House • 18 People • 11

• 9

•

From

€

1,704 /night

Min Stay 1 night

Siena, Italy

€ 1,704 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Vine Vineyard

This gorgeous home boasts its own private pool and breathtaking valley and vineyard views. Ideal for families and large friend groups, there's plenty of space indoors and out. You'll find a games room and a gym, plus a volleyball court and several alfresco dining spots spread over the main house, the extensive gardens, and the separate basement. Wine aficionados can do some tasting in the cellar, and there are ten wineries within 5km. The location is fantastic for enjoying some peace and quiet alongside the picturesque views, but when it comes to exploring you'll find Siena only 15km away, and San Gimignano and Florence are also reachable by car. *Not all bathrooms are photographed, but we expect consistency in style and quality throughout. *There is parking outside for up to six cars. Due to the location, we recommend hiring a car to make the most of your stay. *There is bed space for up to twenty guests, but the maximum guest count ...More Details

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Siena, House for rent

House • 8 People • 5

• 6

•

From

€

591 /night

Min Stay 1 night

Siena, Italy

€ 591 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Olive - Olive Wood

Surrounded by the rolling vistas of a famous wine estate, this Tuscan villa boasts a spacious private pool, stunning views, and space for alfresco dining. The decor is quite traditional and won't be to everyone's taste, but it's certainly not lacking in charm. Opposite the main home, you'll find a stone barn with a kitchen, dining area and second living room, ideal for family dinners. We recommend hiring a car here, with the city of Siena less than an hour's drive away – the road up to the home is unpaved and uneven though, so it won't be suitable for smaller cars. *Not all bathrooms are photographed, but we expect consistent style and quality throughout this home. *There is space to park for free outside this home for up to four cars. We recommend hiring a car here, and the road up to the home is unpaved and uneven so you'll want a high-clearance vehicle. *Your host can provide a free cot and high chair on request if you're travellin...More Details

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Siena, House for rent

House • 26 People • 13

• 13

•

From

€

3,150 /night

Min Stay 1 night

Siena, Italy

€ 3,150 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Marbled with Flowers

Ten minutes from Sarteano town and an easy drive from Montepulciano, this charming Tuscan estate has its own outdoor pool and wellness facilities. The gym and spa are well-equipped, with a heated indoor pool, Finnish sauna and professional exercise equipment. Made up of a main home and an annexe, there's plenty of room for large groups to spread out, and for kids and pets to tire themselves out in the garden. You'll have privacy and countryside views, plus it's a great base to explore the Val d'Orcia and Valdichiana regions by car. *Not all bedrooms and bathrooms are photographed, but we expect consistency in style and quality throughout. *We highly recommend hiring a car to make the most of your stay. *This home is made up of a main house which sleeps sixteen guests, and an annexe which sleeps a further ten. *Several of the bedrooms can be configured as twins or doubles by pushing the beds together. The bedrooms in the annexe are acc...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

642 /night

Min Stay 1 night

Siena, Italy

€ 642 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Valley's Mine

Set amidst rolling Tuscan countryside, this villa promises an escape from it all. With a mix of modern and traditional interiors, there’s something to appeal to all tastes here, and plenty of space for up to ten guests to spread out comfortably. Outdoors, the private pool takes centre stage, while sun-worshippers will be delighted with the expanse of terraced areas and garden from which to soak up the rays. For a day out, nearby Siena is well worth a visit for its beautiful buildings, historic sites and abundance of eateries offering a true taste of Italy. *Due to this home's location, we recommend hiring a car to get the most out of your stay. *The swimming pool is only available for use between 30th April and 1st October, depending on the weather. The pool isn't fenced, so if you're bringing little ones, they'll need to be supervised at all times. *One bedroom is situated in a guest suite, separate from the main home, giving two ...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,246 /night

