Siena Houses for rent With Pool, Rent Furnished or Unfurnished Detached Houses, Villas and Single Family Homes

House in Siena, Italy

€23,268 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Rusticana Retreat

This villa captures the rustic charm of old Italy. Surrounded by 40 hectares of land boasting olive groves, vineyards, orchards, and meadows with grazing horses, it’s an idyllic escape into the Tuscan countryside. A country road leads to the UNESCO hamlet of Castiglione d'Orcia. The garden is home to a rustic outdoor cooking station, a large, shaded table, and a full outdoor lounge. There’s a touch of modernity to the private, heated pool and you’ll find a sauna hidden amid the trees. The main villa is split across two levels and is a vision of old-world Italy and there is a separate annexe with further bedrooms, a second full kitchen and an open-plan living room. *This home consists of a main villa and an annexe with its own full kitchen. *Split across two levels, this place may not suit those with limited mobility. *Access is by a kilometre-long country track which is quite narrow and bumpy. *The swimming pool is only av...

House • 2

• 2

• 700 ft2 • pets

€

15,048 EUR /Month

Term: Monthly

House in Siena, Italy

€15,048 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sweet Vin Santo

Nestled in the heart of Tuscany's renowned Chianti Classico wine region, this villa offers a tranquil escape from it all. Owned by a local winery and surrounded by vineyards, a spot of wine tasting during your stay is a must. The home itself is perfect for a family or small group of friends, and while the interiors are charming, it’s the outdoor space that caught our eye. With far-reaching views, a private pool and terraced dining areas, making the most of the Mediterranean climate will be high on your agenda. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May until October, isn't fenced and there are open tread stairs here. Children will need to be supervised at all times. *The bedrooms can be set up as doubles or twins upon request. *The second bedroom is on the mezzanine level and semi-open to the space below, so privacy is limited.<b...

House • 5

• 5

• 2,949 ft2 • pool

€

40,950 EUR /Month

Term: Monthly

House in Siena, Italy

€40,950 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Glow

Nestled amidst vineyards and olive groves, this villa offers an unforgettable retreat in the heart of Chianti Classico. Set on a winery, it’s no surprise that there are plenty of outdoor spots just made for sipping a glass of wine at the end of a busy day. Add in a private pool and far-reaching countryside views, and this home ticks a lot of our holiday boxes. Ideal for larger groups, we also love how this home flows over three separate buildings, with the cottage and annexe alongside the main villa – perfect for those wanting to holiday together, yet still enjoy some privacy. *This home consists of the main villa (sleeping six), a separate cottage (sleeping two), and an annexe (sleeping two). *The villa is situated on a winery but is private. That said, expect to see staff working at the vineyard from time to time. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Th...

House • 3

• 3

• 1,076 ft2 • pets

€

11,016 EUR /Month

Term: Monthly

House in Siena, Italy

€11,016 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscany Finca

While this home is charming inside and filled with everything you need for a comfortable stay, the outdoor space is the cherry on the cake for us. Made for soaking up the Mediterranean climate, you’ll find secret pockets of garden here, so you can socialise or spend a little quiet time by yourself. The private pool offers some respite from the heat, or sun-seekers may prefer to enjoy the rays from the terrace. Keen to explore the local area? Hop on the bikes, don your helmets, and let two wheels take you away. *We recommend a car to get the most out of your stay – there's parking for three cars here. If you walk to the nearby town of Radda (2km away), take care as it's along a main road with no footpath. *Your host can provide a cot and high chair for free upon request. *The swimming pool, open from May to September (weather permitting), isn't fenced. If you're bringing children, they'll need to be supervised at all times. <...

House • 2

• 2

• 861 ft2 • pets

€

8,904 EUR /Month

Term: Monthly

House in Siena, Italy

€8,904 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

This stone villa ticks all the boxes for a Tuscan getaway. A former barn, the interiors have been given a modern makeover – though it's certainly not lacking in traditional character. When the sun is shining, make a beeline to the garden. Enjoy a dip in the private pool, stretch out on the sun loungers, or fire up the barbecue and dine alfresco on the terrace. Location-wise, the quaint village of Campiglia is just a few hundred metres away. Also nearby are Colle Val d'Elsa, Siena, and Volterra if you're in the mood for a day trip. *One well-behaved dog may be welcome to join you upon request. *The twin beds can be converted into a double on request. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool is available to use between May and September. Please speak to your host for the exact opening and closing dates. *You’ll need a car in this location. On-...

