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    Found 188 Siena properties for vacation rental

    Houses (38) Apartments (145) Rooms (1) Townhouses (1) Cottages (3)
    Apartment • 12 People • 6 5 pets pool wifi
    From
    1,001 /night
    Min Stay 3 nights


    Siena, Italy

    € 1,001 /Night (minimum stay 3 nights)
  • 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...More Details

    • Booked Available
    Apartment • 10 People • 5 6 pets pool wifi
    From
    1,112 /night
    Min Stay 3 nights


    Siena, Italy

    € 1,112 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Sage and Rosemary
    Surrounded by 10 hectares of land, featuring olive groves, lush woods and picturesque vineyards, this home is the perfect introduction to the Tuscan countryside. From the terrace, you can take in the view of the region’s rolling hills, with the hilltown of Poggibonsi rising up in the distance. As you wander through the gardens, breathe in the scent of the lavender, sage and rosemary plants. It’s easy to relax here, whether you’re going for a leisurely swim in the pool, taking some time out in the whirlpool tub or relaxing with a sundowner on the outdoor sofas. Typically Tuscan on the outside, with red-shuttered windows and a terracotta roof, this villa adds a dash of opulence to the occasion inside. From the bright living room with its arched French windows framing the view, to sparkling candelabra above the long, dark-wood dining table. Bedrooms and bathrooms have traditional touches – hand painted wardrobes, vibrat vintage tiling, and...More Details

    • Booked Available
    Apartment • 16 People • 10 9 pets pool wifi
    From
    1,143 /night
    Min Stay 3 nights


    Siena, Italy

    € 1,143 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Texture Like Sun
    A hideaway in the Tuscan countryside, this beautiful home has an air of old Italy about it, without sacrificing modern comforts. Surrounded by the gold and green hills, it's a home for those who want to take a break from the everyday and bring the entire family along to do it with. With two houses and a sprawling garden, there is definitely enough room to accommodate everyone. In the mornings, step outside for an espresso before taking a refreshing dip in the pool. Relax under the Italian sun on one of the loungers — or retreat to the covered pergola with a good book. Inside, the home has retained many of its original features, including wood-beamed ceilings, an open stone hearth in the living room, and tall, arched windows looking out over the grounds. Sunflower-yellow walls throughout are sure to put a smile on your face. When golden hour hits, step outside to take in views of the Tuscan countryside, golden-hued and changing by the se...More Details

    • Booked Available
    Apartment • 14 People • 7 6 pets pool wifi
    From
    975 /night
    Min Stay 3 nights


    Siena, Italy

    € 975 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Rolling In Olives
    This traditional farmhouse, buried deep in the Tuscan hills, offers guests a taste of everything this area is known for – picturesque mountain views, pretty vineyards and lush olive groves. Sat in the heart of 'Chiantishire', you’re surrounded by idyllic villages like Castellina and Radda, and perfectly placed to explore this world-renowned wine region. Back at the home, you’ll find everything you need for the quintessential Tuscan trip, with a glimmering pool overlooking the rolling hills, plenty of seating areas dotted around the lush green gardens and a sun-kissed patio, plus enough space to make sure a large group can sprawl out and unwind. Set across two buildings, both interiors exude rustic charm with beamed ceilings and stone archways. Furnished with plenty of Italian passion, there are comfy sofas, a huge dining table and an authentic kitchen. Fire up the barbecue and wait for the meat to grill while indulging in a sundown aper...More Details

    • Booked Available
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    Apartment • 2 People • 1 1
    From
    234 /night
    Min Stay 3 nights


    Siena, Italy

    € 234 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    WiFi

    Located just outside Cetona in Tuscany, this picturesque home is the perfect place to find peace and tranquility amidst the region’s renowned rolling hills and forests. A renovated stone mill, its romance is clear the moment you step inside. From its beamed ceilings, traditional kitchen and bright study that leads out in the garden, this compact but comfortable villa feels like an intimate country hideaway made for the sole purpose of your relaxation. And then there’s the bedroom with its forest palette, green gothic headboard and access to the terrace. Wake up and head outside for your morning coffee under a shady oak tree, then while away the hours in the pool or discover the babbling brook just beyond the home’s canopy of trees. The medieval town of Cetona with its sandy-hued piazza and palazzo is also just five minutes away by car. After a day luxuriating by the pool or exploring the nearby sights, come back home for a glass of wine...More Details

    • Booked Available
    Apartment • 4 People • 2 2
    From
    382 /night
    Min Stay 3 nights


