Vacation Rentals By Owner In Gaiole In Chianti, TOS

$158.41

Farmhouse apartment in Chianti with garden and pool for 2 people

Gaiole In Chianti, Toscana /Siena, Italy

Stone farmhouse. The apartment is carefully furnished and well-stocked. Satellite TV, Wifi, kitchen, fridge, freezer, washing machine, iron and other small appliances. Lounge corner with armchairs. Very cool apartment in summer. Garden equipped with tables, chairs and sun beds. Private gate. Swimming pool inside the garden to be shared with the owners.brChianti Classico is an area of rare beauty. Unspoiled nature, vineyards and olive groves will be a joy for visitors.

1

Bed

1

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2

Sleeps

$525.95

/ Nightly

Villa

Casa dei Mandorli, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Perched high in the scenic Ama hills, Casa dei Mandorli offers a peaceful retreat for a couple, with sweeping views over a patchwork valley of olive groves and vineyards stretching to the horizon. The nearby hamlets of Ama and Casanova di Ama add charm to the landscape, while the large infinity pool provides a striking focal point for outdoor living.brbrbrbrThe villa is perfectly situated between the hilltop town of Radda in Chianti and the idyllic village of Lecchi in Chianti, offering a balance of tranquillity and convenience. Lecchi is home to the excellent Ristorante Malborghetto and a well-stocked grocery shop, while Radda offers a wider range of shops, restaurants, and a small supermarket. Historic landmarks such as Castello di Brolio and several renowned Chianti Classico wineries are within easy reach. Siena, Florence, Arezzo, and San Gimignano are also ideal destinations for memorable day trips.brbrBuilt from traditional stone, Casa dei Mandorli blends rustic character with modern elegance. The beautifully maintained garden includes lawns and a large terrace set just above the private pool - an ideal spot for al fresco dining or simply enjoying the views.brbrbrbrInside, the villa is bright and welcoming, with contemporary country-style furnishings. The open-plan kitchen, dining and living area features large arched windows and doors that frame the surrounding garden and bring the outdoors in.brbrbrbrThe discreet owners live in a separate villa above, with two friendly dogs kept within a fenced area. They are available if needed and offer helpful local recommendations, contributing to a relaxed and memorable stay at Casa dei Mandorli.brbrGround FloorbrbrbrbrLounge/ DinerbrbrSofa, side tables, dining table, glass cabinet, chairs, fireplace (decoration only), TV, chest of drawers, air-conditioning, French door to terrace.brbrbrbrKitchenbrbrFully equipped, induction hob, fridge/freezer.brbrbrbrBedroom brbrDouble bed (can't be converted into twin beds), bedside tables, wardrobe, desk, chair, air-conditioning.brbrbrbrEn-suite BathroombrbrShower, sink, bidet, WC.brbrbrbrPrivate Pool (infinity)brbrLength: 11 metresbrbrWidth: 5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: May to OctoberbrbrFenced: NobrbrFurnished: Pergola, table, chairs, sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villas: 5 metres

1

Bed

1

Bath

2

Sleeps

$852.92

/ Nightly

Villa

Casa Boccaccio, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Casa Boccaccio is a spacious, design-led apartment nestled in a small historic hamlet within a former medieval castle comprising ten residences. This semi-detached retreat seamlessly blends Tuscan heritage with modern style, offering a private pool, a large furnished terrace, and an elegant interior. It is perfect for guests who value calm, refinement, and privacy. Surrounded by vineyards and olive groves, it commands breathtaking 360-degree views across the Chianti Classico landscape.brbrbrbrLocated in the heart of Chianti Classico, the apartment provides easy access to renowned towns, wineries, and castles. The prestigious Tenuta Perano, owned by the Frescobaldi family and featuring its own osteria, is a ten-minute walk away - ideal for dinner without the need of a car. The famous Castello di Brolio is just a twenty-minute drive. The charming village of Gaiole in Chianti, 2.5 km away, offers restaurants, boutique shops, a COOP supermarket, and bike rental. Siena, Arezzo, San Gimignano, and Florence are all within convenient day-trip range.brbrThe location is wonderfully peaceful, set in the countryside with sweeping vineyard and olive grove views. The apartment spans the ground and first floors. A generous furnished terrace with dining area sits just outside, inviting open-air meals and relaxation. The private pool is adjacent and perfect for unwinding.brbrbrbrInside, original features such as vaulted ceilings, terracotta floors, and wood-beamed ceilings have been meticulously preserved. These traditional elements contrast beautifully with the stylish, contemporary décor created by a Milan-based award-winning interior designer. High-quality furniture and carefully chosen color accents result in a refined yet homely ambiance.brbrbrbrIn addition to its private pool, guests also have access to the estate's larger communal pool, just a short walk away.brbrGround FloorbrbrbrbrLoungebrbrCorner sofa, coffee table, ottoman, smart TV, bookshelves, fireplace (decoration only), air conditioning.brbrbrbrDining RoombrbrDining table and chairs, cupboard, air conditioning, doors to terrace, terrace with outdoor living furniture.brbrbrbrKitchenbrbrFully equipped kitchen, island unit and chairs, gas hob, fridge/ freezer, air conditioning.brbrbrbrGuest ToiletbrbrWC, sink.brbrbrbrBedroom 1brbrDouble bed 1.5 x 2 m (cannot be converted into twin beds), bedside tables, ottoman, chest of drawers, smart TV, side table, air conditioning.brbrbrbrEn-Suite BathroombrbrShower, WC, sink, bidet.brbrbrbrBedroom 2brbrDouble bed 1.5 x 2 m (cannot be converted into twin beds), bedside tables, bench, ottoman, chest of drawers, smart TV, side table, air conditioning.brbrbrbrEn-Suite BathroombrbrWardrobe, bathtub, shower, double sink, WC, bidet.brbrbrbrExtra Area (separate entrance and stairs to 1st floor)brbrbrbrBedroom 3 brbrDouble bed 1.5 x 2 m (cannot be converted into twin beds), wardrobe, bedside tables, chest of drawers, wardrobe, door to terrace, air conditioning. brbrbrbrEn-Suite BathroombrbrBath with shower attachment, double sink, WC, bidet.brbrbrbrUtility RoombrbrWashing machine, dryer.brbrbrbr1st Floor (separate entrance and stairs to ground floor)brbrbrbrLounge/ KitchenettebrbrSofa, armchair, coffee table, sink, coffee machine, table and chairs, side table, stairs to the ground floor bedroom 3, and separate staircase to the entrance, air conditioning.brbrbrbrBedroom 4brbrDouble bed 1.5 x 2 m (cannot be converted into twin beds), bedside tables, chest of drawers, smart TV, TV table, wardrobe, armchair, air conditioning.brbrbrbrEn-Suite BathroombrbrShower, sink, WC, bidet.brbrbrbrPrivate Pool:brbrLength: 8 metresbrbrWidth: 5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: End of May to SeptemberbrbrFenced: NobrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 5 metersbrbrbrbrShared Pool:brbrLength: 15 metresbrbrWidth: 8 metresbrbrDepth: 1.1 - 1.7 metresbrbrEntrance: Metal laddersbrbrOpening times: May to SeptemberbrbrFenced: YesbrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 150 metres

