Chianti Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Apartment • 4 People • 2

• 2

•

From

€

337 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 337 /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

Booked

Available

Apartment • 2 People • 1

• 1

•

From

€

203 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 203 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

A Taste of the Hills

Cosy and quaint, this typically Tuscan apartment is part of a pretty collection of homes, all set inside some historic stone buildings that feel charming and characterful. As such, you'll find terracotta tiled floors, farmhouse-style furniture and exposed stonework, all creating a snug and serene vibe. Staying here means you'll get access to some fantastic shared facilities on site, including a seating terrace with some spectacular views out to the surrounding countryside, as well as an outdoor pool that's ideal for hanging around on hot days. *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 season...More Details

Booked

Available

House • 8 People • 4

• 4

•

From

€

974 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 974 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Olive Tint

Overlooking the Tuscan countryside from its hillside position, this rustic villa boasts some incredible views – best celebrated from the outside dining area and elegant infinity pool. We think it's a great fit for families with a lovely private garden as well as flexible sleeping arrangements – the twin beds can be converted into doubles upon request. Keen cooks will love the modern chef's kitchen for preparing alfresco suppers – though if you feel like dining out, the nearby village of Volpaia and the market town of Radda are both just a short drive away. You will need to hire a car to get around here, and the drive will often be hilly and uneven. *Due to this home's location, you'll need a car to get the most out of your stay. There’s free parking on-site parking. Be prepared for hilly and often uneven roads. *The twin beds can be configured as double if required – you’ll need to request this in advance. *The swimming pool is only a...More Details

Booked

Available

Castellina in Chianti, House for rent

House • 6 People • 3

• 3

•

From

€

333 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 333 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Beyond the Hills

Situated in the heart of Chianti, this stone farmhouse is in a great spot for visiting some of the region’s many vineyards. Whether you’re admiring the countryside views from the wraparound terrace, cooling off in the private pool, or firing up the pizza oven, it’ll be easy to kick back and relax here. While the decor seems a little dated in places, the home boasts lots of traditional Tuscan touches, like terracotta tiled floors and beamed ceilings. Location-wise, you’re near the market town of Radda, and ever-popular Florence and Siena are just a day trip away. *Your host can provide a cot and high chair for free. You'll need to request them in advance. *The swimming pool is available for use between May and September. The pool isn't fenced so children will need to be supervised at all times. *Two well-behaved dogs, weighing up to 30kg each, are welcome to accompany you. *The twin bedroom can be configured as a double if required –...More Details

Booked

Available

House • 6 People • 3

• 2

•

From

€

403 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 403 /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

Booked

Available

Apartment • 10 People • 5

• 3

•

From

€

700 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 700 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Chianti Calm

You’ll find this restored farmhouse in the heart of Chianti, surrounded by vineyards and olive groves. Spread across a main house and a separate cottage, this place is perfect for a group of ten to get together while still having plenty of space to spread out. The home is semi-detached, but the garden, swimming pool, dining terrace, and sun loungers are all yours. The rural location means a car is essential here, especially if you intend on exploring the surrounding towns and villages. We recommend visiting Siena, less than an hour's drive away. *Due to the location of this home, we recommend hiring a car. Please note, access to the property is via an unpaved road. *This is a semi-detached home – the neighbouring villa is occupied by local residents. *The outdoor space is for your exclusive use only. *The swimming pool (open from May to September) isn't fenced. If you're bringing little ones, they'll need to be supervised at all tim...More Details

Booked

Available

Apartment • 10 People • 5

• 6

•

From

€

831 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 831 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Memories

With rolling Chianti hills all around, this traditional villa couldn't feel more Tuscan if it tried. Comprised of a main house and three en-suite bedroom cottages, it's perfect for a large family getaway. While the bathrooms could do with an update, and some of the interiors feel dated, it's all beautifully cared for. Kids will love you for the private pool with dive board –? a fifty-metre flip-flop from the main house. There's also a bocce court and a ping-pong table, and you're welcome to pick fresh vegetables and eggs from the gardens and chicken coop. Location-wise, you're just 5 kilometres from the traditional Chianti towns of Radda and Castellina. *There is ample private parking outside the villa. *The swimming pool is a fifty-metre walk from the villa. It is for seasonal use from May to October, weather permitting. There is a pool house with an additional shower room and an honesty bar. Guests can help themselves and pay upon c...More Details

Booked

Available

Castellina in Chianti, House for rent

Apartment • 4 People • 2

• 2

•

From

€

566 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 566 /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

Booked

Available

House • 8 People • 4

• 5

•

From

€

395 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 395 /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

Booked

Available

Castellina in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

461 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 461 /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

Booked

Available

Apartment • 8 People • 4

• 4

•

From

€

921 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 921 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is a perfect spot for a group seeking a retreat amongst sprawling gardens. There’s a separate cottage for guests seeking a little extra privacy, while the outdoor terrace is perfect for sharing Tuscan dishes all together (your host even produces their own olive oil and wine). Located near the village of Radda in Chianti, you’re perfectly placed for hiking the Tuscan hills or visiting one of the many vineyards that the region is known for. *This home is not suitable for infants or children under the age of 6. *It’s worth noting the approach to the house is on an unpaved lane, and a high-clearance vehicle is recommended. There is parking for three cars. *There's a separate cottage for guests seeking extra privacy. It features a living area and...More Details

Booked

Available

House • 14 People • 7

• 7

•

From

€

1,317 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,317 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Ode to Beauty

This traditional Tuscan home opens its doors to the natural beauty of the Chianti region. Nestled amid the trees, the private garden lends itself perfectly to lazy days by the pool. You’ll also find plenty of shady spots, family-friendly rooms and the welcome addition of an independent cottage with its own kitchen and one bedroom. Guests can enjoy a range of extra services here, including wine tastings and private chefs, plus it’s just a short drive to the nearest amenities – Radda in Chianti is 8 kilometres away. *Due to this home's location, we recommend hiring a car to get the most out of your stay. Please also note there is an unpaved, uneven road leading to the house so a high clearance vehicle is recommended. *There is private parking for up to five cars. *This home consists of a main house with six bedrooms, alongside an independent cottage with a kitchen, living room and a bedroom (located on the mezzanine level). *One pair...More Details

Booked

Available

House • 8 People • 4

• 4

•

From

€

729 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 729 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Eternal Etruscan

Sit back, relax and soak up the sunshine at this characterful villa in Chianti. It may be a little dated inside, but the twin apartment layout is perfect for families and groups that want their own space. Besides, the garden speaks for itself. Surrounded by vineyards and olive groves, you'll be treated to fantastic views day or night. There's a private pool, a hot tub, and a sauna for ultimate relaxation, while the terrace makes the perfect spot to enjoy an Italian feast. Paths lead down to freshwater springs with natural pools, but if you want to venture out, you'll find Radda in Chianti, Siena, and Florence all within easy driving distance. *This home consists of two apartments, each with its own living area and kitchen. They're connected by an outdoor staircase. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *Two double beds can be converted into twins if needed. *If you're travelli...More Details

Booked

Available

House • 9 People • 5

• 4

•

From

€

734 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 734 /Night (minimum stay 1 night)

Swimming Pool

WiFi

A Guide to the Hills

Overlooking the Chianti hills, this home is the ideal setting for a restorative Tuscan getaway. Spread across two floors (connected by external stairs), there are two kitchens, family-friendly rooms and plenty of space for groups to stretch out and enjoy quality time together. Outside, you’ll find the swimming pool takes centre stage, while the hot tub provides the perfect spot to sit back and admire the views. You will need a car to get around here, but it’s just a 7 kilometre drive to the nearest amenities in Radda. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also private parking for two cars. *Please note there is an external staircase between the ground and the first floor. Each floor has its own private entrance. *Two of the bedrooms can be arranged with double beds or two singles beds upon request. *There is no air-conditioning here but fans are provided. Please also note t...More Details

