Castellina in Chianti, Apartment for ren

Apartment • 8 People • 4

• 3

•

From

€

1,818 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,818 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Touch of Chianti

Stylishly rustic, this country home sets the tone for a restorative retreat in the heart of Chianti. Dating back to the 10th century, the house has a wonderful sense of character with plenty of space for groups to relax and enjoy the garden views. There’s also a private swimming pool and a terrace – perfect for alfresco dining. Your host can help organise a range of extra services here, including private chefs and guided tours – a great option for those looking to explore the region. From here, it’s just 4 kilometres to Castellina, while cities such as Florence and Siena are also within driving distance. *Due to this home's location, we recommend having a car to get the most out of your stay – please also note there is a 200-metre track leading to the entrance. *A complimentary mid-stay housekeeping service is included with your stay. *This home is spread across two floors with no internal lift. Please also note one of the bedrooms is...More Details

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Castellina in Chianti, Apartment for ren

Apartment • 6 People • 4

• 4

•

From

€

1,547 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,547 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

First Of The Summer Wine

Surrounded by olive trees and vast swathes of vineyards, this Tuscan home in the heart of the Chianti wine region is a haven of rural relaxation. Its exposed stone exterior gives way to a bright interior, where farmhouse simplicity meets elegant design in the living room. With its giant hearth, plump sofas and tiered chandelier, this is the perfect spot for socialising over a glass of wine or curling up by the fire with a good book on cooler nights. With four comfortable bedrooms boasting postcard-like countryside views and a farm-style kitchen full of traditional charm, you’ll have everything you need to make yourself right at home. Head outside to take cool dips in the pool, or sit back in one of the many sun loungers while taking in the spectacular hillside views. Wander around the vineyards, visit Castellina in Chianti (less than ten minutes away by car), then come back home for a barbecue under the pergola paired, naturally, with a...More Details

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Available

Castellina in Chianti, House for rent

House • 10 People • 5

• 4

•

From

€

1,132 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,132 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Classic Moments

If you’re in search of a rustic retreat in the heart of Chianti Classico, this home delivers a sweet solution. You can enjoy stunning views across olive groves, vineyards and rolling hills. There’s a private pool for leisurely afternoon swims, a shaded pergola for evening meals and a billiard room for family-fun and games. The rooms are spread across the main house and an adjacent annexe – providing plenty of space to stretch out and socialise. You will need a car to get around here, but it’s just a short drive to Castellina in Chianti, while Siena and San Gimignano are both within easy driving distance. *Please note the main house is spread across three floors. You will also find two of the bedrooms are located in the adjacent annexe. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *All fireplaces in this home are ornamental. *The swimming pool is available for use from the last ...More Details

Booked

Available

Castellina in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

1,008 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,008 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Tuscan Moon

Nestled between the pretty hilltop towns of Chianti, this home offers a traditional Italian sanctuary. Enjoy breathtaking views across vineyards while relaxing on the terrace. There’s a private pool for blissful swims and an original stone oven for authentic pizza nights. Inside, you’ll find plenty of space for entertaining with a wine tasting room, a cosy living room and a games room. Your host can also help organise a range of sweet extras – including a private chef, guided tours and walking excursions. And when it comes to explorations further afield, it’s just a short drive to the nearest amenities, while Florence and Siena are also within easy driving distance. *Private parking is available for up to four cars here. *It is possible for the two single beds in bedroom one to be arranged as a double bed on request. *If you’re travelling with little ones, your host can provide a cot for free on request. *The fireplace in this hom...More Details