    Siena, Italy

    € 382 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Silk - Cypress
    A true Tuscan dream, this beautiful home in the middle of the countryside is an elegant rural retreat surrounded by Val d'Elsa's rolling hills, cypress trees and vineyards. It’s the ideal home for those looking to luxuriate in taking things slow. Inside, beamed ceilings, large windows and an elaborate hearth give the upstairs living room a feel of classy decadence, with two beautiful bedrooms completing the ground floor. Downstairs, a homey open-space living area invites plenty of casual socialising, as well as the kitchen and dining area ready to make all your Italian feast fantasies come true. Thanks to its terraced layout, you’re never far from a pair of French doors leading out onto the glorious garden. With its 1,500 square metres of lush, green grounds, you can while away the hours taking sunny walks or cool off with a dive into the glistening pool. Watch the sunset over the horizon with drinks under the poolside umbrella, then si...More Details

    • Booked Available
    Apartment • 12 People • 6 6
    From
    1,405 /night
    Min Stay 3 nights


    Siena, Italy

    € 1,405 /Night (minimum stay 3 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Palatial Peasant
    It might sound impossible but we think the perfect Tuscan villa should manage to give off both a peasant and a palatial vibe at the same time. You know the kind of thing: a rambling country house that despite its impressive size – dozens of high ceilinged rooms, imposing archways, ideally a swimming pool out in the capacious grounds – still gives the impression that its occupants might just be out in their orchard picking olives. That description certainly applies to this gorgeous family-friendly villa: a classic example of super-relaxed luxury. Located in the Tuscan countryside, it’s surrounded by forests and within an hour’s drive of tourist favourites like Siena, Florence, Lucca, Pisa and Assisi. Inside you’ll find a country kitchen with a rustic dining table to seat 12 * Heating and electricity come as an extra charge* The pool is in use from April to October*City taxes are not included in the price of the stay and will be collecte...More Details

    • Booked Available
    Apartment • 11 People • 5 5
    From
    1,088 /night
    Min Stay 3 nights


    Siena, Italy

    € 1,088 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Rustling Oaks
    This period stone villa, filled with antique furnishings, is what we call love at first sight. You will have four spacious floors all to yourself for a dream Tuscan escape with your loved ones. The property sits in the open countryside among rolling hills dotted with cypress trees. Outside, in the manicured gardens, you can make the most of the sunny days and read a book beside the pool or unwind in the Jacuzzi with a cocktail. You will never get weary of listening to the rustling oaks and orchard trees or inhaling the scent of herbs and roses. Sweat out any remaining stresses in the sauna, then whip up some fresh pasta in the kitchen and round up everyone for dinner under the gazebo. Should you need anything more, you’re just a one-minute drive from Sarteano, with its charming medieval houses, wine bars, restaurants and shops. *The pool is open from the last Saturday of April until the first Saturday of October*You have to pay separat...More Details

    • Booked Available
    Apartment • 12 People • 6 7
    From
    1,244 /night
    Min Stay 3 nights


    Siena, Italy

    € 1,244 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    WiFi

    The Orchard Song
    This 19th-century farmhouse has been beautifully restored, preserving all period features like terracotta tiles, oak floors and a travertine marble staircase. The sumptuously decorated dining rooms, living room and rustic-style kitchen are all interconnected without being totally open-plan, and there are as many dining room options as there are meals of the day. Sit up, formal-style under chintsy candelabra, country-style around the hardwood table, or alfresco, under the shade of the pergola. Outside you’re surrounded by rolling hills covered in vineyards and olive groves. Under the shade of oaks, cypresses, peach and apricot trees, and among the fragrant flowers, herbs and figs, you can easily believe the Garden of Eden is in Tuscany. At dusk, let the barbecue sizzle and sip celebrated local wines while listening to the songs of cicadas and crickets. In the morning, tip-toe to the pool for a refreshing swim and breakfast on the sundeck...More Details

    • Booked Available
    Apartment • 12 People • 6 8
    From
    2,289 /night
    Min Stay 3 nights


    Siena, Italy

    € 2,289 /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

    • Booked Available
    House • 10 People • 5 5
    From
    1,637 /night
    Min Stay 3 nights


    Siena, Italy

    € 1,637 /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
    Apartment • 10 People • 5 5
    From
    966 /night
    Min Stay 5 nights


