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Italy  Italy - Holiday Rentals in Siena Italy
Italy Country: Italy (11002) | Region: Tuscany (3452)
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    Found 268 Siena holiday homes for rent

    Siena, Apartment for rent
    Apartment • 2 People • 1 • 1 • wifi
    From
    €
    174 /night
    Min Stay 1 night


    Siena, Italy 

    € 174 /Night (minimum stay 1 night)
  • 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. *There’s f...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 6 People • 3 • 2 • wifi
    From
    €
    485 /night
    Min Stay 1 night


    Siena, Italy 

    € 485 /Night (minimum stay 1 night)
  • Air Conditioning
    WiFi

    Brother Sun

    Sitting within a stone building dating back to the 17th century, this apartment in the hill town of Montalcino mixes Tuscan tradition with contemporary amenities to make for an address that you're unlikely to forget after a visit. Along with the wooden ceiling beams and handsome brick flooring, you'll find comfy leather sofas, a glass dining table sat underneath an equally eye-catching chandelier and a kitchen with a wealth of surface space for whipping up something spectacular. However, the standout feature sits just outside — step onto the home's roof terrace and guests are rewarded with the verdant Val d'Orcia, a UNESCO World Heritage Site. Up here, there's a table for alfresco feasts and a pair of loungers for soaking up the sunshine. The local town may be small, but there are plenty of restaurants, bars and shops selling locally grown produce to keep you occupied. A little further afield, the spas of Bagno Vignoni take twenty-fi...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 10 People • 4 • 3 • pool wifi
    From
    €
    799 /night
    Min Stay 1 night


    Siena, Italy 

    € 799 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Sunflowers - Sangiovese

    Treat yourself to a relaxing stay at this rustic villa in the heart of Chianti, one of the Old World’s best known wine regions. Fully renovated in 2016, this authentic Italian home will delight even the most discerning guest with its characterful design features – think wooden ceilings and gargantuan stone fireplaces – and comprehensive selection of modern amenities. There’s no shortage of activities to keep you busy here – whether it’s relaxing by the pool, playing board games by the fire, or perfecting your forehand on the private tennis court – but we wouldn’t blame you if all you wanted to do was sit back and take in the view. Settle into one of the chairs in the garden and gaze out at the Tuscan hills while your private chef gets to work in the kitchen. When you’re ready to eat, gather everyone round whichever dining table takes your fancy – there are plenty of options here – and enjoy a leisurely lunch under the midday sun befor...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 14 People • 7 • 7 • pool wifi
    From
    €
    2,226 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,226 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Villa Monastero

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


      • Booked Available
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    Siena, Apartment for rent
    Apartment • 10 People • 4 • 4 • pets pool wifi
    From
    €
    780 /night
    Min Stay 1 night


    Siena, Italy 

    € 780 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    An Ode to Tuscany

    Is there anything better than an escape to the Tuscan countryside? How about having two restored barns to call home during your stay? This delightful home is comprised of two traditional barns dating back to the 1800s – they’ve recently been restored to stunning effect. It’s an excellent option for a group of friends or for an extended family, as there’s plenty of space for everyone. Aside from being a wonderfully convenient option, this home is also full of charm. Boasting panoramic views of Chianti Classico, the outside space is dreamy. Spend your days lounging beside the private pool, swimming laps and splashing about with the little ones. Enjoy languid lunches that stretch into alfresco dinners beneath the gazebo. We love sitting out on the terrace as the sun sinks in the sky, watching for the stars to start to emerge. Inside, you’ll find traditional Italian style – think wooden beams and warm colours. If the weather turns chill...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 12 People • 7 • 8 •
    From
    €
    747 /night
    Min Stay 1 night


    Siena, Italy 

    € 747 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Trip To Tuscany

    This sprawling estate in Tuscany is the stuff that dreams are made of. Composed of the main farmhouse, two outbuildings, and a shared hall, along with plenty of outdoor space, it's perfect for large groups planning an escape to the Italian countryside. There are plenty of original features to admire, from the stone exterior to the arched brick doorways and vaulted wooden ceilings. With two kitchens and two indoor living rooms, everyone can make their own schedule and relax in style. Out in the garden, you'll find a sparkling swimming pool that invites you to cool off and plenty of sun loungers where you can catch some rays. And, when evening rolls around, the whole group can gather under the pergola for a fabulous alfresco dinner straight off the barbeque – don't forget the prosecco. It would be easy to while away your days without leaving this fabulous estate, but the rolling Tuscan countryside is waiting just outside the walls. Yo...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 8 People • 4 • 3 •
    From
    €
    370 /night
    Min Stay 1 night


