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

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 • 5

• 4

• 3,229 ft2 • pets

€

19,530 EUR /Month

Term: Monthly

House in Siena, Italy

€19,530 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Jewel

Nestled in the heart of Chianti Classico, this home is an oasis of peace and natural beauty. Surrounded by vineyards, oak trees, and holm oaks, it offers a true Tuscan experience and is an ideal base for anyone looking to get away from it all. Consisting of the main villa and a separate annexe, it gives one couple that extra bit of privacy. Outdoors, you can dine alfresco, kick back with a good book on the sunny terrace, or swim in the private pool. Keen to explore the region? Book a vineyard experience – a must while in the area – or take a day trip to explore the nearby cities of Siena, Florence, or Arezzo. *This home comprises the main villa, sleeping eight, and a separate annexe, sleeping two. *The first-floor bedroom in the villa is accessed via a steep staircase which leads directly into the room with no door. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to re...

House • 9

• 10

• 5,382 ft2 • pets

€

39,081 EUR /Month

Term: Monthly

House in Siena, Italy

€39,081 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Lavender - Jasmine

Tucked away amid gentle hills in the picturesque Val d’Orcia, this home is perfect for large groups. The traditional Tuscan villa and its annex have been elegantly restored, blending rustic charm with modern amenities like a professional kitchen. The jasmine-, rosemary-, and lavender-filled garden features two private swimming pools and a furnished terrace with a pergola – perfect for alfresco dining – overlooking Montalcino. Siena is just a thirty-minute drive away, and you can reach the lively borgo of Buonconvento in no time. Beautiful and peaceful, this home offers a stay to remember. *Your host can provide a cot and high chair for little ones. *The swimming pools are open from the last Saturday in April until the first Saturday in October. *This home is split between two buildings so you won’t all be sleeping under the same roof. *The fireplace is ornamental. *There are stairs to climb at this home so it may not...

House • 4

• 2

• 3,229 ft2 • pets

€

20,664 EUR /Month

Term: Monthly

House in Siena, Italy

€20,664 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Love in Tuscany

Once an old stone barn, this villa has been brought back to life and promises a serene stay in the heart of Tuscany. Sure, the traditional interiors may not be everyone’s cup of tea, but you’ll find all the key ingredients for a comfortable stay here. We love the outdoor space, with sun-kissed terraces, a private pool, and far-reaching views across the hills – what more could you want? Location-wise, San Gimignano is a mere stone’s throw away. A visit to this historic town, with its iconic towers, is a must. *There are steps leading up to the front door here and further steps down to the pool area. It might not be the best option for those with reduced mobility. *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 from the last Saturday in April to the first Saturday in October, isn't fenced. If you're bringing children, t...

House • 4

• 4

• 4,306 ft2 • pets

€

20,076 EUR /Month

Term: Monthly

House in Siena, Italy

€20,076 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Elsa's Outlook

Nestled in the heart of Tuscany, this villa offers breathtaking views of the Val d'Elsa. A former barn dating back to 1620, expect to find plenty of character touches inside – we're talking 5-metre high ceilings, wooden beams, and even fossil shells contained in the external walls. Outside, the panoramic terrace is perfect for alfresco wining and dining. There's also a heated pool, where you can float the afternoon away and admire the scenery. Explore nearby medieval towns like San Gimignano, indulge in local delicacies with private chefs and cooking classes – your host can arrange them for a fee – and create unforgettable memories in this Tuscan paradise. *Not all the bedrooms and bathrooms are photographed but expect consistency in quality and style. *Upon request, two single bedrooms in the basement can be available instead of the fourth double bedroom. Your host can also provide a free cot and high chair. *This villa has ...

House • 6

• 6

• 3,229 ft2 •

€

52,857 EUR /Month

Term: Monthly

House in Siena, Italy

€52,857 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Flower

Immersed in the natural serenity of the Chianti countryside, this home sets the tone for an idyllic Italian escape. From its hillside position, you can enjoy incredible views across the valley. There’s a saltwater swimming pool for refreshing swims, a peaceful garden and a covered terrace with a barbecue for alfresco dining. Inside, you’ll be welcomed by a rich sense of history, charm and plenty of character. Your host is on hand to help organise a range of sweet extras – including grocery deliveries, private chefs and organised excursions. Plus, it’s possible to drive to Siena and Arezzo, while the nearest amenities are in San Gusmè – just 4 kilometres away. *Please note the caretakers live in a private apartment within the house. *This home is set across two floors with stairs. *It is possible for two of the rooms with double beds to be arranged with two singles on request. *If you're travelling with little ones, your...

House • 2

• 1

• 915 ft2 •

€

4,872 EUR /Month

Term: Monthly

House in Siena, Italy

€4,872 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Farmhouse Fair

This charming apartment is on the ground floor of a renovated farmhouse in the Italian countryside. It’s surrounded by vast gardens with a shared swimming pool, and you’ll have private outside space too – what’s better than dining alfresco on holiday? Enjoy views of the surrounding hills while you cook on the barbecue or whip up pasta dishes in the well-equipped kitchen. This comfortable home is ideal for a family seeking a restful escape in a rural setting. You’ll be close to San Gimignano and Siena, giving you great options for day-trips. *The swimming pool is shared with the other residents. It’s open from 1st May to 30th September. *There’s free parking at this home. *Your host can provide a cot for little ones. *The laundry facilities are shared here. Barbeque Carbon Monoxide Detector Central Heating Child Friendly Coffee Maker Cot / Crib Fenced Property Fire Extinguisher Free Parkin...

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 • 9

• 9

•

€

101,304 EUR /Month

Term: Monthly

House in Siena, Italy

€101,304 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Being of Beauty

Experience the beauty of Chianti with a stay in this luxurious Tuscan retreat. Owned by a family for more than a hundred years, now you’re invited to step inside and make your own special memories. From the private woodland and wildflower meadows to the outdoor swimming pool, you’ll find everything you could need to settle in and unwind. A member of the royal family designed the rooms and we don’t think you’ll be disappointed. Plus, your host is on hand to help organise a range of extras – including a private chef and wine tasting. And for explorations further afield, it’s just a short drive to Siena and Florence. *Please note this home can accommodate up to eighteen guests and four staff. *Your host provides a starter supply of toiletries. *If you’re travelling with children, your host can provide a cot and a high chair for free on request. *Well behaved pets are welcome to join you here. Air Conditioning<...

House • 5

• 5

• 4,306 ft2 •

€

29,463 EUR /Month

Term: Monthly

House in Siena, Italy

€29,463 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Tuscan Roses

Located amidst the rolling hills and vineyards of Chianti, this Tuscan oasis makes for a serene retreat. There is plenty of space inside for the whole brood to spread out, thanks to an array of lounges and cosy bedrooms. Sure, the design is traditional, but extras like the welcome hamper and bottle of local wine make it easy to settle in. Out in the landscaped garden, you can splash in the private pool or find a spot to enjoy an alfresco aperitif. Your host can also arrange top-notch services to elevate your stay, from daily housekeeping to guided tours and cooking lessons. *If you're travelling with little ones, your host can provide a cot and high chair upon request. *Daily housekeeping is included with your stay for a maximum of three hours per day. Linen changes will take place every three to four days. *We suggest hiring a car in this location, as it's the easiest way to explore. Private parking is available. *This vi...

House • 8

• 7

• 5,381 ft2 •

€

21,084 EUR /Month

Term: Monthly

House in Siena, Italy

€21,084 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Panorama

Nestled in the rolling hills of Montepulciano, this villa ticks all the right boxes for a heavenly Tuscan holiday. With seven bedrooms set over the main house and a neighbouring annexe, there’s space for all your favourite people to stay, alongside seven bathrooms to make mornings much easier. Outside, the stunning pool is the centrepiece of the lush grounds, which feel peaceful and secluded despite being only a short drive from town. Just bring a good book and good company and you’ll have all you need for an idyllic Italian break. *The accommodation is spread across the main house and a neighbouring annexe. *One of the bedrooms is on the mezzanine level and semi-open to the space below, so privacy is limited. *If you're travelling with little ones, your host can provide two cost and two high chairs for free. You'll need to request them in advance. *The swimming pool is available from 1st May to 30th September. *The swi...