4

Bed

4

Bath

8

Sleeps

$453.8

/ Nightly

Villa

La Fornace di Tremoleto - Villa with exclusive pool in Chianti

Gaiole In Chianti, Provincia di Siena, Italy

La Fornace di Tremoleto is a historic residence that was once the ancient furnace of the famous Castello di Brolio. The house retains many of its original architectural elements, with exposed stone walls, wooden beams, and large open spaces that reflect its origin. The interiors have been tastefully furnished, combining a rustic style with modern comforts to offer an unforgettable stay. Located in the heart of Chianti, right on the route of the Eroica (a historic vintage bicycle race), La Fornace di Tremoleto offers easy access to the region's renowned wineries, where you can taste some of the best wines in the world. Additionally, the proximity to the Castello di Brolio allows you to explore one of the oldest and most fascinating castles in Tuscany, with its historic cellars, gardens, and breathtaking views. The house, spread over two floors, consists of three large double bedrooms on the upper floor, two bathrooms with showers (one on each floor), a kitchen, a living room, and a sitting room. The house is equipped with all the necessary amenities to make your stay as pleasant as possible, including free Wi-Fi, TV, private parking, a fully equipped kitchen (oven, microwave, kettle, dishwasher, washing machine), air conditioning and heating, outdoor spaces with a garden and barbecue area, an exclusive-use swimming pool with an outdoor shower, and children's play equipment .

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Sleeps

$628.35

/ Nightly

Villa

Mulinaccio di Badia, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Mulinaccio di Badia is a charming holiday home set in the gentle hills of the Chianti Classico, surrounded by vineyards and olive trees. Its peaceful rural setting and a beautiful pool with sweeping views of the Tuscan landscape make it the perfect retreat for a relaxing holiday with family or friends.brbrbrbrThanks to its central location in the heart of Chianti Classico, all the region’s highlights are within easy reach. The renowned Castello di Ama winery, also home to a contemporary art collection, is just 15 minutes away. The same distance takes you to the famous Castello di Brolio, which offers wine tastings and a highly regarded restaurant. Gaiole in Chianti, less than 5 km away, provides cafés, restaurants and a small COOP supermarket. Also nearby is the idyllic village of Lecchi, home to the excellent Ristorante Malborghetto and a small grocery shop. Siena can be reached in around 40 minutes, while Florence, Arezzo and San Gimignano are also ideal for day trips.brbrThe two-storey natural stone villa has been lovingly restored, preserving traditional features like terracotta floors and wood-beamed ceilings. Light-coloured walls, comfortable furnishings and thoughtful details create a warm and homely atmosphere.brbrbrbrA special highlight is the separate capanna, opening onto a central courtyard, featuring a summer kitchen, a dining area and a cosy lounge - perfect for long, leisurely meals and shared moments outdoors.brbrbrbrMulinaccio di Badia offers peaceful living in the heart of the Tuscan countryside.brbrFirst FloorbrbrbrbrLounge/ Dining Roombrbr2 sofas, coffee table, smart TV, decorative fireplace, table with 10 chairs, glass cabinet.brbrbrbrKitchenbrbrFully equipped, 4 ring hob full-size fridge/ freezer, dishwasher, decorative fireplace, table.brbrbrbrBedroom 1brbrDouble bed (cannot be converted into twin beds), two bedside tables, wardrobe, two chests of drawers, fan, mosquito screen.brbrbrbrEn-suite BathroombrbrShower, sink, bidet, WC.brbrbrbrBedroom 2brbrDouble bed (cannot be converted into twin beds), two bedside tables, wardrobe, chest of drawers, fan, mosquito screen.brbrbrbrEn-suite BathroombrbrShower, sink, bidet, WC.brbrbrbrBedroom 3brbrDouble bed (cannot be converted into twin beds), two bedside tables, wardrobe, chest of drawers, fan, mosquito screen.brbrbrbrEn-suite BathroombrbrShower, sink, bidet, WC.brbrbrbrBedroom 4brbrDouble bed (cannot be converted into twin beds), two bedside tables, wardrobe, chest of drawers, fan, mosquito screen.brbrbrbrBedroom 5brbrPair of twin beds (cannot be converted into double bed), wardrobe, chest of drawers, fan, mosquito screen.brbrbrbrBathroombrbrShower, sink, bidet, WC.brbrbrbrGround FloorbrbrbrbrGymbrbrWell-equipped gym with bicycle and walking machine, weights and other exercise equipment.brbrbrbrUtility RoombrbrLaundry facilities, washing machine, sink.brbrbrbrBathroombrbrShower, sink, bidet, WC.brbrbrbrBathroombrbrShower, sink, bidet, WC.brbrbrbrOutdoor Stone Barn/ CabanabrbrbrbrKitchen/ Dining areabrbrFully equipped, fridge, barbeque, sink, oven, induction hob, cushioned stone benches and chairs, a large table with two benches, cupboard. brbrbrbrGames RoombrbrTable tennis table.brbrbrbrPrivate PoolbrbrLength: 12 metersbrbrWidth: 4 metersbrbrDepth: 1.10 - 1.80 metersbrbrEntrance: Roman StepsbrbrOpen: June to the end of SepbrbrFenced: nobrbrFurnished: SunloungersbrbrCleansed: SaltbrbrDistance from the villa: 20m

