House • 27 People • 14

• 13

•

From

€

3,808 /night

Min Stay 1 night

Siena, Italy

€ 3,808 /Night (minimum stay 1 night)

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 have the o...More Details

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Siena, House for rent

House • 21 People • 11

• 11

•

From

€

3,868 /night

Min Stay 1 night

Siena, Italy

€ 3,868 /Night (minimum stay 1 night)

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. There a...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

660 /night

Min Stay 1 night

Siena, Italy

€ 660 /Night (minimum stay 1 night)

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 the most out...More Details

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Siena, House for rent

House • 6 People • 4

• 3

•

From

€

513 /night

Min Stay 1 night

Siena, Italy

€ 513 /Night (minimum stay 1 night)

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 double upon reque...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

1,950 /night

Min Stay 1 night

Siena, Italy

€ 1,950 /Night (minimum stay 1 night)

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. *The swimming p...More Details

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Siena, House for rent

House • 6 People • 3

• 3

•

From

€

825 /night

Min Stay 1 night

Siena, Italy

€ 825 /Night (minimum stay 1 night)

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 Utensils Microwave Mosquito Net Outdoor Seating Oven Parking Availa...More Details

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Siena, House for rent

House • 17 People • 9

• 9

•

From

€

3,053 /night

Min Stay 1 night

Siena, Italy

€ 3,053 /Night (minimum stay 1 night)

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 Maker Cot / Crib Dishwasher Dr...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

258 /night

Min Stay 1 night

Siena, Italy

€ 258 /Night (minimum stay 1 night)

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. *One well-be...More Details

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Siena, House for rent

House • 4 People • 2

• 2

•

From

€

627 /night

Min Stay 1 night

Siena, Italy

€ 627 /Night (minimum stay 1 night)

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. *The ceiling ...More Details

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Siena, House for rent

House • 8 People • 4

• 3

•

From

€

547 /night

Min Stay 1 night

Siena, Italy

€ 547 /Night (minimum stay 1 night)

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 a lead when...More Details

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Siena, House for rent

House • 6 People • 3

• 3

•

From

€

476 /night

Min Stay 1 night

Siena, Italy

€ 476 /Night (minimum stay 1 night)

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 available f...More Details

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Siena, House for rent

House • 2 People • 1

• 1

•

From

€

384 /night

Min Stay 1 night

Siena, Italy

€ 384 /Night (minimum stay 1 night)

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 high chair...More Details

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Siena, House for rent

House • 14 People • 7

• 6

•

From

€

732 /night

Min Stay 1 night

Siena, Italy

€ 732 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Cypress

Set on an 8-hectare estate surrounded by cypress trees and vineyards, this 18th-century villa is a dream spot for a Tuscan retreat. While the villa has been renovated, it still offers plenty of traditional charm, with inviting spaces made for gathering – think a cosy living room with a fireplace, board games and books. Outside, there’s a large pool, a shaded lounge and a dining area – your host can also arrange fridge fills to make dining in that little bit easier. And with medieval villages such as Radda and Castellina within easy driving distance, you’re all set to explore the Chianti hills. *The swimming pool is only available for use between May and mid-October. The opening hours are from 8:30am to 8:30pm. *While this home is spread across two floors, there are two ground-floor bedrooms and bathrooms. *If you're travelling with little ones, your host can provide a high chair for free. You'll need to request it in advance. *Due to ...More Details

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Siena, House for rent

House • 16 People • 9

• 8

•

From

€

1,762 /night

Min Stay 1 night

Siena, Italy

€ 1,762 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscany Grace

Surrounded by rolling hills and lush trees as far as the eye can see, this Italian villa in the Lucciola Bella Nature Reserve offers picture-perfect seclusion. Split into five apartments – including an annexe and one suitable for guests with disabilities – it's a dream escape, whether for relaxation or celebrations. Inside, it's as charmingly rustic as you could hope, while outside there's a pool and plenty of space to dine and unwind. A car is essential for reaching amenities, but the idyllic location is totally worth it. *This home consists of five apartments spread out over two floors and across two buildings. *A car is recommended, due to the rural location. *Two baby cots and two high chairs are available on request, free of charge. *The pool is open from 1st May to 30th October. *The villa has five covered parking spaces. *The villa is suitable for hosting weddings. *One apartment in the main building is suitable for guests with...More Details

