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

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 • 8

• 4

• 2,368 ft2 • pets

€

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

• 1,507 ft2 • pool

€

11,640 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€11,640 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Vineyard Sunset

Nestled in the Tuscan countryside with a private pool, serene outdoor space and views across Chianti’s vineyard-laced hills – what’s not to love about this home? Comfortable for a family or group of friends, inside, you’ll find a seamless blend of traditional and modern. And, when you fancy a spot of sightseeing or some authentic Italian cuisine, you can walk to the hilltop town of Radda, just two minutes away, or for jaunts further afield, hop in the car for a day trip to Florence or Siena. *There's no air conditioning here, but fans are provided for guests' comfort. *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 mid-October, isn't fenced. Children will need to be supervised at all times. *There are steps to access this home. It may not be the best option for those with reduced mobility. *We recommend hiring a car to get t...

House • 3

• 2

• 1,938 ft2 • pool

€

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 • 3

• 3

• 1,938 ft2 • pool

€

11,424 EUR /Month

Term: Monthly

House in Siena, Italy

€11,424 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Splendour

With far-reaching views of the rolling Chianti hills, it’s impossible not to relax in this villa. Traditional yet modern, this home promises a true taste of Tuscany, alongside plenty of space to relax. We love the three tiered terraces, each offering something different – alfresco dining on the top terrace, bowls on the middle, and a private pool on the lower. And, being situated next to a working winery, you’re perfectly placed for a spot of wine tasting and some authentic Tuscan food – all of which can be organised by your host. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The twin bedroom can be set up as a double upon request. *There are stairs to climb here, including in the outdoor space to access different terraces. It may not be the best option for those with reduced mobility. *We recommend hiring a car to get the most out of your stay – on-site parking is...

House • 3

• 3

• 1,076 ft2 •

€

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 • 1

• 1

• 495 ft2 •

€

10,704 EUR /Month

Term: Monthly

House in Radda in Chianti, Italy

€10,704 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Cottage

This beautifully restored and furnished Tuscan home is the true epitome of an Italian cottage done right. Right in the heart of the Chianti countryside, with the iconically distinctive cypress trees all around, this is the perfect haven for honeymooners looking for a romantic getaway or a solo tripper after a comfortable home close to Florence. The private pool is perfect for a refreshing dip, while the shaded dining areas invite you to savour leisurely meals alfresco. With its blend of traditional features and elegant touches, this home provides a romantic and restful escape. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There is private onsite parking available. Please be aware that the approach road is unpaved and uneven, so a high clearance vehicle is recommended. *This home has two storeys, so it may not be suitable for those with reduced mobility. *The pool is only available f...

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

• 4

• 1,615 ft2 •

€

10,536 EUR /Month

Term: Monthly

House in Siena, Italy

€10,536 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Memories

This rustic stone villa is located just a short stroll from the historic centre of Gaiole, surrounded by world-class vineyards and sun-drenched olive groves. The traditional building has been thoughtfully restored and now boasts contemporary decor alongside many of its original features. And outside you’ll find plenty of serene spots to soak up the countryside views, from a private pool to an alfresco dining terrace. Because of the layout of this home and garden, we think it’s best suited to groups of friends or families with older children. *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 swimming pool is only available for use between May and September. The pool isn't fenced so children will need to be supervised at all times. *While babies and children are welcome, this home isn't recommended for toddlers. *While the owner lives in...

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 • 4

• 3

• 1,722 ft2 •

€

10,392 EUR /Month

Term: Monthly

House in Siena, Italy

€10,392 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Beyond the Vines

Basking in the Tuscan countryside, this home promises an escape from the daily routine. Sure, some of the bedrooms are a little bit of a squeeze, and the kitchen isn’t the biggest, but the home offers everything needed for a restful stay. Besides, with rolling countryside vistas and a private pool to cool off in, much of your time will be spent outdoors. Perfectly placed to explore the local areas by car, we’d recommend a trip to Pienza, just fifteen minutes away, to sample their famous Pecorino cheese. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There's private parking available here. *As there is no air conditioning available here, it could get a little hot during the summer. *If you're travelling with little ones, your host can provide a cot for free. You'll need to request it in advance. *The swimming pool, open between 1st June and 30th September, isn't fenced. If you'r...