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Sleeps

$649.29

/ Nightly

Villa

Podere Lucignano Secondo - La Villa

Gaiole In Chianti, Provincia di Siena, Italy

In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its green vineyards, you will find the Podere Lucignano Secondo Agriturismo, a mansion built in 1898, now elegantly restored and turned into an exclusive relais.brbrThe Podere Lucignano Secondo Agriturismo, ideal place for lovers of relax and nature as well as food-and-wine connoisseurs, provides its guests with a warm welcome and an exclusive service.brbrThe Villa consists of 5 twin/double bedrooms and 4 toilet/bathrooms, 2 dining rooms, 2 kitchens, 3 fireplaces, 2 sitting rooms, 1 sitting room opening onto the garden, 1 terrace, park, private parking place. The pool is open May-October 24h.brbrThe apartment is independent and for exclusive use.brbrApartment sanitized after each check-out.brbrbrSERVICES:brbrFirst Day Food Shopping Service;brWineries Sightseeing Reservation;brTypical Tuscan Restaurants Reservation;brVan Transfer Service from / to Airports - Private Tour Driver Service.

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Sleeps

$290.4

/ Nightly

Villa

Casa BD in Gaiole - 150 m² apartment with a view & travel guide - sleeps 8

Gaiole In Chianti, Provincia di Siena, Italy

pA short distance from cycling, hiking trails, and more, this family-friendly villa lets you experience it all. Gaiole in Chianti Stadium is an easy 9-minute walk away, so you can leave your car at the property, which offers covered onsite parking, or jump in your vehicle to make short work of the 6-minute drive to Meleto Castle. /ppAfter you return to this 1615-sq-ft villa, you can unwind by the communal pool or sip a drink in the garden; you may also like the deck or patio and outdoor furniture. When you come inside, connect to the free WiFi or get cozy in front of the cable/satellite TV (video library available). There's also table tennis, a DVD player, and a stereo for your enjoyment. /ppA living room, a dining area, air conditioning, and an office are featured at this 4-bedroom, 3-bathroom rental. Bathroom amenities include a hair dryer, a bidet, and towels. The kitchen is equipped with an oven, a stovetop, and a refrigerator, as well as a coffee maker, an electric kettle, and a microwave. And you can even pack a bit lighter because there's a washer and dryer. /p

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Bath

Sleeps

$314.17

/ Nightly

Villa

Podere Lucignano Secondo - Le Logge

Gaiole In Chianti, Provincia di Siena, Italy

In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its green vineyards, you will find the Podere Lucignano Secondo Agriturismo, a mansion built in 1898, now elegantly restored and turned into an exclusive relais.brbrThe Podere Lucignano Secondo Agriturismo, ideal place for lovers of relax and nature as well as food-and-wine connoisseurs, provides its guests with a warm welcome and an exclusive service.brbrThe apartment “Le Logge” at first floor consists of 3 twin/double bedrooms each with private toilet/bathroom, 1 living/dining room with kitchen and fireplace, 1 sitting room with fireplace, 1 sitting room opening onto the garden, 1 terrace, park, private parking place. The pool, open from May to October 24h, is shared with the other apartment.brbrThe apartment is independent and for exclusive use, others guests could be present in the other apartment at ground floor. brbrApartments sanitized after each check-out.brbrbrSERVICES:brbrFirst Day Food Shopping Service;brWineries Sightseeing Reservation;brTypical Tuscan Restaurants Reservation;brVan Transfer Service from / to Airports - Private Tour Driver Service.

3

Bed

3

Bath

6

Sleeps

$1189.2

/ Nightly

Villa

Casale San Vincenti, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Casale San Vincenti is a stylishly restored natural stone villa nestled on a hill in a small hamlet, offering sweeping views across the rolling Chianti hills. The tranquil surroundings, well-kept garden, and spacious pool make this property an ideal retreat for those seeking peace and privacy. A striking contrast between the traditional exterior and the luxurious, minimalist interior highlights its exceptional character - this is where Tuscan authenticity meets contemporary design.brbrbrbrThe holiday home is part of the La Canonica di San Vincenti estate, complete with its own chapel available for weddings. Guests can reach the renowned Tenuta San Vincenti on foot in about 15 minutes. The prestigious wineries Castello di Brolio and Castello di Ama are approximately a 30-minute drive away. Food lovers will delight in the tiny hamlet of Villa a Sesta, just 15 km distant, which hosts two Michelin‑starred restaurants. A supermarket is found in Mercatale Valdarno (13 km), whilst Gaiole in Chianti lies 16km away and offering shops, restaurants, and bike rentals. Siena, Arezzo, Florence, Montepulciano, and Cortona are all within easy reach for day trips.brbrThe villa spans three floors, and an adjoining cottage with a bedroom and kitchenette provides extra privacy for guests. A separate annex features a well-equipped fitness studio. A covered south-facing terrace with a large dining table and comfortable seating steps offers a perfect space for outdoor meals and relaxation.brbrbrbrInside, you’ll find original wood-beamed ceilings painted white, dark stone or marble floors, pale walls, and elegant furnishings in soft jewel tones.brbrbrbrCasale San Vincenti is a retreat with character that harmoniously blends calm, contemporary style, and Tuscan soul.brbrGround FloorbrbrbrbrLoungebrbrSmart TV, large TV cabinet, extra-large U-shaped sofa, 5 soft chairs, 2 circular soft stools, 2 coffee tables, large fireplace, side table, steps to the dining room (no railing careful with small children), French doors to terrace, terrace with large table, and 10 chairs.brbrbrbrDining RoombrbrTable with 14 chairs, glass cabinet.brbrbrbrKitchenbrbrFully equipped professional kitchen, large fridge/freezer, induction hob, glass cabinet.brbrbrbrUtility RoombrbrSink, washing machine and dryer.brbrbrbrBathroombrbrSink, WCbrbrbrbrFirst Floor (access via lift and stairs)brbrbrbrBedroom 1brbrDouble bed (can be converted into twin beds), two bedside tables, and two wardrobes.brbrbrbrEn-suite BathroombrbrLarge shower, sink, WC.brbrbrbrBedroom 2brbrDouble bed (can be converted into twin beds), two bedside tables, wardrobe.brbrbrbrEn-suite BathroombrbrShower, double sink, WC.brbrbrbrBedroom 3brbrDouble bed (cannot be converted into twin beds), two bedside tables, wardrobe, soft chair, circular soft stool.brbrbrbrEn-suite BathroombrbrShower, double sink, WC.brbrbrbrBedroom 4brbrDouble bed (cannot be converted into twin beds), two bedside tables, bench, round table, large wardrobe, door to balcony with table and 2 chairs.brbrbrbrEn-suite BathroombrbrShower, bathtub, double sink, WC.brbrbrbrSecond Floor (low ceilings)brbrbrbrCorridorbrbrLarge wardrobebrbrbrbrBedroom 5brbrDouble bed (cannot be converted into twin beds), two bedside tables, bench, sofa, French door to balcony with table and two chairs.brbrbrbrEn-suite BathroombrbrShower, double sink, WC.brbrbrbrCottagebrbrGround FloorbrbrbrbrSuitebrbrKitchenettebrbrSmall electric hob, fridge, table & 2 chairs.brbrbrbrBedroom 6brbrDouble bed (can be converted into twin beds), two bedside tables, wardrobe, soft chair, bench.brbrbrbrEn-suite BathroombrbrShower, double sink, WC.brbrbrbrCommunal AnnexbrbrbrbrGymbrbrWell-equipped gym with walking machine, bicycle machine and other exercise equipment.brbrbrbrPrivate Pool:brbrLength: 14 metresbrbrWidth: 7 metresbrbrDepth: 1.2 - 2.5 metresbrbrEntrance: Roman stepsbrbrOpening times: May to SeptemberbrbrFenced: YesbrbrFurnished: Sunloungers, parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 25 metres

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Sleeps

$578.89

/ Nightly

Agritourism

Farmhouse in Chianti

Gaiole In Chianti, Toscana, Italy

The Crocino in Chianti offers the opportunity to immerse yourself in the Italian Middle Ages. Here the border disputed for over 100 years by the Guelphs and Ghibellines with their Castles, watchtowers and fortified villages.brbrIn the center of the Chianti Classico, in the center of the little jewel of Lecchi in Chianti, this Agriturismo is the starting point for fantastic walks, bicycle itineraries as well as, simply, the arrival point for relaxing holidays lying in the pool and pampered by breakfasts and dinners of Adam and Alessandra.brHere you will find a familiar, simple and comfortable environment, a classic Italian family ready to meet your needs, teach you about local cuisine or ... chat with good wine!brbrPoolbrpossibility of dinnersbrcooking classes on sitebrbr

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Bath

Sleeps

$302.54

/ Nightly

Villa

Podere Lucignano Secondo - La Mangiatoia

Gaiole In Chianti, Provincia di Siena, Italy

In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its green vineyards, you will find the Podere Lucignano Secondo Agriturismo, a mansion built in 1898, now elegantly restored and turned into an exclusive relais.brbrThe Podere Lucignano Secondo Agriturismo, ideal place for lovers of relax and nature as well as food-and-wine connoisseurs, provides its guests with a warm welcome and an exclusive service.brbrThe rustic apartment “La Mangiatoia” at ground floor consists of 2 twin/double bedrooms with 1 toilet/bathroom, 1 kitchen, 1 living/dining room with fireplace, 1 terrace, park, private parking place. The pool, open from May to October 24h, is shared with the other apartment.brbrThe apartment is independent and for exclusive use, others guests could be present in the other apartment at first floor. brbrApartments sanitized after each check-out.brbrSERVICES:brbrFirst Day Food Shopping Service;brWineries Sightseeing Reservation;brTypical Tuscan Restaurants Reservation;brVan Transfer Service from / to Airports - Private Tour Driver Service.

2

Bed

1

Bath

4

Sleeps

$11634.86

/ Nightly

Private Vacation Home

Traditional Stone House in the Heart of Chianti

Gaiole In Chianti, Toscana, Italy

Perfect for those who want to enjoy a relaxing holiday in the Chianti countryside among vineyards and woods. The place is as charming and peaceful as the photos, built on a hill in the middle of nature, in an ancient Etruscan village.brThe house is well equipped. The kitchen is fully equipped and there are laundry facilities (wash and dry). Siena is only 30 minutes, Florence 50 minutes.brPerfect for up to 4 people.brbrPerfect for 4 people. The house is well equipped. Kitchen is fully equipped and there are laundry facilities (wash and dry). Siena is just 30 min., Florence 50 min.

