House • 2 People • 1

• 2

•

From

€

106 /night

Min Stay 7 nights

Siena, Italy

€ 106 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Credit Cards Accepted

"Triangolo", 2-room semi-detached house 45 m2. Renovated in 2018, beautiful and rustic furnishings: living/dining room with dining table and wood-burning stove. Exit to the garden. 1 room with 1 french bed (160 cm), shower/bidet/WC. Exit to the garden. Kitchenette (mini-oven, 4 gas rings, toaster, kettle, freezer, electric coffee machine). Shower/WC. Gas heating. Comfortable furnishings in the country house style. Terrace, garden 150 m2. Terrace furniture. Beautiful view of the garden, the countryside and the forest. Facilities: children's high chair, baby cot. Internet (WiFi, free). Please note: non-smokers only. Maximum 1 small pet/ dog allowed. Outside Description: Montecagnano 12 km from Siena: Beautiful agricultural estate "Bellaria", 2 storeys, detached, surrounded by trees. 4 houses in the residence. 4 apartments in the residence. 12 km from the centre of Siena, 1.1 km from the centre of Montecagnano, outside the resort, 67 km ...More Details

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Siena, House for rent

House • 2 People • 1

• 1

•

From

€

131 /night

Min Stay 7 nights

Siena, Italy

€ 131 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Credit Cards Accepted

"Il Nespolo", 2-room house 50 m2, on the ground floor. Very beautiful and tasteful furnishings: living/dining room with open-hearth fireplace and dining table. Exit to the garden. 1 double bedroom. Kitchenette (oven, dishwasher, 4 gas rings, toaster, kettle, freezer, electric coffee machine). Shower/bidet/WC. Gas heating. Terrace, garden 150 m2. Terrace furniture. Beautiful view of the countryside and the forest. Facilities: children's high chair, baby cot. Internet (WiFi, free). Please note: non-smokers only. Maximum 1 small pet/ dog allowed. Outside Description: Montecagnano 12 km from Siena: Beautiful agricultural estate "Bellaria", 2 storeys, detached, surrounded by trees. 4 houses in the residence. 4 apartments in the residence. 12 km from the centre of Siena, 1.1 km from the centre of Montecagnano, outside the resort, 67 km from the centre of Firenze, in a secluded position, 92 km from the sea. For shared use: beautiful terraced...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

3,942 /night

Min Stay 1 night

Siena, Italy

€ 3,942 /Night (minimum stay 1 night)

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 a king-sized...More Details

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Siena, House for rent

House • 14 People • 7

• 6

•

From

€

1,108 /night

Min Stay 1 night

Siena, Italy

€ 1,108 /Night (minimum stay 1 night)

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 available for ...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

612 /night

Min Stay 1 night

Siena, Italy

€ 612 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Escape

Tucked away in the vineyard of a prestigious winery, this elegant cottage overlooks the beautiful Tuscan countryside. But not only are the views from the swimming pool and outdoor seating beautiful, but the house itself is also stylish. With only two bedrooms and a guest count of four, it has plenty of space. It would be especially suited to two couples or a small family. It's private and peaceful, located just a 4-minute drive from the historic center of Gaiole in Chianti. For day trips, Siena and Florence are under an hour away by car. *There’s free parking for one car on the driveway. *The swimming pool – available between 1st May and 30th September – isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *The fireplace is for decoration only. *If you want to stock up on essentials during your stay, you'll find the closest supermarket minutes away. Air Conditioning Balcony / Patio Barbeque Dis...More Details

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Siena, House for rent

House • 12 People • 6

• 7

•

From

€

1,377 /night

Min Stay 1 night

Siena, Italy

€ 1,377 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Peace in Tuscany

With idyllic views stretching across vineyards, olive groves and rows of cypresses, it’s not hard to see why this home caught our eye. Dating back to the 18th-century, the house has since been restored into a restorative retreat – one that will leave you feeling refreshed from the moment of arrival. Outside, you can soak in the natural beauty while swimming in the pool or relaxing in the shade. It’s worth noting that some of the furnishings are a little dated, but you will find plenty of rustic charm and family-friendly rooms. Housekeeping is available for an additional fee and children’s amenities can be arranged on request. And for adventures further afield, it’s just 4 kilometres to Montepulciano, while Cortona and Siena are also within driving distance. *There is free private parking for up to four cars here. *Please note this home is spread across three floors. One of the bedrooms and bathrooms is adapted for guests with reduced ...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