Castellina in Chianti House for rent

House • 4

• 3

• 2,239 ft2 •

€

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 • 4

• 2

• 1,507 ft2 •

€

10,224 EUR /Month

Term: Monthly

House in Siena, Italy

€10,224 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Ivy - Olive

Calling all wine connoisseurs – this villa puts Chianti's vineyards at your fingertips. Whether you're touring local wineries or day-tripping to the towns of Radda and Siena, this is a picture-perfect base for a Tuscan getaway. Back home, spend your afternoons lazing by the pool, nibbling on pizza cooked in the built-in barbecue, and playing rounds of outdoor ping-pong. Inside or out, there's no shortage of space to relax. The interiors are a tad dated, but we think that's all part of the charm. *The twin beds can be converted into doubles if needed. You'll need to request this when booking. *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 get in touch with your host for the exact dates. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *You’ll need ...

House • 3

• 3

• 1,292 ft2 •

€

10,032 EUR /Month

Term: Monthly

House in Siena, Italy

€10,032 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Terracotta - Vine

Tucked away in the Tuscan countryside, this villa is just the spot to switch off and relax. We love the seamless blend of traditional and modern and the opportunity to find space for socialising or solitude. The outdoor space is sure to be a firm favourite – with a private pool, sun-kissed terraces, ample opportunity for alfresco dining and far-reaching views, it’s not hard to see why this home caught our eye. When you’re ready to explore, the local village of San Sano has a restaurant and small grocery store, or you can hop in the car for a trip to Siena. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from June until September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *Two of the bedrooms can be set up as doubles or twins upon request. *We recommend hiring a car to get the most out of your stay. ...

Castellina in Chianti House for rent

House • 3

• 2

• 1,830 ft2 •

€

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

• 2

• 1,615 ft2 •

€

9,288 EUR /Month

Term: Monthly

House in Siena, Italy

€9,288 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Terracotta Daze

Swimming pool, sunny garden, and scenic views of the Tuscan countryside – what more could you ask for? There are two separate apartments in this villa, each with a living room and kitchen, so it is an ideal choice for two families travelling together or a group looking for separate yet social spaces. The interiors feature vaulted wooden ceilings, while the garden has a barbecue, ping pong table, and a terrace where you can make the most of the sunshine. A small fitness room is equipped for workouts. Location-wise, this is a great spot for day trips. Volterra, Siena, and even Florence are all easily reached by car. *This villa consists of two apartments. Each apartment has an open-plan living area with a kitchen, two bedrooms, and one bathroom. *If you’re travelling with little ones, your host can provide a cot and high chair upon request. *The swimming pool is available to use between 15th May and 19th October. *We suggest...

House • 1

• 1

• 764 ft2 •

€

9,216 EUR /Month

Term: Monthly

House in Siena, Italy

€9,216 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sweet Tuscany

Tailor-made for two, this charming villa promises a tranquil escape in the Tuscan countryside. We love the character-packed interiors, where you’ll find everything needed to kick back and relax. But for us, the outdoor space is the real winner. Soak up the valley views, peppered with vineyards and olive groves, as you cool off in the private pool or dine alfresco under the warmth of the sun. When you’re ready to explore, you’re conveniently located between Radda and Lecchi. Personally, we’d head to Radda first to sample a bottle of its Chianti Classico. *The owners live in a separate villa above with dogs that are fenced in. They won't disturb you during your stay, but are on hand should you have any questions. *The swimming pool, available from May to October, isn't fenced. 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 h...

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 • 2

• 2

• 861 ft2 •

€

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-...

House • 3

• 2

• 969 ft2 •

€

8,064 EUR /Month

Term: Monthly

House in Siena, Italy

€8,064 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Artist's Cottage

In the heart of the Chianti hills, this cosy villa offers a tranquil escape. Its compact design belies surprisingly spacious rooms, while the wooden beams sprinkle character over the home. That said, it’s the outdoor space that caught our eye. A brief walk away, the secluded garden serves up panoramic vistas, sun-drenched terraces and a private pool. If you can tear yourself away, explore the nearby town of Gaiole, less than ten minutes away by car, or venture further to discover Siena, Florence, and San Gimignano. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from mid-April until mid-October, isn't fenced. Children will need to be supervised at all times. *The owners, who live in the hamlet, may occasionally use the pool when the pool area is unattended by guests. *There are steps to access this home and some of the bedrooms. It may not be t...

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 • 2

• 2

• 1,292 ft2 •

€

7,728 EUR /Month

Term: Monthly

House in Siena, Italy

€7,728 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Hillside Harvest

Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there's a private patio where you can enjoy an alfresco glass of wine. It's also got plenty of character inside – think arched doorways, terracotta floors, and beamed ceilings. Location-wise, you're just a quick car ride from Radda and Gaiole. Whether you're keen to visit the local wineries or venture further afield to Siena or Florence, this is a prime spot to explore the Chianti countryside. *Upon request, the double bed can convert into two singles, while the twin bedroom can convert into a double. *This home sits on a hilltop estate with other apartments and cottages. You'll share access to the grounds and swimming pool. However, the patio is private. *A car is necessary as the home is on top of a steep hill and walking to the near...