House • 2

• 2

• 1,184 ft2 •

€

5,328 EUR /Month

Term: Monthly

House in Siena, Italy

€5,328 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Countryside Cuore

This charming apartment is surrounded by rolling green countryside. It’s just five minutes from the historic centre of Radicondoli, a lively village, and within easy reach of the coast, Siena, and San Gimignano. Staying in this apartment, you’ll have access to the vast grounds and shared swimming pool, as well as a private outside space. This furnished terrace leads from the living room of this delightful, traditional home – you can look forward to beamed ceilings and antique-style art and furniture. *The swimming pool is shared with the property’s other residents. The pool is open from 1st May-1st October. *This apartment is on the first floor of a building with no lift so it may not be suitable for those with reduced mobility. *There’s free parking at this home. *There are mosquito nets in the bedrooms and in the main French window. *Your host can provide a cot for little ones. Air Conditioning Balcony<...

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 • 7

• 5

• 2,982 ft2 •

€

15,528 EUR /Month

Term: Monthly

House in Siena, Italy

€15,528 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

WiFi

Tuscan Cypresses

Nestled amid the rolling hills and vineyards of Tuscany, this beautiful home is a tranquil escape perfect for families and groups of friends. It’s spread between a cottage and three apartments, so couples and small groups can enjoy their privacy – when they’re not dining together outside or admiring the views from the private pool. This home perfectly blends modern furniture and comforts with traditional Tuscan features like terracotta floors and old hearths. From here, you can easily visit Siena, Florence, Radda, and Gaiole. The Chianti Sculpture Park is also close by. *The swimming pool is available from May to October. *There’s parking for four cars here, with one covered space and three uncovered. Access to the villa is via an unpaved road. *This home comprises three apartments and a cottage so you won’t all be sleeping under the same roof. *Four of the bedrooms can be set up as twins or doubles Barbeque Bathtu...

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 • 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 • 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

• 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. ...

House • 3

• 5

• 2,045 ft2 •

€

14,472 EUR /Month

Term: Monthly

House in Siena, Italy

€14,472 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Sangiovesece Scenery

In the Chianti hills, this villa offers vineyard views and easy access to the region's many wineries and picturesque towns. We love the garden – it's where we reckon you'll spend most of your time. There's a private pool, an alfresco dining terrace, and a pool house with a gym that fitness buffs will appreciate. Indoors, the antique furniture and traditional features may feel a bit dated, yet they're all part of its charm. As for location, you'll find Gaiole, Radda, and Castellina a short drive away, making it an ideal base for Tuscan adventures. *One of the double beds can be converted into two singles upon request. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *A separate pool house has a kitchen, living area, bathroom, and gym. *The swimming pool is available to use between May and September. *We suggest hiring a car in this area. Parking is available on the gro...

House • 14

• 13

• 12,056 ft2 •

€

79,968 EUR /Month

Term: Monthly

House in Siena, Italy

€79,968 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti - Vines

Perched on a Chianti hillside, this expansive estate comprises the main villa and two beautifully restored barns – an ideal setting for large groups, retreats or unforgettable celebrations. From the terraces, you’ll enjoy views that stretch from Monte Amiata to Siena, with vineyards unfolding in every direction. Traditional Tuscan through and through, the interiors might not suit modernists, but for those drawn to character and heritage, it’s a dream. Outside, you’ll find a pool, alfresco dining areas and plenty of quiet corners for aperitivos. Your host can arrange everything from private chefs to wine tastings, too. Plus, with medieval hamlets, castles and thermal spas just a short drive away, there’s no shortage of ways to explore the region. *This home is spread across a main house and two converted barns. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms h...

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 • 2

• 2

• 969 ft2 •

€

15,840 EUR /Month

Term: Monthly

House in Siena, Italy

€15,840 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

The Chianti Grape

If you’re looking for an escape from it all, this could be the home for you. Set on a private road deep in the woods, this Chianti villa has tranquillity running through its core. We love the seamless blend of modern furniture with the traditional building here, but the outdoor space is our biggest winner. Sun-kissed terraces, a hot tub, a private pool, alfresco dining areas – what’s not to love? If you can tear yourself away, it’s a mere ten-minute drive to the wine-making town of Gaiole, which is well worth a visit. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool isn't fenced and there are open-sided stairs here. If you're bringing children, they'll need to be supervised at all times. *The second bedroom is on the mezzanine level and semi-open to the space below, so privacy is limited. *Due to this home's location, we recommend hiring a car to get ...