Booked

Available

Castellina in Chianti, Farmhouse for ren

Farmhouse • 16 People • 7

• 6

•

From

€

897 /night

Min Stay 7 nights

Castellina in Chianti, Italy

€ 897 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Credit Cards Accepted

10-room house 314 m2 on 2 levels. Comfortable and cosy furnishings: open living room with open-hearth fireplace and satellite TV. 2 double bedrooms, each room with air conditioning. Living room with open-hearth fireplace and satellite TV. 1 double bedroom with air conditioning. 1 small room with 1 bed and air conditioning. Open gallery with sloping ceilings with 1 bed and air conditioning. Living room with satellite TV. 1 double bedroom with air conditioning. Open kitchen (4 hot plates, oven, dishwasher, freezer). 4 showers/bidet/WC. Upper floor: open living/sleeping room with 1 double bed, open-hearth fireplace and satellite TV. 2 double bedrooms, each room with air conditioning. Open kitchen (4 hot plates, oven, dishwasher, freezer). 2 showers/bidet/WC. Gas heating, air-conditioning (extra). Terrace furniture, barbecue. Very beautiful view of the countryside. Facilities: washing machine, children's high chair, baby cot. Internet (WiFi...More Details

Booked

Available

Castellina in Chianti, House for rent

House • 12 People • 6

• 7

•

From

€

650 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 650 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Farmhouse Serenity

This renovated farmhouse sits within 460 hectares, in a dominant position in the hills of Chianti. It’s surrounded by vineyards and olive groves, and boasts far-reaching views across the countryside, but is just 5 kilometres from Castellina in Chianti and 20 kilometres from Siena. The farmhouse has been renovated to return it to its original splendour – you can look forward to traditional features like wood beams and terracotta tiles. Outside, there’s a pool to swim in, a lush garden, and a loggia with a barbecue, perfect for alfresco dining. *Access to this home is via a 300-metre dirt road. We recommend hiring a car to get the most out of your stay. There’s free parking here. *Your host can provide a cot and high chair for little ones. *There are stairs to climb at this home, so it may not be suitable for those with reduced mobility. There’s a twin bedroom on the ground floor. *While not every bedroom or bathroom has been photograph...More Details

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Castellina in Chianti, Apartment for ren

Apartment • 4 People • 2

• 2

•

From

€

555 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 555 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

A Little Bit of Chianti

This stone-built villa in the heart of Chianti boasts stunning views of the valley and vine-clad hillsides from almost every room. Perfect for two couples wanting to holiday together without crowding each other, each en-suite bedroom feels self-contained, with a kitchenette for morning cuppas. Meanwhile, the free-flowing living spaces downstairs and a private pool with a view are all about socialising. Fringing one of the main Chianti towns, Castellina (a 7-minute drive), there are bars and restaurants close by for evenings out, and you’re just a short drive from Siena and Florence (both less than an hour away). *There is ample private parking outside the home. It’s worth noting the approach to the house is on an unpaved lane. *A cot and high chair are available for little ones. *There are stairs within this home which may be unsuitable for guests with restricted mobility. *The private pool is for seasonal use, from May to October, we...More Details

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Available

Castellina in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

528 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 528 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Orgins

From the countryside views to the traditional character inside, there's no denying that this home is unmistakably Tuscan. It's situated among a working vineyard, offering access to the estate's communal pool and a shared garden. The cottage itself has its own terrace, ideal for relaxing in the fresh air while sharing a bottle of Chianti wine. Some rooms are a tad dated, but there's ample space to relax. When you're ready to venture out, an array of wineries and picturesque villages are within driving distance. Florence, Sienna, and Arezzo are also about an hour away for adventures further afield. *This home is on a family farm with another cottage, a main house, and a barn. You'll share access to the garden and swimming pool with other guests. *The communal swimming pool is open from May to September and is about 50 metres away from this home. *There's a bedroom and bathroom on the ground floor. This room's double bed can be converted...More Details

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Available

Castellina in Chianti, Farmhouse for ren

Farmhouse • 14 People • 7

• 6

•

From

€

510 /night

Min Stay 7 nights

Castellina in Chianti, Italy

€ 510 /Night (minimum stay 7 nights)

