Gaggiano Vacation Villa Rentals
Results 201 - 220 of 532
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Description
Ancient barn situated right outside Siena city center (only 3,5 km away). This property has been recently restored and turned into a modern and bright accommodation ideal for a couple or a family of 4 people. Outside guests can enjoy use of a large, well-groomed garden and of a nice furnished pergola ideal for al-fresco dining.
The house interiors are welcoming and tastefully furnished with modern-design pieces. The property in fenced-in.
A bus stop (with busses to Siena city center) is approx. 150 meters away.
The house's central location is convenient for visiting Tuscany's most important places of interest such as Siena, Florence, San Gimignano and the entire Chianti area with its characteristic villages (Castellina, Greve, Radda, Gaiole, etc.).
A secondary road connecting Siena to the Chianti region passes a short distance away.
Distances: Siena with all kinds of shops and railway station 3,5 km away, the Chianti region (with its characteristic villages of Castellina, Gaiole, Radda, Greve ecc…) is within 30 km, San Gimignano 40 km away, Rapolano Terme (spas) 40 km, Montalcino 45 km away, Volterra 54 km, Pienza (Val d’Orcia) 70 km away, Florence 70 km away.
At guests’ disposal: private furnished outdoor area with sun-umbrellas, sun-beds, table and chairs, barbecue.
WI-FI internet is provided (free of charge).
Extra Services: Baby bed available upon request. Maid service by arrangement (€ 15,- / per hour to be paid on the spot).
Please carefully check if there are any extra costs to be paid on site! Capannino
Book 14 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.
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Description
The Silent Courtyard Retreat: Spacious 2-Bedroom S is a beautiful property (90 sq m) with WiFi internet. The property can accommodate up to four people comfortably in two bedrooms with two bathrooms. The Silent Courtyard Retreat: Spacious 2-Bedroom S is located in the centre of Siena, Italy and only 40 km (25 mi) from San Gimignano in the tourist area "Siena And Surroundings".
The Experience
Upon arrival you’ll find a lovely clean well-maintained property perfect for a splendid holiday in Tuscany. 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. 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 four people.
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: San Gimignano 40 km (25 mi), Greve In Chianti 41 km (26 mi), Montalcino 43 km (27 mi), Montepulciano 62 km (39 mi) and Florence 70 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 70 km (43 mi), Viareggio 164 km (102 mi), Forte Dei Marmi 171 km (106 mi), Rome 239 km (148 mi), Venice 320 km (199 mi) and Milan 364 km (226 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 83 km (51 mi), Pisa (psa) 118 km (73 mi), Bologna (blq) 169 km (105 mi), Roma Ciampino (cia) 248 km (154 mi) and Roma Fiumicino (fco) 260 km (162 mi).
The Silent Courtyard Retreat: Spacious 2-Bedroom S
Book now and save 10%. Offer valid until 15 April 2026 and for a minimum stay of 4 nights.
Book 4 days or less before the arrival date and receive a 10 % discount off the published rental rates.
This Offer is valid only for stays of 3 nights minimum and can not be combined with any other special offers.
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Description
Holiday rental Capanna Di Elfo is a lovely property (180 sq m) that includes air conditioning, WiFi internet and hot tub. The property can sleep up to eight guests comfortably in four bedrooms with four bathrooms. Conveniently located 9 km (5 mi) from Siena, Italy in the tourist area "Siena And Surroundings" and only 42 km (26 mi) from Montalcino.
The Experience
Upon arrival you’ll find a beautiful clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. After a busy day of shopping, spend some time with friends and family enjoying a glass of wine - a perfect way to relax at the end the day. Outdoors you will also find a patio, barbecue grill and hot tub. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the perfect setting to enjoy food, family and the lovely Tuscan weather.
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: Montalcino 42 km (26 mi), San Gimignano 46 km (29 mi), Greve In Chianti 49 km (30 mi), Montepulciano 65 km (40 mi) and Arezzo 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 76 km (47 mi), Viareggio 170 km (106 mi), Forte Dei Marmi 177 km (110 mi), Rome 242 km (150 mi), Venice 327 km (203 mi) and Milan 370 km (230 mi).
Additional Information
Handicapped Accessible - If you or one of your guests needs wheelchair access, you’ll find at least one bedroom and bathroom that are accessible, as well as, most of the main rooms in the house.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 89 km (55 mi), Pisa (psa) 124 km (77 mi), Bologna (blq) 175 km (109 mi), Roma Ciampino (cia) 251 km (156 mi) and Roma Fiumicino (fco) 263 km (163 mi).
