Il Pianello Holiday Rentals
Results 421 - 440 of 473
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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Description
Property Summary
Nestled in the rolling Tuscan countryside of Siena, Italy, the charming detached house "L'Oliviera" offers a truly peaceful and sun-drenched retreat for those seeking an authentic holiday rental experience. Positioned in a quiet, elevated setting just 5 km from the historic centre of Siena, this beautiful property is surrounded by trees, open fields, and sits only 100 metres from the edge of a forest, creating a natural and serene atmosphere. The house benefits from complimentary Wi-Fi throughout, allowing guests to stay connected while enjoying the tranquillity of the Tuscan landscape. Private parking is conveniently available directly at the property, ensuring effortless arrivals and departures for those exploring the surrounding region by car.
Outdoors
The outdoor spaces of "L'Oliviera" are a true highlight of the property, offering guests a private and immersive connection with the natural Tuscan environment. The grounds feature a well-maintained lawn alongside a wildlife garden, thoughtfully designed to blend harmoniously with the surrounding countryside and its native flora and fauna. The property is enveloped by trees and open fields, providing a sense of seclusion and privacy that makes it an ideal setting for relaxing outdoors, breathing in the fresh country air, and enjoying the unspoiled beauty of the Sienese hills.
Other Information
Guests should be aware that heating at "L'Oliviera" is available and billed on-site, applicable during the period from 10 April to 31 October. Baby equipment is provided and included at no additional charge, making the property a practical and welcoming choice for families travelling with young children. The owner resides on the same property, ensuring a reassuring presence and the opportunity for personalised local assistance throughout the stay. Guests should also be aware that the owner keeps a dog on the premises. As the property is situated in a rural setting, the use of a car is strongly recommended in order to fully enjoy the surrounding area and access nearby services with ease.
Distances and Attractions
"L'Oliviera" enjoys a convenient location with easy access to a wide range of everyday amenities and cultural landmarks. A grocery store is located just 3 km away, while a shopping centre can be reached within 4 km, and a restaurant is a short 2 km drive from the property. Public transport is readily accessible, with a bus stop situated only 100 metres from the house, and the railway station "Siena" reachable within 6 km. For those wishing to explore the wider Tuscan region, the thermal baths of "Rapolano Terme" are approximately 35 km away, offering a wonderful opportunity for relaxation and wellness. The medieval village of Monteriggioni lies just 16 km from the property, while the iconic hilltop town of San Gimignano is 36 km away. The breathtaking landscape of the Crete Senesi can be explored within 30 km, and the celebrated wine town of Montalcino is situated 45 km from the house. The Renaissance gem of Pienza is approximately 50 km away, and Montepulciano, renowned for its Vino Nobile, can be reached within 65 km, making "L'Oliviera" an exceptional base from which to discover the very best of Tuscany. L'Oliviera
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- 6
- 3
- 3
| 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
Villa del Mangia, 5Panoramic Pool and Chef Service
Superb private holiday rental with WIFI, A/C, private pool, terrace and panoramic view
- 11
- 6
- 6
Description
Villa del Mangia is a villa located just a few kilometers from Siena.
The villa consists of a main building spread over two floors and an external annex, a former stone barn, which serves as the guesthouse. The total area of the property is 400 sqm. The entire complex was fully renovated in 2024, with incredible attention to detail and the use of high-quality materials, skillfully combining the charm of Tuscan tradition with modern comforts, furnishings, and top-tier materials, offering a luxurious and sophisticated environment. The villa, meticulously curated in every detail, reflects the refined taste of the owner and an emphasis on rare, high-quality materials.
The outdoor spaces have been designed with great care, creating a harmonious connection between the villa and the surrounding natural environment. The garden features lush terraced areas, olive trees, and spacious open areas, ideal for hosting large families or groups of friends seeking a relaxing and convivial vacation.
The interiors, enhanced by marbles that provide luminosity and contemporary design, are equipped with a floor heating and cooling system to ensure maximum comfort. At the same time, original elements such as the ceilings and exposed beams preserve the villa's historic charm, offering a perfect balance between the old and the new.
