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Italy Italy - Long Term Rentals in Siena Italy
Italy Country: Italy (36245) | Region: Tuscany (4438) | Area: Siena
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    Found 390 Siena long term rentals

    Siena Apartment for rent
    Apartment • 3 beds2 baths • 2,583 ft2 • pets pool wifi
    10,416 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €10,416 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    WiFi

    Chianti Soul


    This restored two-storey stone-built home has a hillside location, so it has wonderful vistas (just don’t bring your sports car as the access road is very steep). You can enjoy the glorious views from the two terraces, the pool, and even the bedrooms. There’s an open fireplace here too for cosy evenings, two lounges and an atmospheric dining room for Italian feasts. Go wine and olive oil tasting locally, and stock up on goodies, or simply go for walks among the olive groves and foothills. The town of Gaiole is 1 kilometre away, while charming Radda is 12 kilometres from this lovely home. *For those with reduced mobility, there's a ground-floor bedroom and bathroom. *Your host can provide a cot and high chair for free. You'll need to request them in advance. *The swimming pool is only available for use between May and September. At a depth of 1.2 metres, the non-chlorine pool is too deep for non-swimming children. *Bedroom ...
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  • Siena House for rent
    House • 4 beds3 baths • 1,722 ft2 • pool wifi
    10,392 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €10,392 EUR /Month
    • Term: Monthly (Furnished)

  • 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'r...
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  • Siena Apartment for rent
    Apartment • 1 beds1 baths   • pets wifi
    22,743 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €22,743 EUR /Month
    • Term: Monthly (Furnished)

  • Pets Allowed
    Air Conditioning
    WiFi

    Cypress Drive


    As you travel up this home's drive lined with cypress trees, you can take in the views of the Tuscan countryside and towns. The apartment has a private patio and garden area to enjoy the Italian sun and vistas. Set in an old country house, the characterful open-plan living room also sleeps one guest on a sofa bed at full capacity. Situated just outside the town of Colle Val d’Elsa, known for its crystal glass production, you’ll find plenty of shops, restaurants and cafes to enjoy. The highway to Siena is also only a few minutes away, making this cultural city easy to explore. *There's no lift here. You'll need to be able to climb stairs to reach the entrance of the home. *At full occupancy, one guest will be sleeping on the sofa bed in the living area. *While the home can sleep up to four people, the maximum occupancy is three guests. *If you're travelling with little ones, your host can provide a cot, baby bath and high c...
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  • Siena Apartment for rent
    Apartment • 2 beds2 baths • 990 ft2 • pets pool wifi
    7,680 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €7,680 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Pops of Flowers


    Situated in the beautiful Val d'Orcia in Tuscany, this 200-year-old farm is the setting for fourteen lovely homes. There's a communal outdoor swimming pool to enjoy during the hot summer days and a wine bar where breakfast is served. The apartment itself has oodles of Tuscan charm and a private terrace area for watching the sunset with an aperitif. If you can tear yourself away, explore the gorgeous cities of Florence, Perugia, Siena, Arezzo and Orvieto, which can be reached by car. *While one bathroom isn’t photographed, we expect the style and quality to be consistent with the rest of the home. *There are fourteen homes at this resort, all with mod cons such as geothermal heating/cooling systems. You may be able to book the other homes together to accommodate larger groups – please ask for more information. *The pool and wine bar are communal. *Due to this home's location, we recommend hiring a car to get the most out o...
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  • Advertisement
    Castellina in Chianti Apartment for rent
    Apartment • 4 beds4 baths   • pets pool wifi
    27,153 EUR /Month
    Term: Monthly

    Apartment in Castellina in Chianti, Italy 

    €27,153 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    First Of The Summer Wine


    Surrounded by olive trees and vast swathes of vineyards, this Tuscan home in the heart of the Chianti wine region is a haven of rural relaxation. Its exposed stone exterior gives way to a bright interior, where farmhouse simplicity meets elegant design in the living room. With its giant hearth, plump sofas and tiered chandelier, this is the perfect spot for socialising over a glass of wine or curling up by the fire with a good book on cooler nights. With four comfortable bedrooms boasting postcard-like countryside views and a farm-style kitchen full of traditional charm, you’ll have everything you need to make yourself right at home. Head outside to take cool dips in the pool, or sit back in one of the many sun loungers while taking in the spectacular hillside views. Wander around the vineyards, visit Castellina in Chianti (less than ten minutes away by car), then come back home for a barbecue under the pergola paired, naturally, with a...
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  • House • 6 6 • 2,480 ft2 •
    63,168 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €63,168 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    The Tuscan Embrace