2

Bed

4

Sleeps

$304.86

/ Nightly

Villa

Montelodoli Capanna, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Montelodoli Capanna is a beautifully restored former barn, now a charming holiday home for two. Set within a large natural garden, this single-storey stone house offers a quiet and private atmosphere with sweeping views across the rolling hills of the Chianti Classico. A 16-metre-long infinity pool is the highlight of the property, inviting guests to relax in this perfect setting.brbrbrbrThough rural in setting, the house is centrally located in the Chianti Classico region, putting all nearby towns, villages, wineries and castles within easy reach. The iconic Castello di Brolio, possibly the most famous of all Chianti castles, is just a ten-minute drive away and offers wine tastings, a restaurant, and a stylish bar. The villages of Monti, with a restaurant, and San Regolo, with a trattoria and a small attached bottega, are just two kilometres away. Gaiole in Chianti, about eleven kilometres from the house, has a small COOP supermarket, cafés, and additional dining options. Siena is only 30 minutes away, and Florence, Arezzo, and San Gimignano are all easy to reach for day trips.brbrInside, the house delights with a creative blend of vintage elements, Moroccan touches, and carefully selected furnishings. The interior is warm, inviting, and full of personality.brbrbrbrThe owners live in a separate house on the spacious property with their four friendly dogs and two cats. They are happy to assist guests when needed and occasionally enjoy the pool when it is not in use. They welcome guests’ dogs, but ask that any visiting dogs are friendly with other dogs and comfortable around cats.brbrbrbrMontelodoli Capanna is the perfect place for couples seeking peace, style, and a deep connection to the Tuscan landscape.brbrGround FloorbrbrbrbrEntrance PorchbrbrWooden bench and wicker sofabrbrbrbrKitchen/ Diner/ Lounge/ BedroombrbrFully equipped kitchen with 4 gas hobs, fridge-freezer, dining table with four chairs, sofa, coffee table, TV, two French doors to garden.brbrbrbrExtra King-size double bed (can’t be converted into single beds) bedside tables, clothes rail.brbrbrbrBathroombrbrShower, sink, bidet, WCbrbrNotebrbrThe owner’s live in the main house with their son and two friendly dogs, they occasionally use the pool when the area is untended by guests. The property layout ensures privacy for guests.brbrbrbrPrivate Pool (Infinity)brbrLength: 16 metersbrbrWidth: 4 metersbrbrDepth: 1.4 metersbrbrEntrance: Roman stepsbrbrOpening times: April to OctoberbrbrFenced: Yes brbrFurnished: sunloungers, pergola, cushioned outdoor furniturebrbrCleansed: Chlorine freebrbrDistance from villa: 40 meters

1

Bed

1

Bath

2

Sleeps

$841.28

/ Nightly

Apartment

Le Granchiaie 8, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Le Granchiaie is a spacious and tastefully decorated apartment, perfect for a relaxing holiday with family or friends. Surrounded by olive groves and woodland, it offers tranquillity and beautiful views. The hillside infinity pool is a highlight, ideal for unwinding in the heart of nature.brbrbrbrSet near Gaiole in Chianti, the apartment is in the heart of the Chianti Classico wine region. Guests will find excellent restaurants, wine shops and a small COOP supermarket nearby. Radda in Chianti, the historic Castello di Brolio with wine tastings, and the open-air Parco Sculture del Chianti are all within easy reach. Just 2 km away, the village of San Sano offers a local bottega and a traditional restaurant.brbrThis charming stone-built villa features a terracotta-paved courtyard, a traditional pizza oven, and a cabana offering a generous, sheltered seating area for al fresco dining. Just above the villa, the infinity pool enjoys sweeping views, perfect for relaxing and soaking up the sun.brbrbrbrThe apartment is located on the first and second floors. A private balcony off the master bedroom overlooks the surrounding landscape. Inside, original Tuscan features such as terracotta floors and beamed ceilings blend with elegant furnishings, modern bathrooms, French-style beds and linen-covered armchairs.brbrbrbrThe owner lives on the ground floor but fully respects guest privacy and is happy to help when needed. Bikes can be hired onsite and delivered directly to the property, making it easy to explore the surrounding countryside at your own pace.brbrFirst Floor (external access)brbrbrbrKitchenbrbrFully equipped, gas hob, fridge/freezer, table, chairs, armchairs, fireplace (decoration only), display cabinet, coffee table, air-conditioning, door to sheltered terrace, terrace with a small table and chairs. brbrbrbrBathroombrbrShower, double sink, WC, bidet.brbrbrbrOfficebrbrDesk, chair, chest of drawers.brbrbrbrBedroom 1brbrDouble bed (cannot be converted into twin beds), bedside tables, TV, clothes rail, chest of drawers, mosquito screens, air conditioning.brbrbrbrEn-suite BathroombrbrShower, sink, WC, bidet.brbrbrbrSecond FloorbrbrbrbrBedroom 2brbrTwin beds (can be converted into a double bed), bedside tables, TV, clothes rail, chest of drawers, mosquito screens, air conditioning.brbrbrbrEn-suite BathroombrbrShower, sink, WC, bidet.brbrbrbrBedroom 3brbrDouble bed (cannot be converted into twin beds), bedside tables, TV, clothes rail, mosquito screens, air-conditioning.brbrbrbrEn-suite BathroombrbrShower, sink, WC, bidet.brbrbrbrBedroom 4brbrDouble bed (cannot be converted into twin beds), bedside tables, TV, wardrobe, chest of drawers, air-conditioning, mosquito screens, door to balcony.brbrbrbrEn-suite BathroombrbrShower, sink, WC, bidet.brbrbrbrGround FloorbrbrbrbrUtility RoombrbrWashing machine, dryer. brbrbrbrCabanabrbrSink, table, chairs, fridgebrbrbrbrPrivate Pool (infinity):brbrLength: 10 metresbrbrWidth: 4 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: May to OctoberbrbrFenced: NobrbrFurnished: SunloungersbrbrCleansed: SaltbrbrDistance from villa: 20 metres