The annexed barn is equally welcoming, with a breathtaking view of Siena: every window in this building frames a picture-perfect scene.
The spacious indoor and outdoor areas provide the opportunity to enjoy moments together without sacrificing tranquility or the possibility of retreating to more intimate spaces. Ideal for large families or groups wanting to spend a pleasant vacation together while maintaining privacy, this villa allows you to fully enjoy the Sienese countryside, while being just a short drive from some of Tuscany's most famous destinations, such as Siena, San Gimignano, and Florence. Villa del Mangia, 5Panoramic Pool and Chef Service
Book your vacation for the period from 01 June 2026 to 26 June 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 01 July 2026 to 31 July 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 09 September 2026 to 19 September 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 13 October 2026 to 31 October 2026 and save 10% (minimum 3 nights).
Gaiole in Chianti 649
Pretty multi-unit villa with WIFI, private pool, A/C, TV, terrace, pets allowed and panoramic view
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- 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
| 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
Le Loggine del Pignatello Apartment, Siena City
Comfortable apartment with WIFI and TV
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- 2
- 2
Description
In the heart of Siena’s historic center, a two-level apartment with access from a charming internal courtyard that offers an authentic and peaceful atmosphere.
Stay in this accommodation to explore the city of Siena and nearby attractions. A must-see is Piazza del Campo, the heart of Siena and one of the most beautiful medieval squares in Europe. This is where the famous Palio di Siena takes place (July 2nd and August 16th). Climbing the Torre del Mangia (about 400 steps) rewards you with a spectacular view over the city’s rooftops and the Tuscan countryside. The Siena Cathedral is one of the most fascinating in Italy, featuring unique inlaid floors and works by Michelangelo, Donatello, and Pisano.
Nearby, you can visit San Gimignano with its medieval towers, the Val d’Orcia with its iconic landscapes, Monteriggioni, a fortified village, and Montalcino, famous for its Brunello wine cellars.
The cities of Florence and Arezzo are also easily reachable.
Parking available on request at an extra cost of €35 per day.
Distance to the bus stop: 20 meters from the front door, with a direct connection to the station escalator in less than 5 minutes. Le Loggine del Pignatello Apartment, Siena City
Terre di Giano Private Pool and View, Umbria
Stunning independent villa with private pool, A/C, hot tub, WIFI, TV, terrace, panoramic view
- 18
- 4
- 5
Description
Terre di Giano Private Pool and View, Umbria is located in Paciano, Italy and only 32 km (20 mi) from Cortona. Property Terre di Giano Private Pool and View, Umbria is a beautiful stone building (400 sq m) that includes hot tub, air conditioning and private pool. The property can accommodate up to 18 guests comfortably.
Your Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills perfect for a relaxing holiday in Umbria. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of visiting museums. Outdoors you will also find a hot tub and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 18 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: Cortona 32 km (20 mi), Montepulciano 37 km (23 mi), Perugia 45 km (28 mi), Arezzo 58 km (36 mi) and Montalcino 65 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 148 km (92 mi), Viareggio 234 km (145 mi), Forte Dei Marmi 241 km (150 mi), Rome 176 km (109 mi), Venice 387 km (240 mi) and Milan 436 km (271 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Terre di Giano Private Pool and View, Umbria. 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: 07:00 - 10:00
Pool Open: 15 May - 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) 153 km (95 mi), Roma Ciampino (cia) 185 km (115 mi), Roma Fiumicino (fco) 198 km (123 mi), Pisa (psa) 215 km (133 mi) and Bologna (blq) 239 km (148 mi).
The residence includes also a large living-room on the ground floor of the villa (size 180sqm), equipped with kitchen and tables, fireplace, sofa and armchairs, tv 52″ and facilities, where it is possible to cook for a large number of people (dishes included) and have lunch and dinner on together.
This option is ideal for groups, large families, events or just to enjoy our place without sharing common spaces. Terre di Giano Private Pool and View, Umbria
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.