Min Stay 1 night

Siena, Italy

€ 2,246 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

On Tuscan Hill

Tuscan charm abounds at this rustic villa near Sarteano. Even with dated interiors, every room here conveys cosiness – picture arched stone walls, wood and terracotta ceilings, book-lined shelves, and a traditional fireplace. Outside, dappled terraces, a football field, and a private swimming pool will keep both grown-ups and little ones entertained. What's more, the rural location puts you within striking distance of Tuscany's old-world villages and rolling hills. Sarteano and Cetona are just minutes away, while Perugia and Siena are about an hour's drive and make good options for day trips. *While not all bedrooms and bathrooms are photographed, we expect the style and quality to be consistent with the rest of the home. As this villa is traditionally decorated and somewhat dated, the design may not suit everyone's tastes. *There are two ground-floor bedrooms and bathrooms here, ideal for guests with limited mobility. *The pool is av...More Details

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Siena, House for rent

House • 8 People • 4

• 3

•

From

€

433 /night

Min Stay 1 night

Siena, Italy

€ 433 /Night (minimum stay 1 night)

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're bringing c...More Details

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Siena, House for rent

House • 17 People • 7

• 7

•

From

€

1,028 /night

Min Stay 1 night

Siena, Italy

€ 1,028 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Olive - the Vine

Pictures don't do this elegant farmhouse justice. Ideal for dream weddings, romantic getaways or family holidays, this home offers a private chef and helicopter transfers, amongst other optional luxuries. The wine cellar is stocked with the area's finest wines, and the pool and expansive gardens are perfect for congregating under the sun. You'll definitely want a car here – while this home provides peace and privacy, it's an excellent location for exploring central Italy. Montepulciano is 5km away, and places like Siena, Arezzo, Florence and Rome are easily reached by car or train. *Not all bathrooms are photographed, but expect consistent quality *There's space to park outside for free. Due to the location, we recommend hiring a car. *It's spread over two floors, and all bedrooms are upstairs. Three bedrooms are on a mezzanine level, while the other four are upstairs. *A bi-weekly complimentary housekeeping service is included here. ...More Details

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Siena, House for rent

House • 14 People • 7

• 6

•

From

€

2,593 /night

Min Stay 1 night

Siena, Italy

€ 2,593 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Little Hills

You can't beat the views of the beautiful Val D'Orcia, itself a UNESCO World Heritage Site, from this Tuscan farmhouse lying in the Siena Province on a private two-acre estate. Tear yourself away from the vistas, and you'll find a deft renovation, combining contemporary interiors and historic charm. An excellent choice for a large group of friends or family, there's plenty of space to spill out and feel at home here. Cool off from the Tuscan sun in the infinity pool. Put to use the vast, chef-worthy kitchen (we're talking two dishwashers, two ovens, and some) for a big dinner party – a private chef is bookable for fine dining. Or keep things easy and fire up the barbecue or pizza oven outside as breath-taking views of the valley spread out before you – best seen beneath the pergola at sunset with a glass of something chilled. And on chiller nights, hunker down beside the fireplace with a good book – there are two living rooms to choose ...More Details

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Siena, House for rent

House • 14 People • 6

• 6

•

From

€

2,529 /night

Min Stay 1 night

Siena, Italy

€ 2,529 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Farmhouse Modern

Built in the eighteenth century, this former farmhouse combines rural living with the best of the modern world. Boasting sweeping views of the Val D’Orcia from the infinity pool, we can’t imagine a more perfect place to hang out as the hot Italian sun makes its way across the horizon. Enjoy alfresco dining on the lush patio, fire up the pizza oven for an authentic Italian experience or prepare wonderful meals with ultra-fresh fruit and veg straight from the garden and the famous Chianti wine in the contemporary kitchen inside. Several living areas allow the group to spread out, and have all been immaculately styled and designed – think sleek fireplaces and dazzling modern art against white-wash wooden ceilings and exposed stone walls. Bedrooms are just as stylish and some come with direct garden access and luxurious free-standing tubs. If you want to keep on top of your fitness game, there’s a gym on the first floor with a glorious pict...More Details

