Vacation Rentals By Owner In Radda In Chianti, TOS

Live the Tuscan dream in this stunningly renovated 17th-century farmhouse, in the heart of the Chianti hills! Casale al Sole has been a refuge and a peaceful retreat for many years. It has magnificent views across unspoiled countryside and makes a wonderful holiday destination throughout the year.brbrThe house, which sleeps 6 people, has two floors. The ground floor includes a loggia and a wine room where guests can try the fine, local Chianti wines.brUpstairs, there is another loggia with panoramic views across the vineyards and the village of Radda in Chianti. Here guests can enjoy meals al fresco. Indoors, the spacious living area retains the original terracotta tiled floors and high beamed ceilings. The living area is furnished with a sofa, wooden dining table and chairs and a large, open fireplace not working. The open-plan kitchen is well-equipped with a cooker hob and oven, dishwasher, fridge and Moka coffee maker.brbrThe garden is approximately 1 hectare and surrounds the house. There is a BBQ area with a table and chairs for relaxed meals.brbrSleepingbrBedroom 1: The bedroom is furnished with a double bed, wardrobe and desk.brBedroom 2: The second bedroom has an antique, wooden double bed, with a wardrobe, and a door leads out onto a small balcony with wonderful views.brBedroom 3: Up 3 steps from bedroom 2, this charming room has a double bed with a sofa, large wardrobe and its own wood-burning stove. Steps lead from this room down to the 2nd bathroombrbrBathroomsbrBathroom 1: Off the main living room this split bathroom has a basin in the first room and the second room includes a shower, bidet, washing machine and WC.brBathroom 2: Off bedroom 3, this large, stylish bathroom includes a full bath with showerhead, basin and WC.brbrAdditionalbrFree Wifi • Outside dining area • BBQ • Table tennis & badminton • Books library • Music stereo & Bluetooth speakers • Air conditioning • Central heating • Child friendly • Private garden • Washing machine • Private parking, car essential for your visit • Pets are permitted brbrDeposit for groups under 21 EUR 2500brbrIMPORTANT: To access the property you have to drive 1.5 km along dirt road, the last 900 m must be driven very carefully as it is a stretch of steep unpaved country road through the vineyards. The road becomes narrower and steeper, so it is advisable to keep a steady pace without acceleration. It is not suitable for low cars.brbrLocationbrDespite its secluded location, the house is close to the village of Radda in Chianti (10 minute's drive) where guests will find various shops selling Italian handicrafts, typical local ingredients and delicacies.brbrThe house is in the heart of Chianti Classico which gives guests a wide choice of vineyards to visit for tasting and buying excellent local wines.brbrAll the gems of Tuscany are within easy reach, from Florence (1 hour), Siena (50 minute) and Arezzo (1 hour 10 minutes) to smaller towns like San Gimignano (50 minutes), famous for its medieval towers. brbrFor fashion lovers, the famous Mall in Incisa Valdarno (1 hour) is an Alladin’s Cave of discounted designer outlets from famous Italian brands, including Fendi, Gucci and Armani. Prada’s outlet, Space Outlet, is in Levane (38 minutes).brbrThe closest airports are Florence, (1 hour) or Pisa, which is 1 hour and 50 minutes away.

Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy

Radda In Chianti, Radda in Chianti, Italy

Bed

Bath

Sleeps

$345.59

This 2-bedroom farmhouse situated in Radda in Chianti is suitable for a small group or family. Resting in Tuscany, Italy, it can accommodate 4 people. The farmhouse has a shared swimming pool for rejuvenation at a distance of 250 m._x000D_br_x000D_brRadda In Chianti has a lot to offer in terms of excursions. You can plan a visit to Parco Archeologico di Poggio La Croce and Chianti Sculpture Park. You can also head to Pieve di Santa Maria Novella. Don’t forget to take the kids to Albola Castle. General stores and restaurants rest close to this accommodation, just 2 km away._x000D_br_x000D_brParking is available here. The farmhouse has play equipment,a high chair, and a cot for kids. There is a shared garden and patio where you can have a gala time. Bicycles are offered at this property. WiFi and TV are also available. A maximum of 1 pet is permitted here. Guests also have access to an organic garden where they can pick vegetables. There is a covered parking spac,e and you can rent towels at the accommodation._x000D_br_x000D_brThe nearest airport is only 55 km away.brExpenses related to charging an electric or hybrid car (when possible) are always charged according to use and separatelybrThis holiday home is one of the Belvilla Award winners in: 2021,2022brbrLayout: On the 1st floor: (Living room, open kitchen(TV(satellite), coffee machine, oven, dishwasher, fridge-freezer, terrace), bedroom(double bed), bedroom(double bed), bathroom(shower, washbasin, toilet, bidet))brbrwashing room(washing machine(shared with other guests)), patio, garden(shared with other guests, 1000 m2), garden furniture, parking, swimming pool(shared with other guests, 12 x 6 m., opened from Jun upto and including Sep), play equipment, table tennis table, bicycles available, Charging post for electric carsbrbrThese costs are mandatory and charged on site. They are not included in the rental price.brTourist tax: € 2.00 /person/night (Indication)brFinal Cleaning: € 50.00brElectricity: € 0.75/kWhbrBed linen: PresentbrPets: Max. 1; free of chargebrbrOptional services that you can arrange on sitebrHeating: € 20.00/nightbrHigh chair: free (on request)brCot: free (on request)brBath towels: PresentbrWood: IncludedbrWifi: FreebrKitchen linen: PresentbrMiscellaneous: Order a welcome basket of groceries € 20.00/basketbrUse washing machine: IncludedbrCot + High chair: free (on request)