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
Battisole
Independent Vacation rental with WIFI, private pool, A/C, TV, patio, pets allowed, panoramic view
- 16
- 8
- 11
Description
Battisole is located in Monte Del Lago, Italy and only 26 km (16 mi) from Perugia in the tourist area "Trasimeno Lake". Property Battisole is a lovely property (600 sq m) that includes private pool, WiFi internet and air conditioning. The property can sleep up to 16 guests comfortably in eight bedrooms with 11 bathrooms.
The Experience
When you arrive you’ll find a nice clean well-maintained property with views of the hills and the lake perfect for a relaxing vacation in Umbria. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of visiting museums. Also available outdoors are a patio, tennis court and barbecue grill. Dining with friends and family is a big part of the Italian 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 16 people. Dine 'al fresco' like a real Italian, the fully furnished veranda is the ideal setting to enjoy food, family and the nice Italian weather.
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: Perugia 26 km (16 mi), Cortona 32 km (20 mi), Montepulciano 46 km (29 mi), Assisi 47 km (29 mi) and Gubbio 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 146 km (91 mi), Viareggio 233 km (145 mi), Forte Dei Marmi 240 km (149 mi), Rome 200 km (124 mi), Milan 433 km (269 mi) and Naples 390 km (243 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Battisole. 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
Pool Open: 1 May - 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) 151 km (94 mi), Roma Ciampino (cia) 209 km (130 mi), Pisa (psa) 214 km (133 mi), Roma Fiumicino (fco) 221 km (137 mi) and Bologna (blq) 238 km (148 mi).
Additional Services
Maid Service - If you'd like maid service during your visit that can be arranged by the owner. Inquire for more details about the additional cost.
Battisole
- 8
- 4
- 2
Description
Property Summary
Nestled 750 meters above sea level in the heart of Tuscany, Italy, Caiano is a charming and rustic holiday rental that invites you to slow down and reconnect with the natural world. Surrounded by trees, rolling fields, and vineyards, this distinctive property offers a genuine sense of seclusion without sacrificing access to the region's most celebrated destinations. Located just 7 kilometers from the center of Cavriglia, Caiano strikes an ideal balance between peaceful countryside living and everyday convenience. The property features a private fenced terraced garden of 1,000 square meters, a seasonally available swimming pool, and ample parking for up to 3 cars directly on the premises. Wireless internet connection is available throughout, ensuring you remain connected whenever needed, while the generous yard and surrounding natural landscape provide an exceptional setting for a truly restorative stay.
Outdoors
The outdoor spaces at Caiano are among its most defining and memorable features. The private terraced garden, spanning 1,000 square meters, is fully fenced to ensure your privacy and security, creating an intimate and sheltered environment in which to relax and unwind. Within the garden, you will find a wildlife garden with mature trees, a natural garden area, and an open meadow, all contributing to the property's rich and unspoiled natural character. The swimming pool, available seasonally from May 1st to September 30th, features an unconventional shape that adds a distinctive charm to the outdoor setting. An outdoor shower is conveniently located nearby for use after a swim. A terrace completes the exterior offering, providing an ideal space for outdoor dining, relaxing in the fresh Tuscan air, or simply taking in the surrounding landscape of vineyards and countryside.
Other Information
A car is recommended to fully enjoy everything that Caiano and its surrounding area have to offer, given the property's elevated and rural position. The nearest shop is located 4 kilometers from the property, while a supermarket can be found 8 kilometers away, making it easy to stock up on local produce and essentials during your stay. Guests should be aware that the swimming pool is available on a seasonal basis, operating from May 1st through September 30th.
