La Villaccia-Monastero Vacation Villa Rentals
Results 341 - 360 of 474
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Description
Property Summary
Nestled in the picturesque Tuscan countryside of Terranuova Bracciolini, Italy, Country house "Melograno" is a charming holiday rental that offers guests a truly authentic and tranquil retreat. Set within 10,000 square meters of fully fenced land, this beautiful country property invites you to unwind in a serene natural setting that includes a delightful orchard waiting to be explored. The estate is thoughtfully equipped with all the comforts needed for a memorable stay, including high-speed internet WiFi to keep you connected throughout your visit. A private swimming pool measuring 10 x 5 meters takes center stage among the outdoor amenities, offering a refreshing escape during the warm months. Convenient on-site parking is available for your vehicle, and the expansive yard surrounding the property provides ample space to breathe, relax, and immerse yourself in the beauty of the Tuscan landscape.
Outdoors
The outdoor spaces at Country house "Melograno" are thoughtfully designed to complement the natural beauty of the surrounding Tuscan countryside. The private swimming pool, measuring 10 x 5 meters, is available for your enjoyment from May 1st to September 30th, offering a refreshing retreat during the warmer months of the year. An outdoor shower is conveniently located in the pool area, allowing you to rinse off after a leisurely swim. The extensive grounds, spanning 10,000 square meters of fenced land, provide a generous and secure outdoor environment where you can stroll freely, explore the on-site orchard, and enjoy the peaceful rural atmosphere that defines this exceptional property.
Other Information
Country house "Melograno" is designed to ensure a comfortable and independent stay for all guests. Internet WiFi is available throughout the property, keeping you connected whenever needed. It is worth noting that the owner resides on the same property, though the layout and setup of the estate are arranged so that you can fully enjoy your privacy and independence during your stay.
Distances and Attractions
Country house "Melograno" benefits from an enviable location that places you within easy reach of both local conveniences and renowned Tuscan destinations. The town center of Terranuova Bracciolini is just 800 meters away, where you will find a local shop at the same distance and a supermarket located only 600 meters from the property, making everyday errands effortlessly convenient. For those wishing to explore the wider region, the city of Arezzo is approximately 40 kilometers away, while the magnificent city of Florence can be reached in around 52 kilometers, offering world-class art, culture, and gastronomy. The Montevarchi railway station, situated just 7 kilometers from the property, provides excellent transport connections for day trips and onward travel throughout Tuscany and beyond. Melograno
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Description
Property Summary
Villa il Guscio is an idyllic Tuscan retreat surrounded by stunning landscapes and tranquility. The vacation rental boasts a private fenced garden spanning 1,000 square meters, complete with a seasonal outdoor swimming pool (12x6 meters, depth 140-250 cm) available from May 3rd to September 27th. Enjoy alfresco dining with a barbecue area and outdoor shower. Indoors, you'll find amenities like a fitness room, billiard table, and table football. Parking is available on the premises, and the property offers Internet WiFi access.
Outdoors
The villa's beautiful outdoor spaces beckon adventure and relaxation. Immerse yourself in the Tuscan countryside with hiking trails on the slopes of Pratomagno, offering breathtaking nature walks and spectacular views. Just an example, the sandy beaches of Versilia and Maremma are 150 kilometers away, perfect for a scenic coastal excursion.
Other Information
For added convenience, a cook is available upon request (extra charge). Heating is available from November 1st to April 7th, with costs to be paid on-site. The property is serviced by a gardener responsible for pool maintenance. Nearby, you'll find a grocery store within 900 meters, a supermarket 6 kilometers away, and a restaurant just 300 meters from the villa.
Distances and Attractions
Villa il Guscio is perfectly situated for exploring some of Italy's most beautiful art cities. Within an hour's drive, you can visit Florence (59 km), Siena (63 km), Arezzo (44 km), and Cortona, as well as the charming valleys of Casentino and Val d'Orcia. Nearby attractions include Loro Ciuffenna (3 km), Castelfranco di Sopra (12 km), Gaiole in Chianti (30 km), Greve in Chianti (36 km), Monte San Savino (50 km), and the thermal baths of Rapolano Terme (47 km). The villa is located 7.5 kilometers from the center of Terranuova Bracciolini, Italy. Villa Il Guscio
| Accommodation | |||||
|---|---|---|---|---|---|
| La Rosa | 6 | 2 | 2 | ||
| Il Tulipano | 3 | 1 | 1 | ||
| Orchidea | 4 | 1 | 1 | ||
| All 3 Accommodations | 13 | 4 | 4 |
Description
You will discover that the 'Balze' are a landscape of rare beauty, centuries-old examples of erosion that over the years have formed towers and rocky blades that rise majestically in the valley bottom, and that will catapult you into a suggestive, almost magical world.
The Agriturismo Le Balze is located in the heart of the Alto Valdarno, at the foot of Pratomagno, and 2 km from the village of Castelfranco di Sopra. The nearest shops and supermarkets can be found in Montevarchi or San Giovanni Valdarno, about 10 km away. Here, in the small, pretty towns, you can spend an evening out for dinner or organise an aperitif with friends.