    Nestled in the rolling Tuscan hills not far from Siena, this six-bedroom villa is packed with rustic character. The timber beams, exposed stonework, and other original features make staying here feel a little like stepping back in time – and we think that adds to the charm of the place. There’s lots of space to get comfortable, whether you’re on a family holiday or group getaway, but our favourite feature has to be the scenic swimming pool. With picturesque views over the surrounding countryside, it’s an extra-special spot to relax in the sunshine, whether you’re swimming leisurely laps or lounging poolside. Bellissimo. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *Due to this home's location, we recommend hiring a car to get the mo...
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  • House • 3 2 • 1,722 ft2 •
    7,608 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €7,608 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Views


    Set on a Chianti hillside, this home promises a serene retreat away from the hustle and bustle of everyday life. Sun worshipers will adore the private terrace, and there’s also a communal infinity pool here, perfect for when you need to cool off in the heat of the day. When you’re ready to explore, you’ll find the local villages of Lecchi and San Sano nearby. Alternatively, take to the Dievole Natural Path – twenty-seven kilometres of trails that lead to the Dievole wine-tasting cellar and open terraced restaurant. *This home is set on a resort alongside neighbouring homes. Expect to bump into other guests during your stay. *There's no air conditioning available here. It could get a little hot during the summer. *There's a communal swimming pool here, open between May and September. The pool isn't fenced, so children must be supervised at all times. *Due to this home's location, we recommend hiring a car to get the most o...
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  • Apartment • 7 7 • 4,736 ft2 •
    32,172 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €32,172 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Soul Of Wine


    To say this luxury handcrafted stone villa took our breath away, well, that's an understatement. This place is enchanting with its vistas over a patchwork of Chianti Classico vineyards, olive groves, and oak forests. Relax by the pool or have a stroll around the vegetable garden and take in the fragrance of the Mediterranean herbs. Our favourite spot has to be the spa area with a sauna, Turkish bath, shower and relaxation zone to one side and pizza oven to the other. Inside, you'll find typical Tuscan features, such as traditional terracotta floors and a country-style kitchen. With its multiple living rooms, this home is perfect for a large family or group of friends. Off one of the dining areas is a snug that converts into a bedroom with an ensuite bathroom – ideal for guests with limited mobility. We adore the local travertine stone bathrooms throughout this villa too. Out and about, you'll find woodland streams and netw...
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  • Apartment • 5 5 • 3,013 ft2 •
    44,478 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €44,478 EUR /Month
    • Term: Monthly (Furnished)

  • 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 l...
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  • House • 10 11 • 6,619 ft2 •
    192,339 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €192,339 EUR /Month
    • Term: Monthly (Furnished)

  • 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 Octob...
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  • Apartment • 4 3 • 4,843 ft2 •
    21,021 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €21,021 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Maremma Amara


    Set out over three levels, with a different perspective over the stunning landscapes around every corner, this vast hilltop villa is guaranteed to impress. The interior is pure traditional Tuscany, with brick archways, exposed beams and terracotta flooring to ground you as you wander from room to room. Each of the individually decorated bedrooms brings its own charm, while the main bedroom – with direct patio access and stunning marble en-suite is set to dazzle even the most seasoned of travellers. The open-plan seating area and dining room form an integral heart of the home and would be the focus almost anywhere else. However, life in Tuscany is best lived outdoors, and you're blessed with a number of balconies, rooftop terraces, poolside patios and landscaped gardens (plus seating areas in each one) that ensure there's always a corner to claim as your own. We imagine you'll spend most of your days sprawled out by the pool, onl...
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  • House • 4 4   •
    46,641 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €46,641 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    Sunset on the Landscape


    Take a look at the amazing views of the Tuscan hills and Siena from this traditional home – they really do stop you in your tracks. The gardens are a dream as well – perfect for alfresco dining and drinks as the sun sets on the stunning landscape beyond. There’s a shared pool to enjoy here too. Or relax in the living room with its open fireplace and characterful beams – it’s a cosy place to be. The large, farmhouse-style kitchen has everything you need to prepare unforgettable Italian meals. And, when you want to explore, the beautiful city of Siena, rich in history, is 10 kilometres away. *This house is set over two floors. *The swimming pool is shared with other guests at neighbouring homes. *The garden is terraced. *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. *Due to this home's location, we recommend hiring a car to get the most ...
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  • House • 4 4   •
    29,169 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €29,169 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    The Vittoria


