Views of the verdant hills surrounding this home make it a splendid spot for relaxation. The villa boasts a gym, yoga, and massage space in an annex near the swimming pool, within the well-kept garden. Dine under a pergola while watching the sun set over the Val d’Orcia, after a day spent outside in the sunshine. The stone-clad main house and renovated barn have classic Italian features including exposed wooden beams, but these are combined with modern furniture and art. The result? A stylish home-from-home perfect for a large group. *Your host can provide a cot and high chair for little ones. *There’s free parking at this home. *This home comprises the main house, a barn, and an annex. *Your host has arranged daily housekeeping services. *The caretaker lives on the estate, a ten-minute drive away. *Six of the bedrooms can be set up with double beds or twins Air Conditioning Barbeque Bathtub Blender<b...
With a tennis court, volleyball court, and a five-a-side football pitch, this home is perfect for those seeking an active holiday in Italy. It’s in the green hills of Valdarno Aretino, close to trails for hiking and mountain biking. You’ll also be within easy reach of Siena, Florence, and Arezzo, giving you plenty of inspiration for day trips. When you’re not out exploring, you’ll enjoy having this peaceful space to call home. One swimming pool has a counter-current system, and the other boasts a hydromassage feature for a more relaxing soak. Perfect for several family groups, this home is spread between the main villa and two annexes. *Your host can provide a cot and high chair for little ones. *The swimming pools are open from the last Saturday in April until the first Saturday in October. *Four tennis rackets are provided for the tennis court. *There’s free parking at this home. *This home comprises the main villa a...
Surrounded by lush gardens and typically Tuscan views, this villa is the definition of bliss. It's packed with character – think brick archways, beamed ceilings, and antique furniture. Between the main house and guest annexe, there's plenty of space for all twenty of you to sprawl out, though a couple of the bedrooms sleep three people. Outside, you can gather on the terrace for alfresco meals, laze by the pool with a cocktail, or just sit back and admire the panoramas. Fancy a change of scenery? Hop in the car and head to Bucine, Siena, or Arezzo – they're all within easy driving distance. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *Two bedrooms are located in a guest annexe next to the main villa. Two more bedrooms inside the main house sleep three people – they both have a double bed and a single bed. Some of the other double beds may also b...
Amid the rolling hills and verdant countryside of Tuscany, this home delivers rustic Italian charm and idyllic views. Inside, the rooms unfold across three floors in the main house and two floors in the adjoining annexe – providing an abundance of space and a wonderful sense of character. Outside, the garden lends itself perfectly to lazy days by the pool (open seasonally) and long soaks in the heated jacuzzi. You will need a car to get around here, but it's just 6 kilometres to the nearby town of Ambra (don’t miss the weekly market), plus it’s also within easy reach of Siena, Arezzo, and Cortona. *While not all of the rooms are photographed, expect the style and quality to be consistent with the rest of the home. *Due to this home's location, we recommend having a car to get the most out of your stay – there is also free private parking for up to five cars. *The main house is spread across three floors while the annexe (with...
With views of cypress trees, vineyards and rolling hills, this home delivers the perfect setting for a rustic Italian escape. The rooms are traditional and family-friendly, the garden features a private pool (open seasonally), plus there is a jacuzzi and steam room. Your host can also help organise a range of lovely extras, including private chefs and wine tastings. And while there is plenty to keep you at home, this is a great base from which to explore the region. The nearest small town is just a short walk away, while Arezzo is just a forty-minute drive from here. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also private parking for up to four cars. *This home is spread across three floors with two ground floor bedrooms and bathrooms. Please also note three of the bedrooms have a mezzanine level. *There is daily housekeeping included in your stay (from 9.30am to 12.30...
This Tuscan villa was once a hotel, so it’s well set up for large groups. All of the bedrooms are en-suite, there’s an industrial kitchen, and the huge lounge has plenty of sofas. With an indoor and outdoor pool, you can swim in every season here. Plus there’s a sauna and two of the en-suites have Jacuzzi bathtubs. The decor feels a little dated – particularly the bathrooms – but we love the formal dining room and the conservatory overlooking the Tuscan countryside. Located in the centre of Valdichiana, there are plenty of opportunities for hiking in the area. Or you can jump in the car for a day trip to the hilltop town of Cortona or the Medieval city of Arezzo. *The swimming pools aren’t fenced. If you're bringing little ones, they'll need to be supervised at all times. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *Due to this home's location, we recommend hiring a car to...