The property is divided into three apartments resulting from the restoration of old farm outbuildings close to the main house where the owners live. Traditional materials such as wood, terracotta and stone were used in the renovation carried out to maintain the building's rural and peasant origins. All the apartments overlook a wooden porch on one side, where you will have your own private space equipped with table and chairs to spend the cool summer evenings at dinner or with your family or friends.
In the large, green garden you will have a practical barbecue and a table tennis. The swimming pool in common use is located at the back of the building (size 6x12 m, depth 1.40 m - open from 10 May to 15 September) and is completely fenced. Laundry and ironing facilities in a common room.
At Agriturismo Le Balze you can taste and buy excellent wine and extra-virgin olive oil, vegetables, fruit, and all the farm's products. But certainly one of its highlights is the small restaurant (maximum 25 seats - reservation required) run by the owners and located on the ground floor of their home, open both to the public and to guests of the agriturismo, where you absolutely must, at least for one evening, taste the delicious typical dishes, which are cooked using tasty local products.
We can assure you that you will not regret it! Le Balze
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- 4
- 4
Description
You will find the Agriturismo Le Balze in the heart of the Alto Valdarno, at the foot of Pratomagno, and 2 km from the small village of Castelfranco di Sopra. All around is a natural landscape of rare beauty, which will captivate you from the first moment, characterised by the presence of the 'Balze', secular examples of erosion that over the years have formed towers and rocky blades that rise majestically in the valley bottom.
In about 30 minutes by car you will be able to reach Florence, the cradle of the Renaissance. City of the ancient Medici family, a heritage not to be missed, with its artistic masterpieces, the colourful marble of the churches and the lofty architecture, the ancient bridges over the Arno river and the majestic noble palaces with their immense gardens adorned with fountains, sculptures, grottoes, staircases and paths.
The villa is divided into three independent flats, in one of which on the ground floor there is a double bedroom with a bathroom suitable for persons with disabilities. The structure was born from the recovery of old farm outbuildings close to the main house where the owners live, who will be, albeit in a discreet manner, a point of reference for all your needs.
The owners, thanks to careful renovation using traditional materials such as wood, terracotta and stone and comfortable furnishings, have ensured that the villa is perfect for spending a comfortable and restful holiday.
Villa Le Balze overlooks on one side a wooden porch, equipped with table and chairs and perfect for your dinners and evenings in company, and the lush garden where you will have a barbecue and a table tennis. On the other side, the house overlooks the swimming pool area (size 6x12 m, depth 1.40 m - open from 10 May to 15 September), which is completely fenced off and for the exclusive use of guests.
At Agriturismo Le Balze you can taste and purchase excellent wine and extra-virgin olive oil, vegetables, fruit, and all the products of the farm. In addition, on the ground floor of the house where the owners live you will find a small restaurant (maximum 25 seats), open both to the public and to guests of the villa. We absolutely recommend that you do not miss the delicious typical dishes cooked with love by the owner in the old-fashioned way, and made exclusively with local products. Villa le Balze
Montelucci Chianti Agrivilla
Wonderful independent accommodation with A/C, WIFI, private pool, TV, patio and panoramic view
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- 7
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Description
Vacation rental Montelucci Chianti Agrivilla is a nice stone building (400 sq m) that includes WiFi internet, private pool and air conditioning. The property can accommodate up to 14 guests comfortably in seven bedrooms with six bathrooms. Montelucci Chianti Agrivilla is located 560 m (1795 ft) from Montegrossi, Italy and only 30 km (18 mi) from Greve In Chianti in the tourist area "Chianti".
Your Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills and the mountains ideal for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of sightseeing. For your pleasure, on the grounds there is a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 30 km (18 mi), Siena 37 km (23 mi), San Gimignano 50 km (31 mi), Arezzo 54 km (34 mi) and Montalcino 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 77 km (48 mi), Viareggio 163 km (101 mi), Forte Dei Marmi 171 km (106 mi), Rome 258 km (160 mi), Milan 368 km (229 mi) and Naples 449 km (279 mi).
Additional Information
Check-In Time: 17:00 - 22:00
Check-Out Time: 07:00 - 10:00
Pool Open: 1 May - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 82 km (51 mi), Pisa (psa) 144 km (90 mi), Bologna (blq) 171 km (106 mi), Roma Ciampino (cia) 267 km (166 mi) and Roma Fiumicino (fco) 280 km (174 mi).
More Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a pleasant way to spend time with friends and family while learning the secrets needed to prepare delicious Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Ask for more details and the additional costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours offered, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be scheduled by the owner. Ask for more details about the extra cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Montelucci Chianti Agrivilla. Inquire for more details, including the supplemental cost and how to organize this service.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be arranged. Speak to the owner directly about this service upon arrival.
Montelucci Chianti Agrivilla
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Description
Conveniently located in Gaiole In Chianti, Italy in the tourist area "Siena And Surroundings" and only 29 km (18 mi) from Siena. Property Villa Di Gaiole is a nice stone building (400 sq m) that includes WiFi internet, private pool and air conditioning. The property can sleep up to 12 people comfortably in six bedrooms with four bathrooms.
