Vacation Rentals By Owner In Gaiole In Chianti, TOS

$383.99

Trifoglio, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Trifoglio is a beautifully restored stone cottage set in an authentic 18th-century hamlet in the heart of Chianti Classico. Once renovated by an artist, the villa is tastefully furnished and blends traditional Tuscan style with modern elegance. It’s perfect for a couple or a small family of three looking to enjoy the quiet charm and natural beauty of the Tuscan countryside.brbrbrbrThe house is well located for exploring the region’s highlights. The renowned winery Casanova di Bricciano is just 500 metres away, and Gaiole in Chianti, with its restaurants, shops, and a small supermarket, is only 10 minutes by car. Day trips to Siena, Florence, Arezzo, and San Gimignano are all easily possible from here.brbrbrbrTrifoglio enjoys a peaceful position within a historic rural hamlet, surrounded by olive groves and green hills. Despite its secluded setting, the area’s amenities are easily accessible.brbrThe single-level stone house features a covered terrace directly outside the front door, perfect for enjoying a quiet breakfast. The private pool is surrounded by a well-kept lawn and blooming rose bushes, while a second shaded dining area in the garden offers the perfect spot for long, relaxed meals with a view.brbrbrbrInside, the villa combines traditional elements such as terracotta floors and wooden beam ceilings with stylish contemporary furnishings. Thoughtful details and artistic touches create a warm and inviting atmosphere.brbrbrbrWith its scenic setting, elegant interiors and sense of tranquillity, Trifoglio is a wonderful retreat for those seeking an authentic Chianti experience.brbrGround FloorbrbrbrbrLoungebrbrSofa, two armchairs, stove, table and chairs, fully equipped kitchen, air-conditioning.brbrbrbrBedroombrbrDouble bed (cannot be converted into a twin), wardrobe, chest of drawers, chair, air-conditioning, doors to garden.brbrbrbrBathroombrbrShower, sink, WC.brbrbrbrPrivate Pool:brbrLength: 10 mbrbrWidth: 5 mbrbrDepth: 1.3 metresbrbrEntrance: Roman stepsbrbrOpening times: mid-April to mid-OctoberbrbrFenced: NobrbrFurnished: Gazebo, sunloungers, parasols, table and chairsbrbrCleansed: Chlorine freebrbrDistance from villa: 20 m

1

Bed

1

Bath

2

Sleeps

$229.23

/ Nightly

Apartment

Il Sole, Montefiorile, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across rolling hills carpeted with vines. The hillside structures, all with their own private garden/terrace and charming terra cotta floors and ceilings, are placed to reveal vistas from every corner. While the surrounding oak trees give shaded sanctuary from the midday sun, the swimming pool, private to the resort, offers the chance of a cooling dip. Nights bring out nature, you'll sit back and watch the wildlife play and the twinkling distant stars in the black sky.brbrbrbrWhile taking your front row seat to view the sunset over Castello di Ama's prestigious Montebuoni 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. Foodies will have the Chianti towns of Radda and Gaiole in their sights for typical artisanal delights. If you're feeling more energetic, you may take time out for an early morning run or bike ride among some of Tuscany's finest landscapes.brbrbrbrInside the resort it is car free, the hillside position means there are steps to reach each cottage. We recommend Montefiorile for adults only to promote a quiet and peaceful environment throughout the summer.brbrAbout the villa brbrDetached cottage with stunning views of the surrounding vineyards and olive groves from its garden and furnished terrace.brbrGround FloorbrbrbrbrLounge DinerbrbrTwo sofas, dining table for 4. TV. Double doors open to terrace with magnificent viewsbrbrbrbrKitchenbrbrFully equipped kitchen, gas hob, electric oven and large freestanding fridge-freezerbrbrbrbrBedroom 1brbrDouble bed (Cannot be converted into twins), wardrobe, chest of drawers.brbrbrbrBedroom 2brbrDouble bed (Cannot be converted into twins), wardrobes, chest of drawers.brbrbrbrBathroom 1brbrShower, sink, WC, washing machinebrbrbrbrBathroom 2brbrShower, WC, sinkbrbrbrbrShared PoolbrbrLength: 13 metresbrbrWidth: 5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: April to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: SaltbrbrDistance from villa: Max 90 metres

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Bath

Sleeps

$228.07

/ Nightly

Apartment

Maggiorana, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

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 villabrbrStand alone cottage with furnished terrace and garden for dining and relaxingbrbrGround FloorbrbrbrbrKitchen/diner/loungebrbrFully equipped kitchen with gas hobs, fridge-freezer, dining table for 6, sofabed, 2 armchairs, TV, door to gardenbrbrbrbrFirst FloorbrbrbrbrBedroombrbrDouble bed (Cannot be converted into twin), wardrobebrbrbrbrBathroom brbrSink, WCbrbrbrbrBathroom 2brbrShower, 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