4

Bed

5

Bath

8

Sleeps

$929.72

/ Nightly

Villa

Casa Perano, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Casa Perano is a lovingly restored natural stone villa perched on a hilltop, with far-reaching views across the iconic Chianti Classico landscape. From here you enjoy a postcard-worthy panorama of gentle vineyards, olive groves and the charming village of San Donato in Perano on the horizon. The well-maintained garden and beautiful pool right next to the house make this holiday home ideal for relaxed days with family or friends. Casa Perano is also located close to the route of the famous vintage bike race L’Eroica, an annual highlight for cycling enthusiasts.brbrbrbrThis holiday home sits in the heart of the Chianti Classico, surrounded by wineries, castles and picturesque villages. The Tenuta Perano estate, owned by the renowned Frescobaldi family, is just a 15-minute walk away and features an Osteria for delicious meals accmpanied by local wine . For wine lovers the selection of wineries in this region is a dream, ranging from historic estates such as Castello di Brolio, Castello di Ama and Badia a Coltibuono to small boutique wineries. Castello di Brolio is reachable by car in only 25 minutes. The town of Gaiole in Chianti with its shops, good restaurants, supermarket and bike rentals is less than 3 km away. Siena, Arezzo, Florence and San Gimignano are also easily reached for day trips.brbrThe property is nestled quietly in the hills and surrounded by a large garden. Attached to the house is a south-facing covered terrace with a dining table, chairs and a comfortable seating area - perfect for shared meals and relaxing outdoors.brbrbrbrThe house spans two storeys plus a lower ground floor. Inside, original terracotta floors and wood-beamed ceilings have been preserved, complemented by soft wall colours, murals depicting Tuscan scenes and comfortable furnishings that create a warm and stylish atmosphere.brbrbrbrCasa Perano is a place to feel at home, uniquely combining peace, elegance and the essence of Tuscan living.brbrGround FloorbrbrbrbrKitchen/ Dining RoombrbrFully equipped kitchen, oval table with 6 chairs, island table, Welsh dresser, glass display cabinet, large fridge/freezer, 5 ring gas hobs, French door to terrace, terrace with a table and 8 chairs, comfortable outdoor furniture, air-conditioning.brbrbrbrLoungebrbr2 sofas and 2 armchairs, TV, fireplace (decoration only), coffee table, side table, bookshelf, air-conditioning, mosquito screens.brbrbrbrBedroom 1brbrDouble bed (cannot be converted into twin beds), two bedside tables, bookshelf, chest of drawers, large wardrobe, air-conditioning, mosquito screens.brbrbrbrEn-suite BathroombrbrShower, bath, sink, WC, chest of drawers.brbrbrbrFirst FloorbrbrbrbrBedroom 2brbrDouble bed (cannot be converted into twin beds), two bedside tables, armchair, chair, wardrobe, chest of drawers, air-conditioning, mosquito screens.brbrbrbrEn-suite BathroombrbrShower, sink, WC, chest of drawers.brbrbrbrLower Ground FloorbrbrbrbrBedroom 3brbr2 single beds (can be converted into double), two chest of drawers, round table with two chairs, mosquito screens, subterranean windows.brbrbrbrEn-suite BathroombrbrShower, sink, WC, shelf.brbrbrbrLaundry RoombrbrSink, washing machine.brbrbrbrPrivate PoolbrbrLength: 9 metersbrbrWidth: 4 metersbrbrDepth: 1.4 metersbrbrEntrance: Roman stepsbrbrOpening times: May to SeptemberbrbrFenced: NobrbrFurnished: SunloungersbrbrCleansed: ChlorinebrbrDistance from villa: 2 meters

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3

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6

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$784.27

/ Nightly

Villa

Podere Terrena 10, Gaiole in Chianti, Siena and Chianti

Gaiole In Chianti, Siena and Chianti, Italy

Podere Terrena 10 is a charming holiday home on a small agriturismo in a peaceful hillside setting, surrounded by forests, meadows and unspoiled nature. It offers sweeping views over the wooded hills of the Val d’Ambra and is perfect for families or friends looking to relax in the Tuscan countryside.brbrbrbrLocated on the edge of the Chianti region, well-known towns and wineries such as Gaiole and Radda in Chianti are just a 30-minute drive away. The nearest supermarket, restaurants and cafés 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 easy to organise.brbrThe two-storey stone house is set in a spacious, well-kept garden with flowering roses and terracotta pots. There is a dining terrace next to the house and another larger terrace by the pool, perfect for relaxing or enjoying meals outdoors.brbrbrbrInside, traditional Tuscan elements such as beamed ceilings and terracotta floors are combined with tasteful furnishings and selected antiques. The rooms are bright, comfortable and inviting.brbrbrbrThe property also includes a separate annexe for two additional guests, with its own entrance. It features a living kitchen and a cosy lounge on the ground floor, and a bedroom upstairs. Ideal for those who value privacy and a touch of independence.brbrbrbrThe friendly owners live in the rear part of the house with their dog and are happy to assist. Cooking classes or a private dinner service can be arranged on site.brbrbrbrPodere Terrena 10 is a peaceful and authentic retreat 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.brbrbrbrAnnexbrbrbrbrGround FloorbrbrbrbrKitchen/ Diner/ LoungebrbrFully equipped kitchen, fridge/ freezer, breakfast bar, chairs, corner sofa, coffee table, stairs to 1st floor.brbrbrbrBathroombrbrShower, sink, WC.brbrbrbrFirst FloorbrbrbrbrBedroom 5brbrDouble bed, bedside tables, clothes hanger rack, air-conditioning, stairs to ground floor.brbrbrbrEn-suite BathroombrbrShower, sink, WC.brbrbrbrPrivate PoolbrbrLength: 8 metersbrbrWidth: 4 metersbrbrDepth: 1.2 – 1.5 metersbrbrEntrance: Roman stepsbrbrOpening times: May to OctoberbrbrFenced: NobrbrFurnished: Sunloungers, pergola with a table and 8 chairs.brbrCleansed: ChlorinebrbrDistance from villa: 20 meters