Apartment

Escape to Vineyards, Elba

Radda In Chianti, Radda in Chianti, Italy

Bed

1

Bath

4

Sleeps

$229.23

The traditional holiday apartment 'Rifugio sulla via di Volpaia' is located in Radda in Chianti and is the ideal accommodation for a relaxing getaway. The 45 m² property consists of a living room with a sofa bed for 2 people, a kitchen with a dishwasher, 1 bedroom and 1 bathroom and can therefore accommodate 4 people. Additional amenities include high-speed Wi-Fi (suitable for video calls), air conditioning, heating (with heat pumps) as well as a washing machine. A baby cot is also available.brbrThe highlight of this accommodation is its private outdoor area with an open terrace. A shared outdoor area, consisting of a garden and a barbecue, is also available for your use.brbrThe property is located 2 km from Volpaia, 6 km from the centre of Radda in Chianti, 42 km from Siena and 57 km from Florence.brbrA parking space is available on the property.brbrPets are only allowed upon previous request. brbrBreakfast is available for a fee.brbrDinners, wine tastings, horseback riding tours, forest walks, picnics and an e-bike can be booked in advance for a fee.brbrThe property offers homemade/homegrown produce.brbrThis property has guidelines to help guests with the correct separation of waste. More information is provided on site.brbrThis property has light and water-saving features.brbr- Breakfast payment 15,00 € per person per night

Apartment

Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning

Radda In Chianti, Radda in Chianti, Italy

Bed

Bath

Sleeps

$357.23

Very beautiful, cosy, rustic single-family house Villa del Poggio, surrounded by trees and vineyards. 2 km from the centre of Radda in Chianti, 12 km from the centre of Castellina in Chianti, 23 km from the centre of Montevarchi, in the residential district, in the countryside. Private: beautiful, well-kept garden 5'000 m2 (fenced) with lawn and trees, orchard, lawn for sunbathing, swimming pool (12 x 5 m, seasonal availability: 02.May. - 14.Oct.). Table tennis, arbour, terrace, garden furniture. Available: bicycles (6). Parking (for 3 cars) on the premises. Grocery 2 km, supermarket 3 km, bus stop 2 km, railway station Montevarchi 23 km, outdoor swimming pool 12 km, indoor swimming pool 23 km. Please note: car recommended. Cooking courses bookable on request. The owner lives on the same property. Guided bike and mountain bike tours on request (order, payment on site), mountain bike rental.brVilla del Poggio, 4-room house 95 m2 on 2 levels. Beautiful and tasteful furnishings: living/sleeping room with 1 double sofabed, open-hearth fireplace, satellite TV, radio, CD-player and DVD. Exit to the terrace. 1 room with 1 french bed (160 cm), shower/bidet/WC. Exit to the garden. 1 room with 2 beds and shower/WC. Exit to the garden. Open kitchen (oven, dishwasher, 5 gas rings, toaster, kettle, microwave, freezer, electric coffee machine) with dining table. Exit to the garden. Upper floor: 1 room with sloping ceilings with 1 french bed (160 cm). Shower/WC. Gas heating, air-conditioning. Comfortable furnishings in the country house style. 2 terraces, porch. Terrace furniture, barbecue, deck chairs, box-room. Beautiful view of the garden, the countryside and the forest. Facilities: washing machine, safe, iron, mosquito net, children's high chair, baby cot. Internet (WiFi, free). Please note: non-smokers only. Maximum 2 small pets/ dogs allowed. IT052023C2ZT7IXE8DbrbrIncluded in price:brERV cancellation insurancebrFinal cleaning (Basic cleaning is always carried out by the guest)brLaundry (initial supply of bed linen and towels)brNo Local Tax charged for childrenbroutdoor parking spacebrInterhome plants 100'000 m2 of flowering fields to save the beesbrWireless internet access (WIFI)brbrincl. in the price but needs to be booked beforehand:brCot (up to 2 years) / HighchairbrbrDeposit information: brBreakage deposit in cash: 300.0 EURbr #IT5292.608.1

Private Vacation Home

Villa del Poggio by Interhome

Radda In Chianti, Radda in Chianti, Italy

Bed

Bath

Sleeps

$685.36

Cielo di Radda is a stylish villa in the heart of the Chianti Classico, just a few minutes’ walk from the charming town of Radda in Chianti. With its peaceful setting, well-maintained outdoor spaces and inviting interiors, it is the ideal retreat for a relaxing holiday with family or friends. From both the house and garden, you can enjoy stunning panoramic views across the vineyards and the beautiful town of Radda.brbrbrbrThanks to its central location in the renowned Chianti Classico region, Cielo di Radda is a perfect base for exploring famous wineries, historic castles and typical hilltop villages such as Volpaia and Lecchi. The well-known winery Tenuta di Carleone is just a short walk away. Day trips to Siena, Florence, San Gimignano and Arezzo are easy to organise. In Radda itself, you’ll find a variety of restaurants, charming shops and a well-stocked COOP supermarket – all within walking distance.brbrThe stone villa is surrounded by a lovely garden with a private pool. A shaded terrace with a large dining table under a pergola is perfect for enjoying meals outdoors together.brbrbrbrThis two-storey villa is bright and welcoming, with a tasteful interior that combines traditional Tuscan features with modern comfort. Terracotta floors and wooden beamed ceilings add character, while carefully chosen furnishings and thoughtful details create a warm and homely atmosphere. From the moment you arrive, you’ll feel at home.brbrFirst FloorbrbrbrbrKitchen/ Diner/ LoungebrbrFully equipped kitchen, island unit, hob with 5 gas rings, fridge/freezer, table with chairs, sofas, coffee table, TV, wooden chest, fireplace, stairs to the ground floor, wardrobe French doors to terraces with pergola, table, and chairs.brbrbrbrCloak RoombrbrSink, WC, bidet.brbrbrbrGround FloorbrbrbrbrBedroom 1brbrDouble bed (cannot be converted to twins), bedside tables, table, chair, wardrobe, French doors to garden.brbrbrbrBathroombrbrShower, sink, WC, bidet.brbrbrbrBedroom 2brbrDouble bed (cannot be converted to twins), bedside tables, chair, cupboard, clothes hanger rail.brbrbrbrBedroom 3brbrDouble bed (cannot be converted to twins), bedside tables, chair, two wardrobes, desk, chair, French doors to garden.brbrbrbrBathroombrbrBathtub with shower attachment, sink, WC, bidet.brbrbrbrPrivate Pool:brbrLength: 7 metresbrbrWidth: 3.5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman stepsbrbrOpening times: May to mid-OctoberbrbrFenced: NobrbrFurnished: Sunloungers, parasols and outside showerbrbrCleansed: SaltbrbrDistance from villa: 5 meters

Cielo di Radda, Radda in Chianti, Siena and Chianti

Radda In Chianti, Siena and Chianti, Italy

3

Bed

Bath

Sleeps

$5438.76

Offering panoramic vistas over Chianti’s rolling hills and woodlands, Villa Gaiole is a serene Tuscan retreat that sleeps up to 14 guests across seven luxurious bedrooms. This 400-year-old property, once a rustic farmhouse surrounded by vineyards and olive groves, has been beautifully restored to balance historic charm with modern comfort.brThe villa is divided between the main building and a smaller annexe, both full of character with exposed beams, stonework, and open fireplaces. Inside, you’ll find spacious, light-filled living areas thanks to vast floor-to-ceiling windows that frame the valley views. The ground floor is the social hub, with a welcoming lounge, a feature fireplace, a dining room, and a fully equipped kitchen—though catering packages with a private chef can also be arranged. Additional highlights include a wine cellar, games room, fully equipped gym, and a second sitting room, ensuring plenty of space for everyone.brEach of the seven bedrooms is tastefully decorated and has its own en-suite bathroom. Six boast super king-sized beds, while one can be set up as a twin or double. Two of the bedrooms are housed in the annexe, perfect for families or guests who’d like a little extra privacy.brStep outside to discover two hectares of gardens, olive groves, and vineyards. The heated infinity pool is the star attraction, complemented by numerous terraces, shaded dining spaces, and sun loungers ideal for lazy afternoons.brThe villa’s concierge team can arrange extras such as truffle hunting, pizza-making classes, yoga, or guided tours. Though wonderfully peaceful, Villa Gaiole is close to picturesque Chianti villages and only 28km from Siena, making it an excellent base for exploring Tuscany’s art, food, and medieval history.brVilla Gaiole offers the perfect blend of tradition, elegance, and comfort for an unforgettable group holiday in Tuscany.brbrbrbrFeatures:brbr10-person capacity: main villa only14-person capacity: main villa and annexebrThe Villa (800m2 over two floors)brbrbrbrGround Floor- Living room with sofas, desk fireplace and TV- Games room with seating area, pool table and football table- Dining room with table seating 14- Fully-fitted kitchen with breakfast bar- Guest WC- Gym and Wine cellar- Internal courtyard- Bedroom with super king-sized double bed, seating area an en-suite bathroom with shower (accessible from the courtyard)brFirst Floor- Sitting room with bookshelves and TV- Bedroom with super king-sized double bed, seating area an en-suite bathroom with bath, double sink and WC- 2x bedroom with super king-sized double bed and en-suite bathroom with shower, sink and WC- Bedroom with twin beds or a super king-sized bed and en-suite bathroom with shower, sink and WCbrAnnexe- 2x bedroom with super king-sized double bed and en-suite bathroom with shower, sink and WCbrOutside Grounds (20,000m2)brbrbrbr- Private heated swimming pool, with safety cover (12m x 6m, 1-3m deep) open approximately start of April- end of October- Two hectares of private grounds, olive groves and vineyards- Covered dining pergola- Al-fresco dining terrace- Wraparound terrace with outdoor sofas- Sun loungers and deck chairs - Barbecue- Pizza oven- ParkingbrbrbrbrFacilities brbrbrbr- Wi-Fi- Air-conditioning- Underfloor heating- Home office - TVs- Sound system- Film projector- Iron and ironing board - Gym equipment - Pool table- Football table- Board games and toysbrbrbrbrExtra Sustainability Gems About the PropertybrbrbrbrThe owners have installed solar panels and a wood pellet burner for hot water, as well as their our own fresh water well (natural and treated) which they encourage guests to use as opposed to buying plastic bottles of water. brbrbrbrLocation:brbrVilla Gaiole boasts an enviable position overlooking the rolling hills of Chianti, immersing guests in one of Tuscany’s most iconic landscapes. Scenic walking trails, medieval hamlets, vineyards, and olive groves lie on the doorstep, perfect for countryside exploration at your own pace.brWine enthusiasts can enjoy tastings at local farms or tours at nearby wineries, while food lovers will relish dining in rustic trattorias dotted throughout picturesque villages. Just 5km away, Gaiole in Chianti is a charming spot often ranked among Europe’s best places to live. Its rich history includes a number of castles—some now wineries, others open to the public—and a long tradition of ceramics. Lecchi in Chianti, 6km away, offers shops, cafés, and traditional eateries for an authentic experience.brRadda in Chianti, 12km away, provides a wider array of restaurants and shops. Once the headquarters of the Chianti League in the 15th century, this town enchants with winding medieval streets and historic landmarks such as the Palazzo dei Podestà and the Church of San Niccolò.brFor a longer excursion, Siena lies just 28km from the villa. A medieval jewel, the city is packed with art galleries, museums, and iconic sights, including the Duomo di Siena and the Palazzo Pubblico. Its lively piazzas and rich café culture make it a must-see for visitors seeking Tuscany’s history and charm.brbrbrbrTerms & Conditions:brbr brAn Accidental Damage Waiver of EUR 175 will be added to each booking to protect guests for up to EUR 2,500 in accidental damages at the villa. The waiver provides a limited damage cover in case of any damage to the property or its contents (except in the case of deliberate or reckless acts) up to the value of €2,500. It is essential to report any damage during your stay for the waiver to apply. For damages of a value which is above EUR 2,500 guests will be asked to pay based upon the value of the damage caused.brbr4.00 p.m. Check-in outside this time may be subject to an extra cost. Please enquire for more details.brbr10.00 a.m.brbrYes.brbrYes, with mid-week linen change for one-week stays.brbrPets are not allowed.brbrPlease note home security devices may be installed at the villa, please enquire for further information.brbrbrbrbrbrPlease note that your booking will only be confirmed once we have checked availability with the owner or their property manager.brbrbrbrPlease note that published rates are only valid for the current year. Any bookings for subsequent years will be on request only and correct rates will be confirmed at the time of booking.brbrbrbrPlease note that the use of any external caterers and/or contractors is not permitted.brbrFlexible.brbrIncluded only for one-week stays. However, guests are required to leave the accommodation clean, tidy and in the same condition as on their arrival. Any extra cleaning, laundry, maintenance and/or rubbish disposal required will be charged against the security deposit.brbrOutside only.brbr7 nights from mid-June to mid-August. 4 nights between January to April and October to December. 5 nights in all other periods.brbrEstimated cost will be provided based on the week booked. Please enquire for exact amount, payable locally.brbrIncluded in peak months, and at an extra cost for the low season (October to April), payable locally. Please note that like all heated pools, pool heating and water temperature are reliant on weather and outside temperatures.brbrItalian Visitors Tax payable locally in cash (typically costs €1-€10 per person per night- please enquire if exact amount is required).brbrThe pool is open approximately April to end-October. Please note that pool opening dates are subject to local weather conditions and pool maintenance requirements and that cooler months may not be suitable for swimming.brbrCIR: 052013CAV0037 brbrCIN: IT052013B4ARQLP4UZbrSmoking - not allowed

