Santa Maria Vacation Villa Rentals
Results 381 - 400 of 644
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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 | |||||
|---|---|---|---|---|---|
| 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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| 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
Poggio Mori 20
Private House with sauna, WIFI, private pool, A/C, TV, patio, panoramic view, close to Montepulciano
- 20
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Description
Property Summary
Poggio Mori is an elegant 18th century farmhouse transformed into a luxury villa that stands at the end of a white unpaved road in the heart of the Tuscan countryside south of Siena, just outside the charming borgo of Sarteano in Italy. This exceptional property masterfully combines respect for traditional Tuscan materials including stone, wood and terracotta with contemporary modern design to create an environment of the highest quality. You will enjoy access to a panoramic swimming pool set within the expansive grounds, a private tennis court for your sporting pursuits, and a bowling green for leisurely entertainment. The property ensures you remain connected throughout your stay with internet wifi available across all areas. Ample parking is provided for your convenience, while the surrounding yard extends across an impressive 25 acres of green space. An adjoining annex houses a comprehensive fitness area featuring gym equipment and a dedicated wellness room equipped with both a sauna and Turkish bath, offering you complete relaxation and rejuvenation during your stay.
Outdoors
The exterior of the property encompasses 25 acres of beautifully maintained green space that provides you with numerous opportunities for outdoor enjoyment and recreation. The panoramic swimming pool serves as a stunning focal point where you can refresh yourself while taking in breathtaking views of the surrounding Tuscan landscape. Adjacent to the pool area, you will find a regulation tennis court where you can engage in competitive matches or practice your skills. The grounds also feature a bowling green that offers a more leisurely sporting option for you and your guests. The expansive yard provides ample space for outdoor activities, peaceful walks through the countryside, or simply relaxing in the tranquil natural environment. You can explore the organic farming areas where the property cultivates excellent extra-virgin olive oil, wine, vinsanto and produces organic preserves and jams that authentically represent the traditional agricultural heritage of the region.
Other Information
The property maintains a commitment to organic farming traditions, allowing you to taste excellent extra-virgin olive oil, wine, vinsanto sweet white dessert wine, organic preserves and jams in the fabulous multi-function room located next to the main house. You can arrange for cook service, cooking classes or additional domestic staff upon request to enhance your experience. The villa is equipped with air conditioning throughout to ensure your comfort in warmer months. Entertainment options include satellite TV in both the common areas and bedrooms, with audio and video capabilities in all televisions, a DVD player, and a stereo system with CD player and cable radio in the shared spaces. The property features an advanced I-Pad home control system that allows you to manage lighting, climate and music settings, along with a video projector in the living area for your viewing pleasure. A traditional wood oven is available for authentic cooking experiences, while mosquito screens in the bedrooms and kitchen provide protection during summer evenings. Bicycles are provided for exploring the surrounding countryside. Each bedroom is equipped with its own safe for securing your valuables, and complimentary toiletries are supplied in all bathrooms. You will have access to a PC, fax and printer for any business needs. The annex contains laundry facilities with both a washing machine and dryer for your convenience. The external covered gym in the annex includes a cyclette, tapis roulant and multi-function bench, while the wellness area features a sauna, Turkish bath, relaxation room with beds and a dedicated massage area.