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$848.27

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Villa

Secluded villa between Chianti vineyards, private pool, tennis, large garden

Gaiole In Chianti, Toscana, Italy

Ciao from Petra & Alexa!brWe warmly welcome you in our unbeatable location, halfway between Siena and Florence!brFirst of all we are glad to support you in planning your stay, informing you about the current events in the area in relation to your preferences.brbrVilla LisiDor: Rustic Luxury among Chianti Vineyards with Private Pool and TennisbrbrExperience authentic Tuscany in a 200-year-old farmhouse, where rustic elegance meets modern comfort.brLocated in the heart of the Sienese countryside, among rows of vines and centuries-old olive trees, Villa LisiDor is the perfect retreat for those seeking total relaxation, privacy, and sport.brbrInterior Spaces: A Blend of Tradition and Designbr• Living & Dining Area: A cozy environment with exposed beams and travertine floors. Large French doors flood the living room with light; the fireplace area offers a warm atmosphere, while the dining room provides a breathtaking view of the illuminated pool.br• Professional Kitchen: A stainless, well equipped steel kitchen with a central island.br• Sleeping Area: 4 elegant bedrooms featuring wooden ceilings and original terracotta floors: 2 doubles, one twin (convertible into a double), and the Master Suite with a double bed and private bathroom, boasting an exclusive turret with a double sofa bed and study corner.br• Modern Bathrooms: 3 designer bathrooms with large showers and contemporary finishes for maximum comfort.brbrDream Outdoors and SportbrImmersed in a 1,500 sqm garden, the villa is a true open-air paradise:br• Private Pool: 12 meters of freshness, illuminated for atmospheric evening swims.br• Sport & Fun: Synthetic grass tennis court, ping pong table, and large green spaces.br• Sunset Dining: Outdoor veranda, barbecue, and an ancient wood-burning oven for unforgettable dinners under the stars.brStrategic LocationbrbrIn the heart of Chianti Classico, just minutes from the charming village of Radda in Chianti. An ideal location for exploring Siena (30 min) and Florence (45 min), or for food and wine tours in Lecchi in Chianti.

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3

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$461.95

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Private Vacation Home

Lovely home in Gaiole in Chianti

Gaiole In Chianti, Gaiole in Chianti, Italy

Beautiful detached stone vacation home with private pool, whose origins date back to 1500, on the hills of Chianti Classico in a quiet panoramic position overlooking the valley, vineyards and olive groves near the village of Gaiole in Chianti. Privacy This typical accommodation is located in one of the most prestigious areas of Chianti Classico. Situated on one of these hills, the house enjoys a beautiful panorama. The house is very cozy and furnished in typical Tuscan style. Surrounded by a large property available to guests, equipped with games for children, volleyball net, basketball and petanque balls. Guests can enjoy an exceptional view and spend relaxing moments in the outdoor pool. Another space with table, chairs and barbecue is located in the garden. The convenient location offers numerous tourist attractions: Gaiole in Chianti 2 km, Radda in Chianti 11 km, Greve in Chianti 29 km, Siena 33 km, Florence 68 km, San Gimignano 56 km, Volterra 77 km, Terme di Rapolano 43 km and the Gulf of Bagnaia 50 km. Only 11 km from the house you can reach the castle of Brolio and visit the cellars where you can taste the good wines. Chianti is famous both for the landscape and for the fruits of its land. The exquisite wine produced there is famous all over the world.brbrbrbr- Free parking on sitebrbr- Consumption costs incl.brbr- Bedlinen incl towels (included)brbr- Final cleaning (included)brbrbrbrbrbrbrbr- Pool open May - end Septemberbrbr- Private outdoor swimming pool (50m2)brbr- Fully airconditionedbrbr- Low ceiling heightbrbr- Difficult access roadbrbr- One additional child free of charge (max 4 years old)brbr- Cot: 1brbr- Child's chair: 1