Special Services
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your vacation hassle-free after a long trip. Inquire for more details, including the supplemental cost and how to arrange this service.
Capanna Di Elfo
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky
Cosy holiday home with A/C, hot tub, WIFI, TV, patio and panoramic view
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Description
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky is located in Siena, Italy and only 38 km (24 mi) from San Gimignano in the tourist area "Siena And Surroundings". Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky is a lovely vacation rental (200 sq m) with hot tub, air conditioning and WiFi internet. The property can sleep up to eight guests comfortably in four bedrooms with three bathrooms.
Your Experience
When you arrive you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills ideal for a peaceful holiday in Tuscany. After a busy day of shopping, spend some time with friends and family enjoying a glass of wine - a perfect way to unwind at the end the day. Outdoors you will also find a patio, hot tub and barbecue grill. Dining 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 eight people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the nice Tuscan weather.
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: San Gimignano 38 km (24 mi), Greve In Chianti 40 km (25 mi), Montalcino 43 km (27 mi), Montepulciano 62 km (39 mi) and Florence 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 68 km (42 mi), Viareggio 162 km (101 mi), Forte Dei Marmi 169 km (105 mi), Rome 239 km (148 mi), Venice 318 km (198 mi) and Milan 362 km (225 mi).
Additional Information
Check-In Time: 16:00 - 21:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 April - 30 November (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) 81 km (50 mi), Pisa (psa) 116 km (72 mi), Bologna (blq) 167 km (104 mi), Roma Ciampino (cia) 248 km (154 mi) and Roma Fiumicino (fco) 261 km (162 mi).
Special Services
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky
Casa di Luca, Pool, Castelnuovo Berardenga
Independent House with A/C, WIFI, private pool, TV, patio, pets allowed, panoramic view
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Description
Casa Di Luca, Pool, Castelnuovo Berardenga is a lovely stone building (160 sq m) with private pool, air conditioning and WiFi internet. The property can accommodate up to ten guests comfortably in four bedrooms with three bathrooms. Conveniently located 14 km (9 mi) from Siena, Italy in the tourist area "Siena And Surroundings" and only 39 km (24 mi) from Greve In Chianti.
What to Expect
After arriving you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of shopping. Also available outdoors are a playground, barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people.
Visit the Area
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 39 km (24 mi), San Gimignano 51 km (31 mi), Montalcino 54 km (34 mi), Montepulciano 63 km (39 mi) and Arezzo 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 80 km (50 mi), Viareggio 175 km (108 mi), Forte Dei Marmi 182 km (113 mi), Rome 240 km (149 mi), Milan 375 km (233 mi) and Naples 430 km (267 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Casa Di Luca, Pool, Castelnuovo Berardenga. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 May - 6 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) 93 km (58 mi), Pisa (psa) 128 km (79 mi), Bologna (blq) 180 km (112 mi), Roma Ciampino (cia) 249 km (154 mi) and Roma Fiumicino (fco) 261 km (162 mi).
Front outdoor space of about 100 square meters private and fenced.
Backyard space and pool (4x10 m) occasionally shared with the owner who has reserved a small portion of the house.
Casa Di Luca, Pool, Castelnuovo Berardenga
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Description
Property Summary
Nestled among the rolling hills of the Tuscan countryside, "Casino di Lecceto" is a large, rustic cottage offering an authentic and secluded retreat in Italy, just 8 km from the historic centre of Siena. Set at 400 metres above sea level and spread across 3 storeys, this detached property sits majestically on top of a hill, surrounded by trees and embraced by the natural beauty of the surrounding woodland. As a holiday rental of remarkable character and charm, the cottage accommodates guests seeking privacy and immersion in nature without sacrificing comfort. The property benefits from a generous private estate of 2 hectares, fully fenced and maintained in its natural state, encompassing a wildlife garden, a natural garden, a meadow, and a courtyard. A private swimming pool measuring 10 x 5 metres is available for guests during its seasonal opening period, from 24 April to 4 October, and is maintained by the owner's gardener. The yard surrounding the property provides ample space to enjoy the tranquil outdoor setting, while parking is conveniently available directly on the premises. Internet Wi-Fi connectivity ensures that guests can remain connected throughout their stay, even in this wonderfully remote location.