Distances and Attractions
Poggio Mori enjoys a privileged position between Val di Chiana and Val d'Orcia, providing you with the perfect base to explore the renowned hill towns and destinations of southern Tuscany. The medieval walled town of Sarteano lies just 10 minutes away from the property, offering you immediate access to local amenities, restaurants and historical charm. From this central location, you can easily visit Montepulciano with its magnificent Renaissance architecture and celebrated wine cellars, the ancient Etruscan town of Chiusi with its remarkable archaeological museums, the UNESCO World Heritage site of Pienza known for its perfect Renaissance urban planning and pecorino cheese, and Montalcino famous for its prestigious Brunello wine production. The thermal spa towns of Chianciano Terme and San Casciano dei Bagni are within comfortable reach, allowing you to experience their healing waters and wellness facilities. Numerous other places of timeless charm throughout the Val d'Orcia and Val di Chiana regions await your discovery, each offering unique cultural experiences, exceptional cuisine, local artisan products and stunning landscapes that define the essence of Tuscany. Poggio Mori 20
Gaiole in Chianti 649
Stunning multi-unit property with A/C, private pool, WIFI, TV, terrace, pets allowed, panoramic view
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- 12
- 6
| Accommodation | |||||
|---|---|---|---|---|---|
| Montechioccioli 649.1 | 6 | 2 | 1 | ||
| Montechioccioli 649.2 | 6 | 2 | 1 | ||
| Montechioccioli 649.3 | 6 | 2 | 1 | ||
| Montechioccioli 649.4 | 12 | 6 | 3 | ||
| All 4 Accommodations | 30 | 12 | 6 |
Description
Property Summary
The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the charming hamlet of Rietine, just 4 km from the center of Gaiole In Chianti, Italy. This property features three apartments available for rent, making it an ideal choice for families or groups of friends seeking to experience the beauty of Tuscany. Montechioccioli boasts a range of amenities, including a Swimming Pool, Yard, Internet Wifi, Parking, and an Installment Plan.
Outdoors
Montechioccioli is a true countryside gem with a terraced garden spanning 1,000 m2, adorned with a variety of plants and trees. It offers a serene setting for guests to relax and take in the stunning views of the Tuscan countryside. The property boasts a seasonal swimming pool, measuring 12 x 6 m with a depth of 170 cm, available from May 2nd to October 3rd. The pool area features a shower/WC and a terrace with a barbecue, perfect for alfresco dining and enjoying the warm Italian evenings.
Other Information
The property provides additional conveniences, such as a washing machine for shared use and parking on the premises. It is worth noting that the owner resides on the same property. Montechioccioli offers a truly unforgettable vacation rental experience in the heart of Tuscany.
Distances and Attractions
Montechioccioli is strategically located just 12 km from the center of Radda in Chianti and 40 km from the historic city of Siena, making it an ideal base for exploring the region's many attractions. Nearby, guests can discover the charming town of Gaiole in Chianti, known for its rich cultural heritage and picturesque surroundings. Gaiole in Chianti 649
Last-Minute Offer for Montechioccioli 649.1
Other apartments with last-minute offers:
Montechioccioli 649.2
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Description
It is a semi-detached house, the ground floor part is this holiday home and upstairs lives the owner's brother (with a completely separate entrance).
The private pool is 800 mt distant from the villa, and is located on the owners' property. It is better reachable by car.
The pool will be for the guests' exclusive use. In the pool area, you will also have access to a gazebo with dining table and refrigerator, as well as a bathroom with shower.
There are golf, padel courts and e-bike rental in the vicinity of the villa (about 2 km away).
Conveniently located in the centre of Cavriglia, Italy in the tourist area "Chianti" and only 32 km (20 mi) from Greve In Chianti. Holiday rental Il Campanile is a lovely stone building (120 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to six people comfortably in three bedrooms with two bathrooms. If playing a round of golf is important while on vacation, you are in luck because there is a course nearby.
Your Experience
Upon arrival at Il Campanile you’ll find a nice clean well-maintained property perfect for a relaxing vacation in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of shopping. Also available outdoors are a barbecue grill and patio. 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 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 balcony 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 vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 32 km (20 mi), Siena 42 km (26 mi), Arezzo 46 km (28 mi), San Gimignano 55 km (34 mi) and Florence 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 68 km (42 mi), Viareggio 155 km (96 mi), Forte Dei Marmi 162 km (100 mi), Rome 249 km (155 mi), Milan 355 km (220 mi) and Naples 440 km (273 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Il Campanile. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 11:00
Pool Open: 1 January - 31 December
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 73 km (45 mi), Pisa (psa) 136 km (84 mi), Bologna (blq) 160 km (99 mi), Roma Ciampino (cia) 258 km (160 mi) and Roma Fiumicino (fco) 271 km (168 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques vital 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 enjoyable way to spend time with friends and family while learning the secrets vital to prepare sumptuous 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 vacation? Why not book a professional chef to prepare and serve you a delicious 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 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 when you arrive or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be scheduled by the owner. Inquire for more details about the additional cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you check-in that is possible at Il Campanile. Ask for more details, including the additional cost and how to organize this service.