Immerse yourself in the mystical beauty of this ancient land and its history with a stay at this unique home. Nestled amidst the rolling hills and green fields, this stone gem dates back to the sixteenth century – and while it still preserves all of its original grandeur, it also feels like home, with all the comforts to make your stay a relaxing and restorative one. Arrive to be awed by the impressive façade and the surrounding gardens, with ancient trees and lovingly tended to plots of organic fruit and vegetables. You’ll feel light years away from the hustle and bustle of modernity, and the serene holiday mode will descend upon you the moment you step your foot on this land. Come inside to be welcomed by the cosy interior, with the original wooden beams on the ceiling, stone walls and terracotta floors. We love just how much space there is here to lounge about and enjoy the tranquillity – for those lovely evenings of ...
Escape to Tuscany at this rustic countryside villa, perfect for large groups. Surrounded by rolling hills and expansive gardens, you can unwind by the pool, dine under the shaded gazebo, or simply admire the countryside. Nearby treasures like the Etruscan city of Cortona, the medieval villages of Castiglione Fiorentino and Lucignano, and the historic Montecchio Vesponi Castle are all a short drive away. After a day of exploring Tuscany, fire up the barbecue for an alfresco dinner or challenge your fellow guests to a game of pool. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to request them in advance *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. The pool is only available for use between 1st May and 15th October, with other periods available upon request. *Due to this home's location, we recommen...
Escape to the Tuscan countryside when you stay at this charming villa. The accommodation is set across three traditional buildings and an annexe, providing plenty of space for a big family holiday or group getaway with friends. Lounge by the scenic swimming pool to savour the Italian sunshine. Gather on the terrace for an al fresco feast. Or head out to explore the rolling hills and vineyard vistas that make Tuscany so special. This rustic retreat is ideal for getting away from it all, where the only task on your to do list is embracing what the locals call la dolce vita. *The accommodation is set over three separate buildings and an annexe. *While the home can sleep up to twenty people, the maximum occupancy is eighteen guests. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *The swimming pool is only available for use between May and October. *While not all ...
Overlooking vineyards, rolling hills and woodland, this private estate sits like a gateway to the natural beauty of Tuscany. There are two villas here, one of which dates back to 1700 while the other is a traditional Tuscan farmhouse – together they set the tone for a restorative retreat or intimate celebration. You’ll also find two private pools, a barbecue and multiple terraces to relax and savour the unique charm of this location. From here, it's just a 250-metre stroll to a winery and restaurant – perfect for sampling local produce. And for explorations further afield, it's just a ten-minute drive to the hilltop city of Arezzo. While not all of the rooms are photographed, expect the style and quality to be consistent with the rest of the home. *Please note this home consists of two independent villas each with its own swimming pool. The first villa sleeps 12 guests and has two floors connected by external stairs. The second ...
Time stands still at this 18th-century villa nestled in the heart of the Tuscan countryside. The rooms perfectly embody traditional Italian charm, while the garden offers sweeping views across the hills – making this the ideal setting for a restorative retreat or intimate celebration. There’s also a private pool and jacuzzi (available on request), with multiple lounging spots to sit back and savour the stillness of this rural location. And when you’re in search of adventure, it’s just a short drive to the amenities in Monterchi, while the majestic cities of Arezzo, Siena and Florence are close enough for day trips. *Due to this home's location, we recommend having a car to get the most out of your stay – there is also free private parking. *This home is spread across three levels with no internal lift – there are also steps leading down to the pool. *Please note the swimming pool is only available from the 11th of April to th...
Immerse yourself in the peace and prettiness of the Tuscan countryside from a stunning 15th-century villa. The villa is split into four apartments, making it perfect for several family groups travelling together. It’s perched on a hill within a wine- and oil-cultivating estate, amid beautiful scenery. The views can be admired from the private pool and from the courtyard, where you can dine alfresco. Inside, there’s a wellness area with a gym, a hammam, and a hydromassage tub. You’ll be within easy reach of the shops and restaurants of Monte San Savino, and can take day trips to Siena, Arezzo, and Florence. *This home comprises four individual residential units, each with a separate entrance. Two of the apartments are on the first floor, accessible via a flight of stairs. *Two of the double beds can be unzipped into twin beds if preferred Air Conditioning Barbeque Central Heating Child Friendly Coffee Maker Co...