Outdoors
The outdoor spaces of "Casino di Lecceto" are a true highlight of the property, offering a harmonious blend of cultivated and natural environments across an expansive 2-hectare estate. The private grounds include a wildlife garden, a natural garden, a meadow, and a courtyard, all maintained in a manner that respects and celebrates the surrounding landscape. The swimming pool, measuring 10 x 5 metres, is available seasonally from 24 April to 4 October and is regularly serviced by the owner's gardener to ensure it remains in excellent condition throughout the season. A terrace provides an ideal setting for outdoor relaxation and dining, furnished with garden furniture to allow guests to enjoy meals and leisure time in the open air. A barbecue is also available, perfect for alfresco dining during warm Tuscan evenings. Walking paths begin just 1 km from the property, inviting guests to explore the surrounding countryside and woodland at their own pace.
Other Information
"Casino di Lecceto" is a detached, 3-storey rustic cottage situated in a secluded position, and guests should be aware that part of the house is closed and unoccupied during their stay. Access to the property is via a 400-metre unmade road that is very bumpy, and a 4x4 vehicle is strongly recommended, particularly during the winter months. Please be advised that the tap water at the property does not meet drinking water quality standards, and guests are encouraged to use bottled water for drinking purposes. Baby equipment is included in the rental at no additional charge, making the property a practical choice for families with young children. Groups of teenagers are accommodated on request only and must be arranged in advance. The property is surrounded by trees and positioned 100 metres from the edge of the forest, offering a genuinely immersive natural experience in the Tuscan hills.
Distances and Attractions
"Casino di Lecceto" enjoys a privileged position that provides convenient access to a wealth of destinations and services. Essential amenities are within easy reach, with a grocery store located 1 km away, a supermarket 5 km away, and a restaurant just 2 km from the property. A bus stop is situated 2 km away, while the railway station "Siena" is 8 km from the cottage. The vibrant city of Siena, with its world-renowned historic centre, is just 8 km away, while Florence lies approximately 80 km from the property. The charming medieval town of San Gimignano is 50 km away, and the beautifully preserved walled village of Monteriggioni can be reached in just 14 km. For those interested in history and culture, a former hermitage featuring 15th-century frescoes is located just 1 km from the property. The remarkable ruined abbey of San Galgano is 28 km away, and the ancient Etruscan city of Volterra is 50 km from the cottage. Nature and wellness enthusiasts will appreciate the proximity of the thermal baths at "Rapolano Terme," situated 37 km away. An 18-hole golf course is available 16 km from the property. For those wishing to visit the coast, the sandy beach of "Follonica" is 80 km away, as is the sea. Casino di Lecceto
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Description
Property Summary
Montefienali is a historical holiday village located 15 km from Gaiole in Chianti, Italy, nestled in the countryside at an elevation of 600 meters above sea level. This renovated 13th-century property offers 25 apartments within a hamlet of 25 houses. Guests can enjoy a natural state property spanning 3 hectares with plants, trees, and a seasonal swimming pool (10 x 15 m) available from May 15 to September 30, with pool opening hours from 9:00 AM to 8:00 PM. The property boasts amenities such as a children's pool, outdoor shower, patio, terrace, garden furniture, and a children's playground with a slide, swing, and sandbox. Laundry facilities (shared) are available on-site. While the property is accessible via a 2 km bumpy motor access road, it offers parking on the premises and is within proximity to shops, groceries, supermarkets, restaurants, bars, and bicycle rentals, making it an ideal vacation rental for families seeking a peaceful retreat in the Tuscan countryside.
Outdoors
Immerse yourself in the natural beauty of Montefienali, surrounded by trees on a fenced 3-hectare property. Soak up the sun by the seasonal swimming pool (10 x 15 m), available from May 15 to September 30, with designated pool opening hours from 9:00 AM to 8:00 PM. Children can make a splash in the dedicated children's pool or enjoy the outdoor playground with a slide, swing, and sandbox. Relax on the patio or terrace, surrounded by lush gardens and equipped with comfortable garden furniture. Outdoor showers are also available for your convenience.
Other Information
Montefienali offers convenient on-site amenities, including a shared washing machine for laundry needs. While the property is situated in a secluded location, it is easily accessible via a 2 km bumpy motor access road, with parking available on the premises. A 50-meter footpath leads from the parking area to the accommodations. The property caters to families, with baby equipment provided. Please note that groups of teenagers are accepted upon request only.