Castellina in Chianti House for rent

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 ...

Castellina in Chianti House for rent

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 • 2

• 2

• 1,507 ft2 •

€

4,944 EUR /Month

Term: Monthly

House in Siena, Italy

€4,944 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Sun Beams in Tuscany

Within easy day-trip-reach of Siena, this charming apartment offers a tranquil base amid the picturesque hills and vineyards of Tuscany. Once a haven for travelling priests, this restored home exudes history and character. It’s been converted into delightful individual holiday homes, each with a furnished outside space where you can dine alfresco and drink in the view. You’ll have access to the shared pool and tennis court and will have 27 kilometres of hiking and cycling trails right on your doorstep. Don’t forget your walking boots. *We recommend hiring a high-clearance car as access to this home is via an unpaved road. There’s free parking here. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *You’ll have access to the resort’s shared facilities, including a tennis court and pool. *The shared swimming pool is available from Easter to October. *The twin beds can be...

House • 10

• 11

• 6,619 ft2 •

€

192,339 EUR /Month

Term: Monthly

House in Siena, Italy

€192,339 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

A Truffled Retreat

This Italian villa caught our eye for its panoramic views of the Tuscan countryside. There’s plenty to make your holiday memorable here, including both indoor and outdoor pools, a sauna, and a private wine cellar. While the home is perfectly set up for a large group, you can still get privacy when you need it – all of the bedrooms are en-suite and the second floor of the villa has its own entrance, as well as an extra lounge and kitchenette. And when you’re ready to explore, why not book a wine tasting at one of the local vineyards, or take a scenic drive to the picturesque town of San Gimignano – famous for its medieval towers and gelaterias? *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. *The outdoor swimming pool isn't fenced so children will need to be supervised at all times. The outdoor pool is only available for use between May and Octob...

House • 4

• 3

• 2,153 ft2 •

€

12,312 EUR /Month

Term: Monthly

House in Siena, Italy

€12,312 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Tuscan Escape

Tucked in the Tuscan countryside, yet just five kilometres from Siena, this traditional home is perfect for those seeking a tranquil retreat. Should you need anything during your stay, the owner lives on-site – but your peace won’t be disturbed otherwise. With space to spread out, there are plenty of quiet nooks here when you’d like some privacy. That said, we think everyone will be drawn to the outdoor space. A private pool, sun-drenched terraces, and an alfresco dining spot nestled in the shade – it ticks our holiday boxes. *The swimming pool, available from May to September, isn't fenced and there are open-sided stairs here. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *One well-behaved dog (up to 30kg) is welcome to accompany you during your stay. *The twin bedroom can be set up as a doubl...

House • 7

• 7

• 3,660 ft2 •

€

27,258 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€27,258 EUR /Month
• Term: Monthly (Furnished)

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)...

House • 3

• 2

• 861 ft2 •

€

7,176 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€7,176 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

The Chianti Valley

Nestled amid the rolling hills and lush greenery of the Chianti countryside, this villa offers a tranquil escape to rural Italy. The stone house is as traditional as can be, with terracotta floors, wood-beamed ceilings, and arched doorways. Outside, you’ll find two terraces boasting wonderful views stretching over the valley to the nearby towns of Panzano and Radda – both great options for day trips. There’s also a swimming pool. Rustic and charming, this villa is an oasis in Chianti. *Access to this home is via an unpaved road – we recommend hiring a high-clearance vehicle. There’s free parking here. *The swimming pool is open from May to September. The homeowner and their family may use the pool when you’re not using it. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. A...

House • 8

• 4

• 2,368 ft2 •

€

12,144 EUR /Month

Term: Monthly

House in Siena, Italy

€12,144 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Charming Countryside Villa

This Tuscan villa is perfect for large groups. With a main house and separate annex rented as one home, each with its own living area, kitchen/dining area, and bathrooms, you can holiday together while still enjoying your own space. While the traditional decor may not be to everyone’s tastes, we’re sure everyone will appreciate the outdoor space – with spectacular views across the Tuscan countryside, a private pool, and alfresco dining, what's not to like? Location-wise, you’re 9 kilometres from Casciano di Murlo for shops and restaurants, 6 kilometres from the natural hot springs of Terme di Petriolo where you can enjoy a soak, and 30 kilometres from historic Siena. *This home comprises a main villa sleeping 11 and an annex sleeping four, rented as one property. Both buildings have their own living area, kitchen/dining area, and bathrooms. *While not all of the bedrooms and bathrooms are photographed, expect the style and quali...

House • 3

• 2

• 1,722 ft2 •

€

7,608 EUR /Month

Term: Monthly

House in Siena, Italy

€7,608 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Views

Set on a Chianti hillside, this home promises a serene retreat away from the hustle and bustle of everyday life. Sun worshipers will adore the private terrace, and there’s also a communal infinity pool here, perfect for when you need to cool off in the heat of the day. When you’re ready to explore, you’ll find the local villages of Lecchi and San Sano nearby. Alternatively, take to the Dievole Natural Path – twenty-seven kilometres of trails that lead to the Dievole wine-tasting cellar and open terraced restaurant. *This home is set on a resort alongside neighbouring homes. Expect to bump into other guests during your stay. *There's no air conditioning available here. It could get a little hot during the summer. *There's a communal swimming pool here, open between May and September. The pool isn't fenced, so children must be supervised at all times. *Due to this home's location, we recommend hiring a car to get the most o...

House • 4

• 4

• 1,399 ft2 •

€

10,608 EUR /Month

Term: Monthly

House in Siena, Italy

€10,608 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Sunflower Sunset

In the heart of the Val d'Orcia, this villa offers sweeping views as far as the eye can see. Montepulciano, San Quirico d'Orcia, and Seina further afield are all within driving distance – and all make great options for days out and about in the countryside. But even better than the location is the garden waiting for you back home. There's an ivy-covered pergola ideal for alfresco dining, a private pool overlooking the vineyards, and swings to keep little ones entertained. Inside, modern comforts blend with traditional character. Every bedroom has an en-suite bathroom, making this ideal for families or friends. *This villa is semi-detached. Local residents live next door, but the pool and garden are private. *One bedroom and bathroom are on the ground floor. The other bedrooms and bathrooms, as well as the living area and kitchen, are on the first floor. The rest of the ground level is not accessible to guests. *If you're trav...

House • 3

• 3

• 1,292 ft2 •

€

7,896 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€7,896 EUR /Month
• Term: Monthly (Furnished)

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 i...

House • 5

• 5

• 5,489 ft2 •

€

82,782 EUR /Month

Term: Monthly

House in Siena, Italy

€82,782 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Dream of Beauty

From its privileged spot in the heart of Crete Senesi, this home opens its doors to classic Tuscan views and timeless Italian charm. Nestled within two acres of private land, you'll find the main house consists of two floors, while the independent annexe has a bedroom and private living area with a mini-fridge. You can also enjoy access to a salt-water pool, Jacuzzi and gym along with a range of personal touches – including private-labelled house wine and a concierge service. From here, leisurely days can be spent in the sweeping gardens or out exploring the region – the historic streets of Siena are just 12 kilometres away, while Montalcino is a twenty-minute drive. *Please note the fifth bedroom is located in the independent annexe which has its own entrance and living area with a mini-fridge. *Daily housekeeping and complimentary toiletries are included in your stay. *It is possible for the twin beds to be arranged as ...

House • 4

• 3

• 4,300 ft2 •

€

42,189 EUR /Month

Term: Monthly

House in Siena, Italy

€42,189 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Vine Song

Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding. The interiors have preserved the grace of earlier ages while adding the essential modern cons and amenities. Exposed wood beam ceilings, tiled floors covered with vibrant carpets, and gorgeous vintage furniture make you feel at home, yet so far away from the current era. The master bedroom comes with a four-poster bed, and overall, all sleeping quarters exude a pampering feel accentuated by the gorgeous period furniture. We love the huge dining room, the walls of which are lined with well-stocked bookshelves. After a hearty meal, grab a book, amble outside to the sundeck and lose yourself in another world. When the warmth overwhelms you, take a cooling dip in the massive pool. In the eveni...

House • 3

• 2

• 1,238 ft2 •

€

7,320 EUR /Month

Term: Monthly

House in Siena, Italy

€7,320 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Tuscan Meadows

This traditional home is nestled among the Tuscan hills. You’ll have a private alfresco dining area here, as well as being able to enjoy a swimming pool, garden bar, children’s playground, and outdoor dining area with other guests. Your host can even arrange a private chef to rustle up a feast, or a pizza night in the communal dining spot. The home’s traditional decor won’t appeal to everyone, but we love the views from here, and the on-site garden bar is something you won’t find in many places. Location-wise, you’re 5 kilometres from Berignone Nature Reserve, with its glorious walks and wild swimming, and a short drive from picturesque Casole d'Elsa, where you can stock up on local produce. *The swimming pool, outdoor dining area, children's playground, and garden bar here are shared with other guests. The pool is available for use from May to September. *If you're travelling with little ones, your host can provide a free cot ...

House • 7

• 6

• 2,906 ft2 •

€

20,880 EUR /Month

Term: Monthly

House in Siena, Italy

€20,880 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sun of Splendour

If you’re in search of a traditional Italian stay in a beautiful location, this home delivers a great solution. Nestled in a private garden overlooking the Chianti countryside, you’ll be welcomed by stunning views and a private pool with a Jacuzzi. The main house consists of three independent apartments (each with its own kitchen), while an additional annexe provides a cosy space for two guests. It’s worth noting some of the furnishings and decor are a little dated, but you will find plenty of character. Plus, you can explore some of Tuscany’s most beautiful sights. From here, it’s just a thirty-minute drive to Siena, while San Gimignano and Monteriggioni are also within driving distance. *Please note the main house consists of three independent apartments that are not internally connected. There is also an independent annexe with a double room, bathroom and kitchen. *The traditional decor here might not be to everyone's taste....

House • 4

• 4

• 2,260 ft2 •

€

17,304 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€17,304 EUR /Month
• Term: Monthly (Furnished)

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...

House • 6

• 6

• 6,781 ft2 •

€

61,719 EUR /Month

Term: Monthly

House in Siena, Italy

€61,719 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Golden Tuscan Sun

Traditional charm, stunning views and a private swimming pool – this home has everything you could need for a blissful Italian escape. There are two outdoor seating areas, a barbecue and a pizza oven for delicious evening meals. Inside, the rooms are filled with art along with a range of home comforts to ensure optimum relaxation. Exercise enthusiasts will also appreciate the home gym. Daily housekeeping is included in your stay and your host can help organise a range of extra services – including private chefs and wine tastings. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Sarteano, while Montepulciano, Montalcino and Chianciano Terme are all within easy driving distance. *Housekeeping is included for four hours per day. *Please note this home is set across two floors with stairs. It is also possible for the bedrooms to be arranged with two single beds or as a double on request...

House • 1

• 2

• 753 ft2 •

€

6,144 EUR /Month

Term: Monthly

House in Siena, Italy

€6,144 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Tuscan Couplet

We think this cosy little home is the perfect couple's retreat. Step inside and you'll discover rustic details like stone archways, beamed ceilings, and an open fireplace. Outside, the terrace makes a scenic spot to enjoy an alfresco dinner – your host can organise a private chef for a fee. The cherry on top is the private pool, where you can cool off as the sun goes down. With its convenient location near Florence and Siena, this home is the ideal base for exploring the region's rich history, culture, and culinary scene. *There's a double sofa bed here that may be available on request – please speak to your host for more information. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *The pool is only available to use between 1st June and 21st September. *You’ll need a car i...

House • 1

• 1

• 700 ft2 •

€

5,640 EUR /Month

Term: Monthly

House in Siena, Italy

€5,640 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Hillside Sanctuary

Housed in a restored stone barn, this cottage places you in the heart of Chianti with views of rolling fields, vineyards and valleys as far as the eye can see. The home benefits from a beautifully elevated position, so you can soak up the rural setting from the private outside pool, garden and lovely dining area. On top of that, the kitchen and bedroom both have direct access to the garden and patio. Inside, the home is traditional so the interiors are rustic – which might not be to everyone's taste. Beyond that, you'll need a car to explore the region, however, the market town of Gaiole is just a short drive away, with Siena and Florence well within reach. *Due to this home's location, you'll need a car to get the most out of your stay. There’s free on-site parking but be prepared for an uneven drive at times. *The swimming pool is only available for use from mid-April to mid-October. The pool isn't fenced so children will nee...