1

Bed

1

Bath

2

Sleeps

$870.37

/ Nightly

Villa

Sestuccia, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena, Italy

Sestuccia is a beautifully renovated stone house set in the rolling hills of the Chianti Classico region. This modern villa with character is ideal for a large family or a group of friends. Guests can look forward to a high level of comfort, including a whirlpool, a sauna and a spacious garden with roses, statues and a lovely pool. The entire property is environmentally friendly, with electricity and hot water supplied exclusively through solar energy.brbrbrbrThe setting is particularly appealing. Surrounded by peaceful countryside, the villa is just a three-minute drive from the charming village of Gaiole in Chianti, where you will find restaurants, small shops and a supermarket for everyday needs. Many of the nearby wineries offer guided visits and tastings, giving guests the chance to discover the renowned Chianti wines directly at the source. The castles and towns of the region, including Siena, San Gimignano, Florence and Arezzo, can all be easily reached on day trips.brbrSestuccia is part of a large estate that includes another holiday home as well as the owner’s residence. Guests are welcome to enjoy fresh eggs from the owner’s chickens and organic vegetables from the garden.brbrbrbrThe two-storey house combines the charm of traditional Tuscan architecture with modern elements. Highlights include a fully equipped contemporary kitchen and a large covered terrace with a dining table and comfortable seating areas, ideal for spending time together outdoors.brbrbrbrThe traditional stone building, with its well-maintained garden, pool and spacious whirlpool, offers the perfect setting for a relaxing holiday in the heart of Tuscany.brbrLower LevelbrbrKitchen-DinerbrbrBasic-equipped kitchen area, table and chairs, fireplace, open fireplace, billiard table, sofa, TV.brbrBedroom 1brbrDouble bed (cannot be converted to twins), wardrobe.brbrBathroombrbrHydro-massage bath with shower attachment, sink, WC.brbrLaundry RoombrbrWashing machine.brbrGround floorbrbrbrbrLoungebrbrTwo sofas, wall unit, cupboard, table and chair, TV, stereo, door to garden.brbrDining RoombrbrDining table and chairs, open fireplace, doors to furnished terrace.brbrKitchenbrbrFully equipped, breakfast bar and three stools, door to vegetable garden.brbrBedroom 2brbrDouble bed (cannot be converted to twins), wardrobe, chair.brbrEn-Suite BathroombrbrShower, bidet, sink, WC.brbrFirst FloorbrbrbrbrHallbrbrDoor to small furnished terrace.brbrBedroom 3brbrDouble bed (cannot be converted to twins), glass desk, wardrobe, chest of drawers.brbrEn-suite BathroombrbrShower, sink, WC.brbrBedroom 4brbrDouble bed (cannot be converted to twins), chest of drawers, walk-in wardrobe, table.brbrEn-suite BathroombrbrShower, sink, WC.brbrWellness CenterbrbrSauna, Turkish bath.brbrbrbrPrivate PoolbrbrLength: 11 metersbrbrWidth: 5.5 metersbrbrDepth: 1.5 - 2 metersbrbrEntrance: Roman stepsbrbrOpening times: April to NovemberbrbrFenced: NobrbrFurnished: SunloungersbrbrCleansed: ChlorinebrbrDistance from villa: 5 meters

4

Bed

4

Bath

8

Sleeps

$272.28

/ Nightly

Villa

Sassolaia, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena, Italy

Sassolaia is a Chianti holiday home in a dreamlike secluded location, surrounded by olive groves and vineyards with sweeping panoramic views of the Chianti Classico hills. This single-storey villa with its well-tended garden offers complete peace and is ideal for a family or two couples wanting to enjoy the authentic Tuscan countryside.brbrbrbrThe house is located in the heart of Chianti Classico with easy access to renowned wineries and historic castles. The famous Castello di Ama, known for its collection of contemporary art, is just a few kilometres away. The charming towns of Radda and Gaiole are only 10 to 15 minutes away by car and offer great restaurants, small shops, and a supermarket. The picturesque village of Lecchi, home to the excellent Ristorante Malborghetto, is just 2.5 kilometres away. Siena, Florence, San Gimignano, and Arezzo are all ideal for day trips.brbrSassolaia is peacefully located in the Tuscan hills, offering rural seclusion while still being well connected. The traditional stone façade gives the house its Tuscan character. A large covered terrace is perfect for outdoor meals and relaxed barbecues. The manicured garden with lawn and a beautiful pool invites you to unwind and enjoy the views.brbrbrbrThe house is all on one level and has a practical layout, making it comfortable and easy to live in.brbrInside, the combination of Tuscan country style, exposed wooden beams, and a warm, welcoming interior creates an immediate sense of home.brbrGround FloorbrbrbrbrLounge-DinerbrbrDining table with 4 chairs, sofa, armchair, TV.brbrbrbrKitchenbrbrFully equipped kitchen, gas hob with 4 rings, dining table with 4 chairs, air-conditioning.brbrbrbrBedroom 1brbrDouble bed (cannot be converted into twin beds), 2 bedside tables, wardrobe, chest of drawers, air-conditioning, door to the Garden.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrBedroom 2brbrPair of twin beds (can be converted into a double bed if requested when booking), wardrobe, chest of drawers, air-conditioning.brbrbrbrEn-suite BathroombrbrShower, bidet, sink, WC.brbrbrbrPrivate Pool:brbrLength: 9 metresbrbrWidth: 3.5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: May to SeptemberbrbrFenced: On RequestbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 6 metresbrbrbrbrThe pool at Sassolaia has an optional safety fence which can be set up on request.

