Vacation Rentals By Owner In Gaiole In Chianti, TOS

Vivaio is a spacious holiday home in the heart of Chianti Classico, surrounded by a beautifully landscaped garden with lavender, flowering plants and lovely views over the rolling Tuscan hills. Its peaceful rural setting makes it an ideal retreat for families or groups of friends seeking relaxation and an authentic Tuscan experience.brbrbrbrJust 5.5 kilometres away lies the lively town of Panzano, where you will find a COOP supermarket, small shops, cafés and restaurants. Panzano is also home to Dario Cecchini, a famous butcher known across Italy and beyond, with both his butcher’s shop and the popular restaurant Officina della Bistecca. Other well-known Chianti towns such as Greve, Radda and the picturesque hamlet of Volpaia are within easy reach. The region’s wineries and castles are close by, while Siena, Florence, San Gimignano and Arezzo are perfect for day trips.brbrThe property consists of a two-storey main house and a separate guesthouse with one bedroom, its own living area and a kitchen. It offers generous space and a sense of privacy for guests who appreciate independence.brbrbrbrThe traditional stone house is surrounded by a fragrant garden. Two terraces shaded by a pergola invite you to unwind. One terrace is furnished with a comfortable seating area, the other with a large dining table, ideal for shared meals outdoors.brbrbrbrInside, Tuscan character blends with stylish comfort. Wooden beamed ceilings, terracotta floors and carefully selected antique furnishings create an inviting and charming atmosphere.brbrbrbrVivaio is a wonderful place to enjoy relaxed holiday moments in classic Chianti surroundings.brbrMain HousebrbrbrbrGround FloorbrbrbrbrKitchenbrbrFully equipped, 4 gas hob rings.brbrbrbrDining RoombrbrDining table with 12 chairs.brbrbrbrLoungebrbr2 sofas, 2 armchairs, TV, kitchenette with sink and fridge, desk with 2 chairs, open fireplace, French doors to terrace.brbrbrbrGuest ToiletbrbrWC, sink, bidet, washing machine. brbrbrbrShower RoombrbrShower unit, washing machine.brbrbrbrFirst FloorbrbrbrbrBedroom 1brbrDouble bed (cannot be converted into twin beds), wardrobe, chest of drawers, mosquito screen.brbrbrbrBedroom 2brbrPair of twin beds (can be converted into a double bed if requested when booking), wardrobe, mosquito screen.brbrbrbrBedroom 3brbrDouble bed (cannot be converted into twin beds), wardrobe, mosquito screen.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrBedroom 4brbrDouble bed (cannot be converted into twin beds), chest of drawers, chair, mosquito screen.brbrbrbrBedroom 5brbrDouble bed (cannot be converted into twin beds), wardrobe, mosquito screen.brbrbrbrBedroom 6brbrDouble bed (cannot be converted into twin beds), wardrobe, chest of drawers, mosquito screen.brbrbrbrEn-suite BathroombrbrBath with shower attachment, bidet, sink, WC.brbrbrbrBathroombrbrShower unit, sink, bidet, WC.brbrbrbrBathroombrbrBath with shower attachment, sink, bidet, WC.brbrbrbrBathroombrbrBath with shower attachment, shower unit, sink, bidet, WC.brbrbrbrGuest ToiletbrbrWC, sink.brbrbrbrCottagebrbrbrbrLounge-Dinerbrbr2 sofas, dining table with 4 chairs, open fireplace, TV.brbrbrbrKitchenbrbrHob with 3 gas rings and 1 induction ring, oven, sink, fridge.brbrbrbrBathroombrbrShower, sink, WC.brbrbrbrMezzanine FloorbrbrbrbrBedroom 7brbrDouble bed (cannot be converted into twin beds), wardrobe, sofa, desk and chair, mosquito screen.brbrbrbrPrivate PoolbrbrDiameter: 10 metresbrbrDepth: 1.5 metresbrbrEntrance: Metal ladderbrbrOpening times: May to SeptemberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 50 metres

Vivaio, Radda in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$218.76

An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Originally part of a winery estate, the Tuscan stone buildings have been sympathetically restored into cottages and apartments with their own outdoor space. The pool is exclusive to the cottages and apartments at the resort. There is a delightful family restaurant with small bar/grocery/wine shop within the village, where you can dine al fresco to enjoy seasonal Tuscan food.brbrbrbrWhile enjoying your new Chianti lifestyle, you might plan day trips to the cultural delights of Siena and Florence, or stay closer to home to enjoy the local Chianti towns of Radda and Gaiole. San Sano is found on 'the road of castles' and 10km from the Chianti's most famous castle; Castello di Brolio, a family owned winery open for tours, wine tastings and a first class restaurant.brbrAbout the villabrbrFirst floor apartment with pretty views, a balcony plus private garden space to dine al frescobrbrFirst FloorbrbrbrbrKitchen/diner/loungebrbrFully equipped kitchen with gas hobs, fridge freezer, dining table for 4, 2 double sofasbrbrbrbrBedroom 1brbrDouble bed (Cannot be converted into twins), wardrobe,brbrbrbrBedroom 2brbrDouble bed (Cannot be converted into twins), wardrobe, chest of drawersbrbrbrbrBathroom 1brbrBath with hand held shower head, bidet, sink, WCbrbrbrbrBathroom 2brbrDouble shower/ sink, WCbrbrbrbrShared PoolbrbrLength: 14 metresbrbrWidth: 7 metresbrbrDepth: 1.5 metresbrbrEntrance: Metal ladderbrbrOpening times: May to SeptemberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: Under 70 metres

Casa del Vignaiolo, San Sano, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$795.9