    Siena, Italy 

    € 370 /Night (minimum stay 1 night)
  • 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 towns, hamlets and vin...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 12 People • 6 • 6 •
    From
    €
    1,425 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,425 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Passion Flower

    This isn’t the kind of home that sits discreetly in the Tuscan countryside, rather it radiates like the summer sun inviting you to bask in its warmth. And with its location between Florence and Siena, this is the perfect setting to savour the authentic beauty of Italian living. From the olive groves and vineyards to the luminescent interiors, every detail of this home engages the senses. It’s a wonderful place for families and friends to socialise, relax and simply enjoy the charm of this setting. Days can be spent moving seamlessly between the indoor and outdoor spaces – swimming in the pool, taking long strolls through the countryside and gathering around the table for homemade pizza (prepared in your very own wood–oven). No doubt the spectacular views will inspire you to explore. Florence is just a fifty–minute drive while Siena is thirty–minutes away. Wherever the day takes you, this home is a sanctuary made to experience the joy...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 4 People • 2 • 1 •
    From
    €
    154 /night
    Min Stay 1 night


    Siena, Italy 

    € 154 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    Casa Rosana

    Perched on the hills overlooking the Val d 'Orcia, this traditional farmhouse is immersed in the timeless beauty of the Tuscan countryside. And with its location just a short drive from the charming medieval town of San Quirico, you’ll find everything you could need to experience the beating heart of Italian living. Dating back to 1619, this atmospheric building has been thoughtfully restored into a sanctuary – the perfect setting for a restorative retreat. Anchored around a shared garden with spectacular views across the sweeping landscape, this is the kind of space that feels instantly inspiring. And the uplifting tone extends into this cosy first-floor apartment. From the traditional features to the rustic simplicity of the styling, there’s an abundance of character and warmth here. Days can be spent relaxing on the terrace, hiking, horseback riding, mountain biking and sampling delicious local products from the next-door farm (c...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 2 People • 1 • 1 •
    From
    €
    144 /night
    Min Stay 1 night


    Siena, Italy 

    € 144 /Night (minimum stay 1 night)
  • Pets Allowed
    WiFi

    The Gentle Sage

    With its privileged position in the medieval town of Montepulciano, this traditional apartment abounds with the warmth and beauty of Tuscany. And from the moment you arrive, the picture-perfect views invite a wonderful sense of ease and relaxation. Filled with the atmospheric charm of its setting, this is a wonderful place to experience the richness and joy of Italian living. From the authentic features to the elegant styling, each room has been sensitively restored to honour its heritage, whilst adding contemporary touches. So whether you’re cooking, reading or enjoying a glass of the famous local wine, this home makes it easy to enjoy life’s simple pleasures. Stepping outside, it’s just a five–minute stroll to the Piazza Grande where you’ll also find a wonderful selection of local restaurants, galleries and shops. Days can be spent meandering through the romantic streets of Montepulciano or exploring the cinematic towns and winer...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 2 People • 1 • 1 •
    From
    €
    146 /night
    Min Stay 1 night


    Siena, Italy 

    € 146 /Night (minimum stay 1 night)
  • Pets Allowed
    WiFi

    The Ruby Rose

    Perched in the hilltop town of Montepulciano, this apartment opens its doors to the timeless beauty of Tuscany. From the majestic scenery to the traditional features, there’s a unique presence to this home that feels captivating. The owner has sensitively restored each room to honour its heritage, whilst adding luxurious touches. And the result is an authentic apartment that welcomes you to experience the art of Italian living. With the shutters wide open, the Tuscan breeze invites you to slow down and savour the simple pleasures of this home. And whether you’re enjoying a morning coffee by the window, writing at the ornate desk or reading in the bedroom, it’s easy to settle into the relaxed pace of rural life. Outside, you’ll find an idyllic garden perfectly positioned for golden–hour drinks or simply savouring the charm of this setting. Follow the views and it’s just a five–minute romantic stroll to Piazza Grande as well as a del...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 2 People • 1 • 1 •
    From
    €
    143 /night
    Min Stay 1 night


    Siena, Italy 

    € 143 /Night (minimum stay 1 night)
  • 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 within driving ...More Details


      • Booked Available
    Siena, House for rent
    House • 10 People • 5 • 5 •
    From
    €
    824 /night
    Min Stay 1 night


    Siena, Italy 

    € 824 /Night (minimum stay 1 night)
  • 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 nobody draws th...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 10 People • 5 • 4 •
    From
    €
    1,055 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,055 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    One of the Greats