Distances and Attractions
Nestled in the Tuscan countryside, Montefienali is conveniently located near various attractions and amenities. The charming town of Gaiole in Chianti is just 15 km away, offering shops, groceries, and a supermarket. Restaurants and bars can be found within a 3 km radius, while bicycle rentals are available 15 km from the property. Explore the rich history and culture of nearby cities such as Siena (36 km), Arezzo (44 km), and Florence (66 km), all within a reasonable driving distance from your vacation rental. Il Cinghiale
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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
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 | ||||
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| Mulignone 1 | 4 | 2 | 2 | |
| Mulignone 2 | 3 | 2 | 2 | |
| Mulignone 14 | 2 | 1 | 1 | |
| Mulignone 15 | 2 | 1 | 1 | |
| Mulignone 8 | 3 | 2 | 2 | |
| Mulignone 9 | 3 | 2 | 2 | |
| Mulignone 10 | 3 | 2 | 2 | |
| Mulignone 13 | 3 | 2 | 1 | |
| All 8 Accommodations | 23 | 14 | 13 |
Description
Borgo Mulignone is a large property in the Chianti Hills of Tuscany.
Retrieved from the reastauro of an old Farmhouse, the Borgo includes 10 comfortable apartments, suitable for couples families or friends.
Each apartment is equipped with every comfort and an outdoor area equipped for outdoor dining.
The complex is surrounded by the Tuscan Countryside and a large garden that offers 3 private pools to share with other guests, a perfect place to relax and enjoy the panoramic view on hot summer days.
The owners of Borgo Mulignone live on site and are available to guests for any problems or to recommendations for activities and places to visit.
The strategic location of the property allows guests not only to enjoy nature and the Tuscan Countryside, but also to easily reach the most beautiful cities of the Region such as Siena, Arezzo, Florence and the characteristic villages of San Gimignano, Colle Val d'Elsa, Monteriggioni, Casole d'Elsa and the whole Chianti area.
At guests' disposal: large green areas, three swimming pools of which one is very large (20 x 10 m - maximum depth 1.4 m), a smaller one (10 x 5 m - maximum depth 1 m) and a smaller one equipped with a corner with hydromassage (8 x 5 m - maximum depth 1 m), barbecue, outdoor area with children's games, internet connection via wi-fi. Each apartment has a private outdoor area equipped with a gazebo, table and chairs for outdoor dining, access to the property is via a section of unpaved road of about 700 m in good condition. Parking is available inside the property. Shared laundry (payment on the spot). Free Wi-Fi internet connection is available outside the apartments.
Distances: Pievescola with food shops at 3 km, Casole d'Elsa with all kinds of shops at 15 km, the medieval town of San Gimignano approx. at 20 km, Monteriggioni approx. at 10 km, Siena is at about 20 km.
The abbey of San Galgano (roofless church and sword in the rock) can be easily reached in about 30 minutes by car.
Please carefully check if there are any extra costs to be paid on site! Borgo Mulignone
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| Accommodation | |||||
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| 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
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Stunning private vacation home with A/C, private pool, WIFI and TV
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Description
La Dimora del Chianti Dimora: Stunning Tuscan Vill is located 5 km (3 mi) from Rietine, Italy and only 27 km (17 mi) from Siena in the tourist area "Siena And Surroundings". La Dimora del Chianti Dimora: Stunning Tuscan Vill is a lovely property (200 sq m) with private pool, WiFi internet and air conditioning. The property can accommodate up to eight guests comfortably in four bedrooms with five bathrooms.
What to Expect
After arriving you’ll find a nice clean well-maintained property with views of the hills ideal for a relaxing vacation in Tuscany. Regardless of how you spend your days - visiting museums, sightseeing, shopping or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished garden where you can enjoy the weather while dining outdoors.
Visit the Area
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: Siena 27 km (17 mi), Greve In Chianti 33 km (21 mi), Arezzo 52 km (32 mi), San Gimignano 54 km (33 mi) and Montalcino 62 km (38 mi).
Some other major tourist destinations you should consider visiting are: Florence 65 km (41 mi), Viareggio 159 km (99 mi), Forte Dei Marmi 167 km (103 mi), Rome 240 km (149 mi), Venice 316 km (196 mi) and Milan 359 km (223 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 19 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) 78 km (49 mi), Pisa (psa) 124 km (77 mi), Bologna (blq) 165 km (102 mi), Roma Ciampino (cia) 249 km (155 mi) and Roma Fiumicino (fco) 261 km (162 mi).