The Experience
When you arrive at Villa Di Gaiole you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. Regardless of how you spend your days - sightseeing, visiting museums, shopping or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. There is a kitchen including microwave and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. If you prefer to dine 'al fresco', there is a fully furnished garden where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 29 km (18 mi), Greve In Chianti 30 km (18 mi), San Gimignano 50 km (31 mi), Arezzo 58 km (36 mi) and Florence 62 km (38 mi).
Some other major tourist destinations you should consider visiting are: Florence 62 km (38 mi), Viareggio 156 km (97 mi), Forte Dei Marmi 163 km (101 mi), Rome 251 km (156 mi), Venice 312 km (194 mi) and Milan 354 km (220 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 June - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 75 km (46 mi), Pisa (psa) 121 km (75 mi), Bologna (blq) 161 km (100 mi), Roma Ciampino (cia) 260 km (162 mi) and Roma Fiumicino (fco) 273 km (169 mi).
Villa Radda
Chiara House in Galenda, Chianti, Pool and Nature
Wonderful house with pool, WIFI, TV, terrace and panoramic view, close to Greve In Chianti
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Description
Chiara House In Galenda, Chianti, Pool And Nature is located 13 km (8 mi) from Gaiole In Chianti, Italy and only 24 km (15 mi) from Greve In Chianti in the tourist area "Siena And Surroundings". Chiara House In Galenda, Chianti, Pool And Nature is a nice property (90 sq m) with WiFi internet. The property can accommodate up to six people comfortably in two bedrooms with one bathroom.
What to Expect
After arriving you’ll find a beautiful clean well-maintained property with views of the hills ideal for a peaceful vacation in Tuscany. For your pleasure you will find a pool where you can relax while enjoying a nice cold beverage after a hectic day of visiting museums. There is a kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to six people.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 24 km (15 mi), Siena 29 km (18 mi), San Gimignano 44 km (28 mi), Florence 56 km (35 mi) and Montalcino 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 56 km (35 mi), Viareggio 150 km (93 mi), Forte Dei Marmi 157 km (98 mi), Rome 251 km (156 mi), Milan 350 km (217 mi) and Naples 442 km (275 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 June - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 69 km (43 mi), Pisa (psa) 115 km (72 mi), Bologna (blq) 155 km (96 mi), Roma Ciampino (cia) 260 km (162 mi) and Roma Fiumicino (fco) 273 km (169 mi).
The swimming pool is shared with four apartments in the village. Chiara House In Galenda, Chianti, Pool And Nature
Book your vacation for the period from 10 April 2027 to 15 November 2027 and save 15% (minimum 5 nights).
Book your vacation for the period from 10 April 2027 to 15 November 2027 and save 25% (minimum 7 nights).
Casale Montanare
Unique independent holiday home with private pool, WIFI, TV, patio and panoramic view, near Cortona
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Description
Conveniently located 2 km (1 mi) from Montanare, Italy in the tourist area "Cortona And Surroundings" and only 9 km (6 mi) from Cortona. Casale Montanare is a lovely stone building (220 sq m) with WiFi internet and private pool. The property can accommodate up to ten people comfortably in five bedrooms with six bathrooms.
The swimming pool site is a short walk up a beautiful garden path, 70 mt distant from the villa.
Your Experience
After arriving you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the mountains and the hills perfect for a relaxing vacation in Tuscany. Regardless of how you spend your days - shopping, visiting museums, sightseeing or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Also available outdoors are a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people.
Visit the Area
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 9 km (6 mi), Arezzo 37 km (23 mi), Montepulciano 37 km (23 mi), Perugia 55 km (34 mi) and Gubbio 63 km (39 mi).
Some other major tourist destinations you should consider visiting are: Florence 136 km (84 mi), Viareggio 222 km (138 mi), Forte Dei Marmi 229 km (143 mi), Rome 217 km (135 mi), Venice 375 km (233 mi) and Milan 420 km (261 mi).
Additional Information
Check-In Time: 15:00 - 17:00
Check-Out Time: 07:00 - 10:00
Pool Open: 1 May - 31 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 141 km (88 mi), Pisa (psa) 203 km (126 mi), Roma Ciampino (cia) 226 km (141 mi), Bologna (blq) 227 km (141 mi) and Roma Fiumicino (fco) 239 km (148 mi).
Special Services
Cooking Lessons - Learn from a local chef the techniques needed to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a pleasant way to spend time with friends and family while learning the secrets needed to prepare sumptuous Tuscan meals when you return home. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will organize the meal based on your preferences and dietary needs. The chef will offer suggestions for the various courses and the wine. Inquire for more details and the extra costs.
Il Rifugio
Villa Rosmarino
Independent Vacation home with A/C, private pool, WIFI, TV, terrace, panoramic view, near Cortona
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Description
Conveniently located 6 km (3 mi) from Montanare, Italy and only 13 km (8 mi) from Cortona. Villa Rosmarino is a beautiful stone building (300 sq m) with WiFi internet, air conditioning and private pool. The property can sleep up to 12 people comfortably in six bedrooms with six bathrooms.