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Sleeps

$821.5

/ Nightly

Villa

Torretta Barbischio, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Torretta Barbischio is a characterful Chianti holiday home, ideal for a relaxing stay with family or friends. The building dates back to the 14th century and has been lovingly restored, combining historic charm with modern comfort. Guests enjoy a private pool with views of the rolling Chianti hills and benefit from the excellent Il Papavero restaurant just a few steps away in the same hamlet.brbrbrbrLocated in the Chianti Classico region, Torretta Barbischio offers easy access to renowned wineries, castles, and picturesque villages. The cultural cities of Siena, San Gimignano, Florence, and Arezzo are perfect for day trips. Gaiole, with its restaurants, small shops, and a COOP supermarket, is just 3 km away.brbrThe house sits in a peaceful hamlet and provides an authentic Tuscan atmosphere. The terraced garden includes a covered dining area and several outdoor seating areas , making it perfect for relaxing and enjoying the view.brbrbrbrSpread across three floors, the villa features traditional Tuscan elements such as vaulted ceilings, wooden beams, and terracotta floors, combined with tasteful, comfortable furnishings and many personal touches.brbrbrbrThe large private pool is set within the landscaped garden. A separate pool house with fitness equipment and a sitting area adds extra comfort for guests.brbrbrbrA stay at Torretta Barbischio offeres ideal combination of Tuscan history, natural beauty, and relaxation.brbrGround FloorbrbrbrbrKitchen-DinerbrbrWell-equipped kitchen, dining table and chairs, stairs to first floor, glass door to furnished terrace, door to small covered terrace.brbrbrbrStudybrbrArmchair, bench, table, two chairs, two side tables, sideboard, bookcase.brbrbrbrCloakroombrbrSink, WC.brbrbrbrLaundry RoombrbrFully equipped.brbrbrbrFirst FloorbrbrbrbrLoungebrbrSofa, three armchairs, coffee table, side table, sideboard, pellet stove, stairs to ground and second floors, main entrance.brbrbrbrBedroom 1brbrDouble bed (cannot be converted to twins), wardrobe, chest of drawers, armchair, bench.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrSecond FloorbrbrbrbrBedroom 2brbrDouble bed (cannot be converted to twins), wardrobe, chest of drawers, sofa, armchair.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrBedroom 3brbrDouble bed (can be converted to twins), wardrobe, armchair, writing desk, chair, footstool.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrBathroombrbrShower, sink, WC.brbrbrbrPrivate PoolbrbrLength: 11 metresbrbrWidth: 5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: May to SeptemberbrbrFenced: YesbrbrFurnished: Table and chairs, sunloungers and parasolsbrbrPool house: Fridge and a bathroom with a showerbrbrCleansed: SaltbrbrDistance from villa: 11 metresbrbrbrbrPoolhousebrbrHome gym, sofa, two armchairs, coffee table, fridge.

3

Bed

3

Bath

6

Sleeps

$274.61

/ Nightly

Apartment

Casa Isabella, San Sano, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

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 villabrbrDelightful cottage apartment boasting lovely views of the resort and rolling countryside, a beautiful private garden shaded by a walnut tree, and thick stone walls that keep the heat out, helping the villa stay cool in hot weather.brbrGround FloorbrbrbrbrKitchen/diner/loungebrbrFully equipped kitchen with gas hobs, fridge freezer, dining table for 6, triple sofa and armchair, smart TV, Bluetooth speaker, door to outside area.brbrbrbrBedroom 1brbrDouble bed (Cannot be converted into twin), wardrobe, chest of drawers.brbrbrbrBathroom 1brbrBath with hand held shower head, Bidet, sink, WC.brbrbrbrBedroom 2brbr2 single beds, 2 stowaway beds, wardrobe, chest of drawers.brbrbrbrBathroom 2brbrShower, sink, WC.brbrbrbrShared PoolbrbrLength: 14 metresbrbrWidth: 7 metresbrbrDepth: 1.5 metresbrbrEntrance: Metal ladderbrbrOpening times: May to SeptemberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: Under 70 metres