    This home is a handsome retreat in the heart of Val di Chiana. Outside, you can enjoy stunning views across olive trees and vineyards while lounging by the private pool. There are plenty of shaded areas for lazy afternoon reading sessions, while the terrace lends itself perfectly to evening drinks. The rooms are set across three independent cottages – all of which feature a kitchen and living room. It’s worth noting you will need a car to get around here, but it’s just a short drive to the village of Sinalunga where you’ll find restaurants and shops. It’s also the ideal base for exploring nearby Siena, Arezzo and Montepulciano. *Please note the rooms are set across three independent cottages – two cottages have one double bedroom, and one has two bedrooms. Each house includes a living area, a fully equipped kitchen and a private bathroom. *You may meet the owners and their staff during your stay. *Complimentary toiletries ar...
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  • Apartment • 7 7 • 4,628 ft2 •
    19,104 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €19,104 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    A Tuscan Legacy


    This stunning villa is surrounded by 32 hectares of woods, olive groves, and vineyards. It benefits from a fantastic location close to Tuscany, Umbria and Lazio, making it perfect for families and friends wanting to explore more of Italy. You can reach Siena in forty-five minutes and Rome in ninety – you’ll have your pick when it comes to exciting day-trips. There’s plenty to keep you occupied at the villa, too, with a private pool, barbecue, and billiards. Two guests will be sleeping in an adjacent cottage, which is ideal for a couple seeking more privacy. *We recommend hiring a car to get the most out of your stay. Your host can provide parking on request. *One well-behaved pet is welcome to join you, with prior approval from your host. *The pool is open from 1st May to 15th October. *This home is spread between the main house and an adjacent cottage with a studio layout. *The janitor lives in the former barn next ...
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  • Advertisement
    Apartment • 7 6 • 3,122 ft2 •
    17,568 EUR /Month
    Term: Monthly

    Apartment in Radda in Chianti, Italy 

    €17,568 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    WiFi

    Ceperano is a charming Tuscan farmhouse that has been restored to a high standard and can accommodate up to 14 guests. The property is situated in the heart of the Chianti region, surrounded by olive groves and vineyards, providing a tranquil retreat for families or groups of friends. The farmhouse features four apartments, each offering comfortable traditional furnishings, with three separate kitchens to cater for all dining preferences. Ceperano boasts several furnished terraces and a bamboo-shaded pergola with stunning views, perfect for al fresco dining. The private pool is set in a fenced lawned area, ideal for children playing nearby while adults relax on loungers. Five bedrooms offer flexible sleeping arrangements as they can be either doubles or twins, with plenty of bathrooms throughout the property. Ceperano is within walking distance of the lively town of Radda and an easy day trip from Siena, Florence and San Gimignano. ...

  • Apartment • 3 3 • 1,023 ft2 •
    7,584 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €7,584 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    Ancient Hills


    Just a short drive from historic San Gimignano and its iconic towers, this apartment is a delightful base for six. It’s on a complex in a stunning position close to vineyards and olive groves, and the views of the surrounding hills are breathtaking. You’ll have access to the shared pool, which is perfect for cooling off when the temperature climbs. The apartment is typically Tuscan in style, so you can expect exposed wooden beams and tiled floors. It’s rustic and full of charm. *We recommend hiring a car to get the most out of your stay. *The pool is open from 26th May to 30th September. It’s shared with the other guests staying on the property. *Your host can provide a cot for little ones on request. *There’s a single sofa bed in the living room. *This is a traditional, rustic home so the style may not suit everyone’s tastes. *While not every bathroom has been photographed, we expect the style to be consistent w...
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  • Apartment • 6 4   •
    19,848 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €19,848 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    By The Hearthside


    We immediately fell in love with the view from the swimming pool at this villa tucked into the Chianti hills. Nothing but green hills as far as the eye can see. The grounds are kept blissfully private as a long tree-lined driveway separates the house from the road, so you can dine alfresco and sip a glass of red as the sunsets in complete seclusion. The villa is a picture of Tuscan tradition, from the stone facade and wooden shutters to the original fireplaces and antique furniture inside. Step across the threshold and you’re greeted with the cooling touch of tiled floors and the rustic ambience of timber-beamed ceilings. Our favourite spot has to be the dining room when a long table stands beside the hearth, still adorned with pots and pans as if frozen in the 19th century. The breakfasting kitchen has everything you need for modern-day cooking and there’s a choice between relaxing in the grand lounge by the fireside, or in the cosy fa...
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  • House • 1 1 • 646 ft2 •
    3,408 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €3,408 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Tuscan Wish