The property consists of a main villa (170 square meters) and a cottage (130 square meters) which can accommodate up to 12 people (6 bedrooms and 6 bathrooms); the two buildings are situated just a few meters away from each other.
Your Experience
Upon arrival at Villa Rosmarino you’ll find a lovely clean well-maintained property with views of the hills perfect for a relaxing vacation in Tuscany. Regardless of how you spend your days - sightseeing, shopping, visiting museums or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. If you prefer to dine 'al fresco', there is a fully furnished terrace where you can enjoy the weather while dining outdoors.
Visit the Area
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 13 km (8 mi), Arezzo 40 km (25 mi), Montepulciano 41 km (25 mi), Gubbio 58 km (36 mi) and Perugia 59 km (37 mi).
Some other major tourist destinations you should consider visiting are: Florence 135 km (84 mi), Viareggio 228 km (142 mi), Forte Dei Marmi 235 km (146 mi), Rome 223 km (139 mi), Venice 384 km (239 mi) and Milan 428 km (266 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 148 km (92 mi), Pisa (psa) 209 km (130 mi), Bologna (blq) 229 km (142 mi), Roma Ciampino (cia) 232 km (144 mi) and Roma Fiumicino (fco) 245 km (152 mi).
More Services
Cooking Lessons - Discover from a local chef the techniques vital to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a fun way to spend time with friends and family while learning the secrets needed to prepare mouth-watering Tuscan meals when you return home. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Inquire for more details and the supplemental costs.
Tours - The owner can schedule custom tours for your group. To learn about the tours available, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be organized. Speak to the owner directly about this service after arriving.
Villa Rosmarino
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- 3
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Description
Property Summary
Montefienali is a historical holiday village located 15 km from Gaiole in Chianti, Italy, nestled in the countryside at an elevation of 600 meters above sea level. This renovated 13th-century property offers 25 apartments within a hamlet of 25 houses. Guests can enjoy a natural state property spanning 3 hectares with plants, trees, and a seasonal swimming pool (10 x 15 m) available from May 15 to September 30, with pool opening hours from 9:00 AM to 8:00 PM. The property boasts amenities such as a children's pool, outdoor shower, patio, terrace, garden furniture, and a children's playground with a slide, swing, and sandbox. Laundry facilities (shared) are available on-site. While the property is accessible via a 2 km bumpy motor access road, it offers parking on the premises and is within proximity to shops, groceries, supermarkets, restaurants, bars, and bicycle rentals, making it an ideal vacation rental for families seeking a peaceful retreat in the Tuscan countryside.
Outdoors
Immerse yourself in the natural beauty of Montefienali, surrounded by trees on a fenced 3-hectare property. Soak up the sun by the seasonal swimming pool (10 x 15 m), available from May 15 to September 30, with designated pool opening hours from 9:00 AM to 8:00 PM. Children can make a splash in the dedicated children's pool or enjoy the outdoor playground with a slide, swing, and sandbox. Relax on the patio or terrace, surrounded by lush gardens and equipped with comfortable garden furniture. Outdoor showers are also available for your convenience.
Other Information
Montefienali offers convenient on-site amenities, including a shared washing machine for laundry needs. While the property is situated in a secluded location, it is easily accessible via a 2 km bumpy motor access road, with parking available on the premises. A 50-meter footpath leads from the parking area to the accommodations. The property caters to families, with baby equipment provided. Please note that groups of teenagers are accepted upon request only.
Distances and Attractions
Nestled in the Tuscan countryside, Montefienali is conveniently located near various attractions and amenities. The charming town of Gaiole in Chianti is just 15 km away, offering shops, groceries, and a supermarket. Restaurants and bars can be found within a 3 km radius, while bicycle rentals are available 15 km from the property. Explore the rich history and culture of nearby cities such as Siena (36 km), Arezzo (44 km), and Florence (66 km), all within a reasonable driving distance from your vacation rental. Il Cinghiale
Il Canto del Maggio
Comfortable apartment with WIFI, pool, A/C, TV, patio, pets allowed and panoramic view
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- 14
- 6
- 6
| Accommodation | ||||
|---|---|---|---|---|
| La Castellana | 2 | 1 | 1 | |
| Canto al Sole | 2 | 1 | 1 | |
| Bellina | 2 | 1 | 1 | |
| Canto alla Luna | 4 | 1 | 1 | |
| Lilla | 2 | 1 | 1 | |
| Cecilia | 2 | 1 | 1 | |
| All 6 Accommodations | 14 | 6 | 6 |
Description
Hospitality, Osteria "Gentile" with veg garden, Cooking School and a stunning infinity pool overlooking the valley: il Canto del Maggio, owned by Simona and her family, isn’t just a place to sleep — it’s a place where you meet a family deeply rooted in this land and in its rhythms.