2

Bed

2

Bath

4

Sleeps

$228.07

/ Nightly

Apartment

Salvia, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

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 with terrace.brbrGround FloorbrbrbrbrKitchen/diner/loungebrbrFully equipped kitchen with gas hobs, fridge, dining table for 6, sofa, TV, door to terracebrbrbrbrBedroom 1brbrDouble bed (Cannot be converted into twin), wardrobebrbrbrbrBedroom 2brbr2 single beds (Can be converted into a double), wardrobe, door to terracebrbrbrbrBathroombrbrShower, 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

2

Bed

1

Bath

4

Sleeps

$239.7

/ Nightly

Apartment

Scorpione, Montefiorile, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across rolling hills carpeted with vines. The hillside structures, all with their own private garden/terrace and charming terra cotta floors and ceilings, are placed to reveal vistas from every corner. While the surrounding oak trees give shaded sanctuary from the midday sun, the swimming pool, private to the resort, offers the chance of a cooling dip. Nights bring out nature, you'll sit back and watch the wildlife play and the twinkling distant stars in the black sky.brbrbrbrWhile taking your front row seat to view the sunset over Castello di Ama's prestigious Montebuoni 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. Foodies will have the Chianti towns of Radda and Gaiole in their sights for typical artisanal delights. If you're feeling more energetic, you may take time out for an early morning run or bike ride among some of Tuscany's finest landscapes.brbrbrbrInside the resort it is car free, the hillside position means there are steps to reach each cottage. We recommend Montefiorile for adults only to promote a quiet and peaceful environment throughout the summer.brbrAbout the villabrbrSemi-detached cottage with spectacular views from its garden and balcony over the surrounding vineyards and olive groves and its own private Hot Tub!brbrGround FloorbrbrbrbrKitchen Diner LoungebrbrFully equipped kitchen, gas hobs, fridge with freezer section. Dining table for 4, sofa, two armchairs, TV. Double doors to the terrace.brbrbrbrBedroombrbrDouble bed (Cannot be converted into twins), wardrobe, chest of drawers.brbrbrbrBathroombrbrShower, sink, WCbrbrbrbrShared PoolbrbrLength: 13 metresbrbrWidth: 5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: April to OctoberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: SaltbrbrDistance from villa: Max 90 metres

1

Bed

1

Bath

2

Sleeps

$162.9

/ Nightly

Villa

Ciacchieri, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Ciacchieri is a charming Chianti holiday accommodation with a private pool, ideal for couples or small families. The apartment is located on the ground floor of a residential building in the popular town of Gaiole in Chianti. Thanks to its central location, guests can enjoy authentic Tuscan life right outside their door: cafés, small shops and restaurants are just a short walk away. This is also the perfect base for guests taking part in, or simply watching, the legendary L’Eroica cycling event.brbrbrbrSituated in the heart of the Chianti Classico region, the accommodation offers easy access to renowned wineries and castles. Towns such as Radda, Castellina and Greve in Chianti are just a short drive away , whilst the cultural highlights of Siena, Florence, San Gimignano and Arezzo are all within reach for day trips. If you’d like to explore the beautiful Chianti countryside on two wheels, there are several bike rental shops in Gaiole.brbrCiacchieri is set in a slightly elevated position with lovely views over the rooftops of the town. The central yet quiet location makes it easy to leave the car parked during your stay.brbrbrbrThe apartment offers two furnished terraces: one is directly attached to the house and covered, with a dining table, and the second sits under a leafy pergola covered with grapevines – perfect for relaxing outdoors.brbrbrbrInside, the property is warmly and comfortably furnished, creating a homely and welcoming atmosphere with everything you need for a pleasant stay.brbrbrbrThe friendly owner’s family lives on the upper floor of the same house and is happy to assist with any questions.brbrGround FloorbrbrbrbrLounge-Kitchen-DinerbrbrFully equipped kitchenette, dresser, sideboard, settle, TV, two armchairs, coffee table, table and chairs, fireplace, double doors to terrace.brbrBedroom 1brbrDouble bed (cannot be converted to twins), wardrobe, writing desk and chair.brbrEn-suite bathroombrbrShower, sink, WC, second door to living area.brbrBedroom 2brbr2 single beds (Cannot be convereted to double), wardrobe, writing desk and chair.brbrEn-suite bathroombrbrShower, sink, WC.brbrLaundry RoombrbrFully equipped.brbrbrbrPrivate PoolbrbrLength: 7 metresbrbrWidth: 3 metresbrbrDepth: 1.6 metresbrbrEntrance: Metal ladderbrbrOpening times: May to SeptemberbrbrFenced: NobrbrFurnished: Sunloungers and showerbrbrCleansed: ChlorinebrbrDistance from villa: 6 metres