Canonica di Vertine is a unique holiday home located in the picturesque medieval hamlet of Vertine. This historic building was once the parish house next to the San Bartolomeo church. Today, it offers accommodation for up to eight guests, combining historical charm with modern comfort. The original religious frescoes have been lovingly preserved, making a stay here a truly special experience.brbrbrbrSet peacefully on a hill, the house offers panoramic views over the vineyards and gentle hills of the Chianti. The well-kept garden features a small plunge pool with a whirlpool function, perfect for relaxing on warm days. Two covered terraces provide cosy spots for shared meals or social time outdoors.brbrbrbrLocated in the heart of the Chianti Classico, Canonica di Vertine is just three kilometres from Gaiole, where guests will find excellent restaurants, various shops and a small COOP supermarket. The surrounding region is dotted with wineries offering tastings and tours. Day trips to Siena, San Gimignano, Florence or Arezzo are all easily possible.brbrThe two-storey stone house has been carefully restored. The preserved frescoes, original wooden beam ceilings and terracotta floors are combined with traditional Tuscan furnishings, maintaining the authenticity and historic character of this former parish house.brbrbrbrCanonica di Vertine is an exceptional retreat full of history, charm and Tuscan atmosphere - a perfect place for an unforgettable holiday.brbrGround FloorbrbrbrbrLounge 1brbrSofa, two armchairs, coffee table.brbrbrbrLounge 2brbrSofa, two armchairs, coffee table, side table, fireplace, door to terrace and garden.brbrbrbrDining roombrbrTable and chairs.brbrbrbrKitchenbrbrFully equipped, fireplace.brbrbrbrBedroom 1brbrTwin beds (can be converted into a double), wardrobe.brbrbrbrEn-suite bathroombrbrShower, sink, bidet, WC (please note that there is restricted height in the bathroom due to the sloped ceiling).brbrbrbrCloakroombrbrSink, WC.brbrbrbrFirst FloorbrbrbrbrLounge 3brbrSofa, two armchairs, table and chairs, coffee table, side table, wardrobe, air-conditioning.brbrbrbrBedroom 2brbrFour-poster double bed (cannot be converted into singles), air-conditioning.brbrbrbrEn-suite bathroombrbrShower, twin sinks, bidet, WC.brbrbrbrLounge 4brbrSofa, chair, wardrobe, air-conditioning.brbrbrbrBedroom 3brbrDouble bed (cannot be converted into singles), chest of drawers, chair, air-conditioning.brbrbrbrEn-suite bathroombrbrShower, sink, bidet, WC.brbrbrbrBedroom 4brbrFour-poster bed (cannot be converted into two singles), two wardrobes, side table, chair, air-conditioning.brbrbrbrEn-suite bathroombrbrCorner bath, shower, twin sinks, dressing table, bidet, WC.brbrbrbrPrivate PoolbrbrHydro-massage Jacuzzi-plunge poolbrbrLength: 5 metersbrbrWidth: 3 metersbrbrDepth: 1.20 meterbrbrEntrance: internal stepsbrbrOpening: mid-April - mid-OctoberbrbrFenced: NobrbrFurnished: sunloungersbrbrCleansed: chlorinebrbrHeated: can be heatedbrbrDistance from villa: 50 metersbrbrbrbrGuests are entitled to a discounted entrance to the nearby Castello di Spaltenna, which has a spa and two swimming pools. Please ask for details. Booking in advance is required. brbrClick here to see the La Spatenna Hotel indoor and outdoor swimming pools and spa, 3km away.

Canonica di Vertine, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena, Italy

Bed

Bath

8

Sleeps

$226.9

Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and apartments that recreate the feeling of an authentic Tuscan hamlet. Situated along the crest of its own gently rolling hill, Montebuoni has wonderful, picture postcard views that delight the eye in all directions. This place unwinds you in the beauty of it’s natural setting.brbrbrbrWhile taking your front row seat to view the sunset over Chianti Classico's most prestigious vineyards you can plan a day trip to Siena, Florence and San Gimignano or a walk to the nearby village of Lecchi in Chianti to soak up your new way of life. If you're feeling more energetic, you may take time out for an early morning run, swim or bike ride. Private to the residence of this resort there is a swimming pool, a childrens pool and astro-turf tennis court and it is car free with parking at the entrance.brbrbrbrThe quaint village of Lecchi in Chianti is 4km driving distance from Montebuoni. However it is also possible to walk the 1.5km to Lecchi via a well maintained, hilly path. Also within walking distance is the village San Sano. The popular Chianti town Radda in Chianti is only a 15 minute drive away.brbrbrbrAbout the villa brbrTwo storey villa, covered dining/lounge terrace with garden, open views.brbrbrbrGround FloorbrbrbrbrKitchen Diner LoungebrbrFully equipped kitchen, fridge/freezer, gas hob with 4 rings. Dining table for 4, double sofa, open fire place, TV.brbrbrbrBedroom 1brbrDouble bed (cannot be converted into twin), wardrobe, chest of drawers.brbrbrbrBathroom 1brbrShower, bidet, sink, WC.brbrbrbrFirst FloorbrbrbrbrBedroom 2brbrDouble bed (cannot be converted into twins), wardrobe, drawers.brbrbrbrEn suite Bathroom 2brbrShower, bidet, sink, WC.brbrbrbrShared PoolbrbrLength: 15 metresbrbrWidth: 7.5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: April to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 100 metresbrbrbrbrTennis CourtbrbrSurface: Astro-turfbrbrPlaying equipment: Not providedbrbrDistance from villa: 150 metres