Villa Gaiole - Seven Bedroom Villa, Sleeps 14

Radda In Chianti, Radda in Chianti, Italy

7

Bed

8

Bath

14

Sleeps

$1701.05

Villa Al Bosco: An elegant and welcoming three-story villa situated in a secluded location surrounded by meadows and by green hills, with Free WI-FI.

Radda In Chianti, Radda in Chianti, Italy

Bed

Bath

Sleeps

$600.42

La Casa di Radda is a welcoming holiday home in the Chianti Classico region, notable for its proximity to the charming village of Radda. Just a short walk separates the house from the delightful restaurants, cafés, and small shops in the town center. It is ideal for a family vacation or a getaway with friends, offering the perfect setting for relaxing days in a rural environment.brbrbrbrThe location is excellent for exploring the Chianti region with its renowned wineries, historic castles, and picturesque villages such as Volpaia and Lecchi. Cultural cities like Siena, Florence, San Gimignano, and Arezzo are also easily accessible by car, making for varied day trips.brbrThe single-story stone house is situated in a quiet area, only 500 meters from the center of Radda. It is surrounded by a well-maintained garden with Mediterranean plants. The private pool provides refreshment on warm days. A covered terrace invites guests to enjoy meals outdoors and relaxing moments in the shade.brbrbrbrInside the villa, light colors and traditional Tuscan wooden beam ceilings create a pleasant atmosphere. Every detail of the design has been carefully selected, with the comfort of guests always in mind. The tasteful furnishings are not only functional but also particularly appealing. La Casa di Radda is a place where you immediately feel at home and can fully enjoy the Tuscan way of life.brbrGround FloorbrbrbrbrLounge-Kitchen-DinerbrbrSofa, armchairs, chest with cushions, wood-burning stove, TV, dining table with chairs, sink, oven, gas hob with 5 rings, fridge-freezer, air-conditioning.brbrbrbrBedroom 1 brbrDouble bed (cannot be converted into twins), bedside tables, wardrobe, chest of drawers, chair, air-conditioning, French door leading out onto the terrace.brbrbrbrEn-suite bathroombrbrShower, WC, sink, bidet.brbrbrbrBedroom 2brbrPair of twin beds (can be converted into a double if requested when booking), bedside tables, wardrobe, chest of drawers, chair, air-conditioning.brbrbrbrBedroom 3brbrSingle bed, bedside table, wardrobe, fan, door leading to garden.brbrbrbrBathroombrbrShower, WC, sink, bidet.brbrbrbrLaundry RoombrbrWashing machine.brbrbrbrPrivate PoolbrbrLength: 10 metresbrbrWidth:4 metresbrbrDepth: 1.4 metresbrbrEntrance: Roman steps brbrOpening times: mid-April to mid-October, weather permittingbrbrFenced: NobrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from villa: 2 metres

La Casa di Radda, Radda in Chianti, Siena and Chianti

Radda In Chianti, Siena, Italy

Bed

Bath

Sleeps

$1980.11

Villa Al Borgo: A welcoming two-story villa located in a characteristic village, with Free WI-FI.

Radda In Chianti, Radda in Chianti, Italy

Bed

5

Bath

11

Sleeps

$1352.11

Il Casetto is a luxurious holiday home set in a peaceful countryside location, surrounded by vineyards and rolling hills. The view captures the very essence of the classic Chianti landscape, making this beautifully restored stone house the perfect choice for a stylish holiday with family or friends. Comfort, privacy and proximity to the region’s highlights come together in perfect harmony.brbrbrbrThe medieval village of Volpaia, with a few restaurants, is about a 20-minute walk away. Guests can also enjoy a wine tasting at the historic Castello di Volpaia. Many other wineries are located nearby. Radda in Chianti, with all essential services, is just 6 kilometres away. The cultural cities of Siena, Florence, San Gimignano and Arezzo are ideal for day trips.brbrOutside, the property features a well-kept garden with lawns and a lovely pool overlooking the Tuscan hills. Two furnished terraces provide a choice of sun or shade and are perfect for outdoor dining or relaxing together.brbrbrbrInside, the house offers a tasteful blend of traditional Tuscan style and elegant furnishings. Terracotta floors, wooden beam ceilings and exposed stone walls create a warm, authentic atmosphere. The spacious kitchen with its restored vaulted stone ceiling is particularly striking. Another highlight is the bright lounge with floor-to-ceiling French windows opening onto the garden.brbrbrbrIl Casetto is a place where Tuscan charm, rural peace and refined comfort come together beautifully. to the plush bedrooms, there is much to like about Il Casetto.brbrGround FloorbrbrbrbrLounge 1brbrTwo sofas, two armchairs, table and chairs, coffee table, sideboard, two side tables, shelves, air-conditioning, French windows to garden.brbrbrbrLounge 2brbrFour chairs and occasional table, air-conditioning, stairs to upper floors.brbrbrbrDining roombrbrTable and chairs, easy chair, side table, air-conditioning, doors to garden.brbrbrbrKitchenbrbrFully equipped, fridge-freezer, gas hob with 5 rings, air-conditioning.brbrbrbrBathroom 1brbrSink, WCbrbrbrbrUtility RoombrbrFully equippedbrbrbrbrFirst FloorbrbrbrbrBedroom 1brbrDouble bed, wardrobe, dressing table and chair, easy chair, door to garden, air-conditioning, mosquito screen.brbrbrbrEn-suite bathroombrbrBath, shower, sink, bidet, WC.brbrbrbrBedroom 2brbrTwin beds (can be converted into a double), wardrobe, dressing table and chair, French doors to upper terrace, air-conditioning, mosquito screen.brbrbrbrEn-suite bathroombrbrShower, sink, bidet, WC.brbrbrbrBedroom 3brbrTwin beds (can be converted into a double), wardrobe, chest of drawers, dressing table and chair, air-conditioning, mosquito screen.brbrbrbrEn-suite bathroombrbrShower, sink, WC.brbrbrbrSecond FloorbrbrbrbrBedroom 4brbrTwin beds (can be converted into a double), wardrobe, desk and chair, mosquito screen, air-conditioning.brbrbrbrEn-suite bathroombrbrShower, sink, WC.brbrbrbrPrivate PoolbrbrLength: 8mbrbrWidth: 4mbrbrDepth: 1.4 mbrbrEntrance: Roman stepsbrbrOpening Times: May to OctoberbrbrFenced: NobrbrFurnished: sunloungers, deckchairs, parasolsbrbrCleansed: chlorine freebrbrDistance from Villa: 5 m