Baby Sitting - A babysitter can be organized at Il Campanile. If you're traveling with kids and would like some alone time, speak to the owner directly about this option upon arrival.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
Il Campanile
Book 10 days or less before the arrival date and receive a 8 % 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 Cincinelli
Stunning independent vacation home with WIFI, private pool, TV and pets allowed, close to Arezzo
- 18
- 8
- 5
Description
Vacation rental Villa Cincinelli is a lovely property that includes private pool and WiFi internet. The property can accommodate up to 18 people comfortably in eight bedrooms with five bathrooms. Conveniently located 5 km (3 mi) from Capolona, Italy in the tourist area "Arezzo And Surroundings" and only 18 km (11 mi) from Arezzo.
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.
Upon arrival you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property perfect for a relaxing vacation in Tuscany. After a hectic day of visiting museums, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day.
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: 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
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Description
Property Summary
Podere della Bruciata is a beautiful 18th-century farmhouse nestled in the tranquil hills of Chiusi, Italy, offering an authentic Tuscan retreat with breathtaking views over the surrounding countryside. This historic holiday villa combines rustic charm with modern comfort, accommodating guests in an independent property that consists of a main building and a converted barn. You will enjoy complete privacy in this peaceful corner of Tuscany, surrounded by lush vegetation and scenic walking trails in an area renowned for its fascinating Etruscan heritage. The property features convenient Internet Wifi connectivity throughout and ample Parking facilities for your vehicles. With its impressive swimming pool enhanced by a delightful waterfall feature, this farmhouse provides an idyllic setting for relaxation and memorable gatherings in the heart of the Italian countryside.
Outdoors
The outdoor spaces at Podere della Bruciata are designed to maximize your enjoyment of the stunning Tuscan landscape. The centerpiece is a generous swimming pool measuring 7 by 14 meters with a depth ranging from 1 to 1.50 meters, beautifully enhanced by a cascading waterfall that creates a soothing ambiance. The pool is surrounded by well-maintained green spaces perfect for sunbathing and outdoor relaxation. You will find a spacious porch complete with a gazebo and tables, providing shaded areas for al fresco dining while taking in the panoramic views of the surrounding hills. A barbecue facility is available for your outdoor cooking pleasure, allowing you to prepare delicious meals in the open air. The barn section of the property features its own porch with direct views of the pool area, while the main building offers a charming garden corner with vistas overlooking Chiusi. The swimming pool is open from April 15 to October 15, ensuring availability throughout the warmer months.
Unit Layout
This spacious farmhouse accommodates a maximum capacity of 18 guests across 9 bedrooms and 10 bathrooms, providing generous space and comfort for large families or groups. The main building is distributed over two floors, with the ground floor featuring a welcoming rustic tavern area, a fully equipped kitchen, a service bathroom that doubles as a laundry area, and a rustic dining room. This level also houses 2 double bedrooms, each with a private bathroom with shower, and includes a dedicated corner with internet service. On the first floor, accessed through a charming loggia entrance, you will discover a comfortable living room and a kitchenette equipped with 2 ovens. This floor contains 4 additional bedrooms, comprising 2 double bedrooms and 2 double or twin bedrooms, each accompanied by its own private bathroom with shower. The converted barn provides independent accommodation with 3 more bedrooms, including 2 double bedrooms and 1 double or twin bedroom, each featuring an en-suite bathroom with shower. All 3 bathrooms in the barn are specially designed to be suitable for disabled people, and these rooms benefit from independent entrance access and porch areas overlooking the pool.