Casa Allegra, Montebuoni, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$216.43

San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within easy walking distance from the centre of the village. The hamlet consists of 4 buildings, housing a total of 7 apartments. Each villa have been thoughtfully and tastefully decorated, with each accommodation possessing their own private garden and terrace. In addition, there is also a garage for each individual villa, and there is also a horse-riding school approximately 10km from the hamlet.brbrLocated on a lower terrace to the rear of the hamlet is the shared chlorine-free swimming pool. This is a fantastic location, boasting wonderful views across the vineyards and countryside towards Siena and, in the distance behind the medieval city, Monte Amiata. From the hamlet, it’s a short walk uphill to the famous Brolio castle, which is surrounded by its own vineyards. You can visit the castle where the 32nd Baron Ricasolli and his family still live today. There is a restaurant serving traditional Tuscan food and you can have a wine tasting in the tasting rooms.brbrbrbrGround FloorbrbrKitchen-Diner with LoungebrbrFully equipped kitchen, gas hob with 4 rings, dining table with 4 chairs, sofa, TV.brbrBedroombrbrDouble bed (can be converted into twin beds if requested when booking), wardrobe, desk and chair.brbrEn-suite BathroombrbrShower unit, sink, bidet, WC.brbrNotesbrbrThere is a barbecue which is shared with Villa Girasole.brbrbrbrPool:brbrLength: 15 metresbrbrWidth: 6 metresbrbrDepth: 1.2 to 2.2 metresbrbrEntrance: Roman stepsbrbrOpening times: May to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: Chlorine-freebrbrDistance from villa: 20 metresbrbrThere is a very shallow baby pool, divided from the main pool by a metal railing.

Villa Violetto, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena, Italy

Bed

Bath

Sleeps

$332.79

San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within easy walking distance from the centre of the village. The hamlet consists of 4 buildings, housing a total of 7 apartments. Each villa have been thoughtfully and tastefully decorated, with each accommodation possessing their own private garden and terrace. In addition, there is also a garage for each individual villa, and there is also a horse-riding school approximately 10km from the hamlet.brbrLocated on a lower terrace to the rear of the hamlet is the shared chlorine-free swimming pool. This is a fantastic location, boasting wonderful views across the vineyards and countryside towards Siena and, in the distance behind the medieval city, Monte Amiata. From the hamlet, it’s a short walk uphill to the famous Brolio castle, which is surrounded by its own vineyards. You can visit the castle where the 32nd Baron Ricasolli and his family still live today. There is a restaurant serving traditional Tuscan food and you can have a wine tasting in the tasting rooms.brbrbrbrGround FloorbrbrKitchen-Diner with LoungebrbrFully equipped kitchen, gas hob with 4 rings, dining table with 4 chairs, sofa.brbrBedroom 1brbrDouble bed (can be converted into twin beds if requested when booking), wardrobe, desk and chair.brbrBathroombrbrBath with shower attachment, bidet, sink, WC.brbrFirst FloorbrbrBedroom 2brbrDouble bed (can be converted into twin beds if requested when booking), wardrobe, desk and chair.brbrBathroombrbrShower, bidet, sink, WC.brbrNotesbrbrThere is a barbecue which is shared with Villa Mimosa.brbrbrbrPool:brbrLength: 15 metresbrbrWidth: 6 metresbrbrDepth: 1.2 to 2.2 metresbrbrEntrance: Roman stepsbrbrOpening times: May to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: Chlorine-freebrbrDistance from villa: 20 metresbrbrThere is a very shallow baby pool, divided from the main pool by a metal railing.

Villa Giacinto, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena, Italy

Bed

Bath

Sleeps

$221.08

Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from the town, convenient for traditional niceties. Restored from ancient ruins by the Florentine family who take care of guests at the resort, each holiday cottage/apartment has its own furnished terrace that opens into the resort, ideal for those who seek contact with other guests. The surrounding pine forest means shaded sanctuary from the midday sun and the swimming pool that private to the resort, offers the chance of cooling dip. Nights bring out nature, you'll sit back and watch the wild life play and the twinkling distant stars in the black sky.brbrbrbrFamilies with children appreciate the small playground, table tennis, table football and Tuscan boules court at the resort. Walkers and bikers venture out to drop themselves into nature via the many marked trails through the pine and oak forest of Monte Luco. Day-trippers are enticed to San Gimignano, Florence and Siena or stay locally where the village of Castagnoli is 3.5 Km away and has two restaurants and two wineries.brbrAbout the villabrbrCorner cottage on two floors just a few steps away from the pool with two furnished terraces, perfect to dine al fresco.brbrGround FloorbrbrbrbrKitchen/diner/loungebrbrFully equipped kitchen with gas hobs, small fridge, dining table for 6, double sofa, TV, door to terracebrbrbrbrFirst FloorbrbrbrbrBedroombrbrDouble bed (Cannot be converted into twin), wardrobe, chest of drawersbrbrbrbrBathroombrbrShower, bidet, sink, WCbrbrbrbrShared PoolbrbrLength: 12 metresbrbrWidth: 6 metresbrbrDepth: 0.8 - 2.1 metresbrbrEntrance: Metal laddersbrbrOpening times: May to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 7 metres