Here guests are welcomed into six charming units that reflect a rare and authentic form of hospitality: the Albergo diffuso—literally, a ‘scattered hotel’. Developed in Italy, this model revitalizes once-abandoned villages by blending comfort with local tradition in a truly immersive experience- in fact the "borgo" is a shared community between locals that live here permanently, and travelers that was born in the late 1980's.
Our collaboration with this placa was born to promote a network of local chefs, farmers, winemakers, guides, and hospitality professionals — all working together to create meaningful moments that we hope will make your stay one to remember.
My team (I am Tuscany) and I will take care of the accommodation side of your experience — from the moment you book to the day you arrive. Before your stay, we’ll coordinate with you to plan any extra services or personalized experiences, so everything is ready and tailored to your needs before you arrive.
Simona, the soul of this place, will welcome you into her world: her home, her kitchen, around her table, or walking through the vegetable garden — the orto. On the plate, a cuisine that arises spontaneously: the garden decides the menu, and we simply follow its lead.
Together, we can plan special dinners in the garden or by the pool, enjoy breakfast on the terrace or your private patio, and explore much more — from local farmers’ markets and tastings to our favorite go-to places in the area.
Available experiences include:
-Harvesting ingredients directly from the garden and discovering the joy of simple, farm-to-table cooking
-Themed culinary workshops (vegetarian, pastry-making, regional cuisine)
-Activities that immerse you in the natural beauty, culture, and traditions of the area
-Private meals (including breakfast) served anywhere on the property
-Pop-up events hosted by the restaurant or the outdoor kitchen
-Private events and retreats tailored to your needs Il Canto Del Maggio
Special Offer for La Castellana
Book your vacation for the period from 30 March 2026 to 20 December 2026 and save 15% (minimum 7 nights).
Book your vacation for the period from 30 March 2026 to 30 June 2026 and save 10% (minimum 3 nights).
Apartment:
Canto al Sole
Bellina
Canto alla Luna
Lilla
Cecilia
Description
Property Summary
This charming 2-family house is situated in the heart of Gaiole In Chianti, Italy, offering an ideal vacation rental for those seeking an authentic Tuscan experience. The property provides essential modern amenities including Internet WiFi connectivity and convenient public parking available on the adjacent road (additional fee applies). The residence features a central heating system, available from November 1st to April 4th, with heating costs payable on-site.
Outdoors
The property's central location in Gaiole in Chianti provides an authentic Italian atmosphere with the charm of local architecture and the surrounding Tuscan landscape. The building's position offers easy access to the city center and local amenities while maintaining a peaceful environment.
Other Information
The property benefits from proximity to essential services, including a shop just 100 meters away and a supermarket within 500 meters. A local restaurant can be found 2 kilometers from the property, and public transportation is accessible via a bus stop 200 meters away. The central heating system operates seasonally from November 1st to April 4th.
Distances and Attractions
The property provides excellent access to numerous renowned destinations: Radda in Chianti (10 km), Castellina in Chianti (22 km), and Florence (65 km). Notable nearby attractions include the historic Castello di Meleto (5 km), Castelnuovo Berardenga (21 km), San Donato in Poggio (28 m), Greve in Chianti (29 km), Siena (40 km), and San Gimignano (55 km). For beach enthusiasts, Castiglione della Pescaia's sandy shores lie 125 km away, while the thermal baths of Rapolano Terme can be reached within 42 km. Gaiole Apartament
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| Accommodation | |||||
|---|---|---|---|---|---|
| San Regolo 915.1 | 2 | 1 | 1 | ||
| San Regolo 915.2 | 4 | 2 | 2 | ||
| All 2 Accommodations | 6 | 3 | 3 |
Description
Property Summary
Villa San Regolo is a stunning vacation rental located in the picturesque hamlet of San Regolo, just 10 km from the charming town of Gaiole In Chianti, Italy. This resort boasts 6 houses, offering guests a serene and peaceful escape. The property is equipped with a range of amenities, including a swimming pool, internet WiFi, parking facilities, an EV charging station, and the option for an installment plan.
Outdoors
Immerse yourself in the beauty of the Tuscan countryside at Villa San Regolo. The resort features a shared swimming pool (15 x 6 m, with a depth ranging from 120 to 220 cm) available seasonally from May 1st to October 25th. Guests can also enjoy a children's pool, an outdoor shower, and a beautifully maintained garden with furniture, tended to by the owner/gardener.
Other Information
Villa San Regolo offers a range of additional services and facilities to enhance your stay. The complex features a reception area, and guests can indulge in relaxing massages (at an extra cost). Central heating is available, along with laundry facilities, including a shared washing machine. Heating costs are payable on-site (from March 29th to October 31st) and is available from November 1st to March 28th. Bicycles (6) are available for rent (extra charge), and a cook can be arranged upon request (additional cost). Parking is provided on the premises, and an e-charging station is available for electric vehicles.
