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Italy  Italy - Holiday Rentals in Siena Italy
Italy Country: Italy (11002) | Region: Tuscany (3452)
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    Found 246 Siena holiday homes for rent

    Siena, House for rent
    House • 21 People • 11 • 11 • pool wifi
    From
    €
    3,868 /night
    Min Stay 1 night


    Siena, Italy 

    € 3,868 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Classico Chianti

    This hilltop villa offers panoramas from Monte Amiata to Siena and boasts sweeping vineyard views – what more would you wish from a stay in the Chianti region? Licensed for weddings, it's a magical setting for special occasions – just ask your host for details. The interiors lean traditional, perfect for those who appreciate classic Tuscan charm. That said, you’ll likely want to spend most of your time outdoors – taking dips in the pool, sipping wine on one of the terraces and gathering for alfresco meals – your host can arrange private chefs, too. And with castles, medieval villages, vineyards and thermal spa towns within easy driving distance, you’ll be spoilt for choice here. *This home is spread across a main house and a converted barn. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Two bedrooms have the option to convert the double beds into two singles upon request. There a...More Details


      • Booked Available
    Siena, House for rent
    House • 4 People • 2 • 2 • pool wifi
    From
    €
    660 /night
    Min Stay 1 night


    Siena, Italy 

    € 660 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Chianti Grape

    If you’re looking for an escape from it all, this could be the home for you. Set on a private road deep in the woods, this Chianti villa has tranquillity running through its core. We love the seamless blend of modern furniture with the traditional building here, but the outdoor space is our biggest winner. Sun-kissed terraces, a hot tub, a private pool, alfresco dining areas – what’s not to love? If you can tear yourself away, it’s a mere ten-minute drive to the wine-making town of Gaiole, which is well worth a visit. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool isn't fenced and there are open-sided stairs here. If you're bringing children, they'll need to be supervised at all times. *The second bedroom is on the mezzanine level and semi-open to the space below, so privacy is limited. *Due to this home's location, we recommend hiring a car to get the most out...More Details


      • Booked Available
    Siena, House for rent
    House • 6 People • 4 • 3 • pets pool wifi
    From
    €
    513 /night
    Min Stay 1 night


    Siena, Italy 

    € 513 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    A Tuscan Escape

    Tucked in the Tuscan countryside, yet just five kilometres from Siena, this traditional home is perfect for those seeking a tranquil retreat. Should you need anything during your stay, the owner lives on-site – but your peace won’t be disturbed otherwise. With space to spread out, there are plenty of quiet nooks here when you’d like some privacy. That said, we think everyone will be drawn to the outdoor space. A private pool, sun-drenched terraces, and an alfresco dining spot nestled in the shade – it ticks our holiday boxes. *The swimming pool, available from May to September, isn't fenced and there are open-sided stairs here. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *One well-behaved dog (up to 30kg) is welcome to accompany you during your stay. *The twin bedroom can be set up as a double upon reque...More Details


      • Booked Available
    Siena, House for rent
    House • 10 People • 5 • 5 • pool wifi
    From
    €
    1,950 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,950 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Glow

    Nestled amidst vineyards and olive groves, this villa offers an unforgettable retreat in the heart of Chianti Classico. Set on a winery, it’s no surprise that there are plenty of outdoor spots just made for sipping a glass of wine at the end of a busy day. Add in a private pool and far-reaching countryside views, and this home ticks a lot of our holiday boxes. Ideal for larger groups, we also love how this home flows over three separate buildings, with the cottage and annexe alongside the main villa – perfect for those wanting to holiday together, yet still enjoy some privacy. *This home consists of the main villa (sleeping six), a separate cottage (sleeping two), and an annexe (sleeping two). *The villa is situated on a winery but is private. That said, expect to see staff working at the vineyard from time to time. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming p...More Details


      • Booked Available
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    Siena, House for rent
    House • 6 People • 3 • 3 • pool wifi
    From
    €
    825 /night
    Min Stay 1 night


    Siena, Italy 

    € 825 /Night (minimum stay 1 night)
  • 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 Utensils Microwave Mosquito Net Outdoor Seating Oven Parking Availa...More Details


      • Booked Available
    Siena, House for rent
    House • 17 People • 9 • 9 •
    From
    €
    3,053 /night
    Min Stay 1 night


    Siena, Italy 

    € 3,053 /Night (minimum stay 1 night)
  • 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 Maker Cot / Crib Dishwasher Dr...More Details


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


    Siena, Italy 

    € 175 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Sunlight Embrace

    Set in the pretty town of Gaiole, this apartment makes it easy to experience the magic of Tuscany. From here, you can stroll to local restaurants, shops and cafes. It’s also possible to drive to Siena, San Gimignano, Florence and Arezzo for inspiring day trips. And when it comes to total relaxation, this home has everything you could need. There’s a private pool for refreshing drips and three terraces set across different levels. You can also enjoy freshly picked produce from the vegetable patch and there’s a barbecue for alfresco dining. *Please note the apartment is located in the owner’s house. *It’s worth noting some of the furnishings are a little dated here. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Please note the swimming pool is available for use from May to September. *Private parking is available here. Air Conditioning Barbeque Beach / Pool Towels Child Frie...More Details