Amenities Included
The property is comprehensively equipped to ensure your comfort throughout your stay. The kitchen areas feature modern conveniences including a Dishwasher in both the main kitchen and the first-floor kitchenette, making meal preparation and cleanup effortless. For your entertainment needs, you will find a Television with Satellite TV service available for your viewing pleasure. The cozy rustic tavern on the ground floor is enhanced by an attractive Fireplace, creating a warm and inviting atmosphere for cooler evenings. A Washing Machine is conveniently located in the service bathroom, providing practical laundry facilities during your stay. The outdoor amenities include a Barbecue area perfect for grilling and outdoor cooking experiences. The extensive Private Garden surrounds the property, offering beautiful views and peaceful spaces for relaxation. Heat is Available for your comfort, with heating facilities provided throughout the farmhouse. Every room in the property is fitted with mosquito nets and fans to ensure your comfort during warmer weather, and one bathroom in the main building is specially adapted to be suitable for disabled guests.
Other Information
Check-in is available on Saturday from 3 p.m., and checkout is required on Saturday at 10 a.m. Upon your arrival, you will be required to provide a security deposit of 500 euros, which will be returned at the end of your stay minus any costs for damages incurred. A tourist tax may be required upon arrival according to the regulations of the municipality. The property does not have air conditioning in the rooms, but fans are provided in all bedrooms for your comfort. Daily cleaning services are not included during your stay. Pets are welcome at the property, and dogs are accepted with appropriate arrangements. The kitchen facilities and swimming pool use are fully included in your rental. Pool towels are not included in the standard amenities but are available for your convenience.
Distances and Attractions
The farmhouse enjoys a privileged position in the Tuscan countryside near Chiusi, an area rich in historical and cultural significance. The surrounding region is particularly noted for its fascinating Etruscan settlements, offering you the opportunity to explore ancient archaeological sites and historical treasures. The elevated location provides wide panoramic views over the rolling hills that characterize this beautiful corner of Tuscany. The property is surrounded by areas rich in vegetation, making it an ideal base for scenic walks and nature exploration. The peaceful setting ensures you can enjoy the authentic tranquility of rural Tuscany while remaining within reach of local towns, traditional restaurants, and the cultural attractions that make this region so captivating for visitors seeking an immersive Italian experience.
Costs & Services
Included services
- Consumption of water, gas, and electricity
- Final cleaning
- Linen for rooms and bathrooms
- Kitchen use
- Swimming pool use
Extra costs
- Heating: €4.50 per cubic meter of GPL
- Dog accommodation: €25 per dog per week for extra cleaning
- Extra single bed: €15 per day
- Extra crib: €5 per day
- Tourist tax: payable locally according to municipal regulations
- Security deposit: €500
On request
- Pool towels: €5 per rental Podere della Bruciata
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- 3
- 2
Description
Casa Rossa is a suggestive farmhouse of very remote origins. It stands in a very panoramic and peaceful position, overlooking vineyards and olive groves. It can be reached by following an unpaved road (1,5 km) that winds its way through rows of vineyards, and even before you get there you will feel you have been catapulted into another era. The origins of this house are in fact very old and date back at least to 1500, as documented in the register of souls of the parish of Pieve San Giovanni.
The owners, Leone and Giuseppe, have intentionally maintained its rustic, almost medieval appearance in order to preserve its noble origins. The wooden and brick ceilings, the original terracotta floors and the simple and essential furnishings are a rare example of the rural tradition in Tuscany. The farmhouse is particularly suitable for couples or families who love nature and simplicity and want to get away from modern life for a while.
Pets are welcome (extra charge could be required).
You will find yourself facing an incomparable view on summer evenings, sitting by the pool (size 5 x 9 m, depth 1.20 m, private for guests - open from 16 May to 12 September) or dining in the furnished pergola in front of the house. And if you feel like leaving the quiet of the place for a while, the city of Arezzo is reachable in 15 minutes by car, and throughout the year it offers countless folkloristic and cultural events, including the Giostra del Saracino and the Antique Fair.