Distances and Attractions
Caiano enjoys a privileged position that places some of Tuscany's most celebrated towns and attractions within easy reach. The center of Cavriglia is just 7 kilometers away, while the renowned wine town of Radda in Chianti lies 8 kilometers from the property, offering excellent opportunities to explore the Chianti Classico wine region, its historic villages, and its outstanding local gastronomy. The iconic city of Siena, with its world-famous Piazza del Campo, Gothic cathedral, and vibrant cultural scene, is located 38 kilometers away, making it an ideal destination for a day trip. For those traveling by train, the nearest railway station is San Giovanni Valdarno, situated 12 kilometers from the property, providing convenient rail connections to Florence and other major Tuscan cities. Caiano
Podere
Pretty private holiday villa with WIFI, private pool, TV, terrace, pets allowed and panoramic view
- 14
- 7
- 4
Description
Property Summary
Nestled in the serene Tuscan countryside near Cavriglia, Italy, Podere Filicaia is an exceptional holiday rental that offers a harmonious blend of rural charm and refined comfort. The property, also known as Manor House "Filicaia," sits at an elevation of 150 meters above sea level on the outskirts of Chianti, providing guests with a quiet and sun-drenched retreat far from the demands of everyday life. The estate is divided into 5 apartments in total, making it an ideal choice for families or groups of friends who wish to enjoy the Tuscan landscape together. Of these, 3 apartments are located within the barn, while a fourth occupies the ground floor of the main villa, situated approximately 20 meters from the barn. Each apartment is equipped with a kitchen and/or kitchenette, and all units communicate with one another exclusively through the exterior of the property. The estate offers the flexibility of booking the entire nucleus or individual apartments to suit your travel needs. Guests benefit from a private swimming pool measuring 12 x 6 meters, a spacious yard that captures the natural beauty of the surrounding countryside, complimentary Internet WiFi throughout the property, and convenient on-site parking, all of which contribute to a thoroughly comfortable and memorable stay.
Outdoors
The outdoor spaces at Podere Filicaia are thoughtfully designed to make the most of the property's stunning natural setting. The private swimming pool, measuring 12 x 6 meters with a depth ranging from 120 to 200 cm, is available seasonally from May 7th to September 24th and serves as the centerpiece of the outdoor area. The pool area is complemented by an outdoor shower, allowing guests to refresh themselves with ease after a swim. Garden furniture is provided throughout the exterior spaces, offering comfortable spots to relax and soak in the peaceful Tuscan atmosphere. A barbecue is also available for guests who wish to enjoy outdoor dining under the open sky, making evenings in the yard a truly memorable experience. The surrounding grounds are bathed in sunlight and offer a tranquil environment perfectly suited to leisurely walks, quiet relaxation, and the enjoyment of the unspoiled Chianti countryside.
Other Information
Podere Filicaia benefits from the attentive presence of the owner, who resides on the same property and remains readily available to assist guests with any questions or concerns that may arise during their stay. Heating is available at the property from November 1st to April 7th and is provided for an additional fee, ensuring a warm and comfortable environment during the cooler months of the year. The apartments are interconnected only through the outside, preserving the privacy of each individual unit while still allowing guests to enjoy a sense of community within the estate.
Distances and Attractions
Podere Filicaia enjoys a privileged location that places a wealth of cultural, historical, and gastronomic attractions within easy reach. The property is situated 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. Among the most notable nearby attractions are the Castello di Meleto, the charming village of Greve in Chianti, Castellina in Chianti, and Panzano in Chianti, all of which offer an authentic taste of the Chianti wine region. For those wishing to explore further afield, the Renaissance city of Firenze and the medieval splendor of Siena are both accessible from the property, providing world-class art, architecture, and cuisine within a comfortable driving distance. Podere
Il Canto del Maggio
Comfortable apartment with WIFI, pool, A/C, TV, patio, pets allowed and panoramic view
- 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 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
- 6
- 3
- 2
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).
Il Campanile is a nice stone building (120 sq m) with WiFi internet, private pool and air conditioning. The property can sleep up to six guests comfortably in three bedrooms with two bathrooms. Il Campanile is located in the centre of Cavriglia, Italy and only 32 km (20 mi) from Greve In Chianti in the tourist area "Chianti". There is a golf course nearby if you'd like to get in a round or two while on vacation.
