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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 298 Siena long term rentals

    Siena Apartment for rent
    Apartment • 4 beds2 baths • 1,615 ft2 • pool wifi
    8,256 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €8,256 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    Tuscan Days


    The shared swimming pool takes centre stage at this Italian home. Surrounded by vineyards and olive trees, you’ll be treated to views of the Tuscan hills from the poolside. You’ll also have your own private garden area with a table and chairs – the perfect spot to enjoy an alfresco espresso in the morning or a sundowner in the evening. The traditional decor inside won’t be to everyone’s tastes, but we love the beamed ceilings and imposing fireplace here. The home is surrounded by 300 hectares of unspoiled nature, so there are plenty of opportunities for hiking on your doorstep, and if you want a slice of history, the medieval town of San Gimignano is within easy driving distance. *While one of the bedrooms isn’t photographed, expect the style and quality to be consistent with the rest of the home. *You'll have access to the on-site swimming pool here. It’s shared with the building's other guests. The pool is only available for u...
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  • Siena Apartment for rent
    Apartment • 6 beds5 baths   • pets pool wifi
    23,331 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €23,331 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Green Stables


    This refurbished farmhouse is essentially two homes in one, perfect for two families travelling together. Both segments of the house have three bedrooms, each with direct access to the lush garden. In the living room, floor-to-ceiling windows lead out to the courtyard and lawns, where there’s a private pool and a pond – ideal for game fishing (provided that the fish is thrown back into the water). The interiors pay homage to the home’s initially intended purpose, as a clubhouse for horse riders to relax in, with paintings of horses adorning the walls, and furnishings that have an old-world charm. Despite the antique bed frames and Moroccan rugs, the home itself feels modern, particularly the suspended fireplace in the heart of the living room, and the sleek kitchen flanked by iron columns and picture-frame windows. Your neighbours are of the equine variety, and with stables next door, guests can book horseback riding lessons, and take a...
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  • Siena House for rent
    House • 3 beds2 baths • 1,238 ft2 • pets pool wifi
    7,320 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €7,320 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    WiFi

    Tuscan Meadows


    This traditional home is nestled among the Tuscan hills. You’ll have a private alfresco dining area here, as well as being able to enjoy a swimming pool, garden bar, children’s playground, and outdoor dining area with other guests. Your host can even arrange a private chef to rustle up a feast, or a pizza night in the communal dining spot. The home’s traditional decor won’t appeal to everyone, but we love the views from here, and the on-site garden bar is something you won’t find in many places. Location-wise, you’re 5 kilometres from Berignone Nature Reserve, with its glorious walks and wild swimming, and a short drive from picturesque Casole d'Elsa, where you can stock up on local produce. *The swimming pool, outdoor dining area, children's playground, and garden bar here are shared with other guests. The pool is available for use from May to September. *If you're travelling with little ones, your host can provide a free cot ...
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  • Siena House for rent
    House • 8 beds7 baths • 5,381 ft2 • pets pool wifi
    21,084 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €21,084 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Tuscan Panorama


    Nestled in the rolling hills of Montepulciano, this villa ticks all the right boxes for a heavenly Tuscan holiday. With seven bedrooms set over the main house and a neighbouring annexe, there’s space for all your favourite people to stay, alongside seven bathrooms to make mornings much easier. Outside, the stunning pool is the centrepiece of the lush grounds, which feel peaceful and secluded despite being only a short drive from town. Just bring a good book and good company and you’ll have all you need for an idyllic Italian break. *The accommodation is spread across the main house and a neighbouring annexe. *One of the bedrooms is on the mezzanine level and semi-open to the space below, so privacy is limited. *If you're travelling with little ones, your host can provide two cost and two high chairs for free. You'll need to request them in advance. *The swimming pool is available from 1st May to 30th September. *The swi...
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    Siena Apartment for rent
    Apartment • 3 beds3 baths   • pets pool wifi
    15,216 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €15,216 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    With its backdrop of rolling hills and its flourish of flowers signposting your welcome, this stone villa on the outskirts of Cetona in Tuscany is a vision of rural relaxation waiting to show you just how delicious slow living can be. Inside, exposed beams and tiled floors await you, with the main living area boasting a large hearth and country views for you to enjoy at your leisure. The farmhouse kitchen is a veritable snapshot of Tuscan traditionalism, while upstairs, three comfortable bedrooms wait to cradle you into a serene sleep. From the first floor, walk out on the geranium framed balcony for views of the lush green grounds, then walk down the stone steps to explore them up close. Here, a sunchair-lined pool invites plenty of dips in its refreshing waters while taking in views of medieval Cetona perched on its hilltop, reachable by car in five minutes. After a day luxuriating in the sun or exploring Cetona’s piazzas and palazzos...

