Sandwiched between Siena and Arezzo, this villa is ideally suited to large get-togethers. It consists of three cosy apartments, split between a stone villa (one on each floor) and a cottage. Safe to say, you'll have more than enough space here to spread out – plus plenty of spots to retreat to when you need a little quiet. We love the uninterrupted views across the rolling hills and fields. They're the perfect backdrop for alfresco dining or swimming in the private pool. With archery, table tennis, and a swing set for little ones, dull moments will be few and far between. *This home is divided between a converted barn-style cottage and a stone villa with two apartments. Each has its own kitchen and dining area. The two apartments in the main villa have their own living space. *Well-behaved dogs weighing up to 30kg are welcome to join you here. *Air conditioning is only available in the bedrooms. *Your host provides a free ...
Tucked away in the Tuscan countryside, this home is an ideal base for a group of friends or an extended family. Made up of two bungalows, it’s perfect for those who like to holiday together yet still enjoy some private time, as the second home sleeps two yet still has everything needed for a comfortable stay. Outdoors, everyone can gather together to enjoy the private pool, hot tub, or simply relax on the sun-drenched terraces. Location-wise, nearby Montevarchi is a charming town with shops and restaurants, along with a train station providing easy access to Florence, Siena and Arezzo if you don’t fancy driving. *This home consists of two bungalows – the first with four bedrooms and the second with one bedroom. Both have open-plan kitchens, living rooms and dining rooms. *While the home can sleep up to ten people, the maximum occupancy is eight guests. *The swimming pool is only available for use between May and September.<br...
Sitting on a thousand-hectare olive farm in a rural part of Tuscany, this enchanting villa will win you over with its ancient character. Each morning, slide open the doors of your farmhouse kitchen, where you'll tuck into a traditional breakfast beneath wood beams. From unique oil tastings to dreamy massages, treat yourself to a holiday like no other at this former convent. After cooling down in the shared infinity pool, there's magic to be discovered in the on-site library and theatre – and you can raise your glasses to new friends in the Italian countryside. Perfectly placed, this home awaits midway between charming Arezzo and famous Florence – two cities steeped in rich history. Appreciated by nature lovers and artists for centuries, we're certain that this woodland scenery will inspire you to explore the great outdoors with your loved ones. Perhaps you'll stay by the Resco river, or maybe you'll lace up your hiking boots for ...
This 18th-century villa is located in the rural hamlet of Ripoli, just on the border of Tuscany and Umbria. Overlooking unrivalled views across the valley, this spot is like something straight out of a fairytale. Yet, while the aesthetic is classic Italian countryside, contemporary amenities invite guests to experience a comfortable and luxurious stay centred around leisure. The grounds feature a spacious lawn, a children's play area, a private pool with a Jacuzzi and changing room, and a barbecue area for alfresco dining. It's the perfect place for larger groups to celebrate special occasions. Additionally, the host can help organise a range of excursions and activities, including fishing trips and wine tastings, for a fuss-free stay in rural Tuscany. *Due to the location of this home, we recommend hiring a car to get the most out of your stay – there’s free parking on the premises. *Two of the twin bedrooms can be con...
This Tuscan villa is perfect for those seeking a tranquil country retreat – set amidst the rolling green hills of the Arezzo province, the place offers lovely views and plenty of privacy. The outdoors boasts a large swimming pool and a hot tub, as well as a lush garden and an alfresco dining area. The interior is all about that rustic charm – while some of the furnishings and the overall style may be a bit old-fashioned, we love the authentic character of this home. Bear in mind that a car is necessary here in order to explore the area and reach the shops and restaurants in the town of Gaiole. *A car is recommended here to make the most out of your stay. There's free private parking on the premises for two cars as well as an EV charge point. *The driveway leading up to this home is unpaved. *Please note that this home is spread across two floors with no internal lift. *The swimming pool is fenced and is in operation betw...