Your Experience
Upon arrival you’ll find a lovely clean well-maintained property perfect for a relaxing vacation 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 unwind 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 six people. If you prefer to dine 'al fresco', there is a fully furnished balcony 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: 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 vacation 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 - If you're interested in learning more about Tuscan cooking, ask about the cooking lessons that can be scheduled at the property. It's a pleasant way to spend time with friends and family while learning the techniques vital 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 organize the meal based on your preferences and dietary needs. The chef will offer suggestions for the various courses and the wine. Ask for more details and the extra costs.
Tours - The owner can arrange custom tours for your group. To learn about the tours offered, speak to the owner upon arrival or ask 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 stay that can be scheduled by the owner. Inquire for more details about the additional cost.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Inquire for more details, including the extra cost and how to schedule this service.
Baby Sitting - A babysitter can be arranged at Il Campanile. If you're traveling with kids and would like some alone time, talk to the owner directly about this option when you arrive.
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.
- 4
- 2
- 2
Description
Property Summary
Manor house "Tribolina" is a captivating vacation rental nestled in the rolling Tuscan countryside of Cavriglia, Italy, perched at 550 meters above sea level atop a sun-drenched hill. This distinguished residence comprises 2 separate houses set within a vast estate of 23 hectares, offering guests an unparalleled sense of privacy and space in one of Italy's most celebrated rural landscapes. The property is just 3 kilometers from the village of Cavriglia, providing the ideal balance between peaceful seclusion and convenient access to local amenities. Guests benefit from reliable internet and Wi-Fi connectivity throughout their stay, ensuring they remain connected without compromising the tranquility of their surroundings. The expansive yard, reserved exclusively for guests, invites leisurely afternoons in the open air, surrounded by the natural beauty of the Tuscan hills. Parking is available directly on the premises, with motor access to the property, though guests should be aware that the final 100 meters leading to the house is via an unmade road.
Outdoors
The outdoor spaces at Manor house "Tribolina" are a true highlight of the estate, offering guests an immersive experience in the unspoiled Tuscan landscape. The natural garden, spanning the property's generous 23-hectare grounds, is maintained exclusively for the use of guests and provides a serene setting for relaxation and outdoor living. Garden furniture is thoughtfully arranged throughout the space, allowing guests to sit back and absorb the panoramic views of the surrounding countryside. A barbecue is also available, making the garden an ideal venue for alfresco dining and convivial evenings under the open sky. The elevated position of the property at 550 meters above sea level ensures that the outdoor areas are bathed in sunlight throughout the day, enhancing the sense of warmth and well-being that defines a stay at this remarkable estate.
Other Information
Heating is available at Manor house "Tribolina" from 1st November to 15th April and is payable directly on the spot upon use. The owner of the property resides on the same estate, ensuring that attentive and personal assistance is always available should any queries or needs arise during your stay. Guests are also invited to take advantage of the local sale of farm products offered on the property, providing a wonderful opportunity to sample and purchase authentic regional produce directly from the source.
Distances and Attractions
Manor house "Tribolina" enjoys an exceptionally well-connected location within the Tuscan countryside, placing a wealth of cultural, culinary, and natural attractions within easy reach. The village of Cavriglia is just 3 kilometers away, while the town of Montevarchi can be reached in approximately 12 kilometers. The historic city of Florence lies 65 kilometers from the property, making it an accessible destination for a day of art, architecture, and gastronomy. For lovers of fashion and design, the Prada outlet is located just 14 kilometers away, and The Mall outlet is also conveniently reachable from the estate. The charming Chianti wine villages of Gaiole in Chianti and Radda in Chianti are situated 9 kilometers and 12 kilometers away respectively, offering scenic drives through vineyards and medieval hilltop towns. The celebrated cities of Siena and Arezzo are equally accessible, each offering a rich tapestry of history and culture. For those seeking relaxation and wellness, the Rapolano Terme thermal baths are located 50 kilometers from the property, providing a restorative retreat within the broader Tuscan region. Tribolina
Agriturismo Cincinelli
Comfortable home with pool, WIFI, 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
Agriturismo Cincinelli is a nice stone building with WiFi internet and shared pool. Agriturismo Cincinelli is a apartment / condo having a total of five separate 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.