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Siena, House for rent

House • 18 People • 9

• 8

•

From

€

2,402 /night

Min Stay 1 night

Siena, Italy

€ 2,402 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Journey to Beauty

Experience the timeless beauty of Tuscany with a stay in this historic home. Nestled in the heart of the Val d’Orcia, you’ll be treated to stunning views and a private swimming pool as well as estate grown olive oil and wine. There’s also a yoga shala and plenty of shaded spots for quiet reflection – making this the perfect setting for a retreat or refreshing family gathering. Inside, the rooms make it easy to switch off, unwind and spend quality time together. Your host can also help organise a range of extra services – including massage treatments and yoga sessions. You will need a car to get around here, but it’s just a short drive to Siena and Montepulciano. *Private parking is available here. *Please note the swimming pool is available for use from the 1st of April to the 31st October. Balcony Barbeque Bathtub Central Heating Coffee Maker Dishwasher Drying Rack Espresso Machine Fan Fireplace First Aid Kit Free Parking Freeze...More Details

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Siena, House for rent

House • 14 People • 7

• 7

•

From

€

2,347 /night

Min Stay 1 night

Siena, Italy

€ 2,347 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Hilltop Aria

Rustic charm meets modern luxury in this hilltop Tuscan home. Boasting fantastic views of Montalcino, we think the garden is the perfect spot to enjoy the sunshine and fresh air. Entertain yourself with a dip in the private pool, play a game on the bocce court, or tuck into an Italian feast on the terrace. Step inside and you'll find seven en-suite bedrooms and a living space brimming with traditional character. Siena, Buonconvento, and other picturesque towns are within driving distance, making it easy to explore. There's also the option to arrange wine tastings, private dining, horseback riding, and other experiences – it's no wonder this home caught our eye. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *There's a private suite on the ground floor ideal for guests with reduced mobility. *We suggest hiring a car in this location. Private parking is av...More Details

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Siena, House for rent

House • 16 People • 8

• 9

•

From

€

2,626 /night

Min Stay 1 night

Siena, Italy

€ 2,626 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Sunlight Symphony

This traditional Tuscan farmhouse is nestled in the hills of Chianti. From here, you can enjoy beautiful views across vineyards, long days by the private pool and rejuvenating soaks in the hot tub. There’s also a terrace, a barbecue and a pizza oven for blissful Italian meals. Inside, the rooms offer a simple and peaceful sanctuary for families and groups looking to stretch out and socialise. You’ll find one of the bedrooms is located in an independent annexe – perfect for those seeking a little extra privacy. And when it comes to explorations further afield, it’s a short drive to the nearest amenities as well as Siena and Arezzo. *Please note one of the bedrooms is located in the independent annexe. *If you're travelling with little ones, your host can provide a cot and two high chairs for free on request. *The swimming pool is available for use from May to September. Barbeque Child Friendly Coffee Maker Cot / Crib Dishwasher Dry...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,939 /night

Min Stay 1 night

Siena, Italy

€ 2,939 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Golden Tuscan Sun

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

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

1,497 /night

Min Stay 1 night

Siena, Italy

€ 1,497 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Gaze

Nestled in the heart of the Chianti Classico region, this restored Tuscan farmhouse promises an idyllic escape. Sure, the traditional interiors may not be to everyone’s taste, but this home has all the key ingredients for a relaxing stay. And the cherry on the cake for us is the outdoor space. A private pool, hot tub, sun-drenched terraces and views for miles – what’s not to love? Location-wise, it’s a short 5km drive to Gaiole, where authentic Tuscan eateries and wine tasting await. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open between May and October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *The main bedroom is only accessible from outdoors. *One of the bedrooms can be set up as...More Details

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Siena, House for rent

House • 19 People • 10

• 11

•

From

€

9,159 /night

Min Stay 1 night

Siena, Italy

€ 9,159 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

A Truffled Retreat

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

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy

Siena, Italy