    Siena, Italy

    € 966 /Night (minimum stay 5 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    Peeping over the rolling vineyards of the Val d'Arbia, this hillside home is all soaring beamed ceilings, flagstone floors and antique furnishings. While it retains original features and an unmistakable Tuscan countryside charm, it’s been brought up to the minute with a private pool and access to spa and state-of-the-art gym. In the mornings, take the supplied bicycles for a ten-minute ride into the gorgeous town of Buonconvento—the ancient Via Francigena route is worth it alone. Pick up fresh produce from the greengrocers to be served at lunchtime, alongside homemade wood-fired pizzas, cooked in your open-air oven. In the afternoons, pick a spot under a parasol with your holiday read, moving only for a revitalising dip in the cool water and to top up your glass with the region’s famed wine. *The pool is open from mid-May to the end of September *The spa and gym are shared with a nearby villa—your host will help in coordinating the acc...More Details

    • Booked Available
    Apartment • 10 People • 5 6
    From
    1,561 /night
    Min Stay 4 nights


    Siena, Italy

    € 1,561 /Night (minimum stay 4 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    Sienese Waltz
    This villa dates back to the twelfth century, but you'll be happy to hear that there have been a few additions since then. Most notable of them is the long swimming pool in the verdant grounds, which comes with a large parasol, loungers and an electric cover to keep the water warm over the nighttime. The tennis court is also comparatively new, as are the gym and spa facilities — shared with a neighbouring villa — which include a sauna, steam and hot tub. Inside your home, you'll note a certain sense of decadence with the decor, especially in the dining room filled with an impressive collection of painted portraits in different styles and a grand chandelier. One thing this address is truly blessed with is outdoor seating areas, which, as you can imagine, are just the ticket on those long Tuscan summer evenings. It's from these shady seats that you'll be able to appreciate the peace and quiet that abounds in this corner of the world, but ...More Details

    • Booked Available
    Apartment • 6 People • 3 3
    From
    510 /night
    Min Stay 1 night


    Siena, Italy

    € 510 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Tuscan Serenity
    Amidst the rolling hills and long stretches of vineyards, you'll be captivated by the peace and serenity of this place from the moment you arrive. Stone clad brickwork and cobbled paths set the scene with a backdrop of the surrounding countryside – painting a picture-perfect view of blissful Tuscan serenity. Inside exposed wooden beams and traditional tiled flooring bring charm to the otherwise modern interiors, and you'll have the choice of eating alfresco or at cooler temperatures from the indoor dining area, when it comes to meal times. Take a dip in the outdoor shared pool, or embark on the day's adventures in and around Tuscany. With golfing, horseback riding, cycle paths and walking trails on offer, if you're the. outdoorsy type – this is the place for you. After a day of exploring feel rest assured in knowing that the bubbling jacuzzi awaits your return – but don't forget to pour yourself a glass of wine before getting in. *Some...More Details

    • Booked Available
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    Apartment • 12 People • 6 4
    From
    950 /night
    Min Stay 5 nights


    Siena, Italy

    € 950 /Night (minimum stay 5 nights)
  • 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...More Details

    • Booked Available
    Apartment • 8 People • 3 4
    From
    817 /night
    Min Stay 7 nights


    Siena, Italy

    € 817 /Night (minimum stay 7 nights)
  • Swimming Pool
    Air Conditioning
    WiFi

    In the heart of the Tuscan countryside, spending your time in a remote villa is a rite of passage. Just 3 km from San Gimignano, a UNESCO-heritage-awarded medieval town, this modern country home offers quite the opposite experience. As you roll up to the tree-lined driveway the house will emerge like an oasis, behind which is your private lawn, pool, barbecue, and shady patio for alfresco dining. While it’s tempting to head straight to the sun loungers, we’ve not even reached the house yet. Its warm, terracotta exterior looks incredibly inviting, with huge French windows ushering you into the main living space. Inside, the decor is far from traditional Italian. Find a sleek grey kitchen, cow-print footrests, and a perspex chandelier in this high-ceilinged space. Peep around the corner to find the glass doors to your private sauna, or look up to the mezzanine floor with its reading nook (a perfect place for a glass of chianti in the afte...More Details

    • Booked Available
    Apartment • 10 People • 5 5
    From
    968 /night
    Min Stay 1 night