Il Casetto, Radda in Chianti, Siena and Chianti

Radda In Chianti, Siena, Italy

Bed

Bath

Sleeps

$354.9

Fienile al Corno is a charming holiday home in the Chianti Classico, ideal for a relaxing break with family or friends. Surrounded by olive groves, vineyards, and gently rolling hills, it offers sweeping views of the typical Chianti landscape dotted with cypress trees. A well-kept garden and a private pool create the perfect setting for peaceful days immersed in nature.brbrbrbrThe house is quietly located yet perfectly positioned for exploring the region. The medieval village of Volpaia, home to popular restaurants like Bar Ucci and La Bottega, is a five-minute drive or about a 40-minute walk uphill. Radda in Chianti, with its shops, restaurants, and a COOP supermarket, is just five kilometres away. The organic winery L’Erta di Radda is right next door. Siena, Florence, San Gimignano, and Arezzo are all ideal for day trips.brbrFienile al Corno is nestled in the Tuscan countryside and features a lovely outdoor area with a pergola-shaded terrace, a private pool, and a small play area for children.brbrbrbrThe two-storey house has a slightly unusual layout. The bedrooms are on the ground floor, while the kitchen and living areas are upstairs. French doors open directly from the upper floor onto the terrace with panoramic views.brbrbrbrInside, traditional elements such as wooden beam ceilings and terracotta floors are combined with a mix of antique and modern furnishings to create a bright, inviting, and homely atmosphere.brbrbrbrFienile al Corno is the perfect place to experience the authentic Chianti in peace.brbrGround FloorbrbrbrbrBedroom 1brbrDouble bed (cannot be converted into twins), bedside tables, dressing table, wardrobes, chest of drawers, fan, mosquito screen.brbrbrbrBedroom 2brbrDouble bed (cannot be converted into twins), bedside tables, dressing table, wardrobes, chest of drawers, fan, mosquito screen.brbrbrbrBedroom 3brbrTwin beds (can be converted into double) bedside table, desk, wardrobes, fan, mosquito screen, door to terrace.brbrbrbrBathroombrbrSink, shower, bidet, WC, mosquito screen.brbrbrbrUtility RoombrbrWashing machine, sink, shelves.brbrbrbrFirst FloorbrbrbrbrKitchen/ Lounge/ Diner/ OfficebrbrFully equipped kitchen, fridge/ freezer, island unit, induction hob, table, chairs, sofas, armchairs, coffee tables, TV, bookshelves, desk, fireplace (decoration only), mosquito screens, French door to terrace.brbrbrbrBathroombrSink, shower, bidet, WC, mosquito screen.brbrbrbrPrivate PoolbrbrLength: 10 metersbrbrWidth: 4 metersbrbrDepth: 1.25 metersbrbrEntrance: Roman stepsbrbrOpening times: April to OctoberbrbrFenced: NobrbrFurnished: SunloungersbrbrCleansed: ChlorinebrbrDistance from villas: 8 meters

Fienile al Corno, Radda in Chianti, Siena and Chianti

Radda In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$286.25

Il Cipresso is a lovingly furnished holiday home, ideal for a couple or a small family. It is located on the ground floor of a natural stone house in a small medieval hamlet on a hill in the heart of the Chianti Classico, between Radda and Castellina. The site was once an Etruscan settlement and still retains a unique historical atmosphere. From the private terrace and well-tended garden, guests can enjoy wide views of the typical Tuscan hills.brbrbrbrThanks to the excellent location, many of the region’s best-known towns and villages are within easy reach. Radda and Castellina in Chianti are just six kilometres away and offer excellent restaurants, small shops and supermarkets. A visit to the Gelateria di Castellina, known for its homemade ice cream, is especially recommended. For dining close to home, the restaurant Le Carrozze is only a short walk from the property. Siena, Florence, Arezzo and San Gimignano are also perfect for day trips.brbrThe garden is planted with flowers and a small vegetable patch. Guests are welcome to help themselves to the fresh produce and use it for meals enjoyed on their own terrace. The pool is reserved exclusively for guests and offers peaceful relaxation on warm summer days.brbrbrbrThe interiors reflect traditional Tuscan style. Wooden beamed ceilings, terracotta floors and cosy furnishings create a warm and welcoming atmosphere that makes guests feel at home from the moment they arrive.brbrbrbrThe friendly owners live upstairs and are happy to assist with any questions. Il Cipresso is the perfect base for a peaceful and relaxing stay in the heart of Tuscany.brbrGround FloorbrbrKitchen-diner with furnished lounge, fully equipped kitchen with gas hobs - having 4 rings but no oven -, round dining table with four chairs, an open fireplace, one sofa, mosquito-screens, TV and French doors to gardenbrbrBedroom 1brbrPair of single beds (cannot be converted into a double bed), chest of drawers, mosquito-screens, door to gardenbrbrBedroom 2brbrDouble bed (cannot be converted into twin beds), wardrobe, chest of drawers, mosquito-screens, door to garden.brbrBathroombrbrShower, bidet, sink, WC, mosquito-screens.brbrbrbrPrivate Pool:brbrLength: 12 metersbrbrWidth: 6 metersbrbrDepth: 1.5 metersbrbrEntrance: Metal ladderbrbrOpening times: May to September, weather permittingbrbrFenced: nobrbrFurnished: Sunloungers and parasolsbrbrCleansed: ChlorinebrbrDistance from the villa: 20 meters