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Book now and save 10%. Offer valid until 20 April 2026 and for a minimum stay of 5 nights.
Villa del Mangia, 5Panoramic Pool and Chef Service
Superb private holiday rental with WIFI, A/C, private pool, terrace and panoramic view
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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
- 3
- 24
- 10
- 5
| Accommodation | |||||
|---|---|---|---|---|---|
| Montechioccioli 649.1 | 6 | 2 | 1 | ||
| Montechioccioli 649.2 | 6 | 2 | 1 | ||
| All 2 Accommodations | 12 | 4 | 2 |
Description
Property Summary
Nestled in the picturesque hamlet of Rietine, just 4 km from the centre of Gaiole in Chianti, Italy, Montechioccioli is a charming 3-family house that offers an authentic and rustic holiday rental experience in the heart of Tuscany. Surrounded by rolling vineyards and breathtaking countryside, this property comprises 3 separate apartments, making it an ideal choice for families or groups of friends seeking to immerse themselves in the beauty of the Tuscan landscape. The property features a generous terraced yard spanning 1,000 m2, beautifully landscaped with a variety of plants and trees that frame the surrounding scenery. Guests can take a refreshing dip in the impressive swimming pool, which measures 12 x 6 m with a depth of 170 cm and is available seasonally from 02 May to 03 October. Staying connected is effortless thanks to the internet wifi available throughout the property, while an EV charging station further enhances the convenience and modernity of this countryside retreat. A washing machine is also available for shared use among guests, and parking is provided on the premises.
Outdoors
The outdoor spaces at Montechioccioli are a true highlight of the property, offering guests a wonderful setting in which to unwind and enjoy the Tuscan countryside. The terraced garden, extending across 1,000 m2, is thoughtfully planted with a diverse selection of trees and plants, creating a lush and tranquil environment that invites relaxation at every turn. The swimming pool area, where the pool reaches a depth of 170 cm, is complemented by a dedicated shower and WC facility, ensuring comfort and practicality for all guests. Adjacent to the pool, a terrace equipped with a barbecue provides an ideal space for outdoor dining and socialising, allowing guests to savour al fresco meals while taking in the panoramic views of the surrounding vineyards and hills.
Other Information
The owner of Montechioccioli resides on the same property, ensuring a welcoming and attentive presence throughout your stay. The swimming pool is available on a seasonal basis, open from 02 May to 03 October. A washing machine is available on the premises and is shared among the guests of the 3 apartments. Parking is conveniently provided on site at no additional inconvenience to guests.
Distances and Attractions
Montechioccioli enjoys an enviable location that places guests within easy reach of some of Tuscany's most celebrated destinations. The centre of Gaiole in Chianti is just 4 km away, offering a charming selection of local restaurants, shops, and services that capture the essence of authentic Chiantishire life. The historic town of Radda in Chianti lies approximately 12 km from the property, providing further opportunities to explore the region's renowned wine culture, medieval architecture, and traditional Tuscan cuisine. For those wishing to venture further afield, the magnificent city of Siena, a UNESCO World Heritage Site famed for its Gothic cathedral and the legendary Piazza del Campo, is located approximately 40 km from the property and makes for an unforgettable day trip. Gaiole in Chianti 649
Special Offer for Montechioccioli 649.1
Apartment:
Montechioccioli 649.2
Last-Minute Offer for Montechioccioli 649.1
Other apartments with last-minute offers:
Montechioccioli 649.2
Le Loggine del Pignatello Apartment, Siena City
Comfortable apartment with WIFI and TV
- 4
- 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
Montelucci Chianti Agrivilla
Wonderful independent accommodation with A/C, WIFI, private pool, TV, patio and panoramic view
- 14
- 7
- 6
Description
Vacation rental Montelucci Chianti Agrivilla is a nice stone building (400 sq m) that includes WiFi internet, private pool and air conditioning. The property can accommodate up to 14 guests comfortably in seven bedrooms with six bathrooms. Montelucci Chianti Agrivilla is located 560 m (1795 ft) from Montegrossi, Italy and only 30 km (18 mi) from Greve In Chianti in the tourist area "Chianti".