    Nestled amongst a hamlet of villas on the edge of San Regolo village, this home is tailor-made for two. With traditional Tuscan interiors, it has a cosy, homely vibe – just the spot to relax after a day exploring the local area. The private terrace is a sweet spot for sipping limoncello on a hot day, and you’ll also find a communal pool here. Lined with sunloungers, it’s ideal if you want to sunbathe or beat the heat. Locally, the village is within walking distance, as is Brolio Castle with its restaurant and wine-tasting room – a must-visit in the area. *This home is set on a hamlet alongside neighbouring homes. Expect to bump into other guests during your stay. *You'll have access to the on-site swimming pool here. It's shared with the hamlet's other residents. *The shared pool, open between May and October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling wit...
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  • House • 6 7 • 4,000 ft2 •
    40,950 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €40,950 EUR /Month
    • Term: Monthly (Furnished)

  • Pets Allowed
    Air Conditioning
    WiFi

    Rural Idyll


    Whereas years ago you would have found a farmhouse on this site, visitors are today greeted by a villa that marries rustic charm and modern amenities. Trust us when we say that you won't find it difficult to relax here, thanks to the beautiful views of vineyards and the ancient walled city of Montepulciano in the distance. As you would hope, there are plenty of spots where you can admire this scenic vista, whether it's out on the balcony, the terrace or the large front lawn. Inside, there are a pair of kitchens, dining rooms and living rooms, which offers an extra degree of flexibility if you're travelling in a big group. There are terracotta tiles and wooden ceiling beams throughout to remind you of the home's heritage, but contemporary kitchens and pristine bathrooms show you how much effort the host has gone to in order to bring the address up to date. Montepulciano and its impressive collection of Renaissance-er...
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  • Apartment • 1 1   •
    3,432 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €3,432 EUR /Month
    • Term: Monthly (Furnished)

  • Pets Allowed
    WiFi

    Casa Dolce Vita


    Set within the atmospheric streets of central Montepulciano, this traditional apartment sits like a gateway to the timeless beauty of Tuscany. Overlooking the verdant garden of an ancient fortress, every detail of this home is steeped in the historic charm of its location. From the traditional features to the antique furnishings and artwork, it’s the kind of space that feels authentically Italian – inviting you to slow down and savour life’s simple pleasures. So whether you’re sipping your morning coffee on the little balcony, or preparing a light bite with local delicacies, it’s easy to feel inspired by the small details of this setting. Stepping outside, you’ll find it’s just a short romantic stroll to the medieval piazza, churches, viewing terraces as well as restaurants and cafés. And for explorations further afield, Montepulciano provides easy access to the majestic cities of Tuscany – both Siena and Florence are wit...
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  • Apartment • 4 5 • 4,305 ft2 •
    21,672 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €21,672 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Sunshine Burst


    You’ll find this rustic villa set among Tuscany’s rolling hills and endless countryside. Inside, there’s a warm ambience thanks to the terracotta tiles, homespun furnishings and farmhouse-style kitchen. If you’ll be spending time outside, we bet you’ll be relaxing by the private pool with a refreshing beverage in hand. Spend afternoons dipping in and out of the water before sitting down to an Italian-inspired feast at the alfresco dining table. If exploring sounds like a good idea, take the short drive to charming Chiusi for a stroll around the honey-hued streets and an espresso in a traditional cafe. Should a day trip be on the cards, travel north to Arezzo – visit the hilltop cathedral, Basilica di San Domenico and the imposing Medicean Fortress. Return to your abode in the early evening for a glass of wine or two on the terrace followed by a night of blissful sleep in the comfortable bedrooms. *Due to the location of thi...
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  • Apartment • 3 3 • 2,260 ft2 •
    18,336 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €18,336 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    The Princess of Chianti


    This enchanting home in the Chianti region of Tuscany is set on a tiny hamlet near Gaiole and dates back to the 14th century. Offering picturesque views of Chianti woodland and vineyards, dare we say, it feels like somewhere straight out of a fairytale. Spread over three floors, all with uninterrupted views, the home reveals a blend of traditional and modern designs, creating an authentically Italian countryside vibe wherever you are in the villa. Fitness buffs can stay active at the home gym, yet with views like these, you'll likely spend much of your time outside in the garden. Here, a private swimming pool overlooks the valley, alongside an alfresco dining area and plenty of places to sunbathe. *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 two cars. *The home is split into three indoor levels and three outdoor terraced lev...
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  • House • 6 6 • 4,000 ft2 •
    20,400 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €20,400 EUR /Month
    • Term: Monthly (Furnished)

  • Pets Allowed
    Air Conditioning
    WiFi

    There's nothing more magical and romantic than the sight of an ancient hilltop Tuscan town, surrounded by rolling hills and cypress trees, and here it's what you'll be waking up to each morning. Set just outside the walls of Montepulciano, surrounded by vineyards and olive trees, this traditional farmhouse has been lovingly modernised by your host to create a perfect, authentic experience of life in this beautiful region. Divided into two apartments, each with three good-size bedrooms, it's easily connected to form a really spacious single home. Set on three levels, you'll have all the character features you'd hope for – terracotta floors, arched windows and heavily beamed ceilings – while much of the home has been updated to offer modern kitchens and luxurious ensuite bathrooms. At the front is a large lawn suitable for kids to play on or adults to sit and read, while the rear patio faces that incredible view of the town. <br...