For horse lovers, there is a riding school less than 500 m from the house that organises rides through the vineyards and hills. Casa Rossa
Oliveto del Cantarello
Amazing villa with WIFI, TV and pets allowed, near Montepulciano
- 4
- 2
- 1
Description
Oliveto Del Cantarello is located 7 km (4 mi) from Chiusi, Italy and only 18 km (11 mi) from Montepulciano. Oliveto Del Cantarello is a nice holiday rental (76 sq m) with WiFi internet. The property can accommodate up to four people comfortably in two bedrooms with one bathroom.
The Experience
After arriving at Oliveto Del Cantarello you’ll find a lovely clean well-maintained property perfect for a relaxing vacation in Tuscany. For your enjoyment you will find a private garden where you can relax while enjoying a nice cold beverage after a busy day of sightseeing. A real benefit of renting a home, instead of multiple hotel rooms, is the ability to relax after a busy day of sightseeing with family and friends. Enjoy a meal together along with some local wine to finish the day. 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 vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to four people.
What's Nearby?
Most people enjoy visiting nearby 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: Montepulciano 18 km (11 mi), Montalcino 45 km (28 mi), Cortona 51 km (32 mi), Arezzo 62 km (38 mi) and Siena 81 km (51 mi).
Some other major tourist destinations you should consider visiting are: Florence 135 km (84 mi), Viareggio 221 km (137 mi), Forte Dei Marmi 228 km (142 mi), Rome 168 km (104 mi), Venice 378 km (235 mi) and Milan 423 km (263 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Oliveto Del Cantarello. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 140 km (87 mi), Roma Ciampino (cia) 177 km (110 mi), Roma Fiumicino (fco) 189 km (118 mi), Pisa (psa) 202 km (126 mi) and Bologna (blq) 226 km (141 mi).
Oliveto Del Cantarello
Borgo Dolciano
Nice apartment with A/C, WIFI, private pool, TV, veranda and pets allowed, near Montepulciano
- 35
- 16
- 17
Description
Conveniently located 5 km (3 mi) from Chiusi, Italy and only 20 km (12 mi) from Montepulciano. Borgo Dolciano is a nice stone building (600 sq m) with WiFi internet, private pool and air conditioning. The property can sleep up to 35 people comfortably in 16 bedrooms with 17 bathrooms.
A residence made up of 16 apartments located in the park of the old Medici villa. Guests have at their disposal a park with a swimming pool, a barbecue area and two small internal gardens where they can relax.
Available on request:
LA LIMONAIA, a very bright room that can easily accommodate up to 65/70 people.
THE ANCIENT CELLARS, which can accommodate up to 120 people.
THE CHURCH, still consecrated, ideal for celebrations.
PRIVATE RESTAURANT: the property has a private restaurant available on request for private dinners with or without a chef.
The property is fenced and we accept more than one dog.
The Experience
Upon arrival you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills perfect for a splendid vacation in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of sightseeing. If you enjoy cooking for family and friends there is a well-equipped kitchen including microwave and refrigerator, as well as, plenty of tableware and cutlery for up to 35 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 holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montepulciano 20 km (12 mi), Cortona 35 km (22 mi), Montalcino 51 km (32 mi), Perugia 65 km (40 mi) and Arezzo 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 138 km (85 mi), Viareggio 224 km (139 mi), Forte Dei Marmi 231 km (144 mi), Rome 171 km (106 mi), Milan 424 km (264 mi) and Naples 361 km (224 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Borgo Dolciano. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 15:00 - 18:00
Check-Out Time: 08:00 - 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) 143 km (89 mi), Roma Ciampino (cia) 180 km (112 mi), Roma Fiumicino (fco) 192 km (120 mi), Pisa (psa) 206 km (128 mi) and Bologna (blq) 229 km (143 mi).
Additional Services
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 organize the meal based on your preferences and dietary requirements. The chef will offer suggestions for the various courses and the wine. Inquire for more details and the additional costs.
Meals - If you'd like to have meals provided during your stay, either half-board or full-board is available. If you prefer only breakfast be provided, that can be arranged as well. Ask about the supplemental 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 inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Maid Service - If you'd like maid service during your trip that can be scheduled by the owner. Inquire for more details about the extra cost.