Distances and Attractions
Villa San Regolo is conveniently located near several attractions and points of interest. The Castello di Brolio is just 2 km away, while Castelnuovo Berardenga is 13 km from the resort. The historic city of Siena is a 20 km drive, and Castellina in Chianti is 27 km away. Other nearby destinations include Greve in Chianti (35 km), Monteriggioni (35 km), and Monte San Savino (39 km). For those seeking a beach getaway, the sandy shores of Castiglione della Pescaia are 115 km from the resort, and the thermal baths of Rapolano Terme are just 26 km away. Gaiole in Chianti 915
Gaiole in Chianti 649
Multi-unit villa with WIFI, A/C, private pool, TV, terrace, pets allowed, panoramic view
- 3
- 24
- 10
- 5
| Accommodation | |||||
|---|---|---|---|---|---|
| Montechioccioli 649.1 | 6 | 2 | 1 | ||
| Montechioccioli 649.2 | 6 | 2 | 1 | ||
| All 2 Accommodations | 12 | 4 | 2 |
Description
Property Summary
Nestled in the picturesque hamlet of Rietine, just 4 km from the centre of Gaiole in Chianti, Italy, Montechioccioli is a charming 3-family house that offers an authentic and rustic holiday rental experience in the heart of Tuscany. Surrounded by rolling vineyards and breathtaking countryside, this property comprises 3 separate apartments, making it an ideal choice for families or groups of friends seeking to immerse themselves in the beauty of the Tuscan landscape. The property features a generous terraced yard spanning 1,000 m2, beautifully landscaped with a variety of plants and trees that frame the surrounding scenery. Guests can take a refreshing dip in the impressive swimming pool, which measures 12 x 6 m with a depth of 170 cm and is available seasonally from 02 May to 03 October. Staying connected is effortless thanks to the internet wifi available throughout the property, while an EV charging station further enhances the convenience and modernity of this countryside retreat. A washing machine is also available for shared use among guests, and parking is provided on the premises.
Outdoors
The outdoor spaces at Montechioccioli are a true highlight of the property, offering guests a wonderful setting in which to unwind and enjoy the Tuscan countryside. The terraced garden, extending across 1,000 m2, is thoughtfully planted with a diverse selection of trees and plants, creating a lush and tranquil environment that invites relaxation at every turn. The swimming pool area, where the pool reaches a depth of 170 cm, is complemented by a dedicated shower and WC facility, ensuring comfort and practicality for all guests. Adjacent to the pool, a terrace equipped with a barbecue provides an ideal space for outdoor dining and socialising, allowing guests to savour al fresco meals while taking in the panoramic views of the surrounding vineyards and hills.
Other Information
The owner of Montechioccioli resides on the same property, ensuring a welcoming and attentive presence throughout your stay. The swimming pool is available on a seasonal basis, open from 02 May to 03 October. A washing machine is available on the premises and is shared among the guests of the 3 apartments. Parking is conveniently provided on site at no additional inconvenience to guests.
Distances and Attractions
Montechioccioli enjoys an enviable location that places guests within easy reach of some of Tuscany's most celebrated destinations. The centre of Gaiole in Chianti is just 4 km away, offering a charming selection of local restaurants, shops, and services that capture the essence of authentic Chiantishire life. The historic town of Radda in Chianti lies approximately 12 km from the property, providing further opportunities to explore the region's renowned wine culture, medieval architecture, and traditional Tuscan cuisine. For those wishing to venture further afield, the magnificent city of Siena, a UNESCO World Heritage Site famed for its Gothic cathedral and the legendary Piazza del Campo, is located approximately 40 km from the property and makes for an unforgettable day trip. Gaiole in Chianti 649
Special Offer for Montechioccioli 649.1
Apartment:
Montechioccioli 649.2
Last-Minute Offer for Montechioccioli 649.1
Other apartments with last-minute offers:
Montechioccioli 649.2
Villa Cincinelli
Superb independent property with WIFI, private pool, TV and pets allowed, near Arezzo
- 18
- 8
- 5
Description
Villa Cincinelli is a lovely holiday home with WiFi internet and private pool. The property can accommodate up to 18 guests comfortably in eight bedrooms with five bathrooms. Villa Cincinelli is located 5 km (3 mi) from Capolona, Italy and only 18 km (11 mi) from Arezzo in the tourist area "Arezzo And Surroundings".
The Experience
The villa is internally composed by five independent apartments, each with its own entrance and not communicating internally; in spite of this one offers a large dining area with a table suitable to seat the entire group (ground floor, in front of the pool).
Outside, dining together is possible by joining some tables - in the part of the garden facing the swimming-pool.
in case the clients are less than the villa can sleep and the relative discount is applied, one or two apartments with 1 bedroom each will not be available.
After arriving you’ll find a lovely clean well-maintained property perfect for a relaxing vacation in Tuscany. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of sightseeing.
Visit the Area
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 18 km (11 mi), Cortona 45 km (28 mi), Montepulciano 66 km (41 mi), Greve In Chianti 86 km (53 mi) and Siena 88 km (55 mi).