Your Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills and the mountains ideal for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of sightseeing. For your pleasure, on the grounds there is a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 30 km (18 mi), Siena 37 km (23 mi), San Gimignano 50 km (31 mi), Arezzo 54 km (34 mi) and Montalcino 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 77 km (48 mi), Viareggio 163 km (101 mi), Forte Dei Marmi 171 km (106 mi), Rome 258 km (160 mi), Milan 368 km (229 mi) and Naples 449 km (279 mi).
Additional Information
Check-In Time: 17:00 - 22:00
Check-Out Time: 07:00 - 10:00
Pool Open: 1 May - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 82 km (51 mi), Pisa (psa) 144 km (90 mi), Bologna (blq) 171 km (106 mi), Roma Ciampino (cia) 267 km (166 mi) and Roma Fiumicino (fco) 280 km (174 mi).
More Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a pleasant way to spend time with friends and family while learning the secrets needed to prepare delicious Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Ask for more details and the additional costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours offered, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be scheduled by the owner. Ask for more details about the extra cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Montelucci Chianti Agrivilla. Inquire for more details, including the supplemental cost and how to organize this service.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be arranged. Speak to the owner directly about this service upon arrival.
Montelucci Chianti Agrivilla
Casa Scopeti
Superb private villa with private pool, A/C, hot tub, WIFI, TV, panoramic view, close to Florence
- 12
- 4
- 3
Description
Nice independent villa situated in panoramic location in the heart of the Tuscan country-side. This property has been restored preserving its original architectural features and turned into a comfortable villa with private swimming-pool offering nice interiors furnished in a typical country style.
The access to the property is via an unpaved but well-maintained road.
Distances: the small village of Falciani with food shops 2 km away, San Casciano with all kinds of shops 5 km, Florence 10 km, Greve in Chianti with a charming central square and nice restaurants 20 km, Siena 60 km away.
At guests’ disposal: nice garden furnished with sun-beds and sun umbrellas, private swimming-pool (6 x 12 m – maximum depth 1,4 m – open from 01/04 to 31/10), heated outdoor Jacuzzi (7 seats), barbecue, veranda, playground for children. All of the bedrooms are provided with air-conditioning. Ironing facilities available. WI-FI internet connection available (free of charge for a usage of 15 hours per week - extra consuption to be paid on site at € 0,90 / per hour).
Parking within the grounds.
Extra services: maid service available by arrangement (€ 10,- / per hour to be paid on the spot). It is possible to arrange cooking classes and cooking service.
Small pets are allowed.
Please carefully check if there are any extra costs to be paid on site! Casa Scopeti
Book 15 days or less before the arrival date and receive a 25 % 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.
Cottage Monti Pet Friendly with Shared Pool
Amazing holiday villa with pool, WIFI, A/C, TV, veranda and pets allowed, near San Gimignano
- 4
- 1
- 1
Description
Cottage Monti Pet Friendly With Shared Pool is a beautiful vacation rental (70 sq m) with WiFi internet and air conditioning. The property can sleep up to four people comfortably. Conveniently located 1 km (4699 ft) from La Corsina, Italy in the tourist area "San Gimignano And Surroundings" and only 24 km (15 mi) from San Gimignano.
The cottage has a large private area with a private veranda equipped for outdoor dining. The property is very large and includes the manor house in front of which there is a swimming pool shared with the owners who occasionally stay in the manor house.
Free parking on the property.
Your Experience
After arriving you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills ideal for a peaceful holiday 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 unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. Dining 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.
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: San Gimignano 24 km (15 mi), Siena 41 km (26 mi), Greve In Chianti 49 km (30 mi), Florence 65 km (41 mi) and Montalcino 77 km (48 mi).
Some other major tourist destinations you should consider visiting are: Florence 65 km (41 mi), Viareggio 112 km (69 mi), Forte Dei Marmi 123 km (77 mi), Rome 276 km (171 mi), Venice 314 km (195 mi) and Milan 364 km (226 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Cottage Monti Pet Friendly With Shared Pool. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 1 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) 78 km (48 mi), Pisa (psa) 84 km (52 mi), Bologna (blq) 167 km (104 mi), Genova (goa) 254 km (158 mi) and Roma Fiumicino (fco) 262 km (163 mi).
Special Services
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours offered, 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.
Cottage Monti Pet Friendly With Shared Pool
Book your vacation for the period from 01 April 2026 to 02 November 2026 and save 20% (minimum 7 nights).