4

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2

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8

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$1199.62

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Villa

Villa Barbischio - Gaiole In Chianti ,Tuscany

Gaiole In Chianti, Gaiole in Chianti, Italy

Beautiful independent villa with private pool situated in the heart of the Chianti region, a short distance away from the town of Gaiole in Chianti.brThis villa offers beautiful views over the surrounding landscape and allows easy access to all the places that are featuring the historical, natural and gastronomical characteristics of this wonderful locality in Chianti.Villa Barbischio guarantees privacy and comfort as well as a wonderful pool where you can enjoy precious moments of relax with friends and family, a large garden with a barbecue area that will make unique your holiday during the spring and the summer periods as well as a beautiful fireplace that will make the ambience warmer and comfortable in the colder periods. This villa, nestling deep in quiet position among vineyards and woods, offers full privacy and is the ideal place for those who seek a relaxing stay in contact with nature. Outside guests, can enjoy use of a private pool (heatable upon request) and of a large solarium area with access on to a small wellness center with Finnish sauna.brThe villa offers welcoming interiors furnished in a rustic style and provide air conditioning.brThis property is part of a large farming estate producing Chianti Classico wine which is available for tasting.brThe access to the property is via an unpaved but well-maintained road.brDistances: Gaiole in Chianti with general stores 4 km away, Radda in Chianti 15 km, Siena 30 km away, Florence 50 km away.brAt guests’ disposal: large garden (3000 square meters) furnished with solarium area, private swimming-pool (7 x 3,5 m - depth 1,4 m) that can be heated upon request, Finnish sauna. WI-FI internet connection available free of charge. Washing-machine available.brParking within the grounds.brbrPlease carefully check if there are any extra costs to be paid on site!br240 m2brGround floor: entrance, living-room with dining area, kitchen (oven, freezer, microwaves, dishwasher, toaster, American coffee maker), double bedroom with living area and ensuite bathroom with shower, twin-bedded room with ensuite bathroom with shower. br1st floor: double bedroom with ensuite bathroom with shower and Jacuzzi bathtub. This floor has access to a beautiful terrace with panoramic views over the pool and the surrounding vineyards.br2nd floor (attic room): double bedroom with ensuite bathroom with Jacuzzi bathtub.brbrArrival between 15:00 and 21:00brDeparture between 08:00 and 10:30brbrPool open from 1 May to 30 SeptemberbrbrTo be paid on the spotbrNot included in the rental price:brBed Linen and Towels (additional set) (on request): 15.00€ per person per changebrExtra Bed (on request): 70.00€ per person per daybrRefundable Security Deposit by credit card (mandatory): 500.00€brHeating: 2.00€ per literbrBabycot: 30.00€brPool heating (on request): 100.00€ per daybrPets (on request): 10.00€ per pet per daybrTourist tax (mandatory): 2.00€ per person per daybrbrIncluded in the rental price:brBed Linen and Towels (initial set)brBed linen and towels (weekly changed)brFinal CleaningbrInternet WifibrAir conditioning

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4

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8

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$945.49

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Villa

Villa la Pecine by MMega

Gaiole In Chianti, Gaiole in Chianti, Italy

External DescriptionbrbrbrbrVilla la Pecine, an ancient mill on the Pecine stream from which it takes its name, stands in a sunny valley in the heart of the Chianti Classico countryside. It is surrounded by the lush woods of Lucignano and Monti, just a short walk from the enchanting village of Gaiole.brbrSurrounded by centuries-old oaks, majestic cypresses, and orderly rows of vineyards, the property offers a large private garden, an oasis of greenery with soft lawns and colorful borders of roses, hydrangeas, and fragrant aromatic plants.brbrIn the garden, you will find two inviting outdoor dining areas with umbrella and barbecue, perfect for enjoying pleasant convivial moments under the Tuscan sky and making the most of summer.brbrThe outdoor spaces are enhanced by a beautiful saltwater infinity pool (12 x 6 m, depth from 1.50 to 2.50 m), surrounded by an elegant solarium paved in local Chianti stone, an ideal spot to sunbathe or cool off with a refreshing swim. The pool, open from the last Saturday in April to the first Saturday in October, is equipped with comfortable loungers, an umbrella, and a solar shower.brbrAt the back of the villa, a private uncovered parking area can comfortably accommodate up to 4 cars.brbrbrbrInternal DescriptionbrbrbrbrVilla la Pecine consists of an elegant main building and a charming dependance, located about 20 meters apart, ensuring privacy and comfort for all guests. The entire property can host up to 10 people and features 5 bedrooms and 4 bathrooms. Internet Wifi is included. All rooms, except the bathrooms, are equipped with air conditioning and mosquito screens on the windows. Pets are allowed on request, subject to an extra charge. One baby cot and one high chair are available upon request.brbrOnce an ancient mill, the villa has been beautifully restored, preserving all of its authentic rustic charm. Exposed wooden beams, terracotta floors, and original stone walls tell the story of its centuries-old past, while the interiors, furnished with traditional pieces and precious antiques, create a warm and refined atmosphere.brbrbrbrMain building: The main house, arranged over 3 levels, comfortably accommodates up to 8 guests, offering spacious, functional, and characterful interiors.brbrOn the basement level, there is a practical laundry room equipped with washer-dryer, ironing board, and iron, ideal for longer stays.brbrThe ground floor is dedicated to the living area: a welcoming lounge with two comfortable sofas, a tv, and a piano provides the perfect setting for relaxing and socializing; a bright dining room overlooking the pool, adjacent to the fully equipped kitchen with direct access to the garden.brbrThe kitchen is fitted with everything you need: dishwasher, oven, microwave, kettle, coffee machine, toaster, refrigerator, and stovetop.brbrContinuing along the hallway, you reach the sleeping area, which includes 2 double bedrooms (one featuring a romantic canopy bed), 1 twin bedroom, and two elegant bathrooms (including one with a shower, the other with a bathtub and double washbasin).brbrOn the upper floor, accessed via a steep open staircase, there is a charming attic bedroom with a French bed, ensuite bathroom with shower, and a lovely private terrace, perfect for peaceful moments.brbrbrbrDependance: The dependance, located on the ground floor and completely independent, is ideal for a couple seeking intimacy and comfort.brbrInside, a cozy sitting area with a minibar, breakfast table, and chairs creates a private and pleasant space. Following this, you will find a double bedroom and a bathroom with a hydromassage shower, offering total relaxation and privacy in complete comfort.brbrbrbrIT052013C2GEYXGYQ7brbrbrbrPrices and conditionsbrbrIncluded in the price: Utilities (water, gas, electricity); Internet Wifi; house, garden and pool maintenance.brbrExcluded from the price: Final cleaning (500.00€); heating (200.00€ per week if used); pets allowed on request (50.00€ per pet per week or part of a week). Tourist tax if required (the amount usually varies, depending on location, from 0.50€ to 4.00€ per person per night for a maximum of seven nights, excluding minors, and will be paid upon arrival).brbrSecurity deposit: Customers are required to pay 500.00€ security deposit upon arrival (cash), which will be returned at the end of the stay upon any damages.

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