Il Cipresso, Radda in Chianti, Siena and Chianti

Radda In Chianti, Siena and Chianti, Italy

Bed

1

Bath

4

Sleeps

$5705.09

Summary:brbrVilla Castiglioni is a stunning Chianti villa rental. It is situated in the Chianti region in Tuscany, an area famous for its food, wine and exceptional rural landscape. It has been beautifully furnished and you will even have your very own wine bar within the Medieval tower. As well as this, you have your own gym and wellness area, five stunning bedrooms and a private pool. Guests will be met with a delicious welcome aperitivo and enjoy a welcome dinner on the first Monday of their stay too.brbrbrbrThe Space:brbrInside, the interior of this Chianti villa rental is fresh and contemporary with modern, comfortable furnishings creating an effective contrast against the old stone walls, beamed ceilings and parquet flooring. It's the perfect mix of rustic and modern, whilst large windows bring in plenty of light. brbrbrbrThe property has four beautifully presented double bedrooms in the main villa, each with an equally stylish ensuite bathroom. There is also a separate studio dependence in this Chianti villa rental. In total the house can sleep up to 11 guests in total. brbrbrbrThere is an extremely well equipped and stylish professional kitchen with 4 ring gas stove and 2 ring electric hob. A living area is furnished with two sofas and has a feature fire place to provide a focal point. A dining table seats up to 8 guests. brbrbrbrIn the basement of this Chianti villa rental is a private gym, perfect for those that like to keep fit on holiday, whilst there is also a private health and wellness suite with Turkish bath and sauna where you can relax and unwind along with a gym with weights, rowing machine, exercise bike and more. There is also an additional bathroom on this floor for guests' convenience. brbrbrbrThe property is cleaned daily (except Sundays). The team will work for 5 hours each day, 6 days a week. There is a laundry room at the property. Whilst this is not accessible for guests to use themselves, the housekeeper is available free of charge 5 hours per day (excluding Sundays) and they would be glad to do any washing needed. The housekeeper can also cook for the guests and can remain longer if required at a rate of 20 euros per hour. brbrbrbrBath towels are changed each day for you and pool towels are changed twice weekly. Linen is also changed mid way through your stay but additional changes can be provided at a cost of 12 euros per person. Breakfast is served each day. This can be served either indoors or within the garden. The delicious continental breakfast includes cold meats and cheeses, vegetables, salad, fresh fruit, chia pudding or porridge, yoghurts, home made granola, bread, pastries, juices, smoothies and more. Guests are also invited to a complimentary wine tasting during their stay.brbrbrbrThis Chianti villa rental enjoys incredible 360 degree views of the surrounding countryside. Outside there is a heated swimming pool (12m x 5m, depth 1.4-2.0 metres) which is open from April to October and which is positioned to make the most of the views of the surrounding countryside. Please note that pool heating is charged at 100 euros per day. Plenty of loungers are provided for long days in the sun, whilst there is also a large dining table positioned under the shade of a pergola, perfect for al fresco dining. brbrbrbrThere are numerous other outdoor seating areas at this Chianti villa rental, allowing guests to find a quiet spot to read or to enjoy an afternoon siesta away from the rest of the group! brbrbrbrFor those travelling with children, there is also a small play area to entertain them. brbrbrbrThe property is fenced all the way round and there is ample parking for up to 5 cars.brbrbrbrPlease note that 1000 euros is payable in cash on arrival to cover the cost of any extras during your stay. Any unused funds will be returned to you on departure. A 3000 euro security deposit is also payable. Local tourist taxes are 2 euros per person per day.brbrbrbrThe Neighborhood:brbrThis Chianti villa rental is situated in the heart of the Chianti countryside surrounded by olive groves and wineries, in a small, idyllic village and near the larger town of Radda in Chianti (1.5 km away). Here you will find a selection of shops and restaurants as well as a supermarket, bank and pharmacy. brbrbrbrThe nearest train station is 20 km away in Montevarchi. It's also an easy drive from the house to the main Tuscan cities of Florence and Siena. A plethora of other medieval towns and villages are within a 2-3 hour drive including Lucca, Pisa, Volterra, Arezzo, Cortona, Urbino, Perugia, Assisi, Orvieto, Pienza, Montepulciano, San Gimignano, Vinci and Certaldo.brbrbrbrOther Things to Note:brbrIf you're a wine lover, then look no further than Villa Castiglioni! The owners of this Chianti villa rental happen to own an excellent winery which produces superb wine. We highly recommend guests pay a visit and enjoy a complimentary wine tasting here during their stay! Or if you're more of a foodie, then why not enjoy a cookery lesson in the villa's professional kitchen. Please note that the owner will provide guests with a complimentary welcome cold aperitivo on arrival, a complimentary dinner on the Monday of their stay and a free wine tasting in the nearby wine cellar on the Wednesday.