    Siena, Italy

    € 968 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Italian Dream
    This swoon-worthy Tuscany villa presents a dreamy fairytale-like setting amidst the quiet, green woodland of Sarteano. Unveiling romantic and characteristic scenery, the home itself is also brimming with charm and personality throughout. Stone walls, exposed wooden beams and terracotta tiling invite guests in for a true taste of Tuscan design. With a combination of modern and traditional furnishings, the home boasts both comfort and practicality, all while remaining true to its quintessentially Italian identity. Stylish, warm and welcoming, the space allows guests to soon feel relaxed and at ease upon arrival. A stone patio separates a three-storey annexe from the front of the main building, meaning guests can benefit from the extra added privacy of having two separate living spaces – perfect for groups of multiple families. The annexe features two en-suite double bedrooms, with its own lounge and kitchen. Beyond the house, you'll have ...More Details

    • Booked Available
    Apartment • 10 People • 4 3
    From
    990 /night
    Min Stay 1 night


    Siena, Italy

    € 990 /Night (minimum stay 1 night)
  • 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, only interr...More Details

    • Booked Available
    Apartment • 7 People • 3 2
    From
    186 /night
    Min Stay 3 nights


    Siena, Italy

    € 186 /Night (minimum stay 3 nights)
  • Air Conditioning
    WiFi

    Beyond the Bridge
    This charming apartment is in the old town of Colle di Val d'Elsa, a typically medieval region of Tuscany famous for crystal glass production. It’s a ten-minute stroll into the centre where you’ll find restaurants, cafés and archaeological museums beyond the ancient town walls. Further afield, the city of Siena is a half-hour drive away, ideal for a day trip.The apartment itself is housed in a striking 16th-century building just outside the bridge that leads to il Castello. Wood beams on display hark back to the building’s roots, but the decor is decidedly modern. Vibrant modern art is displayed above the plush, L-shaped sofa and the kitchen is a sleek space of white cabinets. The best bit is the view from French-style windows, which shows off golden fields and hills, even though you’re a short walk from the town centre. *This apartment is up a set of stairs and shares a building with five other apartments*There are also steps into som...More Details

    • Booked Available
    Apartment • 14 People • 6 6
    From
    1,127 /night
    Min Stay 7 nights


    Siena, Italy

    € 1,127 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Antipasti on the Patio
    Just 11km outside of Siena, nestled on a hilltop in the Tuscan countryside, you'll find this idyllic villa. It's a gorgeous spot with over a thousand square metres of grounds to explore, and plenty of space for your friends and family to roam. The home itself is vast, with charming Italian interiors that combine high-end luxury with comfort and cosiness – think chandeliers, sumptuous fabrics, and terracotta tiles. There's a gym with views over the valley, where you can work up a sweat, and an outdoor wood-burning oven for you to refuel yourself alfresco. Outside, there's a covered loggia that extends the entire length of the villa, along with a vegetable patch where you can pick fresh ingredients. There's also a fabulous swimming pool, complete with an outdoor shower, as well as a hot tub for long, revitalising soaks.Exploring the splendid Tuscan landscapes is easy from here – visit picturesque villages, working vineyards, and rolling h...More Details

    • Booked Available
    Apartment • 16 People • 8 8
    From
    1,372 /night
    Min Stay 1 night


    Siena, Italy

    € 1,372 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Arches - Enclaves
    On a hill in the beautiful Val d’Orcia, this traditional stone villa looks out over the undulating countryside. It’s a forty-minute drive to the medieval walled city of Siena, should you fancy a day trip, but the surrounding area has plenty to keep you busy with walking trails and wineries galore.Outside, an immaculate lawn is fringed with herbs and wildflowers, and secluded by ancient trees. Slip into the rectangular swimming pool and float beneath the blue skies in summer, or bag a lounger and while the day away with a book in hand. A handful of terraces and balconies are home to outdoor dining areas and seating nooks with fabulous country views. Inside, the lounge is a vision of old-world charm with brick archways leading from one seating area to another. Pull up an armchair at the arched picture window, which frames the forest-clad hills outside like a work of art. Or, opt for a seat by the old hearth which still has its cooking pot...More Details

    • Booked Available
    Apartment • 10 People • 4 5
    From
    907 /night
    Min Stay 1 night


    Siena, Italy

    € 907 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Rosemary - Quill
    Just like the romantic notion of Tuscany we've all gleaned from books and films over the years, this beautiful, rustic farmhouse stands on an enormous estate, filled with centuries-old olive groves and famed for its high-quality olive oil. Peaceful and secluded, yet only five minutes from the town, it's the quintessential Tuscan retreat – complete with a new pool and a huge private garden dotted with cypress trees, shady oaks and olive trees.Stone-built in the 18th century and packed with character thanks to its terracotta floors and exposed timber ceilings, it's a charming and comfortable home that's been through a careful restoration recently. We love the living room, with its fireplace and archways, but there are modern touches here too – most notably in the contemporary kitchen and the metal staircases. Bedrooms and bathrooms are typically spacious and elegant, and most have views to die for. And there's a unique reading room in the...More Details