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Siena, House for rent

House • 14 People • 6

• 6

•

From

€

1,678 /night

Min Stay 1 night

Siena, Italy

€ 1,678 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Casa Rossa

Tucked away at the end of a four-kilometre dirt road, Casa Rossa provides guests with complete privacy and serenity for a most relaxing stay in the rolling hills of the Valdichiana. Welcoming up to twelve guests, this is an excellent choice for a group of friends or a family gathering. Casa Rossa boasts a contemporary look that creates both a refreshing contrast to its rural setting and offers guests plenty of modern luxuries, from the sleek kitchen to the indoor fire pit. Step outside and make the most of the expansive lawn, large pool and outdoor dining set up. Although you're about an hour and a half from Florence, you can always create your own Bistecca alla Fiorentina on the barbecue. What a way to spend a vacation. *The fireplace here is just for decoration. You won't be able to use it during your stay. Air Conditioning Barbeque Bathtub Central Heating Dishwasher Dryer Electricity Adaptors Espresso Machine Freezer Fridge Garde...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

1,796 /night

Min Stay 1 night

Siena, Italy

€ 1,796 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Emerald Hills

Formerly an olive mill, this Tuscan villa combines rustic charm with modern design elements. Just outside the small hamlet of Iesa, the villa is nestled in the serene Tuscan hills, surrounded by verdant countryside. Downstairs you will find the original stone olive mill, alongside chestnut beams, exposed stone, and terracotta tiling across the house. This preserved charm is compounded by contemporary bathrooms, and a sunroom with floor to ceiling windows, where you can admire the oil painting of a view. On cooler nights, gather here with a drink in hand for a movie or to play some music. Outside there is a table which seats ten, for al fresco dinners before a spot of stargazing. No detail is spared here. From the food and drinks hamper waiting for you in the kitchen on arrival, laden with complimentary wine, olive oil, fruit and cooking supplies, to the range of activities available to book through your host, whether it be horse ridin...More Details

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Siena, House for rent

House • 8 People • 4

• 3

•

From

€

2,009 /night

Min Stay 1 night

Siena, Italy

€ 2,009 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Vine Song

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

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Siena, House for rent

House • 20 People • 9

• 9

•

From

€

2,278 /night

Min Stay 1 night

Siena, Italy

€ 2,278 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Citrus Pavillion

Overlooking vineyards, olive groves, and ancient oak forests, this collection of restored farmhouses offer the ultimate relaxed country retreat. With a refreshingly refurbished interior, saltwater infinity pool, bubbly outdoor jacuzzi, private spa and gym, and enough alfresco dining opportunities to shake a stick at, we are positive that this home offers something for each and every guest. Enjoy poolside sunbathing on plush sun loungers, before taking a dip in the cool, refreshing waters. Mornings are the perfect time to cuddle up on the veranda with a mug of something warm, looking out over rolling hills and lush vistas as the sun begins to warm your day. When the day is just too good to be spent at home, take a walk through the Tuscan countryside, before heading to Radda to sample some of the most refreshing wine and cuisine Chianti has to offer. *Due to the location of this home, we recommend hiring a car to get the most out of y...More Details

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Siena, House for rent

House • 6 People • 2

• 2

•

From

€

380 /night

Min Stay 1 night

Siena, Italy

€ 380 /Night (minimum stay 1 night)

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 you're hoping to dine out,...More Details

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Siena, House for rent

House • 10 People • 5

• 5

•

From

€

824 /night

Min Stay 1 night

Siena, Italy

€ 824 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Well Garden

A traditional Tuscan farm stay, surrounded by olive groves and truffle country, this stone villa is as practical as it is beautiful. With plenty of space for a large group to spread out, there are three living spaces, each with a kitchen, allowing for added flexibility. Here, the name of the game is relaxation, and it's not hard to do in such a peaceful setting. In a quiet, rural area with incredible views of the lush green hills, you'll have country walks and cycling routes on your doorstep, and pretty grounds to explore – plus it's just a walk through the woods to the nearby village. Inside, two entrances each lead to a living area and kitchen. Traditionally styled and oozing Tuscan charm, you'll have tiled floors, chestnut beams and fireplaces, along with archways and shuttered windows. Each section has a large dining table so you can all eat together and each of the five bedrooms upstairs boasts its own bathroom so nobody draws th...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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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

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