Basilico, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$179.19

Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and apartments that recreate the feeling of an authentic Tuscan hamlet. Situated along the crest of its own gently rolling hill, Montebuoni has wonderful, picture postcard views that delight the eye in all directions. This place unwinds you in the beauty of it’s natural setting.brbrbrbrWhile taking your front row seat to view the sunset over Chianti Classico's most prestigious vineyards you can plan a day trip to Siena, Florence and San Gimignano or a walk to the nearby village of Lecchi in Chianti to soak up your new way of life. If you're feeling more energetic, you may take time out for an early morning run, swim or bike ride. Private to the residence of this resort there is a swimming pool, a childrens pool and astro-turf tennis court and it is car free with parking at the entrance.brbrbrbrThe quaint village of Lecchi in Chianti is 4km driving distance from Montebuoni. However it is also possible to walk the 1.5km to Lecchi via a well maintained, hilly path. Also within walking distance is the village San Sano. The popular Chianti town Radda in Chianti is only a 15 minute drive away.brbrbrbrAbout the villabrbrSemi-detached cottage, covered dining terrace with courtyard views.brbrbrbrGround FloorbrbrbrbrKitchen DinerbrbrFully equipped kitchen, fridge/freezer, gas hob with 4 rings. Dining table for 4. double sofa.brbrbrbrLoungebrbrdouble sofa bed, TVbrbrbrbrBedroombrbrDouble bed (cannot be converted into twin beds), wardrobe, drawers, armchair.brbrbrbrBathroombrbrShower, bidet, sink, WC.brbrbrbrLaundry room (communal)brbrwashing machinebrbrGround FloorbrbrbrbrKitchen DinerbrbrFully equipped kitchen, fridge/freezer, fireplace (decoration only), gas hob with 4 rings. Dining table for 4. double sofa.brbrbrbrLoungebrbrdouble sofa bed, TVbrbrbrbrBedroombrbrDouble bed (cannot be converted into twin beds), wardrobe, drawers, armchair.brbrbrbrBathroombrbrShower, bidet, sink, WC.brbrbrbrLaundry room (communal)brbrwashing machinebrbrbrbrShared PoolbrbrLength: 15 metresbrbrWidth: 7.5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: April to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 100 metresbrbrbrbrTennis CourtbrbrSurface: Astro-turfbrbrPlaying equipment: Not providedbrbrDistance from villa: 150 metres

La Contessina, Montebuoni, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$994.88

Borratella is a spacious Chianti holiday home, ideal for a large family or a group of friends. This house offers total privacy: it is entirely surrounded by the vineyards of the eponymous organic winery and woodlands, with no other houses nearby. The expansive property is fenced, allowing guests to fully enjoy the peaceful Tuscan landscape undisturbed. A special highlight: the guests of the holiday home receive a small complimentary wine and olive oil tasting from the Borratella winery on a day of their choice.brbrbrbrThis villa is located in the heart of Chianti Classico, with easy access to the region’s famous wineries, castles and villages. Siena, San Gimignano, Florence and Arezzo are also perfect destinations for day trips. In Gaiole, just a ten-minute drive away, guests will find excellent restaurants, small shops and a COOP supermarket.brbrbrbrBorratella is set in a peaceful, rural location, surrounded by a large garden with manicured lawns. The spacious pool offers stunning views over the Tuscan countryside and invites guests to relax. A furnished loggia with a dining table is perfect for shared barbecues, and there is an additional terrace and seating areas throughout the garden.brbrThe restored stone house spans three floors, with a living area on each level. A separate annex on the ground floor, with a bedroom and private bathroom, can be accessed via the garden or an external staircase, making it ideal for guests seeking extra privacy.brbrbrbrThe interiors are high quality and traditionally Tuscan, featuring terracotta floors, exposed stone walls, high wooden beam ceilings and selected antique furnishings.brbrbrbrThe property manager is available every day at the winery to assist guests and provide local tips.brbrGround FloorbrbrbrbrLounge 1brbrTwo sofas, two armchairs, coffee table, fireplace.brbrbrbrKitchen-DinerbrbrFully equipped, table and chairs, wood-burner, pantry.brbrbrbrBathroombrbrBath with handheld shower, shower, twin sinks, WC.brbrbrbrLaundry roombrbrFully equipped.brbrbrbrLoggiabrbrTable and chairs, barbecue, sink.brbrbrbrAnnexebrbrbrbrBedroom 1brbrDouble bed (cannot be converted into twins), wardrobe, chest of drawers, desk and chair, separate entrance, air-conditioning.brbrbrbrBathroom brbrShower, sink, WC.brbrbrbrFirst FloorbrbrbrbrLounge 2brbrTwo sofas, two armchairs, coffee table, sideboard, access to loggia, air-conditioning.brbrbrbrBedroom 2brbrDouble bed (cannot be converted into twins), two armchairs, wardrobe, two chests of drawers, air-conditioning.brbrbrbrEn-suite bathroombrbrShower, twin sinks, WC.brbrbrbrBedroom 3brbrTwin beds (cannot be converted into a double), wardrobe, chair, decorative fireplace, air-conditioning.brbrbrbrEn-suite bathroombrbrShower, sink, WC.brbrbrbrBathroom brbrShower, sink, WC.brbrbrbrSecond floorbrbrbrbrLounge 3brbrTable and two chairs.brbrbrbrBedroom 4brbrDouble bed (cannot be converted to twins), two armchairs, coffee table, wardrobe, chest of drawers, air-conditioning.brbrbrbrBathroombrbrShower, sink, WC.brbrbrbrPrivate PoolbrbrLength: 15 metresbrbrWidth: 8 metresbrbrDepth: 1.4 - 2 metresbrbrEntrance: Two Roman stepsbrbrOpening times: April to OctoberbrbrFenced: yesbrbrFurnished: Sunloungers, parasols, table and chairs.brbrCleansed: SaltbrbrDistance from villa: 10 metres

Borratella, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

5

Bath

8

Sleeps

$683.03

Podere Terrena is a charming holiday home located on a small agriturismo in a wonderfully peaceful hillside setting, surrounded by forests, meadows and open countryside. It offers wide views over the forest-covered hills of the Val d’Ambra and is an ideal retreat for families or groups of friends looking for a relaxing break in Tuscany.brbrbrbrSituated on the edge of the Chianti region, the house is perfectly placed for exploring the famous towns and wineries of the Chianti Classico. Places like Gaiole and Radda can be reached by car in about 30 minutes. The nearest supermarket and a few cafés and restaurants can be found in Mercatale Valdarno, around ten kilometres away. A wider selection is available in Bucine. Day trips to Arezzo, Siena, Florence and Cortona are also easy to organise.brbrThe two-storey stone house is set within a large, well-kept garden with flowering roses and terracotta pots. Next to the house there is a terrace with a dining table, while a second larger terrace near the pool offers additional seating and dining space. It is a perfect place to relax and enjoy evenings outdoors.brbrbrbrInside, the house features a blend of traditional Tuscan style and modern comfort. Light-filled rooms with beamed ceilings, terracotta floors and carefully chosen antique pieces create a warm and inviting atmosphere.brbrbrbrThe friendly owners live on the ground floor at the rear of the house with their dog and are happy to assist guests if needed. Cooking classes and a private cook-and-dinner service can be arranged on site.brbrbrbrPodere Terrena is a peaceful and authentic base for a relaxing stay in the heart of Tuscany.brbrGround FloorbrbrbrbrKitchen-DinerbrbrFully equipped kitchen, 4 ring gas hob, 2 tables, one with 6 chairs and the other with two chairs, door to terrace with table and 6 chairs under a pergola, air-conditioning.brbrbrbrFirst FloorbrbrbrbrBedroom 1brbrDouble bed (cannot be converted to twins), wardrobe, armchair.brbrbrbrBedroom 2brbrPair of twin beds (cannot be converted into a double), wardrobe, sofa, desk and chair.brbrbrbrBathroombrbrShower, sink, WC.brbrbrbrSecond FloorbrbrbrbrLoungebrbrSofa, antique wooden bench, antique chest of drawers.brbrbrbrBedroom SuitebrbrbrbrBedroom 3brbrDouble bed (cannot be converted to twins), wardrobe, chair, chest of drawers.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrBedroom 4brbrDouble bed (cannot be converted to twins), single bed, wardrobe, chair, little desk.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrPrivate PoolbrbrLength: 8 metersbrbrWidth: 4 metersbrbrDepth: 1.2 – 1.5 metersbrbrEntrance: Roman stepsbrbrOpening times: May to October brbrFenced: NobrbrFurnished: Sunloungers, pergola with a table and 8 chairs.brbrCleansed: ChlorinebrbrDistance from villa: 20 meters

Podere Terrena, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena, Italy

Bed

3

Bath

8

Sleeps

$377.01

Sestuccina is a stylish holiday home in the heart of Chianti Classico, ideal for a couple seeking a romantic retreat, but also perfectly suited for two couples or a small family. With beautiful views over the surrounding vineyards and close proximity to the charming town of Gaiole in Chianti, this modern stone villa offers tranquillity, comfort and a truly privileged location.brbrbrbrSet in the rolling Tuscan hills with a view stretching to the hilltop village of Vertine, the property is just a three-minute drive from Gaiole, where guests will find restaurants, shops and a small COOP supermarket. The cultural centres of Siena, Florence, Arezzo and San Gimignano are all within easy reach for day trips.brbrbrbrSestuccina is part of a larger estate that also includes another holiday home and the owners’ residence. The friendly hosts offer guests seasonal organic vegetables from their garden and fresh eggs from their own hens, adding a personal and authentic touch to the stay.brbrThe house is on one level and features a bright, open layout with a covered terrace for outdoor dining and lounging. The beautifully maintained garden is planted with flowers and elegant cypress trees. A private pool sits just steps from the kitchen, making it easy to cool off throughout the day. A whirlpool adds an extra level of relaxation.brbrbrbrInside, the décor is modern and refined, with clean lines, tasteful details and plenty of natural light. The villa is fully powered by solar energy, making it an environmentally friendly choice for your Tuscan getaway.brbrbrbrSestuccina is the perfect setting for guests who want to unwind in a serene landscape, enjoy modern amenities and experience the magic of Tuscany.brbrGround FloorbrbrbrbrLounge-Kitchen-DinerbrbrSofa-bed, coffee table, sideboard, table, four chairs, TV, well-equipped kitchenette, glass door to furnished terrace.brbrCorridorbrbrWashing machinebrbrBedroom 1brbrDouble bed (cannot be converted to twins), wardrobe, chest of drawers.brbrBathroombrbrShower, sink, WC.brbrBedroom 2brbrDouble bed (cannot be converted to twins), wardrobe, Sofa, double doors to the terrace.brbrEn-suite BathroombrbrDouble shower, sink, WC.brbrbrbrPrivate PoolbrbrLength: 9 metersbrbrWidth: 3.5 metersbrbrDepth: 1.30 metersbrbrEntrance: Roman StepsbrbrOpen: April to the end of NovemberbrbrFenced: nobrbrFurnished: Sounloungers & small dinning areabrbrCleansed: ChlorinebrbrDistance from the villa: 2meters