Chianti villa rental

Radda In Chianti, Toscana, Italy

5

Bed

Bath

11

Sleeps

$610.89

Welcome to La Capanna @ Casa Volpino. A Tuscan farmhouse in the heart of the Chianti Region. Built over the old animal stalls, this cozy, newly renovated 1500 sq foot stone house is nestled in the picturesque hills between the medieval towns of Radda in Chianti and Volpaia. The area offers an abundance of old-world charm, spectacular views, and is ideally situated for exploring the regions wineries and famous Tuscan towns like Florence, San Gimignano, and Siena. brbrThe main floor has a fully stocked kitchen and dining area with an original fireplace.brOur comfy living room is a perfect place to sit and chat. It features 2 sofas one of which is a double couch bed that sleeps 1 -2 people. brOff the living room, you will also find a laundry room with a washer and dryer and a full bathroom with a tub and shower. brbrThe second floor has 3 bedrooms and 3 bathrooms (2 en suite) with luxurious linens and beautiful views. brbrThe garden includes a private pool, where you can relax and soak up the sun while enjoying the breathtaking views. Right off the kitchen, you will find a covered patio with a seating and dining area, perfect for al fresco meals and evening cocktails.brbrIf you are looking for a peaceful retreat or a base for exploring Tuscany, this charming house will be just what you need. brbrIf you have any questions regarding La Capanna, please do not hesitate to ask.brbrPLEASE NOTE THAT YOU AND YOUR GUESTS WILL BE THE ONLY GUESTS ON THE PROPERTY. THE LARGER VILLA IS NOT AVAILABLE FOR RENT AT THIS TIME.brbrImportant Information Regarding local tourist tax and identification:br1. We are required by Italian law to collect identification from each guest before check-in. I will send an email or text message to you after the last deposit is paid, asking you to submit passport information for each guest.brbr2. There is a tourist tax required by law of 2 euros per person (over the age of 14) per night for the first 7 days of your booking We have decided to include this charge in the nightly rent. This avoids having to collect cash from you at check-in.brbrHelpful Information:brIf you plan on staying in Chianti it is highly recommended that you rent a car. brbrDistance from:brFlorence- 31miles / 50 kmbrSiena- 21miles / 34 kmbrSan Gimignano 30 miles / 44 kmbrMontepulciano 48 miles / 78 kmbrbrThere are restaurants, grocery stores, butchers, cheese shops, and fruit and vegetable vendors within 3 miles of the house.

Country House

La Capanna - Radda in Chianti. Newly renovated stone farmhouse with pool & A/C

Radda In Chianti, Provincia di Siena, Italy

Bed

Bath

Sleeps

$658.58

The villa La Petrosa is located in Radda in Chianti and is the ideal accommodation for a relaxing getaway. The 3-storey property consists of a living room with a sofa bed for 2 people, a well-equipped kitchen, 5 bedrooms and 3 bathrooms and can therefore accommodate 11 people. Additional amenities include a TV, a fan as well as a washing machine. A high chair is also available.brbrThis vacation rental offers a private outdoor area with a pool, garden, 6 balconies, a barbecue, and an outdoor shower.brbrThis is a 17th-century Tuscan farmhouse in the heart of Chianti Classico. Equipped with every comfort, it is ideal for peaceful vacations with family and/or friends to relax and enjoy nature and cultural excursions to nearby cities of art.brbrA parking space is available on the property and free parking is available on the street.brbrOne pet is allowed.brbrSmoking and celebrating events are not allowed.brbrAir conditioning and Wi-Fi are not available.brbrBeach/pool towels are provided.brbrThis property has guidelines to help guests with the correct separation of waste. More information is provided on site.brbrThis property features energy-saving lighting.brbrThe electricity at this property is partly generated by photovoltaic panels.brbrSustainable materials have been used in the insulation at this property.brbrHeating is included in the price from October 1st to May 15th.brbr- Pet allowed payment 100,00 € per petbrbr- Energy payment 15,00 € per nightbrbr- Beach/pool towels payment 15,00 € per person

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda In Chianti, Radda in Chianti, Italy

Bed

Bath

Sleeps

$280.43

Located in Radda in Chianti, the cottage Podere in Volpaia has everything you need for a comfortable holiday. The 85 m² property consists of a living room, a fully-equipped kitchen with a dishwasher, 3 bedrooms and 2 bathrooms and can therefore accommodate 5 people. Additional amenities include Wi-Fi, a TV, air conditioning, heating as well as a washing machine. A baby cot is also available.brbrThe highlight of this accommodation is its private outdoor area with a garden, an open terrace, a covered terrace and a barbecue. The property also has a small private lake where you can fish (swimming is prohibited).brbrThe property is located 2 km from Volpaia, 6 km from the centre of Radda in Chianti, 42 km from Siena and 57 km from Florence.brbrA parking space is available on the property.brbrFamilies with children are welcome.brbrPets are only allowed upon previous request.brbrThe property has step-free access and interior, the doors are wide and easy to access.brbrDinners, wine tastings, horseback riding tours, forest walks, picnics and an e-bike can be booked for a fee.brbrAn electric vehicle charging station is available.brbrBreakfast is available for a fee.brbrThe property offers homemade/homegrown produce.brbrThis property has guidelines to help guests with the correct separation of waste, more information is provided on site.brbr- E-Bike payment 60,00 € per daybrbr- Breakfast payment 15,00 € per person per night