This contemporary villa set on the edge of Terontola in southern Tuscany is just the ticket for those seeking a serene escape away from it all. Boasting modern interiors, a private pool and sun-kissed terraces, it’s a real gem. But the cherry on the cake? This home has its very own spa. So, if you fancy a sauna or massage, just wander down the steps to the lower ground floor where your sanctuary awaits. Keen to explore? Drive to historic Cortona, sample the local chocolate of Perugia, or bathe in the hot thermal springs at Bagni San Filippo – you’ll never be lost for things to do. *While not all bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *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. If you're bringing children, they'll need to be supervised at all time...
Escape to your own slice of Tuscan paradise in this beautifully styled villa, tucked away in the heart of the Valdarno. Surrounded by olive groves, vineyards and stunning mountain views, it’s the ultimate spot to unwind. Lounge by the pool, sip local wine under the stars, or fire up the grill for long, lazy lunches al fresco. Inside, rustic charm meets refined comfort with original features and plenty of space to spread out. The location is peaceful and private, so you will need a car to get around. However, the serenity and scenery are more than worth it. For a dreamy getaway with wow factor, this villa certainly delivers. *The swimming pool is only available for use between May and October. It isn't fenced, so if you're bringing little ones, they'll need to be supervised at all times. *There’s free parking for up to six cars. *If you're travelling with little ones, your host can provide a free cot and high chair upon requ...
With a private swimming pool, sun-drenched terraces and a private spa that includes a sauna, Turkish bath and massage table, it’s impossible not to relax here. Set just five kilometres from the centre of historic Cortona, this charming villa is an ideal retreat for a family or group of friends. With daily breakfast included, you can start the day in a leisurely fashion on the terrace, just the spot for sunny alfresco dining. And if having breakfast prepared has given you the taste for taking it easy, you’ll find a selection of eateries nearby for authentic Tuscan food. *While not all bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *If you're travelling with little ones, your host can provide a cot for free. You'll need to request it in advance. *The swimming pool, open between 1st May and 30th September, isn't fenced and there are open tread stairs here. If you're bringing ...
Tucked between olive groves and a pine forest, this cosy villa is a scenic drive away from Cortona, Arezzo and Pienza – but you might not want to leave once you're here. The three bedrooms (each with their own bathroom) are downstairs, while upstairs it’s all about spending time together – cooking in the kitchen, chatting around the travertine island, or sharing a bottle of local wine at the glass-and-timber table made from a tree that once grew on the property. Outside, you’ve got a pool, a jacuzzi, and a rooftop terrace with front-row seats to the sunset over Castiglion Fiorentino. It’s peaceful, spacious and completely private – a proper countryside escape without feeling remote. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s free parking for up to two cars onsite. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. <br...
Set on a 3-hectare estate featuring woodland and olive groves, this rural idyll offers peace and relaxation. Surrounded by a beautiful garden filled with flowers and herbs, there’s an outdoor living area with a gazebo and barbecue, as well as a swimming pool with whirlpool jets. Inside, there’s a large living room, a study, and a dining room connected to the traditional kitchen. There’s also another kitchen and diner with a wood stove in the portico. When you want to explore, Bucine is a short drive, while designer outlets, including Prada, are around 2 kilometres away – Arezzo and Siena can also be easily reached by car. *This home is set over two levels. *The owners live in an annexe about 50 metres from the house and are available if you need them. *The swimming pool is only available for use between the end of April and the beginning of October. *Your host can provide a cot and high chair for free. You'll need to requ...
Set high in the Tuscan hills, this villa has everything you need for a carefree stay. With a private pool and two terraces, you'll probably spend most of your time in the garden. The hot tub is the icing on the cake – it's the best spot to admire those sweeping views. While the traditional interior isn't as impressive, there's no shortage of space. The fifth bedroom is in a separate cottage, complete with a lounge and kitchenette – perfect for grandparents or a couple wanting extra privacy. A car is a must here, but you'll be within driving distance of Arezzo (25km), Cortona (13km), and the small village of Castiglion Fiorentino (5km). *The fifth bedroom is in an independent cottage. It also has a kitchenette, a living area, and a private entrance. *The first floor is divided into two separate areas, with no connecting door between them. *If you're travelling with little ones, your host can provide a free cot and high chair ...