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


    Siena, Italy 

    € 258 /Night (minimum stay 1 night)
  • 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. *One well-be...More Details


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


    Siena, Italy 

    € 627 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Sweet Vin Santo

    Nestled in the heart of Tuscany's renowned Chianti Classico wine region, this villa offers a tranquil escape from it all. Owned by a local winery and surrounded by vineyards, a spot of wine tasting during your stay is a must. The home itself is perfect for a family or small group of friends, and while the interiors are charming, it’s the outdoor space that caught our eye. With far-reaching views, a private pool and terraced dining areas, making the most of the Mediterranean climate will be high on your agenda. *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 until October, isn't fenced and there are open tread stairs here. Children will need to be supervised at all times. *The bedrooms can be set up as doubles or twins upon request. *The second bedroom is on the mezzanine level and semi-open to the space below, so privacy is limited. *The ceiling ...More Details


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


    Siena, Italy 

    € 547 /Night (minimum stay 1 night)
  • Swimming Pool
    WiFi

    Roses of Chianti

    With incredible views across the Tuscan countryside, this home sets the tone for a magical Italian getaway. Nestled in the heart of Chianti, you’ll be welcomed by the sweet sounds of nature, a private swimming pool and a serene terrace for sunset drinks and alfresco dining. Inside, the rooms are traditional and family friendly with plenty of space to stretch out across the three floors. Your host is on hand to help organise extras like private chefs and guided tours. Plus, it’s just a short drive to Gaiole in Chianti where you’ll find the nearest restaurants, bars and shops. *Please note the owners live in an apartment at the rear side of the villa with their dog. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *Please note the swimming pool is available for use from May to October. *Well behaved dogs are welcome to join you here, but please note they need to be kept on a lead when...More Details


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


    Siena, Italy 

    € 193 /Night (minimum stay 1 night)
  • Swimming Pool
    WiFi

    Tuscan Song

    If you’re in search of a traditional Italian escape with plenty of character, this apartment delivers a wonderful solution. Nestled in an old farmhouse, you’ll find snug rooms, original features and all the basics you could need to make it your own. There’s also a private terrace with a barbecue and you’ll have access to a shared swimming pool. You will need a car to get around here, but it’s a great base for exploring the Chianti countryside with Galenda, Florence and Siena all within driving distance. *This apartment is located in a farmhouse with a shared swimming pool. The swimming pool is available for use from 1st June to 30th September. *At full occupancy, two guests will be sleeping on the sofa bed in the living room. *Please note the apartment is set across two levels with steps. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *If you're travelling with little ones, your hos...More Details


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


    Siena, Italy 

    € 476 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Chianti Splendour

    With far-reaching views of the rolling Chianti hills, it’s impossible not to relax in this villa. Traditional yet modern, this home promises a true taste of Tuscany, alongside plenty of space to relax. We love the three tiered terraces, each offering something different – alfresco dining on the top terrace, bowls on the middle, and a private pool on the lower. And, being situated next to a working winery, you’re perfectly placed for a spot of wine tasting and some authentic Tuscan food – all of which can be organised by your host. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The twin bedroom can be set up as a double upon request. *There are stairs to climb here, including in the outdoor space to access different terraces. It may not be the best option for those with reduced mobility. *We recommend hiring a car to get the most out of your stay – on-site parking is available f...More Details


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


    Siena, Italy 

    € 384 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Sweet Tuscany

    Tailor-made for two, this charming villa promises a tranquil escape in the Tuscan countryside. We love the character-packed interiors, where you’ll find everything needed to kick back and relax. But for us, the outdoor space is the real winner. Soak up the valley views, peppered with vineyards and olive groves, as you cool off in the private pool or dine alfresco under the warmth of the sun. When you’re ready to explore, you’re conveniently located between Radda and Lecchi. Personally, we’d head to Radda first to sample a bottle of its Chianti Classico. *The owners live in a separate villa above with dogs that are fenced in. They won't disturb you during your stay, but are on hand should you have any questions. *The swimming pool, available from May to October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host can provide a free cot and high chair...More Details


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


    Siena, Italy 

    € 325 /Night (minimum stay 1 night)
  • 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 Barbeque Beach / Pool ...More Details


      • Booked Available
    Siena, House for rent
    House • 14 People • 7 • 6 •
    From
    €
    732 /night
    Min Stay 1 night


    Siena, Italy 

    € 732 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Chianti Cypress

    Set on an 8-hectare estate surrounded by cypress trees and vineyards, this 18th-century villa is a dream spot for a Tuscan retreat. While the villa has been renovated, it still offers plenty of traditional charm, with inviting spaces made for gathering – think a cosy living room with a fireplace, board games and books. Outside, there’s a large pool, a shaded lounge and a dining area – your host can also arrange fridge fills to make dining in that little bit easier. And with medieval villages such as Radda and Castellina within easy driving distance, you’re all set to explore the Chianti hills. *The swimming pool is only available for use between May and mid-October. The opening hours are from 8:30am to 8:30pm. *While this home is spread across two floors, there are two ground-floor bedrooms and bathrooms. *If you're travelling with little ones, your host can provide a high chair for free. You'll need to request it in advance. *Due to ...More Details