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 • 2

• 2

• 1,292 ft2 •

€

7,392 EUR /Month

Term: Monthly

House in Siena, Italy

€7,392 EUR /Month
• Term: Monthly (Furnished)

Pets Allowed

WiFi

Chianti Lake

Tucked away amid the picturesque Chianti Hills, this charming villa offers a peaceful escape. It’s on an agriturismo with five villas and direct access to a beautiful lake where you can swim and sunbathe. Vineyards, olive groves, and forest surround this home – dining alfresco on the patio gives you the chance to admire stunning views. The villa is a simple home-from-home, with an open-plan living and dining space at its heart. You can walk to Gaiole in Chianti and hop in the car to visit nearby castles and wineries – what more could you ask for? *There’s free parking at this home. We recommend hiring a high-clearance vehicle as access to this home is via an unpaved, uneven road. *Well-behaved pets are welcome to join you during your stay. *This home is within an estate with five villas and the owner’s home. There’s also a small restaurant and bar. *Access to the lake, which is shared with other residents, is via a steep ...

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 • 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 • 2

• 2

• 1,292 ft2 •

€

6,840 EUR /Month

Term: Monthly

House in Siena, Italy

€6,840 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Dream

Set in the picturesque village of San Sano, this home offers the best of both worlds – easy access to amenities and a quiet space to retreat to and relax. You won’t tire of the vineyard views here. Best enjoyed, we think, over a bottle of Chianti on the terrace or from the private pool. You’ll also find a lovely alfresco dining spot, though it’s a mere one-minute walk to the nearest restaurant, so eating out is sure to be on the menu. And when you’re keen to venture further afield, a trip to Siena is a must. *There's no air conditioning here, but fans are provided for guests' comfort. *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 swimming pool, open between May and September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *The single beds in the second bedroom can be set up as double on requ...

House • 2

• 2

• 1,076 ft2 •

€

6,816 EUR /Month

Term: Monthly

House in Siena, Italy

€6,816 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Toast to the Tuscan Sun

Wrapped in Tuscan countryside, this home is an ideal base for friends or a small family seeking a serene retreat to relax. Dine out under the sun on the private terrace, or head to the communal pool or tennis court for something a bit more active – the choice is yours. Within walking distance you’ll find the charming villages of Lecchi and San Sano, or for trips further afield, hop in the car – you can reach mediaeval Radda in a mere fifteen minutes. *This home is set on a resort alongside neighbouring homes. Expect to bump into other guests during your stay. *You'll have access to a swimming pool, open between April and October, a children's pool and a tennis court here. They're shared with the resort's other residents. *The swimming pools aren't fenced. Children will need to be supervised at all times. *There's no air conditioning here. It could get a little hot in the summer. *One well-behaved dog (up to 30kg) is ...

House • 2

• 2

• 969 ft2 •

€

6,792 EUR /Month

Term: Monthly

House in Siena, Italy

€6,792 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Tuscan Hills

Tucked away on the edge of San Regolo village, this is a perfect pad for two couples or a small family on an Italian stay. Sure, its traditional interiors may not be to everyone’s taste, but the outdoor space will be a popular spot with all. The private terrace is just the place for an alfresco family meal, while the communal pool promises some respite from the heat. Locally, we recommend a trip to Brolio Castle. This charming estate serves up a wine-tasting room, castle, and restaurant serving authentic Tuscan food – there’s something for everyone here. *This home is set on a hamlet alongside neighbouring homes. Expect to bump into other guests during your stay. *You'll have access to the on-site swimming pool here. It's shared with the hamlet's other residents. *The shared pool, open between May and October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling wit...

House • 1

• 1

• 700 ft2 •

€

6,624 EUR /Month

Term: Monthly

House in Siena, Italy

€6,624 EUR /Month
• Term: Monthly (Furnished)

Pets Allowed

Air Conditioning

WiFi

Crisp Chianti

Once a hay barn, now a romantic retreat for two, this villa has tranquillity running through its core. Set on an estate surrounded by vineyards that produce some of the region’s most prestigious wines, it’s not hard to relax here. We love the open-plan concept indoors, while outdoors, the hot tub is just the spot to soak up the sun as you watch the world go by. The heart of the estate is two-and-a-half kilometres away, where you can enjoy castle tours, wine tastings, a bar and a restaurant. Further afield, you’ll find Gaiole a short drive away when you’re ready to explore more of the surrounding area. *This home is set on an estate. Expect to see other guests and/or vineyard workers during your stay. *The hot tub is available for use between 1st May and 15th October. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Due to this home's location, we recommend hiring a ca...