Perched on the hills overlooking the Val di Chiana, this beautiful home seamlessly blends rustic charm with elegant Tuscan style to create a truly unforgettable stay. Less than a fifteen–minute walk from the centre of Cortona, the owners have thoughtfully restored this traditional farmhouse into a welcoming space that exudes charm. And with its abundant garden and breathtaking views, this is the perfect setting for a retreat into the heart of nature. Stepping inside, you’ll find an uplifting space designed to enrich your stay with the simple pleasures of Italian living. From luminous mornings watching the sun rise over the valley to cosy evenings curled up by the fire, this is the kind of space that adapts to suit the needs of the moment. And for the ultimate sense of relaxation, the swimming pool is perfectly poised for refreshing swims and lazy afternoons reading under a tree. For explorations further afield, i...
Buried deep within the vineyards and olive groves, this rural retreat offers ample outside space for those wanting a quiet getaway to Tuscany. The interiors are rustic and traditional, so the decor won't be to everyone's taste, but most of your time will be spent outside. With a well-kept garden and private swimming pool, there's plenty of space to while away the afternoons here. Alfresco meals are best enjoyed on the covered dining patio, although, the neighbouring hamlet of Montegonzi offers authentic eateries and bars if you don't feel like cooking. You'll need a car to explore but prepare for a hilly, uneven drive at times. *Due to this home's location, you'll need a car to get the most out of your stay. There’s free parking for up five cars. *There's a double bedroom on the ground floor, although you'll need to climb stairs to reach the other bedrooms. *The double beds can be configured as twins if required – you’ll nee...
This rustic villa caught our eye for its remote location and peaceful countryside surroundings (best enjoyed off the secret terrace accessed from the fifth bedroom). The nearest town of Ambra lies 10km away, so car hire is essential – though there'll be no interruptions here. You'll find plenty of tranquil outside spaces from which to soak up the glorious setting – from the swimming pool, garden and dining area to the tennis court, bocce court and table tennis space (you've also got a well-equipped gym). And, while the traditional interiors might not be to everyone's taste, keen chefs will love the modern kitchen, which makes alfresco cooking a delight. *Due to this home's location, you'll need to hire a car to get around. There's private parking within the grounds for up to three vehicles. The approach road is uneven so please take care upon arrival. *The villa is set over multiple floors with internal stairs. There is one doub...
Made for outdoor living and large family gatherings, this home is sure to jump high up on your wishlist. We love the space this home has, and with two apartments independent from the main villa, it’s perfect for extended families where two couples are seeking a bit of added privacy. With traditional interiors, it’s a comfortable place to call home – but it was the outdoor space that caught our eye. Sun-kissed terraces, alfresco dining opportunities, a private pool and hot tub, and all a short drive from the beautiful hilltop town of Cortona. *This home has two independent apartments on the first floor, accessed via an external staircase. Each apartment has a bedroom, bathroom and kitchenette. *The swimming pool, open between 20th May and 30th September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *The hot tub is available for use between April and October. *If you're travelling...
Nestled on an estate amongst vineyards and olive groves in the Valdarno Valley, this charming villa offers an idyllic escape. Ideal for a family or group of friends, there’s plenty of space to spread out here to enjoy some quiet time, or come together as a group to socialise. And while we love the seamless blend of traditional and modern inside this home, for us, the outdoor space is the star of the show. Relax by the private pool, accessible via a golf buggy, or savour alfresco meals under the vine-clad pergola. Perfectly situated between Florence and Arezzo, this home promises both tranquillity and convenience. *This villa is set on a vineyard. *The swimming pool is 70 metres away from the villa, across the vineyard. A golf buggy is available should you wish to use it to reach the pool. *The pool, open from May to September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you...
Located just one mile from the hilltop town of Cortona, this Tuscan villa is made up of two apartments in one charming and traditional farmhouse. Both apartments have their own separate entrances, making this a great choice for large groups. Outside, the private pool is fenced and perfectly placed for stunning views, and children will love the expansive grounds. Animal lovers can bring their furry friends along, but it's important to note that a couple of dogs and even a friendly donkey live on the land, and the owner of the home lives nearby. Despite this though, you'll be granted full privacy during your stay. *There are three private parking spaces outside this home. Cortona can be reached on foot, but we recommend hiring a car here to get the most out of your stay. *Well-behaved pets are welcome to join you at this home with prior host approval. *Two friendly dogs and a donkey live on the property, so it may not be suitab...