Cottage

Cottage Podere in Volpaia with Garden & Wi-Fi

Radda In Chianti, Radda in Chianti, Italy

3

Bed

Bath

5

Sleeps

$475.91

La Pesa di Mezzo is a beautifully restored Tuscan barn set in the heart of the unspoilt Chianti countryside.The property enjoys a peaceful and secluded position on a gentle slope, offering panoramic views across the Chianti Classico landscape. Surrounded by fragrant rosemary and lavender, this is the perfect retreat for couples or honeymooners seeking privacy, charm, and an authentic Tuscan atmosphere.brbrbrbrA few steps from the villa, guests will find a private pool, ideal for relaxing and soaking in the serene surroundings and sweeping countryside views. Nearby, the two shaded outdoor dining areas provide the perfect setting for leisurely lunches or memorable dinners enjoyed al fresco.brbrbrbrJust 5 km away, the lively town of Radda in Chianti invites guests to browse local shops, enjoy cosy cafés, and dine in excellent restaurants. The surrounding region is renowned for its Sangiovese vineyards and offers easy access to day trips to cultural landmarks in Florence, Siena, and Arezzo.brbrInside, the villa combines traditional features such as terracotta floors and exposed wooden beams with custom-made shelving and wardrobes crafted from reclaimed wood, creating a warm and elegant atmosphere. The kitchen is thoughtfully equipped with a travertine marble sink, SMEG appliances, and carefully selected details that blend comfort and style. The bedroom, decorated in soft pastel tones and illuminated by traditional barn windows, provides a romantic and restful space for quiet evenings.brbrbrbrLa Pesa di Mezzo is more than just a place to stay – it offers a refined and memorable escape surrounded by the timeless beauty of Tuscany.brbrGround FloorbrbrbrbrKitchen / DinerbrbrFully equipped kitchen, fridge / freezer, table, chairs, air-conditioning, doors to sheltered terrace, terrace with table and chairs.brbrbrbrLoungebrbrSofa bed, coffee table, smart TV, wood-burning stove, side tables, air-conditioning, stairs to first floor, doors to sheltered terrace and garden.brbrbrbrBathroombrbrShower, sink, WC, bidet.brbrbrbrBedroom (open in 2026)brbrDouble bed, bedside tables, wardrobe.brbrbrbrEn-suite Bathroom (open in 2026)brbrShower, sink, WC, bidet.brbrbrbrFirst FloorbrbrbrbrBedroombrbrDouble bed (cannot be converted into twin beds), bedside tables, smart TV, ottomans, wardrobe, air-conditioning.brbrbrbrUtility outbuildingbrbrWashing machinebrbrbrbrPrivate PoolbrbrLength: 7.5 metresbrbrWidth: 3.5 metresbrbrDepth: 1.5 metresbrbrEntrance: Roman StepsbrbrOpening times: May to SeptemberbrbrFenced: NobrbrFurnished: SunloungersbrbrCleansed: SaltbrbrDistance from villa: 10 metres

La Pesa di Mezzo, Radda in Chianti, Siena and Chianti

Radda In Chianti, Siena and Chianti, Italy

Bed

Bath

Sleeps

$340.93

Situated in Radda In Chianti, Tuscany, Italy, this 2-bedroom farmhouse is ideal for families and groups with pets. Ideal for 4 people, the farmhouse has a shared swimming pool equipped with sunbeds, at a distance of 250 m.brbrDuring your stay at this property, you can plan several excursion trips including a visit to Parco Archeologico di Poggio La Croce and Albola Castle. On Sundays, you can visit Pieve di Santa Maria Novella to offer prayers. You can also head to Chianti Sculpture Park with kids. Restaurants/cafés, as well as general stores, are situated at a distance of 2 km. This holiday accommodation has play equipment for children. There is a shared garden as well as a private terrace for you to enjoy. You can fetch bicycles on rent. There are TVs in every bedroom along with WiFi connectivity. A cot and a high chair are offered for the comfort of our youngest guests. A maximum of 1 pet is allowed here.brbrGuests also have access to an organic garden where they can pick vegetables. There is a covered parking space and you can rent band towels at the accommodation.brbrThe nearest airport is just 55 km away.brExpenses related to charging an electric or hybrid car (when possible) are always charged according to use and separatelybrThis holiday home is one of the Belvilla Award winners in: 2021,2022brbrLayout: Ground floor: (Living room, open kitchen(double sofa bed, TV(satellite), coffee machine, oven, dishwasher, fridge-freezer, terrace), bedroom(double bed or 2 single beds, TV(satellite)), bedroom(double bed, TV(satellite)), bathroom(shower, washbasin, toilet, bidet), bathroom(shower, washbasin, toilet, bidet))brbrbathroom(shared with other guests, reachable from the outside)(shower, washbasin, toilet), washing room(washing machine(shared with other guests)), terrace(private), garden(shared with other guests, 1000 m2), garden furniture, parking, swimming pool(shared with other guests, 12 x 6 m., opened from Jun upto and including Sep), play equipment, table tennis table, bicycles available, Charging post for electric carsbrbrThese costs are mandatory and charged on site. They are not included in the rental price.brTourist tax: € 2.00 /person/night (Indication)brFinal Cleaning: € 50.00brElectricity: € 0.75/kWhbrBed linen: PresentbrPets: Max. 1; free of chargebrbrOptional services that you can arrange on sitebrHeating: € 20.00/nightbrHigh chair: free (on request)brCot: free (on request)brBath towels: PresentbrWood: IncludedbrWifi: FreebrKitchen linen: PresentbrMiscellaneous: Order a welcome basket of groceries € 20.00/basketbrUse washing machine: IncludedbrCot + High chair: free (on request)

Apartment

Pretty farmhouse with terrace

Radda In Chianti, Radda in Chianti, Italy

Bed

4

Bath

Sleeps

Select Dates for Price

Casa Momi is a charming retreat set in the Chianti Classico countryside, offering views across rolling hills, forests and vineyards, just five minutes from the medieval town of Radda. The property provides a simple, authentic Italian cottage experience, with large windows framing the surrounding landscape and outdoor spaces including a pool, barbecue area and terrace table for sunset drinks. The location combines tranquillity with convenience, making it easy to enjoy both relaxation and exploration of the local area.brbrbrbrThe surrounding region is rich in attractions, from Radda with its many restaurants to nearby Chianti towns Castellina, Panzano and Greve, known for wine fairs and scenic landscapes. Monte San Michele Nature Park offers hiking and guided nature experiences, while Siena, Arezzo and Florence are all within easy driving distance, providing art, culture, food and history for more immersive Italian adventures.brbrbrbrCozy semi-detached cottage for two with a private pool, barbecue, and panoramic outdoor dining. Ground floor has open-plan sitting, dining, and kitchen with hob, gas oven, microwave, and fridge. Spiral staircase leads to a double bedroom with en-suite shower and air-conditioning.

Private Pool Retreat in Chianti

Radda In Chianti, Radda in Chianti, Italy

1

Bed

Bath