    Nestled away in the countryside outside the idyllic hilltown of San Gimignano, this extraordinary villa combines exquisite interior design and a sprawling collection of amenities to make for an address that is sure to win over even the most discerning of guests. As you walk about the house for the first time, you might find it difficult to single out a favourite room. There's a timeless elegance to the dining room surrounded by floor-to-ceiling windows and centred around a grand piano, while the neighbouring kitchen is surprisingly modern in style and is sure to excite those with a culinary calling. And that's before we've even got around to the impressive grounds. On summer days, the swimming pool surrounded by leafy vegetation is sure to beckon, but there's also a wealth of peaceful spots out on the various terraces. As if that wasn't enough, guests are also blessed with a tennis court, which can be found about 500m from the home. ...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 6 People • 3 • 3 •
    From
    €
    905 /night
    Min Stay 1 night


    Siena, Italy 

    € 905 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Gioia Pura

    If you’re in search of picture-perfect Tuscan views, this apartment could be the one for you. It sits within a beautifully restored rural building and overlooks the chianti vineyards. The grounds are shared with four other apartments and there’s a communal pool – ideal for soaking in the unique charm of this setting. You can follow hiking or cycle trails from here and find amenities in Pianella village – just 1.5km away. Also, Siena is just a twenty-minute drive away, making this an ideal location for sightseeing as well as total relaxation. There are lots of steps here so it may not be ideal for those with limited mobility, but it’s well-equipped and your host can arrange grocery deliveries for your arrival. *Due to the location of this home, we recommend having a car to get the most out of your stay – there is also private parking available *This home is spread over two floors, with no internal lift so it may not be suitable for th...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 8 People • 4 • 5 •
    From
    €
    1,032 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,032 /Night (minimum stay 1 night)
  • 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 this home, w...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 32 People • 16 • 16 •
    From
    €
    3,299 /night
    Min Stay 1 night


    Siena, Italy 

    € 3,299 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Sweetest Life

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


      • Booked Available
    Siena, Apartment for rent
    Apartment • 6 People • 3 • 2 •
    From
    €
    849 /night
    Min Stay 1 night


    Siena, Italy 

    € 849 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Chianti Chic

    In the heart of Chianti sits this stunning holiday home, perched up on a hill and featuring gorgeous views over the surrounding Siena landscape. It’s a classic stone villa with charming interiors and characterful features, such as ornate light fittings, retro tiled floors and elegant furniture. We love the lovely living area that has a fireplace that you can cosy up to on chilly evenings and the lavish dining space that’s great for feasting on pizzas and pasta dishes. You’ll be even more impressed with the outside, where you’ll find a beautiful outdoor pool where you can have an invigorating swim as the sun comes up, as well as loads of sitting areas to relax and admire the views out over the olive groves and vineyards around you. When you want to head out, you’ll find yourself perfectly located for exploring Siena, as well as the medieval villages of Vagliagli, Radda and Gaiole where you’ll find an idyllic atmosphere and picturesque...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 6 People • 3 • 3 •
    From
    €
    1,500 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,500 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Rustic Idyll

    It's homes like this that give Tuscany its reputation as a blissful place which to retreat for a week or three. The surrounding landscape of vineyards and rolling hillsides is as picturesque as you could possibly imagine, while the home itself is bursting with character. Much of this is down to its long history. Built at the end of the 18th century as a mill, it was converted into a farmhouse before becoming the handsome getaway you see today. This heritage is writ large across the interior, with stone archways, wooden ceiling beams and terracotta tiles underfoot a treat for those that melt at the sight of rustic design – which includes us. The more contemporary features – including the freestanding bathtub and modern kitchen – have been tastefully added to retain this inimitable charm. Outside, it's a slightly different story. The hot tub and swimming pool in the middle of the garden are comparatively recent additions to the address ...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 12 People • 6 • 6 •
    From
    €
    995 /night
    Min Stay 1 night


    Siena, Italy 

    € 995 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Yellow Harvest Moon

    With a traditional farmhouse style and situated within some of the most beautiful landscapes that this part of the Tuscan countryside has to offer, this warm, welcoming, and characterful home is perfect for anyone looking to slow down and experience the simple pleasures of life in an idyllic location. Nestled in the shadow of Montepulciano, the home is ideally placed for those with a penchant for hiking and biking, not to mention those hoping for a taste of 'la dolce vita' by exploring sleepy local villages and typically Tuscan towns. Here you will find a relaxed atmosphere and plenty of great food (and loads of lovely local bars in which to sit and enjoy a glass or two of regional wine). The home itself is finished in a wealth of natural materials, including plenty of stone and wood, lending to the sense that the farmhouse is entirely at home in its beautiful environment, while luxurious touches such as the marble fireplace create an ...More Details


      • Booked Available
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