What to Expect
After arriving you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills perfect for a splendid holiday 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 relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Outside you will also find a barbecue grill and patio. This vacation rental is a multi-unit property which is ideal for a group of friends or acquaintances traveling together that prefer to have private living and sleeping quarters while sharing the common areas, like the pool or garden, with the group. Each apartment is equipped with its own fully-equipped kitchen for meal preparation.
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: 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 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).
Agriturismo Cincinelli
Last-Minute Offer for Capanno
Book 15 days or less before the arrival date and receive a 30 % 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.
Other apartments with last-minute offers:
Forno
Bottegaccia
Borgo
Caratello
Casa Rossa
Wonderful private house with WIFI, private pool, veranda and pets allowed, close to Arezzo
- 7
- 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
- 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
Nestled at an elevation of 150 meters above sea level in the serene Tuscan countryside of Cavriglia, Italy, Manor House "Filicaia" is an exceptional vacation rental that combines rural tranquillity with refined comfort. The property comprises 5 individual apartments set within a quiet and sun-drenched landscape, offering guests an authentic experience of the Italian countryside. Throughout your stay, you will benefit from a range of carefully considered amenities designed to enhance your comfort and relaxation. The expansive yard surrounding the property provides a peaceful natural setting where you can unwind and immerse yourself in the beauty of the Tuscan hills. A shared swimming pool is available for guests to enjoy during the warmer months, offering a refreshing retreat after a day of exploration. For those who need to remain connected, high-speed internet WiFi is provided throughout the property, ensuring seamless connectivity without compromising the sense of escape that Manor House "Filicaia" so effortlessly delivers.
Outdoors
The outdoor spaces at Manor House "Filicaia" have been thoughtfully arranged to offer guests a complete al fresco experience in the heart of the Tuscan countryside. The shared swimming pool measures 12 x 6 meters with a depth ranging from 120 to 200 cm, and is available for seasonal use from 07 May to 24 September, providing ample opportunity to enjoy the warm Italian summer. Complementing the pool area, an outdoor shower is conveniently available for guests returning from a swim. The garden is furnished with outdoor furniture, creating a welcoming space where you can relax, dine, and socialise in the open air. A barbecue is also at your disposal, inviting you to make the most of the long Tuscan evenings with al fresco dining surrounded by the natural beauty of the countryside.
Other Information
To ensure a comfortable and well-organised stay at Manor House "Filicaia," several practical amenities and house policies are in place for your convenience. A washing machine is available for shared use among guests, making longer stays particularly comfortable. Heating is provided seasonally, available from 01 November to 07 April, and is subject to an additional charge. Private parking is available directly on the premises, offering ease of access for guests arriving by car. Please be aware that the owner of the property resides on the same premises, which ensures attentive and responsive hospitality throughout your visit.
Distances and Attractions
Manor House "Filicaia" enjoys a privileged position in the Tuscan countryside, placing you within easy reach of some of the region's most celebrated destinations and attractions. The centre of San Giovanni Valdarno is just 3.8 km away, offering a convenient base for everyday needs including shops, restaurants, and local services. For those wishing to explore the renowned Chianti wine region, the centre of Gaiole in Chianti is approximately 18 km from the property, while Radda in Chianti lies at a distance of 26 km. Further afield, the historic Castello di Meleto, the charming villages of Greve in Chianti, Castellina in Chianti, and Panzano in Chianti are all within comfortable driving distance, each offering a unique glimpse into the rich cultural and viticultural heritage of Tuscany. For those seeking the grandeur of Italy's most iconic cities, the art-filled streets of Firenze and the medieval splendour of Siena are both easily accessible by car, making Manor House "Filicaia" an ideal base from which to discover the very best of this extraordinary region. San Giovanni 801