Tucked away in vineyards and verdant pastures as far as the eye can see, this home promises tranquillity with breathtaking views to boot. You'll find it tucked away in Terranuova Bracciolini, surrounded by natural beauty and just a thirty-minute drive from Arezzo. Here, you're in a convenient spot for exploring Tuscany, with Siena and Florence both just shy of an hour's drive away. We're completely infatuated with this home's rustic charm. It's set across two pastel-hued and ivy-clad villas, making it the perfect base for families and large groups. We especially love the majestic glass-walled recreation space, dressed to the nines for entertaining, with a banquet-style dining table, cosy lounge, ping pong and billiards table. Inside, it's a quaint canvas of terracotta tiled floors, shuttered windows and timber beamed ceilings, while contemporary comforts promise a want-for-nothing stay. After a restful slumber in the cosy...
Not far from the hilltop town of Arezzo, this villa offers a chic and rustic stay in the Italian countryside, with gorgeous views and a private pool. We think this home is well-suited to two families or friend groups travelling together – the two floors act as separate apartments, each with its own kitchen, living room and entrance. The ground floor enjoys direct access to the alfresco dining area, while the first floor benefits from lovely views across the Tuscan landscape. We recommend having a car here – the cities of Siena and Florence are just over an hour's drive away. *Not all bathrooms are photographed, but we expect consistency in style and quality throughout this home. *There is space to park for free outside this home. Due to the location, we recommend hiring a car to make the most of your stay. *There are bedrooms on the ground floor here, accessible for guests with reduced mobility. *Both floors in this home a...
This Tuscan farmhouse sits within a renowned winery, just a ten-minute drive from Arezzo. 250 metres away, guests can enjoy wine tasting and delicious Tuscan food in the winery’s garden. A cosy farmhouse living room and kitchen await inside. We love the dining room with its walls of glass doors offering unobstructed views of the rolling hills, along with a rustic-style semi-outdoor kitchen with a wood-burning oven. Outside, the villa has a beautiful garden with a private corner swimming pool overlooking the valley and city of Arezzo. Start your Tuscan dream the right way with dinner offered by the owners on arrival and a welcome basket for next day's breakfast. *While the kitchen isn’t photographed, we expect the style and quality to be consistent with the rest of the home. *For those with reduced mobility, there's a ground-floor bedroom and bathroom here. *The swimming pool is only available for use between 28th April and 6t...
Nestled among the olive groves of Chianti, this home welcomes you to enjoy mesmerising views and ultimate relaxation. There’s a private pool and a perfectly positioned terrace for sunset drinks and alfresco dining. Inside, the rooms are traditional, simple and well suited to families. You’ll also find one of the bedrooms is located in the pool house – providing a sweet and private sanctuary for two guests. You will need a car to get around here, but it’s just a short drive to the nearest amenities, while the beautiful Castelnuovo Berardenga (renowned for its delicious wine, restaurants and castles) is also just a short drive away. *This home can accommodate eight guests with prior approval from the host. *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. *Private parking is available for up to three...
On the border between Valdarno and Chianti, this hilltop villa in the heart of Tuscany is just a short drive from the town of Montevarchi and within an hour of Arezzo. The rustic interior may feel dated to some, though we think it’s part of the charm. Outside, the well-kept garden offers views of the surrounding valley, a furnished portico, and a private swimming pool, open from the last Saturday of April until the first Saturday of October. *Due to this home's location, we recommend hiring a car to get the most out of your stay. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. Your host can also provide a cot and a high chair upon request. *If you need to pick up provisions during your stay, the closest supermarket is a fifteen-minute drive away. Air Conditioning Balcony Barbeque Bathtub Blender Central Heating Coffee Maker Cooking Essentia...
Flanked by Tuscany's postcard-perfect cypress trees and commanding magnificent views of the rolling hills and vineyards beyond, the setting for this farmhouse villa would be hard to beat. Spend lazy mornings exploring nearby Cortona, one of the oldest Etruscan towns in the region (a sixteen-minute drive). Or discover the little borghis (that's little villages to us) perched in the hillsides surrounding this home. When it's time to cool off from the Tuscan sun, head back home to while away an afternoon beside the pool, enclosed by vineyards and olive trees. Set within a fifteen-hectare farm estate, the owners produce an exceptional extra virgin olive oil and a mean Syrah and Sangiovese, which they'll happily invite you to sample in the wine cellar adjacent to the house. The perfect accompaniments for evening barbecues on the vast outdoor terrace, wouldn't you agree? Group of friends or families sharing will love ho...