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Bath

Sleeps

$491.04

/ Nightly

Villa

Villa Riecine, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Villa Riecine is a luxurious holiday home located on the grounds of the renowned winery of the same name. Surrounded by vineyards and wooded hills, it offers breathtaking views of the classic Chianti landscape. With its well-maintained garden, two covered terraces, and a private whirlpool, the villa is an ideal retreat for a small family or two couples travelling together. Wine enthusiasts can look forward to a complimentary tasting at the Riecine estate. Guests who appreciate contemporary interior design will also feel right at home.brbrbrbrThe villa enjoys a peaceful hilltop position in the Chianti Classico region, with easy access to the area's famous wineries, castles, and picturesque towns and villages. The cultural highlights of Siena, San Gimignano, Florence, and Arezzo can all be reached by car in under an hour. The charming town of Gaiole is just a five-minute drive away and offers restaurants, shops, a bike rental service, and a small Coop supermarket.brbrThe single-storey stone villa features a private garden with lovely outdoor areas, including a furnished terrace perfect for al fresco meals and a separate area with a whirlpool.brbrbrbrInside, the atmosphere is bright, spacious, and refined. Wooden-beamed ceilings, contemporary art, and a neutral colour scheme come together in a harmonious blend of elegance and comfort. The large living room with a generous designer sofa and modern kitchen creates a welcoming space for guests. The thoughtfully designed interior extends to the bedrooms and bathrooms, making this villa not only highly comfortable but also aesthetically pleasing.brbrOpen-Plan Kitchen-Diner and LoungebrbrLounge AreabrbrLarge corner sofa, TV, open fireplace, French door leading to terrace.brbrDining Room AreabrbrWooden dining table with 8 cushioned chairs, stereo, French doors leading to garden.brbrKitchen AreabrbrGas hob with 1 ring, induction hob with 5 rings, twin oven, breakfast bar with 4 stools, American-style fridge-freezer, wine-cooler fridge, twin-basin sink.brbrBedroom 1 – MasterbrbrDouble bed (cannot be converted into twins), wardrobe, TV, chest of drawers, wood-burning stove, stereo, French door leading to garden and terrace.brbrEn-Suite BathroombrbrShower unit, WC, bidet, sink.brbrBedroom 2brbrDouble bed (can be converted to twins), walk-in wardrobe, chest of drawers, TV.brbrBathroombrbrShower unit, WC, sink.brbrbrbrPrivate PoolbrbrThere is no pool.

2

Bed

2

Bath

4

Sleeps

$216.43

/ Nightly

Apartment

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

Gaiole In Chianti, Siena, Italy

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.brbrBedroombrbrDouble bed (can be converted into twin beds if requested when booking), wardrobe, desk and chair, chest of drawers.brbrBathroombrbrShower, bidet, 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.

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Sleeps

$529.44

/ Nightly

Villa

Casa Virginia, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Casa Virginia is a welcoming Chianti holiday home, ideal for a relaxing break with family or a small group of friends. Set on the edge of the picturesque village of San Sano, the house enjoys peaceful surroundings and beautiful views over rolling hills and vineyards. The large garden is filled with terracotta flower pots and fragrant lavender, and guests can choose between three furnished terraces and a covered loggia to enjoy meals and moments outdoors.brbrbrbrThe house is perfectly placed for exploring the Chianti Classico region. Famous wineries, castles and charming villages are all nearby, and cities like Siena, Florence, San Gimignano and Arezzo can be easily reached for day trips.brbrbrbrThe location is peaceful but convenient. San Sano has a small grocery store and a local restaurant just a short walk away. The surrounding area is ideal for hiking and cycling. The nearby village of Lecchi is also within walking distance, while Gaiole in Chianti is only 10 minutes away by car, with several good restaurants, shops, a small COOP supermarket and bike rentals.brbrCasa Virginia is a traditional Tuscan stone house spread over two floors. The exterior is built from local stone, and the property has been carefully maintained to preserve its rustic charm.brbrbrbrInside, the interiors are light and welcoming. Wooden beam ceilings and terracotta floors create a classic Tuscan atmosphere, complemented by a comfortable and practical décor throughout.brbrbrbrCasa Virginia offers a warm and peaceful base for discovering the heart of Chianti, with everything you need for a memorable Tuscan escape.brbrGround FloorbrbrbrbrHallbrbrChest of drawers, side table, double doors to furnished loggia and main entrance.brbrbrbrLoungebrbrSofa, armchair, TV, air-conditioning.brbrbrbrDining roombrbrTable and chairs, two sideboards, side table, air-conditioning.brbrbrbrKitchenbrbrFully equipped, free-standing cupboard, double doors to furnished terrace.brbrbrbrBedroom 1brbrDouble bed (can be converted to twins), wardrobe, desk and chair, bedside table, corner cupboard, air-conditioning.brbrbrbrBedroom 2brbrDouble bed (cannot be converted to twins), wardrobe, two bedside tables, air-conditioning.brbrbrbrBathroom brbrShower, sink, WC, bidet.brbrbrbrBathroom brbrShower, sink, WC, bidet.brbrbrbrFirst FloorbrbrbrbrBedroom 3brbrTwin beds (can be converted into a double), wardrobe, air-conditioning.brbrbrbrEn-suite bathroombrbrShower, sink, WC.brbrbrbrbr Private Poolbrbr Length: 12 metresbrbr Width: 6 metresbrbr Depth: 1.1 - 2.6 metresbrbr Entrance: Roman steps, diving board and ladder accessbrbr Opening times: June to Septemberbrbr Fenced: nobrbr Furnished: Sunloungers and parasolsbrbr Cleansed: Chlorinebrbr Distance from villa: 20 metres