House • 11

• 11

• 10,764 ft2 •

€

81,228 EUR /Month

Term: Monthly

House in Siena, Italy

€81,228 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Classico Chianti

This hilltop villa offers panoramas from Monte Amiata to Siena and boasts sweeping vineyard views – what more would you wish from a stay in the Chianti region? Licensed for weddings, it's a magical setting for special occasions – just ask your host for details. The interiors lean traditional, perfect for those who appreciate classic Tuscan charm. That said, you’ll likely want to spend most of your time outdoors – taking dips in the pool, sipping wine on one of the terraces and gathering for alfresco meals – your host can arrange private chefs, too. And with castles, medieval villages, vineyards and thermal spa towns within easy driving distance, you’ll be spoilt for choice here. *This home is spread across a main house and a converted barn. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms have the option to convert the double beds into two singles upon request...

House • 1

• 1

• 700 ft2 •

€

4,104 EUR /Month

Term: Monthly

House in Siena, Italy

€4,104 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Blush

This cottage overlooks Chianti's vine-covered hills, providing an idyllic background for a romantic Tuscan stay. We love the private terrace – there's no better spot to savour a glass of locally-made wine and soak up the views. Inside, the design is equal parts modern and rustic. The cherry on top is the private hot tub, though you'll also have access to a communal swimming pool shared with the resort's other guests. Keen to get out and explore? Lecchi is less than a 2-kilometre walk through the countryside, while the medieval town of Radda is only a fifteen-minute drive away. *This home is set on a resort with other holiday homes. While you’ll likely bump into other guests during your stay, the patio and hot tub are private. *There's a car park here, but much of the resort is car-free, so you'll need to be able to climb steps to the cottage. It might not be the best option for those with reduced mobility. *You’ll have access...

Castellina in Chianti House for rent

House • 5

• 4

• 4,844 ft2 •

€

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 • 2

• 2

• 1,023 ft2 •

€

9,120 EUR /Month

Term: Monthly

House in Siena, Italy

€9,120 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Landscape Artist

In years gone by, this building in the countryside surrounding Siena was a farmhouse. Today, however, those paying a visit to the address will find a really rather dreamy Tuscan getaway. We're willing to wager the first things that guests notice upon arrival is the invitingly blue swimming pool that sits in the middle of the garden, which in turn, is surrounded by beautiful views of Val d'Orcia — a UNESCO World Heritage Site, no less. The panorama is no less spectacular from underneath the home's shady verandah, either. Inside, there are traditional aspects, like the wooden ceiling beams and terracotta tiling underfoot, but the white walls and furnishings add a contemporary flourish, too. It must be said that the kitchen is modest in size, but there's also a barbecue in case you fancy cooking alfresco. There is a recently added sauna, minipool and chromotherapy hot tub for those looking to fully relax. If yo...

House • 3

• 2

• 1,938 ft2 •

€

11,544 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€11,544 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Tuscan Vine

In the heart of Chianti Classico, this charming old stone villa offers a haven for wine enthusiasts. Surrounded by vineyards producing world-renowned wines, you can easily explore local wineries and historic towns like Radda. If you’re not sampling the local grapes, back home, you’ll find everything needed for a comfortable stay. Granted, there’s no air conditioning here, but with sun-dappled terraces, panoramic views and a private pool, you’re sure to be drawn outdoors anyway. Locally, a trip to Radda is a must, reached easily in under ten minutes in the car. *There's no air conditioning here. It could get a little hot during the summer. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May until September, isn't fenced. Children will need to be supervised at all times. *The twin bedroom can be set up as a double upon request. *We...

House • 7

• 5

•

€

50,169 EUR /Month

Term: Monthly

House in Siena, Italy

€50,169 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Super Tuscan

Whether you're swimming laps in the pool, lounging in bed or sipping a sundowner in the garden, this country home serves up breathtaking views from almost every angle. Surrounded by olive groves, world-famous vineyards and just a short drive from Siena, it’s a picture-perfect base for exploring the Chianti region. Inside, it’s packed with character — grand but with a touch of eccentricity, from exposed beams and stone staircases to chandeliers and canary-coloured walls. Did we mention it comes with staff, including a chef? After a hard day of wine tasting, nothing beats coming home to find dinner ready and waiting. *While not all of the bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *This home comes with its own private chef and team of staff who can help with anything you might need while always respecting your privacy. *The swimming pool isn't fenced. If you...