Sestuccina, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$309.52

Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and apartments that recreate the feeling of an authentic Tuscan hamlet. Situated along the crest of its own gently rolling hill, Montebuoni has wonderful, picture postcard views that delight the eye in all directions. This place unwinds you in the beauty of it’s natural setting.brbrbrbrWhile taking your front row seat to view the sunset over Chianti Classico's most prestigious vineyards you can plan a day trip to Siena, Florence and San Gimignano or a walk to the nearby village of Lecchi in Chianti to soak up your new way of life. If you're feeling more energetic, you may take time out for an early morning run, swim or bike ride. Private to the residence of this resort there is a swimming pool, a childrens pool and astro-turf tennis court and it is car free with parking at the entrance.brbrbrbrThe quaint village of Lecchi in Chianti is 4km driving distance from Montebuoni. However it is also possible to walk the 1.5km to Lecchi via a well maintained, hilly path. Also within walking distance is the village San Sano. The popular Chianti town Radda in Chianti is only a 15 minute drive away.brbrbrbrAbout the villabrbrSemi-detached cottage, covered dining terrace, large aromatic garden with extensive views and its own private Hot Tub!brbrGround FloorbrbrbrbrKitchen DinerbrbrFully equipped kitchen,fridge/freezer, gas hob with 4 rings. Dining table for 6, spiral stairs.brbrbrbrLoungebrbr2 double sofas, open fire place, TVbrbrbrbrFirst FloorbrbrbrbrBedroom 1brbrDouble bed (can be converted into twins), wardrobe, armchair, air-conditioning,brbrbrbrBathroombrbrShower, sink, WC.brbrbrbrBedroom 2brbrDouble bed (can be converted into twins), wardrobe, armchair, air-conditioning.brbrbrbrShared PoolbrbrLength: 15 metresbrbrWidth: 7.5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: April to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 100 metresbrbrbrbrTennis CourtbrbrSurface: Astro-turfbrbrPlaying equipment: Not providedbrbrDistance from villa: 150 metres

La Vigna, Montebuoni, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$841.28

Villa San Michele enjoys a wonderfully private location on a Chianti hilltop and was once the residence of wealthy landowners. Today, this spacious country home offers an ideal setting for relaxed holidays with family or friends, surrounded by a vast garden filled with mature trees and views of the surrounding countryside.brbrbrbrSet between the picturesque villages of Lecchi in Chianti and San Sano, both easily reached on foot, the villa offers excellent access to local life and the timeless beauty of the Chianti Classico region. The town of Gaiole is just a short drive away and offers restaurants, grocery shops and other amenities. Siena can be reached in about 30 minutes by car, while San Gimignano, Florence and Arezzo are all within easy reach for day trips.brbrThe property features five distinct living areas arranged across two floors of a handsome stone-built villa. A spacious covered terrace provides the perfect spot for outdoor dining, and the private pool is set apart in a peaceful area of the garden. Additional seating areas around the grounds invite guests to relax and enjoy sun or shade throughout the day.brbrbrbrInside, traditional Tuscan details such as terracotta floors and exposed beam ceilings are combined with elegant furnishings and carefully selected antiques. With its generous layout, historic charm and serene setting, Villa San Michele is a wonderful base from which to enjoy the beauty and culture of Tuscany.brbrGround FloorbrbrbrbrLounge-StudybrbrSofa, table with chairs, armchairs, coffee table, fireplace, sofa, desk with chair, bookshelf, doors to garden.brbrbrbrFirst FloorbrbrbrbrLoungebrbrTwo sofas, desk with chair, cupboard.brbrbrbrDining RoombrbrTable with chairs, desk with chair, cupboard, sideboard, fireplace, main entrance.brbrbrbrKitchenbrbrFully equipped, fridge-freezers, gas hob with 5 rings.brbrbrbrUtility RoombrbrWashing machine.brbrbrbrBedroom 1brbrFrench bed, wardrobe, dressing table with chair, mosquito screen.brbrbrbrBedroom 2brbrTwin beds (cannot be converted into a double), wardrobe, bureau, chairs, mosquito screen.brbrbrbrEn-suite Bathroom (shared with Bedroom 1)brbrShower, sink, WC, bidet.brbrbrbrBedroom 3brbrDouble bed (cannot be converted to twins), wardrobe, chest of drawers, desk with chair, footstool, mosquito screen.brbrbrbrBedroom 4brbrDouble bed (cannot be converted to twins), wardrobe, dressing table with chair, shelves, chair, mosquito screen.brbrbrbrEn-Suite BathroombrbrShower, sink, WC, bidet.brbrbrbrBathroombrbrShower, sink, WC, bidet.brbrbrbrPrivate PoolbrbrLength: 10 metresbrbrWidth: 5 metresbrbrDepth: 1.2 - 1.8 metresbrbrEntrance: Roman stepsbrbrOpening times: April to OctoberbrbrFenced: NobrbrFurnished: Loungers, shaders, outside showerbrbrCleansed: ChloorbrbrDistance from villa: 20 metres