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...
This 17th century Tuscan villa is brimming with old world charm. It has been expertly restored and renovated, while maintaining a magical ancient aura. Terracotta floors, bronze busts, wooden roof beams, original fireplaces and deep stone basins compound the villa’s traditional appeal, while outside there is a stunning 14 by 6 metre pool, and plenty of chill out zones and deck chairs so you can sunbathe and relax in comfort. There are seven bedrooms, each with their own distinct character. We love the emerald green tiled bathroom, and the classic Tuscan stripes. Downstairs there are three living rooms, as well as a cards table for a late night game of Poker. On warm summer evenings dinner can be eaten al fresco, or at the long banqueting table inside. The kitchen is fully modernised, and there is also an outdoor wood fired oven, so you can try your hand at pizza making. The villa is located in verdant countryside, about an ei...
This is an excellent base from which to explore Tuscany and Chianti. The stone villa is a classic example of Tuscan style, which has been renovated into a comfortable home – it has everything you might need and is still full of authentic charm. You’ll wake up under an authentic wood-beamed ceiling in one of the elegant bedrooms. Making your way downstairs, past antique paintings and a grandfather clock, you’ll enter the dining and living space. As in any Italian home, this is the heart – you’ll likely spend hours sitting around the dining table. Outside, the covered veranda is the perfect place to sip coffee – or vino in the afternoon. The pool is a short stroll away, surrounded by lush lawns and trees. It’s a dreamy place to be whether you’re swimming laps, soaking up the sun by the water, or reading a book in the Jacuzzi. The villa is a twenty-nine-minute drive from Siena, which is a great city for day trips. Di...
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. ...
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 ...
Overlooking the lush Chiana Valley, this former farmhouse boasts views you won’t be forgetting any time soon. There are plenty of spots to sit back and soak it all in, but the pergola’s one of our favourites, perched right next to the pool and offering plenty of room for dining alfresco. The vineyard at the bottom of the garden is lovely too – and, while the interior’s a little dated, there’s a gorgeous stone fireplace to cosy up by if you’re visiting out of season. *While the fourth bathroom isn’t photographed, we expect the style and quality to be consistent with the rest of the home. *We love the traditional stone stairs here, but they may not be accessible for everyone. Those with limited mobility might prefer to use the bedroom and bathroom on the ground floor. *The swimming pool is only available for use between 15th May and 15th September. It isn't fenced, so little ones will need to be supervised when playing outside...
In and of itself, this stone and brick villa is rather dreamy. The timber roof trusses and tiled floor bring an easy rustic charm, and the furnishings are unshowy. Large glass doors can be opened on warm afternoons — plenty of those in Tuscany — to let a cooling breeze circulate through the interior. They also look out to a lovely view of the Pratomagno mountains. However, the home is part of a compound with some excellent communal amenities. Pass through the lemon grove, for instance, and you'll come across a large infinity pool with a covered pavilion at the side for alfresco lunches. Elsewhere, there's a well-stocked library and a theatre space where musical and artistic events often take place. Guests can embark upon a stroll in the surrounding private park, where you'll find olive trees, traditional stone walls and waterfalls on the Resco River. You might find there's very little need to leave the address, but the local town of Pia...
Built as a farm at the end of the 19th century, this rural home has oodles of charm and Tuscan character. We're swooning over the original terracotta-vaulted ceilings, the exposed cork beams and the huge fireplace, which is the perfect spot to snuggle up with a cup of tea on wintery nights. Every room captures the essence of old-world Tuscany – warm, cosy and pastoral – but there are modern conveniences too, like rainfall showers and a ping-pong table in the garden. Surrounded by a sea of olive trees and with vistas of the mountains, the garden is utterly enchanting. Start the morning off with an espresso on the outdoor sofa, cool off on sunny afternoons with a swim in the pool, then fire up the stone barbecue and dine under the wisteria-covered pergola on summer evenings. If you fancy exploring, there are plenty of places to discover. Just down the road is artsy Cortona, an Etruscan town with views across the Chiana Vall...