Baby Sitting - A babysitter can be arranged at Borgo Dolciano. If you're traveling with kids and would like some alone time, talk to the owner directly about this option after arriving.
Borgo Dolciano
- 6
- 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 Canto al Sole
Book now and save 10%. Offer valid until 30 June 2026 and for a minimum stay of 7 nights.
Last-Minute Offer for Lilla
Book 10 days or less before the arrival date and receive a 15 % discount off the published rental rates.
This Offer is valid only for stays of 5 nights minimum and can not be combined with any other special offers.
Podere
Superb independent villa rental with private pool, WIFI, TV, terrace, pets allowed, panoramic view
- 14
- 7
- 4
Description
Property Summary
Podere Filicaia is a tranquil vacation rental located in the heart of Tuscany's countryside. This manor house sits 150 meters above sea level and features 5 apartments, making it perfect for families or groups of friends traveling together. The property boasts a private swimming pool, a yard, internet WiFi, and ample parking spaces.
Outdoors
One of the highlights of Podere Filicaia is its private swimming pool, measuring 12 x 6 meters with a depth of 120 - 200 cm. The pool is available seasonally from May 7th to September 24th and comes complete with an outdoor shower, garden furniture, and a barbecue.
Other Information
The owner lives on the same property, ensuring that someone is always available to answer any questions or address any concerns you may have during your stay. Heating is available from November 1st to April 7th for an additional fee.
Distances and Attractions
Podere Filicaia is conveniently located 3.8 kilometers from the center of San Giovanni Valdarno, 18 kilometers from the center of Gaiole in Chianti, and 26 kilometers from the center of Radda in Chianti. Nearby attractions include Castello di Meleto, Greve in Chianti, Castellina in Chianti, Panzano in Chianti, Firenze, and Siena, allowing you to explore the rich cultural heritage of Cavriglia, Italy. Podere
- 8
- 4
- 2
Description
Property Summary
Caiano is a charming and rustic vacation rental located in the heart of Tuscany, 750 meters above sea level. Surrounded by nature, including trees, fields, and vineyards, it offers a peaceful escape from city life. The property boasts a private terraced garden spanning 1,000 square meters, complete with a wildlife garden, natural garden, meadow, and a seasonal swimming pool available from May 1st to September 30th. The pool's unconventional shape adds to the property's unique charm. Additionally, Caiano provides an outdoor shower, terrace, and parking for up to three cars.
Outdoors
Caiano's private terraced garden is a true highlight, spanning 1,000 square meters and fenced for privacy and security. The garden features a wildlife garden, natural garden, and meadow, creating a serene and natural environment. The seasonal swimming pool, available from May 1st to September 30th, is a standout feature with its unconventional shape, adding to the property's charm. An outdoor shower and terrace further enhance the outdoor experience.
Other Information
A car is recommended to fully explore Caiano and the surrounding area. The nearest shop is 4 kilometers away, while a supermarket is located 8 kilometers from the property. The closest railway station, San Giovanni Valdarno, is 12 kilometers away, providing convenient access to transportation options.
Distances and Attractions
Caiano is strategically located in Cavriglia, Italy, offering a balance of seclusion and convenience. The property is situated 8 kilometers from the center of Radda in Chianti and 7 kilometers from the center of Cavriglia. Additionally, the famous city of Siena is just 38 kilometers away, providing easy access to some of Tuscany's most renowned sights and attractions. Caiano
- 4
- 2
- 2
Description
Property Summary
Manor house "Tribolina" is a charming holiday rental situated on a sunny hill in the countryside of Cavriglia, Italy. With a vast area of 23 hectares and a natural garden exclusively for guests, it offers a tranquil escape surrounded by scenic beauty. The property boasts amenities like a yard, internet Wi-Fi, and parking facilities, ensuring a comfortable stay.