Villa San Michele, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$454.97

Casetta Kiwi is a charming Chianti holiday home in the historic hamlet of Bricciano, made up of 18th-century buildings and full of authentic character. Peacefully located amidst olive groves and green hills, this semi-detached house is ideal for a couple or a small family with one child. The large pool, surrounded by lavender and Mediterranean plants, invites you to relax and enjoy views across the Tuscan countryside.brbrbrbrThe property lies in the heart of Chianti Classico, with easy access to the region’s famous wineries, castles and hilltop villages such as Radda, Gaiole and Lecchi. The Casanova di Bricciano winery is just 500 metres away. The small hamlet of Barbischio, home to the excellent restaurant Il Papavero, is a 20-minute walk. Gaiole in Chianti, with shops, restaurants and a small supermarket, is a 10-minute drive. Siena, San Gimignano, Florence and Arezzo can all be reached comfortably on day trips.brbrCasetta Kiwi occupies the first and second floor of a traditional stone house. The property features its own terrace with a dining table, making it the perfect spot for outdoor meals. The single bedroom upstairs also offers a private balcony with lovely views.brbrbrbrInside, the house combines traditional Tuscan elements such as terracotta floors and wooden beamed ceilings with a light, welcoming atmosphere and stylish modern furnishings.brbrFirst FloorbrbrbrbrKitchen-DinerbrbrFully equipped kitchen, gas hob with 5 rings/burners, dining table with 4 chairs, air-conditioning.brbrbrbrLoungebrbrSofas, smart TV, wood-burning stove.brbrbrbrSecond FloorbrbrbrbrBedroom 1brbrKing size double bed (cannot be converted into twin beds), extensive wardrobe space, full length mirror, air-conditioning.brbrbrbrBedroom 2brbrSingle bed, wardrobe, French door to balcony, ceiling fan.brbrbrbrBathroombrbrShower, sink, bidet, WC, and washing machine.brbrNo infants or children under 6 years.brbrbrbrPrivate Pool:brbrLength: 18 metresbrbrWidth: 4 metresbrbrDepth: 1.4 metresbrbrEntrance: Roman stepsbrbrOpening times: May to OctoberbrbrFenced: YesbrbrFurnished: Pergola with sunloungersbrbrCleansed: chlorine freebrbrDistance from villa: 70 metres

Casetta Kiwi, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$228.07

Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from the town, convenient for traditional niceties. Restored from ancient ruins by the Florentine family who take care of guests at the resort, each holiday cottage/apartment has its own furnished terrace that opens into the resort, ideal for those who seek contact with other guests. The surrounding pine forest means shaded sanctuary from the midday sun and the swimming pool that private to the resort, offers the chance of cooling dip. Nights bring out nature, you'll sit back and watch the wild life play and the twinkling distant stars in the black sky.brbrbrbrFamilies with children appreciate the small playground, table tennis, table football and Tuscan boules court at the resort. Walkers and bikers venture out to drop themselves into nature via the many marked trails through the pine and oak forest of Monte Luco. Day-trippers are enticed to San Gimignano, Florence and Siena or stay locally where the village of Castagnoli is 3.5 Km away and has two restaurants and two wineries.brbrAbout the villabrbrGround floor apartment with furnished terrace at the front overlooking the pool plus a larger furnished terrace at the back, perfect for dining al fresco.brbrGround FloorbrbrbrbrKitchen/diner/loungebrbrFully equipped kitchen with gas hobs, fridge-freezer, dining table for 4, double sofa, TVbrbrbrbrBedroom 1brbrDouble bed (Cannot be converted into twins), wardrobebrbrbrbrBedroom 2brbr2 single beds (Cannot be converted into a double), wardrobe, chest of drawersbrbrbrbrBathroombrbrShower, bidet, sink, WCbrbrbrbrShared PoolbrbrLength: 12 metresbrbrWidth: 6 metresbrbrDepth: 0.8 - 2.1 metresbrbrEntrance: Metal laddersbrbrOpening times: May to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 7 metres

Rosmarino, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$201.3

Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from the town, convenient for traditional niceties. Restored from ancient ruins by the Florentine family who take care of guests at the resort, each holiday cottage/apartment has its own furnished terrace that opens into the resort, ideal for those who seek contact with other guests. The surrounding pine forest means shaded sanctuary from the midday sun and the swimming pool that private to the resort, offers the chance of cooling dip. Nights bring out nature, you'll sit back and watch the wild life play and the twinkling distant stars in the black sky.brbrbrbrFamilies with children appreciate the small playground, table tennis, table football and Tuscan boules court at the resort. Walkers and bikers venture out to drop themselves into nature via the many marked trails through the pine and oak forest of Monte Luco. Day-trippers are enticed to San Gimignano, Florence and Siena or stay locally where the village of Castagnoli is 3.5 Km away and has two restaurants and two wineries.brbrAbout the villabrbrTwo storey apartment with furnished terrace at the front plus a second furnished terrace and garden at the back.brbrGround FloorbrbrbrbrKitchen/diner/loungebrbrFully equipped kitchen with gas hobs, fridge-freezer, dining table for 4, sofa, TVbrbrbrbrFirst FloorbrbrbrbrBedroombrbrDouble bed (Cannot be converted into twin), wardrobe, chest of drawersbrbrbrbrBathroombrbrShower, bidet, sink, WCbrbrbrbrShared PoolbrbrLength: 12 metresbrbrWidth: 6 metresbrbrDepth: 0.8 - 2.1 metresbrbrEntrance: Metal laddersbrbrOpening times: May to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 7 metres

Peperoncino, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$252.5

San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within easy walking distance from the centre of the village. The hamlet consists of 4 buildings, housing a total of 7 apartments. Each villa have been thoughtfully and tastefully decorated, with each accommodation possessing their own private garden and terrace. In addition, there is also a garage for each individual villa, and there is also a horse-riding school approximately 10km from the hamlet.brbrLocated on a lower terrace to the rear of the hamlet is the shared chlorine-free swimming pool. This is a fantastic location, boasting wonderful views across the vineyards and countryside towards Siena and, in the distance behind the medieval city, Monte Amiata. From the hamlet, it’s a short walk uphill to the famous Brolio castle, which is surrounded by its own vineyards. You can visit the castle where the 32nd Baron Ricasolli and his family still live today. There is a restaurant serving traditional Tuscan food and you can have a wine tasting in the tasting rooms.brbrbrbrGround FloorbrbrKitchen-Diner with LoungebrbrFully equipped kitchen, gas hob with 4 rings, dining table with 4 chairs, sofa, TV.brbrBedroom 1brbrDouble bed (can be converted into twin beds if requested when booking), wardrobe, desk and chair.brbrBathroombrbrShower, sink, WC.brbrFirst FloorbrbrBedroom 2brbrDouble bed (can be converted into twins if requested when booking), wardrobe, desk and chair.brbrBathroombrbrShower, sink, WC.brbrbrbrPool:brbrLength: 15 metresbrbrWidth: 6 metresbrbrDepth: 1.2 to 2.2 metresbrbrEntrance: Roman stepsbrbrOpening times: May to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: Chlorine-freebrbrDistance from villa: 20 metresbrbrThere is a very shallow baby pool, divided from the main pool by a metal railing.

