Castellina In Chianti Houses for rent, Rent Furnished or Unfurnished Detached Houses, Villas and Single Family Homes

House • 4

• 3

• 2,239 ft2 • pets

€

10,344 EUR /Month

Term: Monthly

House in Castellina in Chianti, Italy

€10,344 EUR /Month
• Term: Monthly (Furnished)

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 w...

House • 5

• 5

• 4,628 ft2 • pool

€

22,806 EUR /Month

Term: Monthly

House in Castellina in Chianti, Italy

€22,806 EUR /Month
• Term: Monthly (Furnished)

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 firepl...

House • 5

• 4

• 4,844 ft2 • pets

€

24,423 EUR /Month

Term: Monthly

House in Castellina in Chianti, Italy

€24,423 EUR /Month
• Term: Monthly (Furnished)

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 fr...

House • 6

• 7

• 5,167 ft2 • pets

€

15,864 EUR /Month

Term: Monthly

House in Castellina in Chianti, Italy

€15,864 EUR /Month
• Term: Monthly (Furnished)

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 bee...

House • 3

• 2

• 1,830 ft2 • pets

€

9,456 EUR /Month

Term: Monthly

House in Castellina in Chianti, Italy

€9,456 EUR /Month
• Term: Monthly (Furnished)

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 ...

House • 4

• 5

• 2,691 ft2 •

€

10,440 EUR /Month

Term: Monthly

House in Castellina in Chianti, Italy

€10,440 EUR /Month
• Term: Monthly (Furnished)

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 Ba...

House • 5

• 5

• 2,691 ft2 •

€

13,632 EUR /Month

Term: Monthly

House in Castellina in Chianti, Italy

€13,632 EUR /Month
• Term: Monthly (Furnished)

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 ...