  • House • 9 9   •
    101,304 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €101,304 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Being of Beauty


    Experience the beauty of Chianti with a stay in this luxurious Tuscan retreat. Owned by a family for more than a hundred years, now you’re invited to step inside and make your own special memories. From the private woodland and wildflower meadows to the outdoor swimming pool, you’ll find everything you could need to settle in and unwind. A member of the royal family designed the rooms and we don’t think you’ll be disappointed. Plus, your host is on hand to help organise a range of extras – including a private chef and wine tasting. And for explorations further afield, it’s just a short drive to Siena and Florence. *Please note this home can accommodate up to eighteen guests and four staff. *Your host provides a starter supply of toiletries. *If you’re travelling with children, your host can provide a cot and a high chair for free on request. *Well behaved pets are welcome to join you here. Air Conditioning<...
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  • House • 5 5   •
    37,716 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €37,716 EUR /Month
    • Term: Monthly (Furnished)

  • 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...
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  • House • 4 3 • 2,153 ft2 •
    12,312 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €12,312 EUR /Month
    • Term: Monthly (Furnished)

  • 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 doubl...
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  • Apartment • 9 6   •
    52,941 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €52,941 EUR /Month
    • Term: Monthly (Furnished)

  • 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 groun...
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  • Apartment • 1 1 • 915 ft2 •
    4,176 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €4,176 EUR /Month
    • Term: Monthly (Furnished)

  • WiFi

    Artistic Grapes


    If you love the artsy side of life, you'll thrive in this contemporary loft. Colourful art pieces stand out, with some splashes of colour added by the feature walls. Natural light pours in through the large kitchen windows – the perfect chance to watch the morning birds fly by. You even get a lovely view of the courtyard from the bedroom too. Spend the day at Constanti winery – this is where your host works, so she will be more than happy to give you a tour of the place. Beautiful vineyards surround the loft and a wide range of wineries to sample some of the tastiest glasses of red. Return home to sit at the dining table while the scent of a home-cooked Italian meal fills the room from the nearby kitchen. After you've eaten, pick a book off of the shelf, and snuggle up on the sofa while the moonlight shines through the windows. Pop the TV on for background noise or simply enjoy the peace and quiet that Montalcino brings. ...
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  • Cottage • 2 2 • 1,184 ft2 •
    7,368 EUR /Month
    Term: Monthly

    Cottage in Siena, Italy 

    €7,368 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    Tuscan Flow


    Nestled in the heart of the Tuscan countryside, this charming cottage offers a tranquil retreat for families or small groups. Set on a resort, if you’re not enjoying the privacy of the cottage garden or hot tub, you can take a refreshing dip in the shared pool, just a short stroll away, or challenge your friends to a game on the tennis court. With walking trails including the Dievole Natural Path on your doorstep, wine tasting, and nearby villages to explore, you’ll find the perfect blend of relaxation and adventure. *This home is set on a resort. Expect to bump into other guests during your stay. *You'll have access to the communal swimming pool and tennis court here. They're shared with the resort's other residents. *The swimming pool is only available for use between Easter and October. *Playing equipment is not provided for the tennis court. If you'd like to play tennis, you'll need to bring your own racquets and balls...
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  • Apartment • 1 1 • 861 ft2 •
    6,168 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €6,168 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Rigomagno Rustico


    While away spectacular sunny days lost in the pages of a good book by the pool, drink fantastic local wines as you relax in the bubbling Jacuzzi, and tuck into Tuscan classics cooked on the brick barbecue at this beautiful countryside chic apartment located within a spectacular villa close to the charming hilltop village of Rigomagno. The interior is a typically Tuscan affair, with terracotta tiled floors underfoot, a large brick fireplace to gather around, and earth tones that soothe the soul, all sitting beneath an exposed beam ceiling. In the bedroom, elegantly draped material adds a touch of Renaissance drama, while the spacious marble bathroom is perfect for post-pool pampering sessions. Step into the shared outdoor space, and you'll find yourself surrounded by eighteen acres of pristine protected forest, with breathtakingly beautiful walks departing right from the front door. In addition to the stunning gardens (comp...
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