Villa Rosabella, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena, Italy

Bed

Bath

Sleeps

$353.74

La Fontanella is a traditional stone farmhouse located on the edge of the charming village of San Sano. Surrounded by vineyards and nestled in the rolling hills of Chianti, this inviting villa is ideal for a relaxing holiday with family or a small group of friends. The large garden offers a peaceful retreat with a private pool, a covered dining terrace, and wonderful views over the surrounding countryside.brbrbrbrSituated in the heart of the Chianti Classico, La Fontanella is perfectly placed for exploring the region's famous wineries, castles, and towns. Siena, San Gimignano, Florence, and Arezzo are all within easy reach for day trips. From the villa, you can walk to the centre of San Sano, where you’ll find a local restaurant and small grocery shop. The nearby village of Lecchi is also reachable on foot, while Gaiole is just 10 minutes away by car and offers further dining options, shops, a small COOP supermarket and bicycle rentals.brbrThe villa is divided into two self-contained apartments, providing privacy for two families or groups while offering shared spaces for time together. The covered terrace is ideal for outdoor dinners, and the garden features a children’s play area, pizza oven and barbecue. The interior is cosy and authentic, with terracotta floors, wooden beamed ceilings and traditional Tuscan furnishings.brbrbrbrPlease note that the owner lives in Siena but may occasionally spend a night during the summer in a small separate building on the property.brbrApartment 1 (Ground Floor)brbrbrbrLoungebrbrSofa, writing table, chair, entrance.brbrKitchen-DinerbrbrFully equipped kitchenette, bar table, three stools.brbrBedroom 1brbrDouble bed (cannot be converted to twins), wardrobe, chest of drawers, air-conditioning.brbrBathroombrbrShower, sink, WC, bidet.brbrLaundry RoombrbrFully equipped, washing machine.brbrApartment 2 (First Floor)brbrbrbrLounge-DinerbrbrSofa, two armchairs, cabinet, table and chairs, fireplace, spiral stairs to ground floor, door to balcony, main entrance.brbrKitchenbrbrFully equipped, washing machine.brbrBedroom 2brbrTwin beds (can be converted to a double), wardrobe, air-conditioning.brbrEn-suite BathroombrbrShower, sink, WC, bidet.brbrBedroom 3brbrDouble bed (cannot be converted to twins), wardrobe, settle, air-conditioning.brbrBathroom brbrShower, sink, WC, bidet.brbrbrbrPrivate Poolbrbr(pre-fabricated pool is partly raised above the ground)brbrLength: 7,5 metresbrbrWidth: 4,5 metresbrbrDepth: 1,1 metresbrbrEntrance: Metal ladderbrbrOpening times: May to September, weather permitting.brbrFenced: NobrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 5 metres

La Fontanella, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

3

Bed

3

Bath

6

Sleeps

$335.12

A Chianti Classico hamlet resort, Galenda's cottages lay on a ridge with magnificent views across rolling hills draped with olives and vines. The individually owned Tuscan stone structures, all with their own private garden/terrace and charming terracotta floors and ceilings, are tucked into a tree shaded wooded corner. The swimming pool, private to the resort, offers the chance of a daytime cooling dip by an amazing Chianti hills backdrop while night skys are no less spectacular, our advice Sit back with a glass of Chianti wine, watch the wild life play and distant stars in the black sky.brbrbrbrDay trippers are spoilt for choice between Siena, Florence and San Gimignano. Walkers and bike riders will want to reach nearby Lecchi in Chianti to experience the warm welcome of Chianti village life. Foodies will have the Chianti towns of Radda and Gaiole in their sights for typical artisanal delights. There really is something for all at Galenda!brbrAbout the villabrbrGround floor apartment with garden and furnished terrace, perfect to dine under the Tuscan starry sky.brbrGround FloorbrbrbrbrKitchen/dinerbrbrFully eqpuiped kitchen with gas hobs, fridge-freezer, dining table for 4brbrbrbrLoungebrbrDouble sofa, 2 armchairs, TVbrbrbrbrBedroom 1brbrDouble bed (Cannot be converted into twin)brbrbrbrBathroom 1brbrShower, bath, bidet, twin sinks, WCbrbrbrbrBedroom 2brbrDouble bed (Cannot be converted into twin), wardrobebrbrbrbrBathroom 2brbrShower, sink, WCbrbrbrbrCommunal laundry roombrbrWashing machine.brbrbrbrShared Pool brbrLength: 14 metresbrbrWidth: 4-6 metresbrbrDepth: 1.35 metresbrbrEntrance: Metal LadderbrbrOpening times: May to SeptemberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 100 metresbrbrBaby pool is circular with a diameter of 3 metres and a depth of 0.5 metres

Mantegna, Galenda, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena, Italy

Bed

Bath