Swimming Pool

Air Conditioning

WiFi

Credit Cards Accepted

"Cerretino + Tettoia", 10-room cottage 180 m2 on 2 levels. Spacious, renovated, tasteful and cosy furnishings: open living/dining room with dining table and satellite TV (flat screen), air conditioning. Living room with dining table and air conditioning. 2 double bedrooms, each room with air conditioning. Open living/dining room with dining table, kitchen corner and air conditioning. 1 room with 2 beds (80 cm, length 190 cm), air conditioning. Open kitchen (oven, dishwasher, 8 gas rings, toaster, kettle, microwave, electric coffee machine) with dining table. 2 showers/WC. Upper floor: 2 double bedrooms, each room with shower/WC and air conditioning. 1 double bedroom with air conditioning. 1 small double bedroom with sloping ceilings, without wardrobe with air conditioning. 2 showers/WC. Gas heating (extra), air-conditioning. Natural stone floors. Comfortable furnishings in the country house style. 3 terraces, patio. Terrace furniture, d...More Details

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Available

Castellina in Chianti, Apartment for ren

Apartment • 10 People • 5

• 2

•

From

€

481 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 481 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Stuff of Dreams

With a truly picturesque location in the Chianti hills, this rustic villa is the ideal choice for anybody that has fantasised at any point about eloping to Tuscany for a short while — which is surely most people, right? Thanks to the elevated position, the address benefits from sweeping views of the countryside and these can be admired while dining on the terrace or gliding through the swimming pool, which is shared with the other four houses in the tiny village. Once you step through the home's large vaulted entrance — formerly the property's stables — you'll be greeted with an interior heavy on period features, including the fireplace, wooden ceiling beams and antique furnishings. The walls are covered in a great variety of artwork, while the four-poster beds add an extra touch of grandeur. When it comes to days out, you're firmly in wine territory here and there are local vineyards to visit not too far from the home. There are wal...More Details

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Castellina in Chianti, Apartment for ren

Apartment • 6 People • 3

• 2

•

From

€

462 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 462 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Brick - Green Shutters

There are many great things to say about this 18th century villa in Chianti, so let’s start with the most obvious, shall we? Overlooking the breathtaking Chianti Classico hills, the view here is something that shouldn’t be missed. We can picture it already, sitting out on the sunlounger simply basking in the sunshine and fresh air whilst you admire the incredible vistas. Then there’s the location itself which puts you on the doorstep of many of the finest wineries of the region. Sample all the farms and vineyards have to offer, or go on a hike when you’re in the mood to reconnect with nature. The interior of this home is another big tick – rustic but cosy, you’ll be especially drawn to the traditional Tuscan fireplace that, although ornamental, adds such warmth to the space. If it’s a fire you want, however, light it up in the barbecue outside where you can enjoy everything you brought back from the cellars and shops. *Due to the lo...More Details

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Castellina in Chianti, House for rent

House • 8 People • 4

• 3

•

From

€

458 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 458 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Like Sweetness

If you’re looking to experience the natural beauty of Chianti, this home delivers a charming solution. You’ll be welcomed by stunning views across the surrounding vineyards and there’s a private swimming pool for leisurely dips. Inside, the rooms are traditional, family-friendly and full of character. Your host is on hand to help organise sweet extras like private chefs, walking excursions and guided tours. Plus, it’s just a short drive to the nearest amenities while Siena is also within easy driving distance. *Please note the owners live next door with a dog and a cat – you may see them during your stay. *It is possible for the two single beds in the second bedroom to be arranged as a double bed on request. *Please note the swimming pool is open from May to September. *If you’re travelling with little ones, your host can provide a cot for free on request. *Private parking is available for up to three cars. *One well behaved dog is...More Details

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Castellina in Chianti, House for rent

House • 8 People • 4

• 5

•

From

€

441 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 441 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

This charming cottage is tucked away on an authentic working vineyard, beside a family farmhouse. It’s just 1 kilometre from Castellina in Chianti, and within driving distance of Sam Gimignano, Siena, and Florence – you’ll have plenty of options for day trips. There’s a sloped garden with a furnished terrace and a shared swimming pool, and exquisite views of the Chianti countryside to be enjoyed from almost every angle. The cottage feels typically Tuscan, with its terracotta tiles and wooden beams. It’s a comfortable holiday home in an idyllic setting. *There’s free parking at this home. *This home is spread over two floors so it may not be suitable for those with reduced mobility. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool is shared between the other homes on the property. It’s open from May-September. Air Conditioning Barbeque Bathtub Child Friendly Cot...More Details

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Available

Castellina in Chianti, Farmhouse for ren

Farmhouse • 12 People • 6

• 6

•

From

€

400 /night

Min Stay 7 nights

Castellina in Chianti, Italy

€ 400 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Credit Cards Accepted

9-room semi-detached house 267 m2 on 2 levels, on the ground floor. Renovated, tasteful and cosy furnishings: living/dining room with open-hearth fireplace, dining table and satellite TV. Exit to the garden. 1 double bedroom. Exit to the garden. Living/dining room with open-hearth fireplace, dining table and satellite TV. Exit to the garden. 1 double bedroom. Exit to the garden. Living/dining room with open-hearth fireplace, dining table and satellite TV. Exit to the garden. 2 double bedrooms. Exit to the garden. Kitchenette (4 hot plates, mini-oven, electric coffee machine). 4 showers/bidet/WC. Upper floor: 1 large double bedroom. 1 double bedroom. Shower/WC, shower/bidet/WC. Large terrace, garden. Terrace furniture, barbecue. Facilities: Internet (WiFi, extra). Suitable for families. 2 pets/ dogs allowed. No internal connecting door between the separated properties. IT052005B42PTXEB5T Outside Description: Podere Gioia consists of tw...More Details

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Castellina in Chianti, House for rent

House • 6 People • 3

• 2

•

From

€

388 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 388 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Dreaming of Chianti

After a day touring world-class vineyards, this home is the perfect place to unwind with a glass of Chianti. Sure, there’s no air conditioning here, and the traditional interiors may not be to everyone’s taste, but there’s no denying the beauty of the outdoor space. And, where better to cool off in the Tuscan heat, than the private pool? If you’re not dining alfresco and soaking up the countryside views, take the short drive to Quercegrossa for some authentic Italian food with the locals. *The owners live next door to the villa and have a dog and a cat, and there's an apartment that they occasionally use for family and guests. The apartment doesn't overlook the villa – it overlooks the pool slightly from a distance – they don't use the swimming pool and won't disturb you during your stay. *There's no air conditioning here. *The swimming pool, open between May and September weather permitting, isn't fenced. Children must be supervise...More Details

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Castellina in Chianti, Apartment for ren

Apartment • 3 People • 2

• 1

•

From

€

386 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 386 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Cheers to Chianti

You've got all the perks of a private home combined with the palatial shared grounds of a hamlet at this apartment complex nestled between the Chianti villages of Panzano and Castellina. The views of the rolling hills and iconic cypress trees are delightful from the estate's shared swimming pool. But if you're after more privacy, the panoramas from the apartment's private terrace are just as impressive. Besides a restaurant in the neighbouring village of Piazza, there are no local amenities to walk to. You'll need a car to explore but prepare for a hilly, uneven drive at times. *Due to the unpaved, uneven access roads and uphill segments, a high clearance vehicle is recommended, and the roads may be better suited to experienced drivers. *This home is part of a collection of eight cottages and apartments within communal grounds. The swimming pool and parking area are shared, but this semi-detached home has a private entrance and garden...More Details

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Castellina in Chianti, Apartment for ren

Apartment • 5 People • 2

• 1

•

From

€

342 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 342 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Grape Juice

Situated on the first floor of a traditional Tuscan stone building, this apartment puts you right at the heart of rural Tuscany, surrounded by glorious rosemary bushes, grape vineyards and olive groves. Here, you'll enjoy access to the site's fantastic communal facilities, including a terrace area with seating where you can gaze out at the countryside views, plus an outdoor swimming pool that's surrounded by loungers for afternoon naps. Inside, you'll find traditional Tuscan decor that makes the home feel warm and welcoming. *Due to the unpaved, uneven access roads and uphill segments, a high clearance vehicle is recommended, and the roads may be better suited to experienced drivers. *This home is part of a collection of eight cottages and apartments within communal grounds. The swimming pool and parking area are shared, but this semi-detached home has a private entrance and gardens. *The shared pool is for seasonal use from May to Oc...More Details

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Castellina in Chianti, Apartment for ren

Apartment • 4 People • 2

• 2

•

From

€

327 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 327 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Chianti Rosemary

Sitting on the hillside in Chianti's countryside, this apartment is part of a small collection of cottages and apartments. Typically Tuscan, the interior may be a tad dated – and you'll have to share laundry facilities – but it'll suit those craving a bit of character. You'll also have access to all the on-site amenities, including a communal terrace for alfresco dining and a shared swimming pool open from May to September. We highly suggest hiring a car here, as you'll want to get out and about to explore the local area. Vineyards, charming hamlets, and sightseeing hotspots like Florence and Castellina are all within easy reach. *Due to the unpaved, uneven access roads and uphill segments, a high clearance vehicle is recommended, and the roads may be better suited to experienced drivers. *This home is part of a collection of eight cottages and apartments within communal grounds. The swimming pool and parking area are shared, but this...More Details

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Available

Castellina in Chianti, Farmhouse for ren

Farmhouse • 6 People • 2

• 1

•

From

€

300 /night

Min Stay 7 nights

Castellina in Chianti, Italy

€ 300 /Night (minimum stay 7 nights)

Swimming Pool

Air Conditioning

WiFi

Credit Cards Accepted

4-room house 120 m2 on 2 levels, on the ground floor. Renovated in 2023, comfortable and cosy furnishings: living/dining room with open-hearth fireplace, satellite TV and air conditioning. Exit to the garden. Open gallery with 1 double bed and air conditioning. Kitchenette (4 hot plates, oven, dishwasher, freezer). Shower/bidet/WC. Upper floor: living/dining room with 1 double sofabed, open-hearth fireplace and satellite TV. 1 double bedroom with air conditioning. Exit to the garden. Kitchenette (4 hot plates, oven, dishwasher, toaster, kettle, microwave, freezer). Terrace furniture, barbecue. Panoramic view of the countryside. Facilities: washing machine, iron, children's high chair, baby cot for up to 2 year olds, hair dryer. Internet (WiFi, free). IT052005C2P4EUFYD7 Outside Description: Pretty stone farmhouse. The property, made up of two connected units, is immersed in the countryside in the heart of Chianti, an ideal area for vis...More Details

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Castellina in Chianti, Apartment for ren

Apartment • 8 People • 3

• 1

•

From

€

262 /night

Min Stay 7 nights

Castellina in Chianti, Italy

€ 262 /Night (minimum stay 7 nights)

Swimming Pool

Credit Cards Accepted

"Tipologia Quadrilocale", 4-room apartment 98 m2 on 2 levels, on the ground floor. Comfortable and rustic furnishings: entrance hall. Living/dining room with open-hearth fireplace and TV. 1 room with 1 bed, 1 double bed and separate WC. Kitchenette (4 hot plates, dishwasher, microwave, freezer). Upper floor: 1 double bedroom. 1 room with 1 bed and 1 double bed. Bath/shower/bidet/WC. IT052022B5K2YANYJD Outside Description: The farm surrounded by olive groves and vineyards of Chianti. Each of 12 apartments are located in the main house and a former barn has its own outside area with a table on the terraces surrounding with the main building. The location is very central and ideal for trips to discover the natural and cultural beauties of the region large working farm "La Moraia", renovated. 14 km from the centre of Castellina in Chianti, 18 km from the centre of San Gimignano, 50 km from the centre of Firenze, in an elevated position, i...More Details

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Luxury Rentals Castellina In Chianti Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 47 Castellina In Chianti holiday homes for rent

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Luxury Rentals Castellina In Chianti Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 47 Castellina In Chianti holiday homes for rent

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina In Chianti Property for rent