  • Apartment • 4 4 • 3,229 ft2 •
    19,488 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €19,488 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Beauty


    This Tuscan home is a bit special. It’s situated in the medieval hamlet of Vertine, close to the market towns of Gaiole in Chianti – just 2 kilometres away – and Radda, which is 7 kilometres away. The richness of the area’s history is reflected in the home’s decor, which includes frescoes, wooden beams, and antique furniture. Outside, you can admire views of the hamlet’s main square, as well as vistas of the rolling Chianti hills. The private pool has hydrotherapy jets, so you can unwind as you take in the marvellous views. We also love the covered terrace, which is a great spot for dining alfresco. *Your host can provide a cot and high chair for little ones. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *The twin beds can be pushed together and set up as a double bed if preferred. Just let your host know. *Air conditioning is only found throughout the first floor. *Gu...
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  • House • 2 2 • 861 ft2 •
    6,192 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €6,192 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Vines - Serenity


    Wrapped in vineyards and olive groves, this cosy villa in the heart of the Chianti countryside promises a serene escape from daily life. It’s not the biggest inside, but it’s more than comfortable for a family, and with the Tuscan sun shining, everyone will naturally be drawn to the outdoor space. We love the private pool and choice of sunny and shaded spots to relax, all whilst soaking up the far-reaching views. Location-wise, hop in the car and you can reach Lecchi in three minutes or Radda in ten. Peppered with restaurants, they’re both perfect options when you crave authentic Italian cuisine. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May to September, can be fenced upon request. Speak to your host for more details. *The twin bedroom can be set up as a double upon request. You'll need to let your host know at the time of booking. ...
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  • Apartment • 4 4   •
    20,517 EUR /Month
    Term: Monthly

    Apartment in Sovicille, Italy 

    €20,517 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Breathe The Green


    Ah, Tuscany. There’s no better way to explore the verdant Italian countryside than from a rustic farmhouse, and this home has tradition (and charm) in spades. Dating back to the early 1900s, this stone-walled villa with authentic wooden beams has plenty of modern assets, like a luxe swimming pool and cleverly hidden solar panels for those all-important eco-credentials. Whether you’re swinging on a hammock, taking a stroll beneath the majestic oaks that make up the enormous woodlands surrounding the home, or sipping wine on the terrace, you’ll find yourself instantly rejuvenated by the fresh air and natural beauty of the Italian hills. And there’s no chance the kids will get bored – between splashing about in the kidney shaped pool, getting a table-tennis tournament going, or hanging out in their very own private playroom, this home is a paradise for children as well as adults. *Air Conditioning is only available in the bedrooms. <b...
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  • Apartment • 3 3 • 1,270 ft2 •
    7,968 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €7,968 EUR /Month
    • Term: Monthly (Furnished)

  • 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 ava...
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  • House • 5 5   •
    19,776 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €19,776 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Well Garden


    A traditional Tuscan farm stay, surrounded by olive groves and truffle country, this stone villa is as practical as it is beautiful. With plenty of space for a large group to spread out, there are three living spaces, each with a kitchen, allowing for added flexibility. Here, the name of the game is relaxation, and it's not hard to do in such a peaceful setting. In a quiet, rural area with incredible views of the lush green hills, you'll have country walks and cycling routes on your doorstep, and pretty grounds to explore – plus it's just a walk through the woods to the nearby village. Inside, two entrances each lead to a living area and kitchen. Traditionally styled and oozing Tuscan charm, you'll have tiled floors, chestnut beams and fireplaces, along with archways and shuttered windows. Each section has a large dining table so you can all eat together and each of the five bedrooms upstairs boasts its own bathroom so nob...
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  • Apartment • 2 1 • 1,475 ft2 •
    8,040 EUR /Month
    Term: Monthly

    Apartment in Castellina in Chianti, Italy 

    €8,040 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    WiFi

    Grape Juice


    Situated on the first floor of a traditional Tuscan stone building, this apartment puts you right at the heart of rural Tuscany, surrounded by glorious rosemary bushes, grape vineyards and olive groves. Here, you'll enjoy access to the site's fantastic communal facilities, including a terrace area with seating where you can gaze out at the countryside views, plus an outdoor swimming pool that's surrounded by loungers for afternoon naps. Inside, you'll find traditional Tuscan decor that makes the home feel warm and welcoming. *Due to the unpaved, uneven access roads and uphill segments, a high clearance vehicle is recommended, and the roads may be better suited to experienced drivers. *This home is part of a collection of eight cottages and apartments within communal grounds. The swimming pool and parking area are shared, but this semi-detached home has a private entrance and gardens. *The shared pool is for seasonal use from ...
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  • House • 5 5   •
    52,101 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €52,101 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    Jade Hamlet


    Located in the heart of Tuscany, this expansive villa spans fifty hectares and is ideally suited for families or groups of friends. A tasteful blend of traditional features and luxurious interiors include impressive stone fireplaces, rustic wooden beams, and French doors. Enjoy alfresco dining for up to twenty guests, or spend your day lounging by the heated infinity pool, accompanied by the sound of the nearby river. With such a serene setting, it’s easy to forget that the Chianti region — with its wealth of places to see and things to do — lies just beyond the door. *While the bedrooms and bathrooms aren't photographed, expect the style and quality to be consistent with the rest of the home. *The fifth and final king-size bedroom is built into the original tower of the homestead. It's accessed via a preserved wooden staircase and offers 360-degree views of the property. *Three-hour morning cleaning is included daily with e...
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  • Apartment • 5 5   •
    67,578 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €67,578 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Sunflower Hill


    This home, composed of three suites and two cottages, sits on an exclusive estate just 1 kilometre from the historic centre of Montepulciano. It’s in a breathtaking spot overlooking a vineyard-filled valley, with the marvellous views visible from inside and out – the living room boasts floor-to-ceiling arched windows. The outside space is stunning, with a private pool and gardens filled with fragrant roses, fruit trees, and even a vegetable patch. We love the rustic touches that sit alongside modern amenities – you get the best of both worlds here. *This home is composed of three suites and two cottages, so you won’t all be sleeping under the same roof. *There are stairs to climb at this home, so it may not be suitable for those with reduced mobility. *While not every bedroom or bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *Well-behaved pets are welcome to j...
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  • House • 4 2 • 1,507 ft2 •
    10,224 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €10,224 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    WiFi

    Ivy - Olive


    Calling all wine connoisseurs – this villa puts Chianti's vineyards at your fingertips. Whether you're touring local wineries or day-tripping to the towns of Radda and Siena, this is a picture-perfect base for a Tuscan getaway. Back home, spend your afternoons lazing by the pool, nibbling on pizza cooked in the built-in barbecue, and playing rounds of outdoor ping-pong. Inside or out, there's no shortage of space to relax. The interiors are a tad dated, but we think that's all part of the charm. *The twin beds can be converted into doubles if needed. You'll need to request this when booking. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool is available to use between May and September. Please get in touch with your host for the exact dates. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *You’ll need ...
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  • Advertisement
    House • 9 9 • 8,611 ft2 •
    64,113 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €64,113 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Winery Way


    This beautiful home is perfect for celebrations and special occasions. The hilltop villa boasts panoramic views from Monte Amiata to Siena in the lap of Val d’Orcia, a UNESCO World Heritage Site. The restored stone property is a winery licensed for events, and with its terracotta floors, vaulted ceilings, and antiques, it’s bound to impress. There are multiple living areas and a professional kitchen, as well as a garden with stunning vistas and a gorgeous alfresco dining space. Whether you’re staying here for an event or just want an elegant home-from-home in Italy, this villa is sure to make for a memorable stay. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms are suitable for those with reduced mobility. *Bedroom eight can be set up with twin beds or a double Air Conditioning Barbeque Bathtub Beach / Pool Towels Child Friendly Coffee Mak...
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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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  • House • 6 6 • 3,875 ft2 •
    22,239 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €22,239 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Forever Light


    This Tuscan home is set within a peaceful garden just outside the small town of Sarteano. Offering tranquility and privacy, it’s the perfect setting for a slow Italian escape. There’s a private pool for refreshing swims, a terrace with a barbecue and outdoor games for family fun. Inside, the rooms are set across two independent apartments – making this a great option for groups looking to stretch out and spend quality time together. You will need a car to get around here, but it’s just a short drive to the nearest amenities, while some of the most beautiful spots of Tuscany and Umbria are within easy reach. *Please note this home consists of two independent apartments. They are not connected internally. *It is possible for the bedrooms with single beds to be arranged as doubles on request. *If you're travelling with little ones, your host can provide a cot and high chair for free on request. *Please note the fireplace is ...
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  • Apartment • 3 4   •
    18,792 EUR /Month
    Term: Monthly