    • Booked Available
    Apartment • 10 People • 5 5
    From
    2,089 /night
    Min Stay 1 night


    Siena, Italy

    € 2,089 /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

    • Booked Available
    House • 12 People • 6 7
    From
    1,563 /night
    Min Stay 7 nights


    Siena, Italy

    € 1,563 /Night (minimum stay 7 nights)
  • 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-era architecture can be re...More Details

    • Booked Available
    House • 6 People • 6 6
    From
    784 /night
    Min Stay 7 nights


    Siena, Italy

    € 784 /Night (minimum stay 7 nights)
  • 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.Walk or drive i...More Details

    • Booked Available
    Apartment • 6 People • 3 3
    From
    897 /night
    Min Stay 7 nights


    Siena, Italy

    € 897 /Night (minimum stay 7 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    Vista a Montepulciano
    One of two three-bedroom apartments set within a traditional Tuscan farmhouse, it offers a welcome respite from the hustle and bustle of everyday life, overlooking the hilltop town of Montepulciano.Despite its recent renovation, your hosts have done their utmost to maintain the period features that made this villa so special in the first place, so the original archways, exposed beams and wooden windows remain. However, stylish contemporary furnishings and a sleek kitchen bring it firmly up to date. All en-suite bedrooms complete the interior offering, each with views over the medieval town of Montepulciano, while guests staying in the main suite benefit from direct access to the balcony. *Some of the outdoor spaces are shared with the other apartment in the building*The villa is set over three levels, so it may not be suitable for those with limited mobility*We'd recommend a car to fully explore the area – there's ample on-site parking...More Details

    • Booked Available
    House • 20 People • 9 9
    From
    2,423 /night
    Min Stay 3 nights


    Siena, Italy

    € 2,423 /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

    • Booked Available
    Apartment • 14 People • 7 7
    From
    1,569 /night
    Min Stay 3 nights


    Siena, Italy

    € 1,569 /Night (minimum stay 3 nights)
  • 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 networks of ancient ...More Details

    • Booked Available
    Apartment • 12 People • 4 4
    From
    1,104 /night
    Min Stay 3 nights


    Siena, Italy

    € 1,104 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    My Chianti Heart
    Surrounded by vineyards tumbling down hillsides and towering trees, this stone villa sits in the heart of the Chianti Hills. The beautiful village of Lecchi with its ancient castle is just a six-minute drive away if you’re not too busy discovering the family-run wineries and vineyards on your doorstep.This villa was designed for entertaining, inside and out. In the lush garden, you’ll find seating for a huge group, shaded by a pergola. Perhaps unwind in the hot tub after a session in the gym. There’s also a sauna for post-workout relaxation. If swimming laps is more your style, there’s a shared swimming pool at the bottom of the estate, lined with loungers.Inside, the grand lounge is set around an old hearth, just like you’d expect in a traditional old Tuscan farmhouse. Wooden ceilings and terracotta floors are a nod to the past, while the pops of vibrant colour throughout keep things lively and modern. Especially in the dining room, wh...More Details

    • Booked Available
    Apartment • 6 People • 3 3
    From
    860 /night
    Min Stay 3 nights


    Siena, Italy

    € 860 /Night (minimum stay 3 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Olive Stone
    Enjoying a secluded spot in the Chianti countryside, this traditional stone villa is packed with things to keep you entertained. The gardens are a delight, where olive groves provide a spot for a shady stroll, and vineyards tumble down the hillside around you. Set up for a lazy lunch beneath the pergola – there’s dining for the whole group here. Shared between a handful of stone villas on the same estate, there’s a swimming pool at the bottom of the garden.Inside, whitewashed wooden ceilings speak of days gone by and there’s a traditional Tuscan farmhouse vibe throughout. Terracotta floors keep things cool underfoot and bedrooms and bathrooms are all super spacious. The kitchen in jolly aquamarine-blue is more than big enough to handle the hustle and bustle of a busy breakfast time too.Exploring the area, you’ll find the charming village of Lecchi to be a six-minute drive away where the ruins of an ancient castle await. Plus you’re in t...More Details

    • Booked Available
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