the signs for Certaldo, arrived at Certaldo follow the signs for San Gimignano and after 100 meters follow indication Badia a Elmi, after 300 meters follow the indication Pulicciano, take the dirt road, go about 700 meters and you have arrived.brComing from the South: motorway A1, exit Valdichiana direction Siena. Few km before Siena follow direction Firenze, exit Poggibonsi Nord, follow the signs for Certaldo, arrived at Certaldo follow the signs for San Gimignano and after 100 meters follow the sign Badia a Elmi , after 300 meters follow the indication Pulicciano , take the dirt road, go about 700 meters and you have arrived. brbrFrom the farm Villino del Grillo, located in the center of Tuscany, all the main cities are easily reachable.br brGPS coordinatesbr Pulicciano: N 43 ° 31'57. 4 '' - E 011 ° 02'03. 8 ''; N 43 ° 31. 954 '- E 011 ° 02. 060 '; N 43. 532611 - E 11. 034389.brbr Villino del Grillo: N 43 ° 31'40. 9 '' - E 011 ° 02'03. 8 ''; N 43 ° 31. 681 '- E 011 ° 01. 483 '; N 43. 528028 - E 11. 02475.brbrSan Gimignano is an Italian town of 7. 770 inhabitants, located in the province of Siena in Tuscany. For the characteristic medieval architecture of its historic center it has been declared a UNESCO World Heritage Site. The site of San Gimignano, despite some eight-twentieth-century restorations, is mostly intact in the two-fourteenth-century appearance and is one of the best examples in Europe of urban organization of the municipal age.brLocated in the hills of the Val d'Elsa, in the heart of the Chianti, San Gimignano owes its fame mainly to its countless medieval towers. In the past, symbol of power and prestige of the rich bourgeois families to which they belonged, make today this country, with an ancient flavor, one of the most evocative and characteristic of Tuscany. A place where time has stopped, which has kept its structure of a fortified village intact, with a treasure of history, art and culture.brThe extraordinary spectacle that San Gimignano offers its visitor is represented by its towers. Tall and powerful, the nobles competed to erect the highest, the most solid, the most beautiful tower; it represented a symbol of prestige, such as the 'Torre Grossa' of the Palazzo del Popolo, now seat of the Municipality, of 54 meters. Monumental center is Piazza del Duomo. On this square there is the Collegiata di Santa Maria, a building dating back to 1056 which houses masterpieces by Taddeo di Bartolo, Benozzo Gozzoli, Lippo Memmi and Bartolo di Fredi, the wooden statues by Jacopo della Quercia depicting the Annunciation and the Archangel Gabriel. A real gem is the Chapel of Santa Fina, patron saint of San Gimignano, a refined Renaissance building by Giuliano and Benedetto da Maiano, decorated by Domenico Ghirlandaio. At the Collegiata are the Museums of Sacred and Etruscan Art, with paintings, sculptures and sacred vestments, as well as archaeological evidence from Etruscan excavations of the surroundings.brIn the same Piazza del Duomo is the Palazzo del Podestà, built in 1239. In the contiguous Piazza della Cisterna, the center of the village, there is a medieval cistern that supplied water to the population. It is bounded by ancient buildings of inestimable beauty and historical interest.brFrom the highest point of the city, the Rocca, which still preserves part of the ancient walls and a tower, one can admire one of the most evocative views of the town and the surrounding countryside.brIn the beautiful countryside surrounding San Gimignano, the famous Chianti and Vernaccia di San Gimignano wines are produced.brbr
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Exceptional(2)

$666.74

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San Gimignano Town Garden - 10 pax

San Gimignano, Toscana, Italy

San Gimignano Town Garden is a one in a million apartment characterized by a central location and wide internal spaces, including a gorgeous green and relaxing garden.brbrThe building was freshly renovated.brbrThe vaulted ceilings and the ancient wellbrbrThe entrance of San Gimignano Town Garden is at street level.brbrOnce entered, the door to the left will lead our guests to the ample, beautiful living room with vaulted ceilings and a very peculiar well, protected by a thick glass.brbrThanks to the wide glass doors from which the garden is accessed, the living room benefits from a smooth natural light throughout the day.brbrIn the furnished garden, a nice awning guarantees the right proportion of sun and shadow.brbrSince the whole ground floor area was thought and designed as a chill out zone to be enjoyed by all the guests together, it features a big table with chairs, two sofas, a big tv, an equipped kitchen and a guest bath.brbrTwo double bedrooms and their ensuite bathrooms with shower are at the first floor.brbrOne of the bedrooms also features a nice panoramic terrace with table and chairs for four people.brbrOn this same floor, an equipped kitchen is also at guests' disposal.brbrThe same layout is repeated on the second floor, which hosts two double bedrooms with ensuite bathroom with shower and another equipped kitchen.brbrOne of the two double bedrooms' feature is a comfortable terrace with table and chairs for four people.brbrThe fifth double bedroom with its ensuite bathroom with shower is set on the third floor, where a small but functional kitchenette is.brbrbrbrbrbrbrbrThe vaulted ceilings and the ancient well in the living room were valorized and perfectly combined with modern elements.
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