Some other major tourist destinations you should consider visiting are: Florence 102 km (63 mi), Viareggio 189 km (117 mi), Forte Dei Marmi 196 km (122 mi), Rome 238 km (148 mi), Venice 345 km (214 mi) and Milan 387 km (240 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Cincinelli. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 15:30 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 June - 15 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 109 km (68 mi), Pisa (psa) 170 km (105 mi), Bologna (blq) 194 km (120 mi), Roma Ciampino (cia) 247 km (154 mi) and Roma Fiumicino (fco) 260 km (161 mi).
Villa Cincinelli
Book 15 days or less before the arrival date and receive a 20 % discount off the published rental rates.
This Offer is valid only for stays of 7 nights minimum and can not be combined with any other special offers.
- 10
- 5
- 5
Description
Conveniently located 2 km (1 mi) from Adatti, Italy in the tourist area "Central Tuscany" and only 18 km (11 mi) from Cortona. Villa Il Biancospino is a lovely vacation rental (180 sq m) with private pool and WiFi internet. The property can accommodate up to ten people comfortably in five bedrooms with five bathrooms.
The Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property ideal for a peaceful vacation in Tuscany. Regardless of how you spend your days - visiting museums, shopping, sightseeing or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. If you enjoy cooking for family and friends there is a well-equipped kitchen including plenty of tableware and cutlery for up to ten people.
Places Nearby
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 18 km (11 mi), Arezzo 38 km (23 mi), Montepulciano 48 km (30 mi), Gubbio 66 km (41 mi) and Perugia 77 km (48 mi).
If you'd like to visit the beautiful Tuscan coast, it's just a short driving distance to the sea from the property, only 15 km (9 mi).
Some other major tourist destinations you should consider visiting are: Florence 125 km (78 mi), Viareggio 209 km (130 mi), Forte Dei Marmi 219 km (136 mi), Rome 229 km (142 mi), Venice 373 km (232 mi) and Milan 412 km (256 mi).
Additional Information
Pool Open: 3 April - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 132 km (82 mi), Pisa (psa) 193 km (120 mi), Bologna (blq) 217 km (135 mi), Roma Ciampino (cia) 238 km (148 mi) and Roma Fiumicino (fco) 250 km (155 mi).
Villa Il Biancospino
Villa Ginestra
Unique private house with WIFI, private pool, A/C, TV, patio and panoramic view, close to Cortona
- 6
- 3
- 3
Description
Villa Ginestra is a beautiful stone building (100 sq m) with air conditioning, WiFi internet and private pool. The property can sleep up to six people comfortably in three bedrooms with three bathrooms. Conveniently located 5 km (3 mi) from Poggioni, Italy in the tourist area "Cortona And Surroundings" and only 14 km (9 mi) from Cortona.
The Experience
Upon arrival at Villa Ginestra you’ll find a lovely clean well-maintained property with views of the mountains and the hills ideal for a peaceful vacation in Tuscany. After a hectic day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. For your pleasure, on the grounds there is a barbecue grill and patio. Sharing a meal with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to six people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the perfect setting to enjoy food, family and the lovely Tuscan weather.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 14 km (9 mi), Arezzo 42 km (26 mi), Montepulciano 44 km (27 mi), Perugia 66 km (41 mi) and Gubbio 69 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 135 km (84 mi), Viareggio 229 km (142 mi), Forte Dei Marmi 236 km (147 mi), Rome 224 km (139 mi), Venice 376 km (233 mi) and Milan 428 km (266 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 149 km (93 mi), Pisa (psa) 210 km (130 mi), Bologna (blq) 230 km (143 mi), Roma Ciampino (cia) 233 km (145 mi) and Roma Fiumicino (fco) 245 km (152 mi).
Special Services
Cooking Lessons - Discover from a local chef the techniques required to master Tuscan cuisine. The owner can organize to have a chef come to the property for a cooking lesson for any number of people in your group. It's a pleasant way to spend time with friends and family while learning the secrets needed to prepare delicious Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will schedule the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Inquire for more details and the extra costs.
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours offered, speak to the owner after arriving or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be arranged. Speak to the owner directly about this service after arriving.
Villa Ginestra
Cerretalta
Pretty private villa rental with private pool, WIFI, A/C, TV, patio, panoramic view, near Montalcino
- 14
- 7
- 8
Description
Villa Cerretalta is in a wonderful position on a small hill surrounded by Brunello vineyards, within the national park of Val D'Orcia. The 7 bedroom, 6 bath property is set between the cities of Montalcino and San Quirico D'Orcia (both are about 10 km away), yet in few minutes you can reach the little town of Torrenieri (5 km) where you can find the nearest shops, supermarket and restaurants.
The owner occasionally uses the independent building nearby and whilst respecting your privacy will be at your disposal if you should need any help.
Cerretalta is completely surrounded by hedges and fences to guarantee total privacy. Nonetheless, you have a wonderful sight over the countryside.
Once you enter the gateway, there is a large courtyard plenty of tables and chairs at guests’ disposal as well as the brick barbeque. Across the court there is a lovely area with a big round stone table and matching benches sheltered from the sun by a pergola. Here there is also a second way out from the property, down a stone staircase and through a small iron gate.