Book your vacation for the period from 01 April 2026 to 02 November 2026 and save 25% (minimum 10 nights).
Book your vacation for the period from 01 April 2026 to 02 November 2026 and save 28% (minimum 14 nights).
Alice - Podere Ribatti - Casole D'Elsa, Toscana
Lovely accommodation with WIFI, pool, A/C and terrace, close to San Gimignano
- 2
- 1
- 1
Description
Conveniently located 3 km (2 mi) from Casole D'elsa, Italy in the tourist area "San Gimignano And Surroundings" and only 22 km (14 mi) from San Gimignano. Property Alice - Podere Ribatti - Casole D'elsa, Toscana is a nice property (100 sq m) that includes air conditioning and WiFi internet. The property can sleep up to two guests comfortably in one bedroom with one bathroom.
What to Expect
Upon arrival at Alice - Podere Ribatti - Casole D'elsa, Toscana you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful 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. Dining with friends and family is a big part of the Tuscan culture. Take advantage of the kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to two people.
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: San Gimignano 22 km (14 mi), Siena 38 km (23 mi), Greve In Chianti 56 km (35 mi), Florence 63 km (39 mi) and Montalcino 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 63 km (39 mi), Viareggio 155 km (96 mi), Forte Dei Marmi 165 km (102 mi), Rome 272 km (169 mi), Venice 310 km (193 mi) and Milan 358 km (222 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 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) 76 km (47 mi), Pisa (psa) 87 km (54 mi), Bologna (blq) 163 km (101 mi), Roma Ciampino (cia) 281 km (175 mi) and Roma Fiumicino (fco) 294 km (183 mi).
Alice - Podere Ribatti - Casole D'elsa, Toscana
Book your vacation for the period from 17 June 2025 to 06 January 2027 and save 15% (minimum 10 nights).
Book your vacation for the period from 17 June 2025 to 06 January 2027 and save 18% (minimum 14 nights).
Book your vacation for the period from 17 June 2025 to 06 January 2027 and save 20% (minimum 21 nights).
Book your vacation for the period from 07 April 2026 to 03 May 2026 and save 15% (minimum 3 nights).
Book your vacation for the period from 03 May 2026 to 31 May 2026 and save 15% (minimum 4 nights).
Lina - Podere Ribatti - Casole D'Elsa, Toscana
Comfortable home with WIFI, pool, TV and terrace, close to San Gimignano
- 2
- 1
- 1
Description
Conveniently located 3 km (2 mi) from Casole D'elsa, Italy in the tourist area "San Gimignano And Surroundings" and only 22 km (14 mi) from San Gimignano. Vacation rental Lina - Podere Ribatti - Casole D'elsa, Toscana is a nice property (50 sq m) that includes WiFi internet. The property can accommodate up to two people comfortably in one bedroom with one bathroom.
What to Expect
When you arrive you will be greeted by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills ideal for a relaxing vacation in Tuscany. After a hectic day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day. There is a kitchen including coffee machine, microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to two people.
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: San Gimignano 22 km (14 mi), Siena 38 km (23 mi), Greve In Chianti 56 km (35 mi), Florence 63 km (39 mi) and Montalcino 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 63 km (39 mi), Viareggio 155 km (96 mi), Forte Dei Marmi 165 km (102 mi), Rome 272 km (169 mi), Venice 310 km (193 mi) and Milan 358 km (222 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 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) 76 km (47 mi), Pisa (psa) 87 km (54 mi), Bologna (blq) 163 km (101 mi), Roma Ciampino (cia) 281 km (175 mi) and Roma Fiumicino (fco) 294 km (183 mi).
The swimming-pool is to be shared with 4 further apartments, one of which is where the owners live. Lina - Podere Ribatti - Casole D'elsa, Toscana
Book your vacation for the period from 17 June 2025 to 02 November 2026 and save 15% (minimum 10 nights).
Book your vacation for the period from 17 June 2025 to 02 November 2026 and save 18% (minimum 14 nights).
Book your vacation for the period from 17 June 2025 to 02 November 2026 and save 20% (minimum 21 nights).
Book your vacation for the period from 03 April 2026 to 03 May 2026 and save 15% (minimum 3 nights).
Book your vacation for the period from 03 May 2026 to 31 May 2026 and save 15% (minimum 4 nights).