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...
Tucked away in the heart of Tuscany, this serene stone house sets the scene for many happy holiday memories made with your loved ones. It sits on a green and leafy spot, with some wonderful views over the Tuscan hills in the distance that you can enjoy from one of the many sitting areas in the gardens and on the terrace. There's a dreamy private pool here so you can stay refreshed in the Tuscan heat, as well as an outdoor kitchen with a barbecue and wood oven for alfresco feasts. Inside, the interiors are a little lacking in light, but they feel peaceful and secluded, and feature all you need for a home-from-home stay. *One of the bedrooms is located in a separate annexe with its own lounge area, ideal for couples who'd like more privacy. *The swimming pool is only available for use between 1st May and 30th September. It isn't fenced, so if you're bringing little ones, they'll need to be supervised at all times. *If you're tr...
Made up of a main building and two annexes, nestled on a promontory and enjoying stunning views of the city and surrounding countryside, this home is a gorgeous blend of the traditional and the super modern. Sit by the fireplace in the main building or admire the art adorning the walls, or out by the private pool and catch some sun on the poolside loungers under the trees. While one annexe houses primarily bedrooms, the second can be enjoyed as an impressive modern gazebo with a fully-equipped kitchen and dining area, and large windows that can be lowered at the touch of a button. Read under the trees and enjoy picnics on the vast grounds, and dine alfresco in the furnished gazebo. Although you'll enjoy tranquillity and serenity during your stay, there's only a ten-minute drive between you and the city of Arezzo. History buffs can visit the Roman amphitheatre and Medici Fortress, or dine like a local at the range of fantastic res...
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...
Like many traditional homes in Tuscany, this gorgeous old farmhouse is full of rustic elegance, with ivy and vines creeping over the exterior, beautifully matching it to its country surroundings. With traditional wooden floors boasting large woollen rugs and thick wooden beams on the ceilings, there’s no mistaking this home's authentic and historic character. Each of the three comfortable bedrooms is bright and full of country flair while the bathrooms are fitted with Italian patterned tiles. Outside, the garden runs down to the cool, inviting swimming pool and the wide terrace is the perfect place to sit for a barbecue lunch while taking in hilltop views of the Tuscan countryside. Just a 25-minute drive over the border from Tuscany to Umbria and you’ll reach the beautiful shore of Lago Trasimeno, a large freshwater lake where you can take a boat out or enjoy a meal in a taverna on the water’s edge. *At maximum capacity, one of...
Situated near Monte San Savino, this farmhouse invites guests to experience an authentic taste of the Tuscan countryside, including a complimentary wine tasting and a visit to the owner's winery. With a large garden and private swimming pool overlooking the vineyards and hills, you'll likely choose to spend much of your time out here taking in the surrounding scenery. Inside, classic designs nod to the home's Italian countryside location through features including an original oven and fireplace. While its traditional styling may not be to everyone's tastes, modern finishing touches ensure comfort and practicality are met here. *Due to the location of this home, we recommend hiring a car to get the most out of your stay – there’s free parking on the premises. *One of the twin bedrooms can be set up as a double upon request. *The swimming pool is open from May to September. *A complimentary wine tasting and a visit...
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...
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...
This villa is one of six on a complex, nestled among olive trees with views of the Tuscan hills. You’ll have use of the large, communal infinity pool as well as your own private outdoor space here. While the home has a fully equipped kitchen if you want to cater for yourself, there’s also an on-site restaurant serving breakfast, lunch, and dinner. Location-wise, you’re perfectly placed for walks in the countryside and we suggest hiring a car to explore the vineyards and historic villages that the region is known for. *While one of the bathrooms isn’t photographed, expect the style and quality to be consistent with the rest of the home. *This is one of six villas in a complex so you’ll have direct neighbours here. *While you’ll have some private outdoor space, the swimming pool is shared with four other villas. It isn't fenced, so children will need to be supervised at all times. *If you're travelling with little ones, yo...
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...
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...