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 • 5

• 5

• 2,949 ft2 •

€

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

• 2,153 ft2 •

€

19,800 EUR /Month

Term: Monthly

House in Siena, Italy

€19,800 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Air Conditioning

WiFi

Chianti Hilltop

This beautiful, traditional villa sits in the Chianti countryside between the wine towns of Radda and Gaiole in Chianti. It’s a splendid spot, whether you plan on exploring the local vineyards or just want to laze beside the private pool and admire the view – you can look forward to a 180-degree panorama of the countryside and a nearby hilltop town. The villa is charming and cosy, with authentic terracotta tiles and beamed ceilings. The terrace is perfect for alfresco dining. *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. Air Conditioning Barbeque Bathtub Beach / Pool Towels Child Friendly Coffee Maker Cot / Crib Dishwasher Fan Fenced Property Fireplace Freezer Fridge Garden Hair Dryer High Chair Kitchen Kitchen U...

House • 9

• 9

• 8,611 ft2 •

€

64,113 EUR /Month

Term: Monthly

House in Siena, Italy

€64,113 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Winery Way

This beautiful home is perfect for celebrations and special occasions. The hilltop villa boasts panoramic views from Monte Amiata to Siena in the lap of Val d’Orcia, a UNESCO World Heritage Site. The restored stone property is a winery licensed for events, and with its terracotta floors, vaulted ceilings, and antiques, it’s bound to impress. There are multiple living areas and a professional kitchen, as well as a garden with stunning vistas and a gorgeous alfresco dining space. Whether you’re staying here for an event or just want an elegant home-from-home in Italy, this villa is sure to make for a memorable stay. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms are suitable for those with reduced mobility. *Bedroom eight can be set up with twin beds or a double Air Conditioning Barbeque Bathtub Beach / Pool Towels Child Friendly Coffee Mak...

House • 2

• 2

• 861 ft2 •

€

6,192 EUR /Month

Term: Monthly

House in Siena, Italy

€6,192 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Vines - Serenity

Wrapped in vineyards and olive groves, this cosy villa in the heart of the Chianti countryside promises a serene escape from daily life. It’s not the biggest inside, but it’s more than comfortable for a family, and with the Tuscan sun shining, everyone will naturally be drawn to the outdoor space. We love the private pool and choice of sunny and shaded spots to relax, all whilst soaking up the far-reaching views. Location-wise, hop in the car and you can reach Lecchi in three minutes or Radda in ten. Peppered with restaurants, they’re both perfect options when you crave authentic Italian cuisine. *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 to September, can be fenced upon request. Speak to your host for more details. *The twin bedroom can be set up as a double upon request. You'll need to let your host know at the time of booking. ...

House • 2

• 2

• 700 ft2 •

€

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 • 4

• 3

• 1,938 ft2 •

€

13,128 EUR /Month

Term: Monthly

House in Siena, Italy

€13,128 EUR /Month
• Term: Monthly (Furnished)

Swimming Pool

WiFi

Roses of Chianti

With incredible views across the Tuscan countryside, this home sets the tone for a magical Italian getaway. Nestled in the heart of Chianti, you’ll be welcomed by the sweet sounds of nature, a private swimming pool and a serene terrace for sunset drinks and alfresco dining. Inside, the rooms are traditional and family friendly with plenty of space to stretch out across the three floors. Your host is on hand to help organise extras like private chefs and guided tours. Plus, it’s just a short drive to Gaiole in Chianti where you’ll find the nearest restaurants, bars and shops. *Please note the owners live in an apartment at the rear side of the villa with their dog. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Please note the swimming pool is available for use from May to October. *Well behaved dogs are welcome to join you here, but please note they need to be kept on...

House • 3

• 3

• 1,938 ft2 •

€

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...