Outdoors
Immerse yourself in the serene ambiance of the natural garden, thoughtfully equipped with garden furniture and a barbecue area. Soak in the tranquility and embrace the picturesque surroundings, creating cherished memories in this idyllic outdoor space.
Other Information
The property comprises two houses, with the owner residing on-site, ensuring attentive assistance whenever required. Guests can conveniently park their cars on the premises, although the final 100 meters to the house requires traversing an unmade road. Heating is available from November 1st to April 15th, with charges payable on location. For those seeking local produce, a nearby farm offers a delightful opportunity to explore the flavors of the region.
Distances and Attractions
Nestled in a prime location, Manor house "Tribolina" is just 3 kilometers from the charming village of Cavriglia, 12 kilometers from Montevarchi, and 65 kilometers from the vibrant city of Florence. Nearby attractions include the renowned Rapolano Terme thermal baths (50 kilometers away), Gaiole in Chianti (9 kilometers), Radda in Chianti (12 kilometers), the Prada outlet (14 kilometers), and easy access to Siena, Arezzo, and The Mall outlet, offering a diverse array of experiences for visitors to indulge in. Tribolina
Agriturismo Cincinelli
Fantastic apartment with WIFI, pool, TV, patio, pets allowed and panoramic view, close to Arezzo
- 5
- 19
- 8
- 5
| Accommodation | |||||
|---|---|---|---|---|---|
| Capanno | 2 | 1 | 1 | ||
| Forno | 2 | 1 | 1 | ||
| Bottegaccia | 4 | 2 | 1 | ||
| Borgo | 6 | 2 | 1 | ||
| Caratello | 5 | 2 | 1 | ||
| All 5 Accommodations | 19 | 8 | 5 |
Description
Property Agriturismo Cincinelli is a beautiful stone building that includes pool and WiFi internet. The apartment / condo has a total of five private units. The property can accommodate up to 19 people comfortably in eight bedrooms with five bathrooms. Conveniently located 5 km (3 mi) from Capolona, Italy in the tourist area "Arezzo And Surroundings" and only 18 km (11 mi) from Arezzo.
Your Experience
When you arrive you’ll find a nice clean well-maintained property with views of 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 unwind at the end the day. For your pleasure, on the grounds there is a barbecue grill and patio. Each apartment has its own private living area with a kitchen with plenty of utensils, tableware and cutlery, a bedroom and bathroom. Many people traveling with friends prefer a multi-unit property where they can spend time together in the common areas, such as the pool or garden, but still have their own private living quarters.
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: Arezzo 18 km (11 mi), Cortona 48 km (30 mi), Montepulciano 66 km (41 mi), Siena 79 km (49 mi) and Greve In Chianti 86 km (53 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 388 km (241 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Agriturismo Cincinelli. If you have a large dog or multiple pets, please ask 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).
Agriturismo Cincinelli
- 4
- 21
- 8
- 4
| Accommodation | |||||
|---|---|---|---|---|---|
| Girasole 801.1 | 4 | 1 | 1 | ||
| Lavanda 801.2 | 6 | 3 | 1 | ||
| Rosmarino 801.3 | 5 | 2 | 1 | ||
| Corbezzolo 801.4 | 6 | 2 | 1 | ||
| All 4 Accommodations | 21 | 8 | 4 |
Description
Property Summary
Manor House "Filicaia" is a beautiful vacation rental located in Cavriglia, Italy, situated at an elevation of 150 meters above sea level. The property comprises five apartments and offers a range of amenities, including a swimming pool, yard, internet WiFi, parking, and the option for an installment plan. Guests can enjoy a comfortable stay with the shared use of a washing machine and heating (charges apply from 01.11 to 07.04). The owner of the property resides on the premises.
Outdoors
The vacation rental boasts a shared swimming pool that measures 12 x 6 meters with a depth of 120-200 cm, available for seasonal use from 07.May to 24.Sep. Guests can unwind in the garden area, complete with outdoor shower facilities, garden furniture, and a barbecue area.