A few kilometres from Cortona, this old farmhouse makes a rustic retreat for families. With a private pool, sprawling gardens, and a panoramic terrace, you'll have plenty of time to enjoy the Tuscan sun. The inside, meanwhile, is filled with traditional details like wooden beams and exposed stone. You'll need to be comfortable climbing stairs here, and it's worth noting that air conditioning is only available in the bedrooms. Still, we think this villa is perfect if you want a characterful, cosy home in the heart of Tuscany. *If you're travelling with little ones, your host can provide a cot and high chair upon request. *Air conditioning is only available in the bedrooms. *Two bedrooms are connected internally and share a terrace, though they also have independent entrances from the outside. *The swimming pool is only available to use between the last Saturday in April and the first Saturday in October. *There are two i...
Halfway between Arezzo and Siena, this 18th-century farmhouse makes a fantastic base for exploring Tuscany. The garden will surely be a hit, featuring a private pool (open seasonally), a loggia with a brick barbecue, and a terrace where you can tuck into alfresco meals – not to mention plenty of lawn space where kids and pets can let off some steam. Inside, though dated, certainly doesn't lack charm. We love all the character features, from the timber beams on the ceiling down to the terracotta floors. With seven en-suite bedrooms (including two on the ground floor), it’s a great option for extended families and large friend groups. *Up to two well-behaved pets are welcome to join you. *If you're travelling with little ones, your host can provide two cots and two high chairs on request. *The dated interiors here aren’t up to Plum’s typical standards. We let this one into our collection on behalf of the garden and the location...
This traditional Tuscan home is located in the stunning Chianti hills. Made up of two stone farmhouses rented as one, it’s a great choice for a family reunion or group getaway. You’ll be doubling up on living rooms, kitchens, and dining rooms so there’s plenty of space for everyone, and two of the bedrooms have three beds – perfect for families or children. While the rustic decor inside won’t appeal to everyone, we think the outdoor space, with its panoramic views, private pool, and alfresco dining terrace, will be a crowd-pleaser. Location-wise, you’ll find a shop and a restaurant 1 kilometre away, and for day trips, the Medieval town of Arezzo is a 25-kilometre drive. *This home comprises two farmhouses, each with its own bedrooms, bathrooms, living room, kitchen, and dining room, rented as one. *The swimming pool is only available for use between 27 April and 19 October. The pool isn't fenced so children will need to be super...
Escape to the beautiful Tuscan countryside, with a stay in this traditional Italian home. You’ll be welcomed by a serene garden with a pool and a covered veranda with an outdoor kitchen for alfresco dining. There’s also a wellness area with a sauna and a hot tub to ensure optimum relaxation. Inside, you’ll find tradition and contemporary comfort with all five bedrooms featuring en-site bathrooms for privacy. We recommend hiring a car to get around here, but it’s just a short drive to Ambra where you’ll find the nearest restaurants and shops. You can also drive to Arezzo, Florence and Siena for inspiring day trips. *Private parking is available for up to eight cars. There is also a charging station for electric vehicles. *A weekly linen change is included in your stay. *Please note this home is set across two floors with stairs. *If you're travelling with little ones, your host can provide a cot and two high chairs ...
Tucked away in the town of Santa Maria alla Rassinata, amid the hills of Arezzo, this delightful holiday home promises beautiful views. The house dates back to the mid-16th century and has been expertly restored, showcasing retro charm. Outside, you’ll have a swimming pool surrounded by panoramic views, and a terrace with a pool house and a minibar. The well-maintained gardens feature antique roses, hydrangeas, and aromatic plants. The setting is ideal for long walks and bike rides, and you’ll be just an eighteen-minute drive from Palazzo del Pero. *While not every bedroom or bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *The swimming pool is available from the last Saturday of April until the first Saturday of October. The pool is 150 metres from the villa, accessed along a path and down seven stone steps. *The caretakers live in the annex adjacent to the villa. ...
This beautiful Tuscan home caught our attention due to its inspiring views and ample outside living space. Consisting of a farmhouse and a cottage, you'll have access to the well-kept gardens and lovely terraces to help you soak up the rural setting. We think it's a perfect fit for families, due to the abundance of space and fully-fenced swimming pool (complete with a diving board) – plus you've got a table tennis area, sun loungers, a pergola with deck chairs and a covered patio for alfresco suppers. Though you will need a car to explore the region, you'll find the beautiful town of Levane nearby for local amenities. *Due to this home's location, you'll need a car to get the most out of your stay. There’s free parking on-site parking for two cars. *The swimming pool is only available for use from mid-May to September. *If you're travelling with little ones, your host can provide a cot and high chair for free. You'll need to...