There are two garden areas.
The first one is bordered by mature trees, should the guests enjoy a peaceful shady lawn, and it is situated next to a white travertine floored space with tables, chairs and parasol. This is the perfect location where you can have your meals, while taking in the beautiful view over the surrounding farmland.
From here, few stone steps lead to the second garden that is located near the poolside. A small gate possibly delimits the way so as to prevent little children from reaching the swimming-pool area without permission. Some fruit trees, flowers and shrubs brighten the place and there is also a gazebo with table and chairs. An extensive hedge marks the limits of the patch.
Distances: Torrenieri 5 km, San Quirico D'Orcia 10 km, Montalcino 12 km, Bagno Vignoni 14 km, Pienza 18 km, Montepulciano 32 km, Siena 36 km, Monte Amiata 45 lm, Grosseto 70 km, Firenze 100 km, Roma 200 km.
At guests' disposal:The salt water swimming pool is 12 x 6 meters, and has a depth from 1.20 to to 1.60 m.
Here there are parasols and several sun-loungers to relax in.
The seventh bathroom of the property is situated here at the poolside. In addition there is also an outdoor shower. Baby bed and highchair available on site free of charge.
Wi Fi connection is available in the villa.
Tennis table available free of charge.
children playground.
Motor vehicle access to the house: 3 km via unpaved road.
Air conditioning is also available in each of the bedrooms, to be charged according to consumption.
Extra Services: Four extra bed are available upon request at € 200,- / for week / each (to be paid on the spot).
Please carefully check if there are any extra costs to be paid on site! Cerretalta
Book 15 days or less before the arrival date and receive a 20 % discount off the published rental rates.
This Offer is valid only for stays of 7 nights minimum and can not be combined with any other special offers.
Villa Magnolia
Private Villa with hot tub, WIFI, private pool, A/C, TV, terrace, panoramic view, close to Cortona
- 10
- 5
- 5
Description
Villa Magnolia is a lovely stone building (240 sq m) with air conditioning, hot tub and WiFi internet. The property can accommodate up to ten guests comfortably in five bedrooms with five bathrooms. Conveniently located 5 km (3 mi) from Poggioni, Italy in the tourist area "Cortona And Surroundings" and only 15 km (9 mi) from Cortona.
What to Expect
When you arrive at Villa Magnolia you’ll find a nice clean well-maintained property with views of the hills and the mountains ideal for a splendid holiday in Tuscany. Regardless of how you spend your days - visiting museums, sightseeing, shopping or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. For your pleasure, on the grounds there is a hot tub and barbecue grill. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people. Dine 'al fresco' like a real Tuscan, the fully furnished terrace is the ideal setting to enjoy food, family and the beautiful Tuscan weather.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 15 km (9 mi), Arezzo 42 km (26 mi), Montepulciano 44 km (27 mi), Perugia 66 km (41 mi) and Gubbio 69 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 135 km (84 mi), Viareggio 229 km (142 mi), Forte Dei Marmi 236 km (147 mi), Rome 224 km (139 mi), Venice 376 km (234 mi) and Milan 428 km (266 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Magnolia. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 31 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 149 km (93 mi), Pisa (psa) 210 km (130 mi), Bologna (blq) 230 km (143 mi), Roma Ciampino (cia) 233 km (145 mi) and Roma Fiumicino (fco) 246 km (152 mi).
More Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be arranged at the property. It's a enjoyable way to spend time with friends and family while discovering the techniques needed to master Tuscan cuisine. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will schedule the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Inquire for more details and the additional costs.
Tours - Custom tours can be organized by the owner for your group. For more details about the tours available, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Baby Sitting - A babysitter can be arranged at Villa Magnolia. If you're traveling with kids and would like some alone time, speak to the owner directly about this option upon arrival.
Villa Magnolia
Villa Ulivacci
Wonderful private holiday home with A/C, WIFI, private pool, TV, patio and panoramic view
- 9
- 5
- 2
Description
Villa with private pool, close to Montevarchi, just a few kilometres away from some of the most important farms and wine producers of Tuscany.
The villa is a spacious country house and is perfect for guests who want to relax surrounded by nature and explore little villages and art cities in Tuscany such as Gaiole in Chianti, Castellina in Chianti, Radda in Chianti, Panzano, and also Florence, Siena, Arezzo.
The house has a private garden with swimming pool at the guests' exclusive use, there is also a covered patio equipped with tables and chairs and barbecue.
At the guest disposal: private swimming pool, private garden, covered veranda equipped with table and chairs for al fresco dining, internet wi-fi (free wi-fi), with PC and printer, barbecue, private parking; air contioned bedrooms.
Distances: Cavriglia (all kind of shops) 1,5 km, Gaiole in Chianti 11 km, Arezzo 40 km, Siena 40 km, San Gimignano a 60 km, Florence 60 km, Montepulciano 80 km, Montalcino 85 km, Pienza 85 km, Orvieto 135 km.
Please carefully check if there are any extra costs to be paid on site! Villa Ulivacci