Other Information
The property is conveniently located just 3.8 km from the center of San Giovanni Valdarno, 18 km from the center of Gaiole in Chianti, and 26 km from the center of Radda in Chianti.
Distances and Attractions
Surrounding attractions within driving distance include the Castello di Meleto, Greve in Chianti, Castellina in Chianti, Panzano in Chianti, Firenze, and Siena. With its prime location and proximity to nearby villages and attractions, Manor House "Filicaia" offers the perfect holiday rental for exploring the Tuscan countryside. San Giovanni 801
Villa Ulivacci
Fabulous independent property with WIFI, A/C, private pool, TV, patio and panoramic view
- 9
- 5
- 2
- 10
- 5
- 6
Description
An original stone farmhouse at the gateway to the green Casentino valley and north of the city of Arezzo. The villa Casale Lorenzo with its beautiful fenced park, the large private swimming pool (size 15 x 8 m - depth 1,00 - 2,40 m - open from 01st May to 30th September) with changing room, bathroom with shower and equipped solarium, the relaxing Jacuzzi (Extra payment required) offers wide space for everyone to enjoy an unforgettable holiday with family or friends. You won't be able to give up a dip in the pool, a barbecue on the cool furnished porch or an afternoon in the Jacuzzi with a good glass of wine. Also your small size four-legged friends are welcome here (extra charge could be required).
3 km away from the villa is the small village of Subbiano, where you will find shops, supermarkets and restaurants. Absolutely not to be missed, on hot summer days, is a trip to the nearby Park of the Casentino Forests, among ancient castles and remote monasteries, which will give you moments of true wonder.
The villa Casale Lorenzo is luxuriously equipped with air-conditioning, a billiard room, a large, well-equipped kitchen and an indoor barbecue. A décor composed of local antiques offers countless nooks and crannies for you to relax while reading your favourite book. For you and your children, there is an infinite, safe green space and a billiard table where you can play tournaments and games.
An extra touch comes from the extremely cordial welcome of Massimo and Nadia, the owners, who are always attentive to make you feel welcome and at home. Casale Lorenzo
Capanna al Lago
Stunning independent property with hot tub, WIFI, A/C, private pool, TV, patio and panoramic view
- 6
- 3
- 3
Description
Capanna Al Lago is a lovely stone building (200 sq m) with hot tub, air conditioning and private pool. The property can accommodate up to six people comfortably in three bedrooms with three bathrooms. Conveniently located 8 km (5 mi) from Siena, Italy in the tourist area "Siena And Surroundings" and only 35 km (22 mi) from Greve In Chianti.
What to Expect
After arriving you’ll find a lovely clean well-maintained property with views of the hills and the lake ideal for a peaceful vacation in Tuscany. Regardless of how you spend your days - shopping, sightseeing, 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. Outdoors you will also find a playground, patio, barbecue grill and hot tub. Dining 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 and refrigerator, as well as, plenty of tableware and cutlery for up to six people.
Places Nearby
Most people enjoy visiting nearby 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 35 km (22 mi), San Gimignano 36 km (22 mi), Montalcino 48 km (30 mi), Florence 66 km (41 mi) and Montepulciano 67 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 66 km (41 mi), Viareggio 160 km (99 mi), Forte Dei Marmi 167 km (104 mi), Rome 244 km (151 mi), Venice 316 km (196 mi) and Milan 360 km (224 mi).
Additional Information
Check-In Time: 16:00 - 21:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 10 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) 79 km (49 mi), Pisa (psa) 114 km (71 mi), Bologna (blq) 165 km (103 mi), Roma Ciampino (cia) 253 km (157 mi) and Roma Fiumicino (fco) 265 km (165 mi).
Special Services
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Capanna Al Lago. Inquire for more details, including the supplemental cost and how to organize this service.
Capanna Al Lago
Book now and save 10%. Offer valid until 31 March 2026 and for a minimum stay of 6 nights.
Book your vacation for the period from 08 April 2026 to 23 April 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 01 March 2026 to 10 March 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 29 June 2026 to 10 July 2026 and save 10% (minimum 5 nights).