    Apartment in Radda in Chianti, Italy 

    €18,792 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    The Fruits of Chianti


    Nestled within the iconic green hills of Tuscany, close to the charming hilltop town of Radda, this beautifully restored farmhouse has everything you need for a good time – delicious food, great wine and quality time with loved ones. Both the interior and exterior boast traditional features, with wooden-beamed ceilings, terracotta tiles and exposed brick creating a cosy atmosphere and a sense of authenticity. The lawn is beautifully kept and offers a private pool and outdoor shower, which provide an invigorating start to the day. Once you're feeling refreshed, it's time to explore – get the mountain bikes out from the bike shed and go for a scenic cycle into town for a cultural adventure. This quintessential Tuscan town is home to upmarket boutiques, art galleries and 360-degree panoramic views thanks to its high position. Wine lovers will be in their element in Chianti – we highly recommend spending an afternoon wine tasting in...
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  • Apartment • 5 7   •
    23,457 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €23,457 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Moonlight Moments


    Surrounded by flourishing trees with sweeping views across the hills of Chianti, every detail of this home sings with the natural beauty of Tuscany. From the rustic interiors to the antique furnishings and personal touches, the owners have retained the authentic spirit of this traditional country home. And while its foundations date back to 1900, it now exists as a contemporary sanctuary – a private space to lose yourself in the timeless magic of Italian living. Stroll through the verdant garden, spend lazy mornings sipping coffee in the shade, take cooling dips in the pool and savour delicious Italian meals – served straight from the barbecue. By night, the soft glow of sunset transforms the terrace into the perfect setting for intimate candlelit meals and stargazing, while the sauna (available on request) provides an idyllic spot to relax before slipping into bed. Beyond this rural haven, it’s just a short scen...
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  • Apartment • 2 1 • 753 ft2 •
    4,752 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €4,752 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    WiFi

    Where Time Stops


    Situated on the outskirts of the charming town of Poggibonsi, this rustic apartment is an idyllic escape for a small family or two couples looking to spend some time in Tuscany. We loved the traditional features, particularly the timber ceiling beams and the terracotta tiles. Outside, there’s a private terrace for enjoying home-cooked dinners or an evening glass of wine. You also have access to a communal swimming pool and a tennis court. For those keen to explore, Florence is an ideal day trip destination, less than an hour’s drive away. *Due to the location of this home, we recommend hiring a car for ease of getting around. Parking is available on the premises. *If you’ll be staying with a little one, your host can provide a cot and high chair upon request. *Guests staying here have access to a communal swimming pool (open from the 18th of May to the 18th of September) and a tennis court. Barbeque Central ...
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  • Apartment • 2 2 • 1,345 ft2 •
    7,800 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €7,800 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Sweet Tuscan Dreams


    This apartment makes it easy to experience the timeless charm of Tuscany. Nestled within a private estate, you’ll find a communal pool and peaceful gardens with a barbecue and alfresco dining area – perfect for leisurely evening meals. The apartment is simple, fresh and well suited to families in search of ease and comfort in a fantastic location. From here, you can stroll to a traditional restaurant and it’s possible to drive to Siena and Florence for day trips. Your host is also on hand to help organise a range of extras – including private chefs and guided tours. *Please note this home is set within a private estate. There is a communal swimming pool which is available for use from May to September. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Well behaved pets are welcome to join you here. *Parking is available for up to two cars. Air Conditioning B...
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  • House • 6 6   •
    47,166 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €47,166 EUR /Month
    • Term: Monthly (Furnished)

  • 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 p...
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  • Apartment • 3 2 • 1,615 ft2 •
    7,560 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €7,560 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Pets Allowed
    WiFi

    Wine in the Hills


    This delightful holiday home is located in the beautiful countryside of Tuscany. It’s just a ten-minute drive to the Pietraporciana Nature Reserve and fifteen minutes to the Sarteano Civic Archaeological Museum, so there’s plenty to see and do nearby. The home boasts wonderful views over a valley and Mount Amiata, which can be admired from the private pool and garden. Your host offers free wine tastings in the homeowner’s family wine cellar – what more could you ask for from a Tuscan escape? *One well-behaved pet is welcome to join you during your stay, with prior approval from your host. *There’s free parking at this home. We recommend hiring a car to get the most out of your stay. *The pool is open from 1st May to 14th October. *Your host can provide a cot for little ones. *Your host can arrange a wine tasting for you at the owner’s family’s wine cellar in the historic centre of Cetona. *There are stairs to cl...
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  • Apartment • 4 3   •
    8,880 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €8,880 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    WiFi

