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, Apartment for rent

Apartment • 17 People • 9

• 9

•

From

€

2,601 /night

Min Stay 1 night

Siena, Italy

€ 2,601 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Lullaby

Situated in southern Tuscany, offering sweeping views of the rolling hills and vineyards, this villa is the perfect location for a peaceful holiday. The town of Radicofani is a ten-minute drive away, home to restaurants, shops and supermarkets, while sleepy San Casciano dei Bagni is reached in twenty. The abode features modern amenities including a sauna, private pool, and a tennis court – though the ground is uneven, so it won’t be suitable for serious players. There’s also a covered gazebo for alfresco dining and a comfortable seating area from where you can watch the sunset. *Due to the location of this home, we recommend hiring a car for ease of getting around. You’ll find parking available on the premises. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *For those with reduced mobility, there's a ground floor bedroom and bathroom here. *Some of the twin beds can be arr...More Details

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Siena, Apartment for rent

Apartment • 10 People • 6

• 5

•

From

€

1,422 /night

Min Stay 1 night

Siena, Italy

€ 1,422 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

A Country Garden

Perfect for a rural retreat, this converted farmhouse provides an excellent base for families seeking relaxation in the Tuscan countryside. Surrounded by gardens, you’ll enjoy peace and tranquillity here. While the interiors feel a little rustic, there’s plenty of charm and amenities to enjoy. The two living areas provide plenty of space for the whole group to spread out while the stone hearth brings the group together on cooler evenings. The outdoor pool and alfresco dining room are a highlight, too. This area is great for hiking and biking, with La Foce and the Amiata mountains nearby. *A car is recommended here to make the most of your trip. There's free parking on site. *This home is spread over two levels. While there's a ground-floor bedroom and bathroom here, there are steps in and around the property – this may not suit those with limited mobility. *Two interconnecting bedrooms on the first floor share a bathroom. *The pool is...More Details

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Siena, Apartment for rent

Apartment • 18 People • 9

• 6

•

From

€

2,521 /night

Min Stay 1 night

Siena, Italy

€ 2,521 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Tulip Moment

Located in the Tuscan countryside, this traditional villa offers plenty of privacy thanks to its rural location. The home is set across three levels and split into the main house and a separate annex, which is ideal for a couple or small family who need their own space. Boasting all of the amenities you could ever want, inside you’ll find a wine cellar, Jacuzzi and Turkish bath and workspace, whilst outside you won't be short of things to do thanks to a private pool, tennis court and football pitch. In addition to all of this, just fifty metres from the house a private gym and sauna await. *This home comprises of two separate buildings – the main house and a separate annex with two double ensuite bedrooms. If the guest count is below 14, the annex with not be available for use. *Your host allows pets at no extra cost but we recommend seeking their approval before arrival. *The housekeeper lives on-site in a room on the ground floor a...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

1,142 /night

Min Stay 1 night

Siena, Italy

€ 1,142 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Olive House

This villa is a rural oasis just south of Siena in the peaceful countryside, surrounded by woodlands and hills with panoramic views of Montalcino and Monte Amiata. You're just 24km from the charming city, while the Tuscan coast and Florence are also just over an hour's drive away, making it the ideal destination for those wanting to explore the area. The villa provides plenty of outdoor living space, including an alfresco dining area, a shaded lounge space and a poolside deck with a private pool. Inside, a bright and spacious living area with traditional features awaits you, as well as a country-style kitchen and five welcoming bedrooms, benefitting from wood beams and exposed brick. *Due to the location of this home, we recommend hiring a car during your stay. There's parking here. The villa is accessed via 3km of uneven road, which is not suitable for sports cars. *The villa is spread over two floors with a marble staircase, so it ...More Details