      • Booked Available
    Siena, House for rent
    House • 16 People • 9 • 8 •
    From
    €
    1,762 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,762 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    Tuscany Grace

    Surrounded by rolling hills and lush trees as far as the eye can see, this Italian villa in the Lucciola Bella Nature Reserve offers picture-perfect seclusion. Split into five apartments – including an annexe and one suitable for guests with disabilities – it's a dream escape, whether for relaxation or celebrations. Inside, it's as charmingly rustic as you could hope, while outside there's a pool and plenty of space to dine and unwind. A car is essential for reaching amenities, but the idyllic location is totally worth it. *This home consists of five apartments spread out over two floors and across two buildings. *A car is recommended, due to the rural location. *Two baby cots and two high chairs are available on request, free of charge. *The pool is open from 1st May to 30th October. *The villa has five covered parking spaces. *The villa is suitable for hosting weddings. *One apartment in the main building is suitable for guests with...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 10 People • 5 • 5 •
    From
    €
    2,953 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,953 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Savour the Tuscan Sun

    This beautiful 450-year-old villa boasts a majestic setting in Tuscany. Its Radda in Chianti location puts you within easy reach of vineyards and historic towns and villages, whether you plan on exploring by car, on foot, or by bike. You can look forward to breathtaking views of the rolling hills *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. *There’s free parking here. We recommend hiring a car to get the most out of your stay. -Hour Security Air Conditioning Balcony Barbeque Bathrobes Bathtub Beach / Pool Towels Black-Out Blinds Breakfast Included Cafetiere Carbon Monoxide Detector Ceiling Fans Child Friendly Cleaning Products Coffee Maker Cooking Essentials Desk Dishwasher Dryer Drying Rack Electricity Adaptors Espresso Machine Exercise Equipment Extra Pillows and Blankets Fan Fenced Garden Fenced Property Fire Extinguisher Free Parking On Premises Free Parking On Street Free...More Details


      • Booked Available
    Siena, House for rent
    House • 18 People • 9 • 8 •
    From
    €
    2,402 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,402 /Night (minimum stay 1 night)
  • Swimming Pool
    WiFi

    Journey to Beauty

    Experience the timeless beauty of Tuscany with a stay in this historic home. Nestled in the heart of the Val d’Orcia, you’ll be treated to stunning views and a private swimming pool as well as estate grown olive oil and wine. There’s also a yoga shala and plenty of shaded spots for quiet reflection – making this the perfect setting for a retreat or refreshing family gathering. Inside, the rooms make it easy to switch off, unwind and spend quality time together. Your host can also help organise a range of extra services – including massage treatments and yoga sessions. You will need a car to get around here, but it’s just a short drive to Siena and Montepulciano. *Private parking is available here. *Please note the swimming pool is available for use from the 1st of April to the 31st October. Balcony Barbeque Bathtub Central Heating Coffee Maker Dishwasher Drying Rack Espresso Machine Fan Fireplace First Aid Kit Free Parking Freeze...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 12 People • 6 • 6 •
    From
    €
    2,460 /night
    Min Stay 1 night


    Siena, Italy 

    € 2,460 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Tranquil Tuscan Retreat

    Situated in the Val D’Orcia, with stunning views of Montalcino, this home has an idyllic, secluded setting. There’s a pool to cool off from the Tuscan weather, as well as a barbecue, a wood-burning oven, and several relaxation areas. Ideal for families or friends, the accommodation consists of the main house and a one-bed guest barn. We love the mix of modern with the kitchen and the character features such as the barrel-vaulted ceiling in the dining room. Location-wise, you’ll be near Buonconvento, described as one of the most beautiful villages in Italy. *This home is set over two levels and consists of a five-bedroom main house and guest barn with one bedroom and an en-suite. *For those with reduced mobility, there's a ground-floor bedroom and bathroom here. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The bedrooms have air conditioning. *There's no tumble dryer here. *Due t...More Details


      • Booked Available
    Siena, Apartment for rent
    Apartment • 10 People • 5 • 5 •
    From
    €
    1,331 /night
    Min Stay 1 night


    Siena, Italy 

    € 1,331 /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    A Tuscan Rhapsody

    Peaceful Tuscan retreats don’t get much better than this. This stunning home – spread between the main villa and an annex – is a special base in Italy, tucked amid the Tuscan Hills yet within easy reach of the art and culture of nearby Montepulciano and Pienza. This is a refined, stylish home designed to blend the antique and the modern. You can look forward to the villa’s original beamed ceilings and stone walls as well as a steel kitchen and contemporary features. We love the alfresco dining setup and the private infinity pool – it’s a breathtaking spot for admiring sunsets over Val D’Orcia. *This home is split between the main villa and an annex, connected via a courtyard. *While not every bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *This home is spread over two floors so it may not be suitable for those with reduced mobility – the bedrooms are accessible via a flight...More Details


      • Booked Available
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