    A Fine Vintage


    Surrounded by olive groves and vineyards, the surrounding landscape of this home in the Chianti Hills is as idyllic as you might imagine and the living quarters are equally as rustic. The main stone tower dates back to the 17th century, while the farmhouse is covered almost completely in foliage. The interiors of both buildings overflow with historic character, with wooden ceiling beams and terracotta tiling playing host to traditional fireplaces, vintage furnishings and ornate bed frames. It's only the sleek bathrooms that lean on the contemporary side. Step outside and you'll find terraces that look out over the bucolic Tuscan countryside, as well as a swimming pool surrounded by loungers, an alfresco dining area and a barbecue. In addition, there's a well-kept garden in which you can find a shady spot to while away sunny afternoons. Although the location certainly feels isolated, there are plenty of quaint town...
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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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  • Apartment • 3 3 • 1,184 ft2 •
    9,240 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €9,240 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    The Bishop's Garden


    This charming apartment is located in the beautiful Tuscan countryside, in a quiet village along the Via Francigena. San Gimignano is just 8 kilometres away, and the home is surrounded by gentle hills, vineyards, and olive trees – it’s a peaceful base for a family break but you’ll still be within easy reach of restaurants and shops. We love the views outside, and the shared swimming pool. Inside, you’ll find 19th-century furniture, including a stunning wooden bed in the main bedroom. *There’s free parking here. We recommend hiring a car to get the most out of your stay. *The shared swimming pool is open from 26th May to 30th September. *Your host can provide a cot for little ones on request. *Each apartment in this complex has a garden space with a table and chairs. *There are stairs to climb to reach the entrance to this home, so it may not be suitable for those with reduced mobility. Air Conditioning ...
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  • House • 3 3 • 2,153 ft2 •
    19,800 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €19,800 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Hilltop


    This beautiful, traditional villa sits in the Chianti countryside between the wine towns of Radda and Gaiole in Chianti. It’s a splendid spot, whether you plan on exploring the local vineyards or just want to laze beside the private pool and admire the view – you can look forward to a 180-degree panorama of the countryside and a nearby hilltop town. The villa is charming and cosy, with authentic terracotta tiles and beamed ceilings. The terrace is perfect for alfresco dining. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. Air Conditioning Barbeque Bathtub Beach / Pool Towels Child Friendly Coffee Maker Cot / Crib Dishwasher Fan Fenced Property Fireplace Freezer Fridge Garden Hair Dryer High Chair Kitchen Kitchen U...
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  • 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 • 1,119 ft2 •
    7,224 EUR /Month
    Term: Monthly

    Apartment in Siena, Italy 

    €7,224 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    A Touch of Tuscany


    Surrounded by vineyards and olive trees in the Tuscan countryside, this apartment ensures a restful stay for a family or a group of friends. We loved the traditional features, particularly the exposed stone walls and the timber beams. Outside, there’s a dining table and chairs for alfresco lunches and a communal swimming pool for keeping cool in the summer. You???ll need to hire a car for stress-free exploring – the medieval city of Siena is less than an hour’s drive away. *Due to the location of this home, we recommend hiring a car for ease of getting around. *At capacity, one guest will sleep on the sofa bed in the living space. *Please note that only one of the bathrooms has a window. *If you’ll be staying with a little one, your host can provide a cot upon request. *The communal swimming pool is open from the 26th of May to the 30th of September. Air Conditioning Barbeque Central Heating Co...
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  • House • 2 2 • 969 ft2 •
    14,688 EUR /Month
    Term: Monthly

    House in Siena, Italy 

    €14,688 EUR /Month
    • Term: Monthly (Furnished)

  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Escape


    Tucked away in the vineyard of a prestigious winery, this elegant cottage overlooks the beautiful Tuscan countryside. But not only are the views from the swimming pool and outdoor seating beautiful, but the house itself is also stylish. With only two bedrooms and a guest count of four, it has plenty of space. It would be especially suited to two couples or a small family. It's private and peaceful, located just a 4-minute drive from the historic center of Gaiole in Chianti. For day trips, Siena and Florence are under an hour away by car. *There’s free parking for one car on the driveway. *The swimming pool – available between 1st May and 30th September – isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *The fireplace is for decoration only. *If you want to stock up on essentials during your stay, you'll find the closest supermarket minutes away. Air Conditioning Balcony...
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