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Siena, Apartment for rent

Apartment • 11 People • 5

• 5

•

From

€

591 /night

Min Stay 1 night

Siena, Italy

€ 591 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Dream of Tuscany

This charming old farmhouse is between Buonconvento and Monteroni d'Arbia, southeast of Siena (25km away). It is a perfect place for a relaxing break with friends or family, made up of three beautifully restored apartments that share a private swimming pool. Each kitchen is brimming with Tuscan rusticana and has everything you need for self-catering. That’s if you’re not too busy using the stone barbecue outside and dining beneath the vine-dappled pergola. To top it all off, there are killer views of the Tuscan countryside at every turn. *While not all of the bathrooms are photographed, we expect the style and quality to be consistent with the rest of the home. *One of the single beds is on an open mezzanine level above a double bedroom and would best suit a child. *This home consists of three separate apartments each with its own entrance. *For those with reduced mobility, there's a ground-floor bedroom and bathroom here. *The swimm...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 6

•

From

€

820 /night

Min Stay 1 night

Siena, Italy

€ 820 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Pienza

Offering panoramic valley views over the surrounding olive groves, this countryside spot invites guests to experience rural Tuscany at its finest. Just a short drive from Monticchiello, you'll have easy access to the town's shops and restaurants despite your countryside location. And with miles of valley routes in the local vicinity, it's the perfect spot for hikers and cyclists. At the villa, you'll have a private swimming pool and a covered terrace annexe with a fireplace, pizza oven and alfresco dining area to enjoy the Tuscan sunsets. While the interiors feel a little dated in terms of design, they don't seem out of place amid the traditional lifestyle of this part of Italy. *While not all of the bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *Due to the location of this home, we recommend hiring a car to get the most out of your stay – there’s free parking on the premises for...More Details

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Siena, Apartment for rent

Apartment • 18 People • 9

• 8

•

From

€

4,887 /night

Min Stay 1 night

Siena, Italy

€ 4,887 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Rose of Time

This 18th-century Tuscan farmhouse is set to impress. It’s in the heart of the Tuscan countryside south of Siena, close to Sarteano, where you’ll find a maze of narrow streets, a medieval castle, and plenty of bars and restaurants. Tucked away in 25 acres of olive trees, cypresses and vines, this home is a haven. Spend your days swimming in the private pool or unwinding in the sauna or Turkish bath. Play tennis, hit the bowling green, or pootle around on bikes, soaking up the tranquillity of the luxurious setting. Begin each day with a breakfast buffet and let your host take care of your every need. *There’s free parking here. *This home comprises the main house – which is spread over three floors – and two cottages, in addition to an annex and a separate fourth building with a dining room. One of the cottages is wheelchair accessible. *The swimming pool is open from May to mid-October. The pool is closed from and on Tue...More Details

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Siena, Apartment for rent

Apartment • 19 People • 8

• 9

•

From

€

2,134 /night

Min Stay 1 night

Siena, Italy

€ 2,134 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Hilltop Sanctuary

Stop scrolling and pack your bags if you’re seeking an unforgettable retreat to rural Tuscany. Here, you’ll be surrounded by the rolling hills of Montepulciano, three hectares of sprawling gardens, an orchard and a vegetable plot. With eight bedrooms, all of which are en-suite, this is a perfect spot for a large family getaway. Outside, soak up the Tuscan sun by the pool, or enjoy an alfresco meal prepared with your produce pickings on the covered terrace. And after a day exploring the local vineyards, you can sink into the Jacuzzi tub under the stars. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there's parking here. *Though this home is spread over three floors and may not suit those with limited mobility, there is a ground-floor bedroom and en-suite. *One of the twin bedrooms has an independent entrance and en-suite bathroom – perfect for guests seeking extra privacy. Another staircase ...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

1,207 /night

Min Stay 1 night

Siena, Italy

€ 1,207 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Carmine Sunset

Providing sweeping views of the Tuscan countryside, this rustic villa guarantees a restful break for a family or group of friends. While the traditional, worn-in interior won’t be to everyone’s taste, we think it’s charming. Outside, there’s a heated swimming pool, a dining terrace and loungers for sunbathing sessions. Plus, there is a vegetable patch and orchard – feel free to help yourself to fresh produce. If you’d prefer to let the professionals take care of dinner, the closest restaurant is 3 kilometres from the home while Sarteano town is 8 kilometres away. *Due to the location of this home, we recommend hiring a car for ease of getting around. You’ll find parking available on the premises. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *For those with reduced mobility, there's a ground-floor bedroom and bathroom here. *One of the beds is raised with a small step lad...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, Apartment for rent

Apartment • 48 People • 25

• 21

•

From

€

2,625 /night

Min Stay 1 night

Siena, Italy

€ 2,625 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Campanella Rose

Nestled amid a medieval country estate, this home welcomes guests to enjoy its sprawling gardens, private pool, tennis court and beautiful views. There are 11 individual apartments here, each offering a wonderful sense of privacy, peace and rustic charm. It’s also a great base from which to explore the region. From here, it’s just 25 kilometres to Siena, while the nearest shops and restaurants can be found in Monteroni d’Arbia and Asciano – both just a short drive away. *The estate has one main villa which sleeps 11 guests and 11 annex apartments that sleep 48 guests. *Unless you are renting the entire estate, the outdoor facilities such as the tennis court, bikes, boccia ground and children’s playground may be shared with other residents. *Weekly housekeeping is included in your stay. *The swimming pool is only available for use from the 14th of April to the 22nd of October. *Due to this home's location, we recommend having a 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, Apartment for rent

Apartment • 18 People • 8

• 6

•

From

€

2,729 /night

Min Stay 1 night

Siena, Italy

€ 2,729 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Toasted Oak

You might think it doesn't get much better than a swimming pool, a garden in bloom and panoramic views of the Italian countryside, but this home's heritage is what caught our eye. The villa has stood within the Montagnola nature reserve for over a thousand years, and though it has been modernised since, it has kept hold of a lot of the original charm. Surrounding apartments means it isn't always private, especially around the shared pool, but the home is a retreat for big groups and a good base when you're exploring Siena, San Gimignano, or beyond. Having breakfast included is a nice touch, especially when it's alfresco. *We suggest hiring a car for ease – there's free parking here. *You'll have access to the swimming pool and garden here. They're shared with the building's other residents. *At full occupancy, two guests will be sleeping on the sofa bed in the living area. *Breakfast is included here, but you'll also find restaurants ...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

212 /night

Min Stay 1 night

Siena, Italy

€ 212 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Sweet

This apartment near Torrita di Siena has lovely views over this little slice of Tuscany from the terrace – perfect for alfresco meals. Or have a stroll through the communal gardens to the shared swimming pool. When you feel like exploring, visit Torrita di Siena with its pretty streets lined with stone-built houses or go for a hike around Mount Amiata. Alternatively, spend the day in one of the many parks in the area, such as Giardini Pubblici and Parco Via Ruffilli. *The gardens and swimming pool are communal. *The pool is open from April to November, from 8.30 am to 7.30 pm. *Due to this home's location, we recommend hiring a car to get the most out of your stay (there's free parking on the premises). A cot, high chair and travel cot are available upon request, at no extra cost. *There are stairs to climb here, so it may not suit those with limited mobility. *While one bathroom isn’t photographed, we expect the style and quality t...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

214 /night

Min Stay 1 night

Siena, Italy

€ 214 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan White

Situated on a private resort, this villa drops you in the heart of the Tuscan countryside to indulge in pure rest and relaxation. Set over two floors, there’s plenty of space for guests to spread out, plus an inviting private terrace to soak up the rural vistas. Cool off from the Italian heat in the seasonal communal pool, while a visit to the on-site wine bar is a must to taste some local delights. For an additional fee, you can also enjoy a delicious breakfast buffet, an Italian cooking class or a truffle hunting experience. *Your host operates several villas here, so the exact view, layout and furnishings may differ slightly from the photos. While not all bedrooms are photographed, expect the style and quality to be consistent with the rest of the home. *The twin bedroom can be prepared as a double or two singles upon request. *If you're travelling with little ones, your host can provide a free cot and high chair with advance noti...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

332 /night

Min Stay 1 night

Siena, Italy

€ 332 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Getaway

Nestled in a Tuscan country estate, this pet-friendly home offers the best of both worlds – a private terrace for alfresco dining and the option to share breakfast with your neighbours at the buffet. After snoozing by the communal pool, why not join a truffle hunt? Or rent a bike and cycle through the area. Maybe sipping local sundowners in the on-site bar will inspire a next-day trip to medieval Montepulciano, so you can see where that regional wine comes from. *For those with reduced mobility, this is a ground-level home. *There’s free parking here. Due to this home's location, we recommend hiring a car to get the most out of your stay. *If you're travelling with little ones, your host can provide cots with bedding, high chairs, plastic bowls, and plates for free. You'll need to request them in advance. *The swimming pool is shared with the building's other residents. It is open between 8.30am and 8pm, and it is only available for u...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

301 /night

Min Stay 1 night

Siena, Italy

€ 301 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Casa di Siena

Located in the Tuscan countryside, this home in Torrita di Siena offers endless peace, quiet and picturesque scenery. With views stretching to Lake Trasimeno, it's a spot for those keen to reconnect with nature while discovering the attractions of Tuscany. There's a shared swimming pool on-site, and you'll have your own private garden space here. The alfresco dining area is perfect for sitting with a glass of local wine and an Italian aperitivo. Meanwhile, the open-plan living area makes for a sociable living space to kick back after a long day of exploring. *Due to this home's location, we recommend hiring a car to maximise your stay. There’s free parking for up to two cars on the driveway. *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 rooftop swimming pool is shared with other building residents and is only available for use between 1st April...More Details

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Siena, Apartment for rent

Apartment • 6 People • 3

• 3

•

From

€

294 /night

Min Stay 1 night

Siena, Italy

€ 294 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Tuscan Vineyard

Set on a farm, parts of which are more than 200 years old, you’ll find this apartment, which is light and bright thanks to the large arched windows. Outside, as you’d hope for – there are gorgeous vistas over the Tuscan countryside and instead of a farm pond, there’s now a beautiful shared pool, which is a short walk through the communal gardens. When you fancy exploring the area – go for a hike in the Val di Chiana, discover the medieval hilltop town of Montepulciano, or spend the day at one of the beaches at Lake Trasimeno. *Your host operates several villas here, so the exact view, layout and furnishings might differ slightly from the photos. However, the overall quality should remain the same. *If you're travelling with little ones, your host can provide a cot, high chair and children's dinnerware for free. You'll need to request them in advance. *This home is located within a resort, with a shared pool and communal grounds. Expec...More Details

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Siena, Apartment for rent

Apartment • 4 People • 2

• 2

•

From

€

331 /night

Min Stay 1 night

Siena, Italy

€ 331 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Alighieri

This converted Tuscan home provides a great base to explore one of Italy’s most iconic areas from. Though the interior perhaps lacks a bit of cosiness, it is well-kept and provides you with all you need for a comfortable stay, including a fully-equipped kitchen and a nice open-plan dining area which leads onto a private terrace. Guests can also make use of the resort’s facilities, such as the shared outdoor pool and rooftop. Make the most of the area by sampling some of its famous wines and visiting the picturesque towns. *While one of the bathrooms isn’t photographed, we expect the style and quality to be consistent with the rest of the home.\u2028 *The decor may have been updated and differ slightly from the photos.\u2028*Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s free parking on-site. *You won't find a welcome hamper or basic essentials here, so we'd recommend packing some bits...More Details

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Siena Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

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Siena Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Found 268 Siena holiday homes for rent

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