3

Bed

3

Bath

6

Sleeps

$221.08

/ Nightly

Apartment

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

Gaiole In Chianti, Siena and Chianti, Italy

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 brbrGround floor apartment with dining terrace, sun terrace and garden.brbrbrbrGround FloorbrbrbrbrCellar Loungebrbr2 Triple sofas, double sofa, bar, pool table, open fire place, TVbrbrbrbrFirst FloorbrbrbrbrKitchen DinerbrbrFully equipped kitchen,fridge/freezer, gas hob with 4 rings. Dining table for 6, double sofa, TV.brbrbrbrBedroom 1brbrDouble bed (cannot be converted into twin), wardrobe, chest of drawers.brbrbrbrEn suite Bathroom 1brbrShower, bidet, sink, WC.brbrbrbrBedroom 2brbrTwin beds (can be converted into double), waredrobe, armchair.brbrbrbrBathroom 2brbrShower, 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

2

Bed

2

Bath

4

Sleeps

$228.07

/ Nightly

Apartment

Vaniglia, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

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 villabrbrFirst floor Tuscan apartment with a pretty furnished terrace in the gardens of the resort for al fresco diningbrbrFirst FloorbrbrbrbrKitchen/diner/loungebrbrFully equipped kitchen with gas hobs, fridge, dining table for 4, double sofa.brbrbrbrBedroom 1brbrDouble bed (Cannot be converted into twin), wardrobebrbrbrbrBedroom 2brbr2 single beds (Cannot be converted into a double), 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

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Bath

Sleeps

$273.45

/ Nightly

Villa

La Rana, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

La Rana is a welcoming Chianti holiday home on the edge of the pretty village of San Sano, ideal for a family of four or two couples. The well-maintained garden offers beautiful views over vineyards and the gentle Chianti hills. Two furnished terraces invite guests to relax: one with a comfortable seating area and another with a dining table, perfect for shared meals outdoors. The private pool is quietly set within the garden and provides a refreshing escape on warm days.brbrbrbrThe villa enjoys an excellent position in the Chianti Classico region, with easy access to the area’s renowned wineries and castles, as well as its medieval towns and villages. The cultural highlights of Siena, San Gimignano, Florence and Arezzo can all be reached on day trips. Gaiole in Chianti is just ten minutes away by car and offers several restaurants, small shops, a COOP supermarket and bike rentals.brbrbrbrSan Sano itself is a picturesque village full of Tuscan charm. Just a few minutes’ walk from the villa is the popular restaurant La Grotta della Rana, which also stocks a small selection of groceries. The surrounding countryside is ideal for walking and cycling, and the lovely village of Lecchi in Chianti can also be reached on foot.brbrLa Rana is a two-storey stone house with a thoughtful layout. The ground floor living area opens to the garden, while the bedrooms on the upper floor offer peace and pleasant views. A covered terrace beside the house is perfect for long evenings with good food and wine.brbrbrbrInside, the villa combines traditional Tuscan style with warm comfort. Wooden beam ceilings, terracotta floors and thoughtfully chosen furnishings create a relaxed and inviting atmosphere. It’s a wonderful choice for guests who appreciate authenticity and comfort.brbrbrbrWith its private garden, lovely pool, proximity to a charming village and peaceful rural setting, La Rana offers a delightful Tuscan holiday experience for families or friends.brbrGround FloorbrbrbrbrLoungebrbrStairs to the first floor, sofa, armchair, smart TV, side table, two sideboards, fireplace, door to furnished terrace.brbrbrbrKitchen-DinerbrbrFully equipped kitchen, table and chairsbrbrbrbrBathroom brbrBath with handheld shower, sink, WC.brbrbrbrLaundry roombrbrFully equipped.brbrbrbrFirst FloorbrbrbrbrLoungebrbrSofa, armchair, TV, coffee tablebrbrbrbrBedroom 1brbrDouble bed (cannot be converted to twins), wardrobe, chest of drawers, chair, balcony.brbrbrbrBedroom 2brbrTwin beds (can convert to a double), wardrobe with chest of drawers.brbrbrbrBathroom brbrShower, sink, WC, bidet.brbrbrbrPrivate PoolbrbrLength: 7 metresbrbrWidth: 4 metresbrbrDepth: 1.4 metresbrbrEntrance: Roman stepsbrbrOpening times: May to SeptemberbrbrFenced: NobrbrFurnished: sunloungers, parasols, tables and chairsbrbrCleansed: ChlorinebrbrDistance from villa: 10 metres

2

Bed

2

Bath

4

Sleeps

$326.97

/ Nightly

Apartment

Nicchio, Agriturismo Vinci, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Surrounded by the rolling Chianti hills covered with vineyards and olive groves, this property is wonderfully positioned to enjoy all the local castles and wine estates. At the agriturismo, there is a small restaurant with a bar that has a pretty terrace overlooking the Tuscan countryside. Agriturismo Vinci is composed of 5 little Tuscan villas, plus the owner’s residence. It's located within walking distance of the lovely Tuscan town of Gaiole in Chianti. Day trips to Florence, Siena, or San Gimignano are perfectly possible, too! brbr brbrThere is no pool at Agriturismo Vinci - however, there is a beautiful lake shared with other residents of the property and nearby houses. The lake is surrounded by a pretty Tuscan forest on two sides while a third has a lovely olive grove. The last side has a grassy area and a small, paved area to sunbathe, complete with some sun beds. A little wooden jetty provides access to the clear water. The water is tested regularly to ensure that it is clean and safe to swim.brbrbrbrAbout the villa brbrDetached cottage with terrace and garden with lawn plus extensive views over the countryside and lake.brbrGround FloorbrbrbrbrKitchen Diner with LoungebrbrFully equipped kitchen, gas hob with 4 rings, wood-burning stove, dining table with 6 chairs, 2 sofas, TV.brbrbrbrBedroom 1brbrDouble bed (cannot be converted into twin beds), wardrobe, desk and chair, access to garden via French doors.brbrbrbrEn-suite BathroombrbrShower unit, bidet, twin sinks, WC.brbrbrbrLower Ground FloorbrbrbrbrBedroom 2brbrDouble bed (cannot be converted into twin beds), wardrobe, access to garden via French doors.brbrbrbrEn-suite BathroombrbrBathtub with shower attachment, bidet, twin sinks, WC.brbrbrbrLake:brbrLength: 300 metresbrbrWidth: 150 metresbrbrDepth: 10 metresbrbrEntrance: NobrbrOpening times: Jan to DecbrbrFenced: NobrbrFurnished: NobrbrCleansed: NobrbrDistance from villa: 100 metres

2

Bed

2

Bath

4

Sleeps

$755.18

/ Nightly

Villa

Valliole, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Valliole is a 17th-century villa in the Chianti region with breathtaking postcard-perfect views across the vineyards of Chianti Classico. Set on a hill in peaceful countryside, this spacious and beautifully maintained property comfortably accommodates up to eight guests and is ideal for a relaxing holiday with family or friends. The large infinity pool with panoramic views is one of many highlights. A covered terrace and several outdoor seating areas provide plenty of space to come together or retreat for quiet moments.brbrbrbrThe location is perfect for exploring the region’s renowned wineries and castles. The prestigious Castello di Ama is just over a kilometre away and also features an impressive collection of contemporary art. The Chianti towns and villages are within easy reach, and cities such as Siena, San Gimignano, Florence and Arezzo are perfect for day trips. Radda, with its restaurants, shops and supermarket, is 15 minutes away by car. The charming villages of Lecchi and San Sano can also be reached on foot in under 30 minutes. Each has a restaurant and a small grocery store.brbrThe property comprises a two-storey main house and a separate guesthouse for two guests, ideal for those seeking extra privacy.brbrbrbrInside, original terracotta floors and wooden beam ceilings are combined with elegant furnishings and contemporary art.brbrbrbrValliole is a timeless Tuscan retreat that combines history, beauty and comfort in one unforgettable setting.brbrGround FloorbrbrbrbrHallbrbrCupboard, console table, chair, fireplace, stairs to first floor, entrance.brbrLounge-DinerbrbrTwo sofas, two chairs, woodburning stove, table and chairs, cupboard, two sets of doors to terrace.brbrKitchenbrbrFully equipped.brbrFirst FloorbrbrbrbrLibrarybrbrTable, two chairs, wood burning stove.brbrBedroom 1brbrTwin beds (can be converted into a double bed), two wardrobes, table.brbrEn-suite BathroombrbrShower, sink, WC.brbrBedroom 2brbrDouble bed (cannot be converted into twin beds).brbrEn-suite BathroombrbrBath, shower, WC, SinkbrbrBedroom 3brbrDouble bed (cannot be converted into twin beds)brbrBathroombrbrBath, shower, twin sinks, WC.brbrSeparate AnnexebrbrbrbrKitchen-DinerbrbrWell-equipped kitchenette, table and chairs, door to terrace.brbrMaster Bedroom brbrDouble bed (cannot be converted into twin beds), wardrobe, two chairs.brbrBathroombrbrJacuzzi bath, shower, sink, WC.brbrbrbrPrivate PoolbrbrLength: 12 metersbrbrWidth: 6 metersbrbrDepth: 1.4 metresbrbrEntrance: Roman stepsbrbrOpening times: Easter to OctoberbrbrFenced: NobrbrFurnished: Sunloungers, parasols, pergola, benches and outside shower, WCbrbrCleansed: ChlorinebrbrDistance from villas: 3 meters

4

Bed

4

Bath

8

Sleeps

$529.44

/ Nightly

Villa

Le Cerreta, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena, Italy

Le Cerreta is a traditional Tuscan stone villa in a secluded setting, offering breathtaking panoramic views, an elegant infinity pool, and two furnished terraces, making it the ideal retreat for a relaxing holiday with family or friends. Surrounded by fields, woodlands, and gently rolling hills, the property is immersed in the unspoilt Chianti countryside, perfect for those seeking peace, nature, and comfort.brbrbrbrJust 5 km away lies the charming town of Gaiole in Chianti, where guests will find everything they need, from local shops and welcoming cafés to excellent restaurants. The area is renowned for its vineyards, historic castles, and authentic Tuscan lifestyle. Cultural gems such as Siena, San Gimignano, and Florence are all within easy reach for day trips.brbrbrbrSet on a hillside, Le Cerreta enjoys sweeping views across the Chianti landscape. Its elevated position brings a sense of tranquillity and spaciousness, allowing guests to fully connect with the surrounding nature.brbrThe detached villa is spread over two floors and features a well-maintained garden. Outdoors, two terraces provide inviting spaces at any time of da - one is a furnished balcony terrace with comfortable seating, the other equipped with a dining table and chairs, ideal for al fresco meals or unwinding in the shade.brbr brbrInside, the villa showcases traditional Tuscan architecture with terracotta floors and exposed wooden beams, while the interiors blend rustic charm with modern, elegant touches to create a warm and stylish atmosphere.brbrbrbrWith its unique combination of authentic character, stunning location, and convenient access to the region’s culinary and cultural highlights, Le Cerreta offers a truly special Tuscan holiday experience.brbrGround FloorbrbrOpen Plan Kitchen, Diner and Lounge AreabrbrGas oven and hob, extractor fan, fridge-freezer, twin-basin sink, cooking island, dining table with four chairs, desk with chair, sofa, 2 armchairs, flat-screen TV.brbrLower Ground FloorbrbrBedroom 1brbrDouble bed with cushioned headboard, wardrobe, mosquito screens, access to garden via French doors.brbrEn-Suite BathroombrbrBathtub with shower attachment, bidet, sink, WC.brbrBedroom 2brbrDouble bed with wrought iron frame, wardrobe, mosquito screens, access to garden via French doors.brbrBedroom 3brbrPair of twin beds with wrought iron frames, wardrobe, mosquito screens.brbrBathroombrbrWC, sink, shower.brbrBathroombrbrWC, sink, shower.brbrbrbrPrivate PoolbrbrInfinity poolbrbrLength: 12 metersbrbrWidth: 4.5 metersbrbrDepth: 1.2 – 1.6 metersbrbrEntrance: Roman stepsbrbrOpening: May to SeptemberbrbrFenced: nobrbrFurnished: sunloungers, table and chairs, outdoor showerbrbrCleansed: chlorine free

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Bath

Sleeps

$349.08

/ Nightly

Villa

Villa Montemarcoli, a haven of peace and love in Gaiole in Chianti

Gaiole In Chianti, Provincia di Siena, Italy

pA short distance from cycling, hiking trails, and more, this welcoming villa lets you experience it all. Jump into your car and make short work of the 10-minute drive to Meleto Castle or the 10-minute drive to Cantalici Winery (and enjoy the property's convenient onsite parking in the meantime). /ppAfter you return to this 1076-sq-ft villa, you can unwind by the outdoor pool or sip a drink in the hot tub; you may also like the garden and deck or patio. As for the great indoors, you can come inside and enjoy the WiFi, TV, and stereo. /ppAs you settle into this 2-bedroom, 2-bathroom rental, you'll find a living room, a BBQ grill, air conditioning, and a desk. Bathroom amenities include a hair dryer, a bidet, and towels. Prepare a home-cooked meal in the kitchen, complete with an oven, a stovetop, and a refrigerator, as well as a coffee maker, an ice maker, and a microwave. And you can even travel light because you'll have access to laundry facilities. /p

2

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2

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4

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