964 /night

Min Stay 1 night

Siena, Italy

€ 964 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Light

Anyone looking to experience the natural beauty of the Tuscan countryside will love this home. Nestled amid a sanctuary of oak trees, you’ll be welcomed by a wonderful sense of peace and privacy. There is also a swimming pool, a terrace with a barbecue and plenty of shaded spots to sit back and admire the views. Inside, the rooms are traditional, simple and full of rustic charm. Your host can arrange children’s amenities on request. Plus, one of the bedrooms is located in an adjoining annexe – making this a great option for large groups. You will need a car to get around here, but it’s just a 12-kilometre drive to Radicondoli and the nearest amenities, while San Gimignano and Siena are both within driving distance. *Please note this home consists of a main house with two floors and an adjoining annexe with one bedroom and bathroom. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There is also...More Details

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Siena, House for rent

House • 12 People • 6

• 7

•

From

€

1,735 /night

Min Stay 1 night

Siena, Italy

€ 1,735 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Land of Beauty

Surrounded by olive and cypress trees, this home perfectly embodies the timeless charm of Tuscan living. Dating back to the 15th-century, it began its life as a monastery, transitioned into a farm and now exists as the ideal setting for an immersive Italian escape. Inside, you’ll be welcomed by a wonderful sense of character along with plenty of space to stretch out and enjoy quality time together. There is also a games room, a fitness room and a wine cellar. Outside, you can stroll through the gardens, relax by the private pool and enjoy games of tennis on the private court. You will need a car to get around here, but it’s just 10 kilometres to Siena, while Florence and Arezzo are also within driving distance. *This home consists of a main house with three floors and an adjoining annexe with a laundry room, fitness room and wine cellar. *The tennis court can transform into a basketball court. Rackets are available to use. *Due to thi...More Details

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Siena, House for rent

House • 15 People • 8

• 4

•

From

€

506 /night

Min Stay 1 night

Siena, Italy

€ 506 /Night (minimum stay 1 night)

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 quality to ...More Details

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Siena, House for rent

House • 10 People • 5

• 4

•

From

€

930 /night

Min Stay 1 night

Siena, Italy

€ 930 /Night (minimum stay 1 night)

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 request the...More Details

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Siena, House for rent

House • 20 People • 9

• 10

•

From

€

1,861 /night

Min Stay 1 night

Siena, Italy

€ 1,861 /Night (minimum stay 1 night)

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 be suitable fo...More Details

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Siena, House for rent

House • 7 People • 4

• 2

•

From

€

861 /night

Min Stay 1 night

Siena, Italy

€ 861 /Night (minimum stay 1 night)

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, they'll ne...More Details

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Siena, House for rent

House • 8 People • 4

• 4

•

From

€

956 /night

Min Stay 1 night

Siena, Italy

€ 956 /Night (minimum stay 1 night)

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 three flo...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,517 /night

Min Stay 1 night

Siena, Italy

€ 2,517 /Night (minimum stay 1 night)

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 host can pr...More Details

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Siena, House for rent

House • 4 People • 2

• 1

•

From

€

203 /night

Min Stay 1 night

Siena, Italy

€ 203 /Night (minimum stay 1 night)

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 Parking Freezer Fridge Garden Kitchen Microwave ...More Details

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Siena, House for rent

House • 8 People • 4

• 2

•

From

€

387 /night

Min Stay 1 night

Siena, Italy

€ 387 /Night (minimum stay 1 night)

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 hiring a ca...More Details

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Siena, House for rent

House • 18 People • 9

• 9

•

From

€

4,824 /night

Min Stay 1 night

Siena, Italy

€ 4,824 /Night (minimum stay 1 night)

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 Balcony / Patio Barbe...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

1,403 /night

Min Stay 1 night

Siena, Italy

€ 1,403 /Night (minimum stay 1 night)

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 villa is set o...More Details

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Siena, House for rent

House • 16 People • 8

• 7

•

From

€

1,004 /night

Min Stay 1 night

Siena, Italy

€ 1,004 /Night (minimum stay 1 night)

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 swimming pool isn'...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

222 /night

Min Stay 1 night

Siena, Italy

€ 222 /Night (minimum stay 1 night)

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 Barbeque Bathtub Carbon ...More Details

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Homes for rent in Siena Holiday rentals Italian vacation rentals of Detached House and Villas, Single Family Homes - Short term lettings

Found 102 Siena Houses for rent

Siena, Italy

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Siena, Italy

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Siena, Italy

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Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy