Italy - Holiday Rentals in Siena Italy

Country: Italy (7128) | Region: Tuscany (2161)

Found 185 Siena properties for vacation rental

Houses (37) Apartments (143) Rooms (1) Townhouses (1) Cottages (3)

Siena, House for rent

House • 27 People • 14

• 14

•

From

€

5,453 /night

Min Stay 1 night

Siena, Italy

€ 5,453 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Art of Tuscany

With a team of staff on-hand to help at this decadent home, you won't have to lift a fingertip during your stay. Spread across a main house, guest house and suite, you also won't have to compromise on space. The swimming pool, Roman baths, and sauna ensure relaxation. When you're not traversing the hundreds of acres on bicycle or horseback, the on-site observatory allows you to admire the stars. We think some of the decor is a little dated, and it might not be to everyone's taste. But whether you're throwing a wedding, a yoga or tai chi retreat, or you're simply looking for a scenic escape to the Tuscan countryside, this home has it all. *This home consists of a main house (sleeping nineteen), a guest house (sleeping six), and a guest suite (sleeping two). Each has a combination of living rooms, bathrooms, and bedrooms. Some bedrooms may only have external access. Several beds can be configured as twins or doubles on request.\n *Not al...More Details

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Siena, Apartment for rent

Apartment • 19 People • 8

• 9

•

From

€

4,158 /night

Min Stay 1 night

Siena, Italy

€ 4,158 /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.\n *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.\n *One of the twin bedrooms has an independent entrance and en-suite bathroom – perfect for guests seeking extra privacy. Another stairca...More Details

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Siena, House for rent

House • 26 People • 13

• 13

•

From

€

3,958 /night

Min Stay 1 night

Siena, Italy

€ 3,958 /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.\n *We highly recommend hiring a car to make the most of your stay.\n *This home is made up of a main house which sleeps sixteen guests, and an annexe which sleeps a further ten.\n *Several of the bedrooms can be configured as twins or doubles by pushing the beds together. The bedrooms in the annexe ar...More Details

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Siena, Apartment for rent

Apartment • 18 People • 9

• 8

•

From

€

3,841 /night

Min Stay 1 night

Siena, Italy

€ 3,841 /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.\n *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.\n *The swimming pool is open from May to mid-October. The pool is closed from and on ...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 7

•

From

€

3,478 /night

Min Stay 6 nights

Siena, Italy

€ 3,478 /Night (minimum stay 6 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Paradise

This recently restored country home, nestled in the heart of the wilds of Tuscany, offers the perfect escape for those seeking luxurious tranquillity, with astounding views, entertainment and opportunities for adventure. Get a taste of the Tuscan life with an on-site winery and views out over lush vistas and spanning farmland. Relax in ultimate comfort by the pool, catching the perfect holiday tan, while others man the barbecue, cooking up a storm of delicious local delicacies by the alfresco dining area. Younger guests will have the time of their lives playing out on the lawn, making a splash in the azure infinity pool, and hiding out in the games room and library, while adults make the most of the peace and comfort this beautiful home has to offer.If you can bring yourself to venture out of your front door, there are ample places to explore, whether your preference is to grab your walking boots and go for an adventurous country ramble...More Details

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Siena, House for rent

House • 14 People • 7

• 6

•

From

€

2,907 /night

Min Stay 4 nights

Siena, Italy

€ 2,907 /Night (minimum stay 4 nights)

Swimming Pool

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, Apartment for rent

Apartment • 15 People • 7

• 7

•

From

€

2,884 /night

Min Stay 1 night

Siena, Italy

€ 2,884 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Treasure

Sitting pretty on sixty-five hectares of rolling countryside, this 16th-century villa has been renovated into a luxury retreat with designer touches. Even though an indoor pool, gym, wine cellar and billiard room ups the ante inside, the outdoors is where this home truly shines. Admire the views from the sprawling garden. You'll also find a private pool with ample poolside seating and a shaded veranda for alfresco dining. Location-wise, it's within driving distance of thermal spas, Siena, Florence and several other art cities. And for more active guests, Lucciola Bella Nature Reserve has various hiking trails. *There’s free covered parking available.*At full occupancy, one guest will be sleeping on the sofa bed in the tower.*This home is spread across three floors, so you'll have to be able to climb stairs here, but there is a guest house with a ground-floor bedroom and bathroom. *The outdoor swimming pool is only available for use bet...More Details

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Siena, Apartment for rent

Apartment • 18 People • 8

• 6

•

From

€

2,857 /night

Min Stay 3 nights

Siena, Italy

€ 2,857 /Night (minimum stay 3 nights)

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 and ...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

2,851 /night

Min Stay 7 nights

Siena, Italy

€ 2,851 /Night (minimum stay 7 nights)

Swimming Pool

Air Conditioning

WiFi

Villa Monastero

Formerly a 16th century convent, this enchanting villa is bursting with character and has been renovated with every comfort and enjoyment in mind. Step into the cool stone entrance hall and you will instantly note the attention to detail. There are two distinctive reception rooms, decorated with a curated selection of original furniture, paired with custom creations from local artisans and designer touches. The kitchen is fully stocked with high spec appliances, and the dining room is the perfect place for breakfast, with views of the rolling green olive groves out of the window. Outside, there are plenty of spots to relax in the sun and the shade, and there is no better way to start the day than plunging into the sparkling pool. There is also an indoor hydro massage pool to relax and unwind in after a day's activities. At sunset, gather everyone for an aperitivo under the pergola, whether it’s a negroni or a bottle of red from neighbou...More Details

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Siena, Apartment for rent

Apartment • 14 People • 7

• 7

•

From

€

2,810 /night

Min Stay 7 nights

Siena, Italy

€ 2,810 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sunlight On The Hills

If you’re in search of a rustic getaway, head to this 18th-century home overlooking the Chianti hills. It was the former residence of a noble Florentine family who have left their fashionable mark, along with a range of impressive features. Inside, the rooms are elegant, traditional and family-friendly with plenty of space across the seven bedrooms to rest and recharge. Outside, there are stunning views across the hills which you can admire from the private pool, or whilst lounging under the trees. It’s also just 14 kilometres from Siena, with San Gimignano and Florence both near enough for inspiring day trips. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also free parking. *This home is spread across two floors with no internal lift – there are three bedrooms and bathrooms located on the ground floor. *Please note the housekeeper and staff live in a separate building within the gr...More Details

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Siena, Apartment for rent

Apartment • 30 People • 14

• 13

•

From

€

2,782 /night

Min Stay 5 nights

Siena, Italy

€ 2,782 /Night (minimum stay 5 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Titiro Toscano

Located in the Tuscan countryside, this impressive estate is an excellent choice for a couple of large families looking for an easygoing stay. Set across a main building and two guest houses, the residence, dating back to the 1600s, has been carefully restored and boasts fantastic views of Val d’Orcia. Although the traditional interiors may not be to everyone’s taste, the space is functional and perfectly suited to group dining and relaxing. Need a hand planning activities? Your host provides a wide range of experiences from truffle hunting to wine tasting – all on your doorstep. *Due to the location of this home, we recommend hiring a car to get the most out of your stay*This home is spread across a main building and two residences*Your host can provide a cot and high chair for free upon request*Wifi is only available in the communal spaces*Pets are allowed upon request*You'll need to bring your own toiletries with you to use during y...More Details

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Siena, House for rent

House • 14 People • 6

• 6

•

From

€

2,739 /night

Min Stay 4 nights

Siena, Italy

€ 2,739 /Night (minimum stay 4 nights)

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, Apartment for rent

Apartment • 20 People • 9

• 9

•

From

€

2,592 /night

Min Stay 5 nights

Siena, Italy

€ 2,592 /Night (minimum stay 5 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Masterpiece

This incredible Tuscan villa dates back to the 1600s and has been lovingly transformed into an organic and eco-sustainable farm. The landscape surrounding this home is impressive too – especially from the panoramic pool – as it's situated in Val d'Orcia, a UNESCO World Heritage Site. Spread over two floors, the space includes a fully-equipped kitchen and plenty of outdoor dining space, as well as BBQ facilities and a wood-burning oven for alfresco cooking. If any guests have mobility issues, three of the en-suite bedrooms on the ground floor are easily accessible from outside. We recommend a car to explore the area with ease – the Medieval village of Trequanda is just 5km away. *There's private parking on the premises*The kitchen has been designed to a professional standard and is well equipped*There is wifi throughout the property so remote working is possible – but there isn't a designated office space*The pool is open from late Apri...More Details

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Siena, House for rent

House • 20 People • 9

• 9

•

From

€

2,430 /night

Min Stay 3 nights

Siena, Italy

€ 2,430 /Night (minimum stay 3 nights)

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 you...More Details

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Siena, Apartment for rent

Apartment • 17 People • 9

• 9

•

From

€

2,426 /night

Min Stay 1 night

Siena, Italy

€ 2,426 /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.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. \n *For those with reduced mobility, there's a ground floor bedroom and bathroom here.\n *Some of the twin beds can b...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 8

•

From

€

2,392 /night

Min Stay 3 nights

Siena, Italy

€ 2,392 /Night (minimum stay 3 nights)

Swimming Pool

Air Conditioning

WiFi

Botticelli's Primavera

Just driving up to this fabulous Tuscan home is a pleasure in itself. Surrounded by manicured lawns, tall cypress trees and rolling hills, it's an imposing place in a secluded setting. Within the private estate of Arceno, it comprises a main stone-built villa and an Annesso – a historic barn converted into a separate intimate home. The main house is dominated by its central courtyard, while the lush gardens are home to a stunning pool and outdoor dining spots. We love the thought of gathering the whole gang around the long dining tables for lazy lunches of lemon ravioli and chilled white wine, lasting far into the afternoon. Inside, this home is elegant and comfortable, with period features, antique furniture and grand reception rooms. The concierge service makes things even easier, providing items ranging from the basic (oil and selected toiletries) to the delectable (spirits and house wine). One of the best ways to acquaint yourself w...More Details

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Siena, Apartment for rent

Apartment • 32 People • 16

• 16

•

From

€

2,252 /night

Min Stay 1 night

Siena, Italy

€ 2,252 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Sweetest Life

Staying at this sprawling Tuscan estate is like having your own ancient borgo (small village). Hectares of grounds are dotted with cypress trees, dense woodland, ancient olive groves and gardens blossoming with flowers. You could get your daily steps in just wandering the grounds. Following a woodland path, you’ll find the private swimming pool in complete seclusion, lined with loungers and shaded by towering trees. There are seating areas aplenty and spots to dine outdoors. For a real celebration, a banqueting table can be set up in the flower-filled courtyard.The villa itself is set around a traditional courtyard-style with a separate annexe housing some of the bedrooms. It’s a vision of Tuscan tradition – wooden ceilings, tiled floors and antique furniture in every room. The huge dining table can fit the whole group for breakfasts and the chrome, the professional kitchen could rival that of a Michelin-starred restaurant. Bedrooms are...More Details

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Siena, Apartment for rent

Apartment • 48 People • 25

• 21

•

From

€

2,137 /night

Min Stay 1 night

Siena, Italy

€ 2,137 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Lady 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. *This home is split across 11 apartments, with each apartment sleeping between 2 and 6 guests – please speak with your host to request a full breakdown.\n *Please also note this home is located within a private estate – the facilities such as the tennis court, bikes, boccia ground and children’s playground are all shared. \n *Weekly housekeeping is included in your stay.\n *The swimming pool is only available for use from the 14th of April to the 22nd of October.\n *The...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

2,098 /night

Min Stay 1 night

Siena, Italy

€ 2,098 /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.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. \n *For those with reduced mobility, there's a ground-floor bedroom and bathroom here.\n *One of the beds is raised with a small ste...More Details

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Siena, House for rent

House • 14 People • 6

• 6

•

From

€

2,089 /night

Min Stay 4 nights

Siena, Italy

€ 2,089 /Night (minimum stay 4 nights)

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 ConditioningBarbequeBathtubCentral HeatingDishwasherDryerElectricity AdaptorsEspresso MachineFreezerFridgeGardenHair DryerH...More Details

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Siena, House for rent

House • 11 People • 6

• 7

•

From

€

2,075 /night

Min Stay 1 night

Siena, Italy

€ 2,075 /Night (minimum stay 1 night)

Swimming Pool

WiFi

Olive Garden

Charming and traditional, this Tuscan villa sits in a serene spot near San Casciano Dei Bagni, and is ideal for those looking to get away from it all and enjoy some relaxing days amongst nature. Featuring a main house and a separate annexe, this home is ideal for large groups who'd occasionally like to split up and enjoy more privacy. The interiors are dreamy and elegant, with a neutral colour scheme that invokes a sense of calm. This vibe carries through to the outside of the home, where you'll find a gorgeous private pool that you can soak in while you stare out at the stunning views that surround you here. *While the home can sleep up to twelve people, the maximum occupancy is eleven guests.\n *The house is made up of the main house and a separate annexe.\n *For those with reduced mobility, there's a ground floor bedroom and bathroom here.\n *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervis...More Details

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Siena, Apartment for rent

Apartment • 10 People • 5

• 5

•

From

€

2,060 /night

Min Stay 1 night

Siena, Italy

€ 2,060 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Beneath The Autumnal Sun

Sitting proudly in the Chianti landscape, surrounded by woods, olive trees and row upon row of vines – this ancient farmhouse is the dream. It’s located in the prestigious setting of the Tolaini organic winery, one of the most esteemed in the area and produces delicious extra virgin olive oil and a fine selection of wines exported worldwide. You can taste a selection of these wines in the estate’s cellars a short distance away.That’s if you can tear yourself away from the gorgeous gardens with their fragrant lemon trees, lavender and rosemary bushes. Fire up the wood oven or barbecue, then dine alfresco under the pergola covered in exquisitely scented jasmine. After lunch, take a dip in the swimming pool with its vistas over the stunning countryside. Inside, a renovation has maintained the charm and character features such as the brick arches and vaulted ceilings. We love the huge dining table, which follows the curved lines of the kitc...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

2,020 /night

Min Stay 1 night

Siena, Italy

€ 2,020 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

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.\n *There are two ground-floor bedrooms and bathrooms here, ideal for guests with limited mobility.\n *The pool is...More Details

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Siena, House for rent

House • 12 People • 6

• 7

•

From

€

1,872 /night

Min Stay 1 night

Siena, Italy

€ 1,872 /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 mo...More Details

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Siena, Apartment for rent

Apartment • 10 People • 6

• 5

•

From

€

1,852 /night

Min Stay 1 night

Siena, Italy

€ 1,852 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Tuscan Green

This marvellous villa, nestled in the verdant countryside, will rise to every occasion. With plenty of space for up to twelve guests, it's the ideal gateway to the wonders of Tuscany – or, if you'd prefer to just chill out, you can press pause and relax in style. There's plenty of character here – from the oil paintings to the wooden ceilings and tiled floors, lovers of all things traditional will find plenty of features to admire. The cosy living room is the perfect place to find some peace and quiet, while the games room is ideal for a competitive game of pool with your guests. The fun continues outside, where you can stretch out on a sun lounger then take a dip in the pool when the heat gets too much. And, come evening, you can gather your guests around the alfresco dining table for a delicious feast – don't forget some local red wine. It would be easy to never leave this little patch of heaven, but if you want to get out and about t...More Details

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Siena, Apartment for rent

Apartment • 12 People • 6

• 6

•

From

€

1,697 /night

Min Stay 1 night

Siena, Italy

€ 1,697 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Tuscan Dreamland

Escape to this Tuscan villa that offers a rural setting and a host of amenities. From here, you can explore the hiking routes through the Riserva Naturale Lucciola Bella, then enjoy a Shiatsu or Ayurveda massage in the garden upon your return – just speak to your host. The home is a little dated but perfectly comfortable for a large group. Spread across a main house and two annexes, it's also ideal for those seeking privacy. From playing pool in the games room, to relaxing poolside, this home offers an idyllic setting to unwind with family and friends. And when it comes to mealtimes, you can cook organic produce straight from your host’s vegetable garden. *While some rooms aren't photographed, expect the style and quality to be consistent with the rest of the home.\n *This home is comprised of a two-storey main house and two annexes.\n *The pool is open between June and September. \n *Your host provides a cleaning service and a change ...More Details

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Siena, House for rent

House • 12 People • 6

• 6

•

From

€

1,687 /night

Min Stay 1 night

Siena, Italy

€ 1,687 /Night (minimum stay 1 night)

Swimming Pool

WiFi

The White Vine

Looking for the wow factor? This home fits the bill. Each room effortlessly blends Tuscan tradition with contemporary aesthetics – none more so than the living area, with its brick archways, stone walls and beamed ceilings. There's also an annexe offering even more space for groups, containing an additional kitchen and living room, as well as the fifth and sixth bedrooms (one of which is wheelchair-accessible). Outside, the swoon-worthy views from the infinity pool and Jacuzzi are hard to resist. Meanwhile, the shaded pergola is perfect for Aperol Spritzes at sundown. And did we mention daily maid service is included? If you can tear yourself away from this stunning home, Montefollonico is a thirty-minute walk, while Siena is an hour's drive. *Bedrooms five and six are located in the annexe, which has its own living area and kitchen. Bedroom six and its en-suite are both suitable for wheelchair users.*If you're travelling with little o...More Details

Booked

Available

Siena, House for rent

House • 10 People • 5

• 5

•

From

€

1,660 /night

Min Stay 3 nights

Siena, Italy

€ 1,660 /Night (minimum stay 3 nights)

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 riding...More Details

Booked

Available

Siena, Apartment for rent

Apartment • 8 People • 4

• 6

•

From

€

1,640 /night

Min Stay 3 nights

Siena, Italy

€ 1,640 /Night (minimum stay 3 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Kisses

Nestled among the lush greenery of an expansive 1,000-acre private estate, this beautifully restored stone villa is ideally located to allow you to enjoy the ultimate holiday with your family or a group of close friends. Picture yourself serenely floating in the infinity pool while taking in the view of the rolling Tuscan hills below. Imagine sipping a medium-bodied Chianti and tucking into fresh pasta on the sun-drenched terrace while waiting for the Instagram-worthy sunset. There are a couple of barbecues, so you can always indulge in plenty of Florentine steaks if you get weary of pizza and pasta (is that even possible?). When you've had your fill of sumptuous Italian fare, play your favourite tunes on the Bose sound system and chill out with some board games by the fireplace. If you feel like you might have over-indulged, fear not. You can keep up your workout regime by sweating it out in the fitness room or hiking through the surro...More Details

Booked

Available

Siena, House for rent

House • 18 People • 11

• 9

•

From

€

1,633 /night

Min Stay 1 night

Siena, Italy

€ 1,633 /Night (minimum stay 1 night)

Swimming Pool

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 is ...More Details

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