Booked

Available

House • 10 People • 5

• 6

•

From

€

5,401 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 5,401 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Sangria

At this rustic villa, rolling vineyards are on your doorstep. We mean that quite literally – the owners are local winemakers, and they offer tastings in the medieval tower-turned-wine bar. They'll also arrange welcome dinners, cooking classes, private chefs, continental breakfasts, and other special touches during your stay. As for the home itself, we think it's pretty spectacular. A private pool, sun-kissed garden, and Chianti views await outside, while the somewhat traditional interior has a few surprises in store – namely, a chef's kitchen, a small gym and a wellness centre boasting a Turkish bath and steamy sauna. Location-wise, Radda is less than 2 kilometres away, and Florence and Siena are great options for day trips. *The fifth bedroom is located in a guest annexe. It has a kitchen, double bedroom and bathroom.*Daily housekeeping (excluding Sundays) is included. Bath towels are changed daily, while pool towels and bed linen ar...More Details

Booked

Available

Apartment • 8 People • 4

• 3

•

From

€

1,951 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,951 /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

Booked

Available

Apartment • 6 People • 2

• 1

•

From

€

204 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 204 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Dreamers

This apartment is a comfortable base from which to explore all that Tuscany has to offer. Siena, around 27 kilometres away, is an ideal day trip destination, while the small town of Castellina in Chianti is just a short drive away. The home’s rustic interior design won’t be to everyone’s taste as the place feels a little dated in parts, but access to a communal swimming pool and barbecue area certainly makes up for it. If you’d like to make your mornings extra special, your host provides breakfast for an additional fee. *Due to this home's location, we recommend hiring a car to get the most out of your stay. Parking is available on the premises. *Heating and the use of Air Conditioning are charged extra upon consumption. *The communal swimming pool (open from the 1st of May to the 1st of October) isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *Your host can also provide a high chair, at no ...More Details

Booked

Available

Apartment • 6 People • 3

• 3

•

From

€

801 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 801 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Stonehill Vines

This grand stone villa looks the perfect part in a region known for its Renaissance history and castles. Located on a gentle hillside slope, this 16th century home sings of rural Tuscany. With its two floors connected by an external staircase, you can easily dip in and out of its beautiful beamed main room and bedrooms and into the gorgeous sunshine. Outside, a covered dining pergola, panoramic terrace, and raised pool garden offer views from every angle, celebrating country living amidst the home’s surrounding woodlands, olive trees, and endless rows of vines. Taste Tuscany's infamous Chianti grapes with an inclusive tour and guided tasting at the Castello d’Albola and explore the hills’ rustic trails and hidden paths on horseback. Discover the nearby ‘road of the castles’ and live out your own royally decadent stay at this home that’s a true feast for the senses. *All the beds can be separated or pushed together to make singles or d...More Details

Booked

Available

Apartment • 10 People • 5

• 6

•

From

€

1,357 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,357 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Wild Roses

Tucked away in the Tuscan countryside, this idyllic villa promises plenty of rest, relaxation and rustic charm. Famous for its rolling hills, acres of vineyards and quaint, historic hamlets, there's no better spot to explore all this region has to offer. Both Florence – an hour away – and Siena – a thirty-minute drive away – are great options for day trips, though it will be hard to pull yourself away from the serene gardens back at home. Enjoy your morning espresso on the cosy outdoor sofa, go for a relaxing swim in the pool and soak up the sun on the poolside lounge chairs. Surrounded by olive trees, rose bushes and dense woodland, you'll feel a sense of calm wash over you as you take it all in. Even inside, the bright, classically styled rooms feel warm and welcoming. Whether you're whipping up meals in the mint-green kitchen – which are best enjoyed alfresco – or snoozing in the comfy elegant bedrooms, you'll love calling this hidea...More Details

Booked

Available