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...
For a peaceful garden retreat close to the coast, look no further. Bright and welcoming, this colourful home has a beach-house vibe, which is fitting – the beach is mere moments away. You’ll also be just 2 kilometres from the little town of Castiglione della Pescaia, which you can reach on foot or by bike. When you’re not out exploring or splashing in the surf, you’ll likely spend most of your time in the garden. Doze on sun loungers before dining alfresco in the shade of the portico, or unwind inside. The villa is contemporary and cheerful, thanks to bold splashes of colour. *Your host can provide a cot and high chair for little ones. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility – there are some ground-floor bedrooms. *There’s free parking here. Air Conditioning Barbeque Blender Central Heating Child Friendly Coffee Maker Cot / Crib Dishwash...
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...
Rustic charm meets modern luxury in this hilltop Tuscan home. Boasting fantastic views of Montalcino, we think the garden is the perfect spot to enjoy the sunshine and fresh air. Entertain yourself with a dip in the private pool, play a game on the bocce court, or tuck into an Italian feast on the terrace. Step inside and you'll find seven en-suite bedrooms and a living space brimming with traditional character. Siena, Buonconvento, and other picturesque towns are within driving distance, making it easy to explore. There's also the option to arrange wine tastings, private dining, horseback riding, and other experiences – it's no wonder this home caught our eye. *While not all bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *There's a private suite on the ground floor ideal for guests with reduced mobility. *We suggest hiring a car in this location. Private park...
In the heart of the Chianti hills, this cosy villa offers a tranquil escape. Its compact design belies surprisingly spacious rooms, while the wooden beams sprinkle character over the home. That said, it’s the outdoor space that caught our eye. A brief walk away, the secluded garden serves up panoramic vistas, sun-drenched terraces and a private pool. If you can tear yourself away, explore the nearby town of Gaiole, less than ten minutes away by car, or venture further to discover Siena, Florence, and San Gimignano. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from mid-April until mid-October, isn't fenced. Children will need to be supervised at all times. *The owners, who live in the hamlet, may occasionally use the pool when the pool area is unattended by guests. *There are steps to access this home and some of the bedrooms. It may not be t...
Nestled in the picturesque hills of Valdarno, this secluded country home is ideal for nature lovers seeking a restful stay in Italy. Spread between the main building and five annexes, this home is perfect for large groups – smaller family units will have their own space but everyone can come together to celebrate, in the large dining room or the beautiful outside space. The estate sits within 36 hectares and is framed by oaks, olive trees, and rows of vines in one of the most beautiful and varied landscapes in Tuscany, between the Pratomagno ridge and Chianti. You’ll be within easy reach of Florence and Arezzo, which are ideal destinations for day trips. *Your host can provide a cot and high chair for little ones. *The swimming pool is open from the last Saturday in April until the first Saturday in October. *This home comprises the main building and five annexes, so you won’t all be sleeping under the same roof. *There’...
There are some homes that are simply made for entertaining. And this beautiful villa in Tuscany invites guests to come together and celebrate in style. Located in the village of Cevoli, there’s an authentic charm to this home that feels inspiring. From the moment you step inside, you’ll want to pause and admire the eclectic styling. Art and objects fill this space with a sense of depth and elegance, transporting you to another time and place. And wherever you find yourself, there’s something beautiful to see. From the ornate bedrooms to the tranquil gardens, every detail of this home enriches the moment – making it the perfect setting for families and friends to enjoy quality time together. Whether your relaxing by the pool or cooking in the kitchen, it’s easy to feel at home here. Days can be spent exploring the Tuscan countryside – wind your way through vineyards and olive groves towards the stunning villages o...
Nestled in the rolling hills, this villa offers a tranquil retreat in the heart of Tuscan wine country. Perfect for families or friends, it blends rustic charm with modern comforts for a truly restful stay. Spend your sunny days lounging by the private pool or unwind in the spa with a Turkish bath, sauna and Jacuzzi. You'll find everything you need inside the elegant living spaces, including a billiard room and six serene bedrooms split between the main house and annexe. Finish your day of relaxation at the BBQ and alfresco dining area for a long, lazy evening under the stars. With charming villages, historic abbeys, and world-class wine estates a short drive away, this is timeless Tuscan living. *This home is situated over three floors and may not be the best option for those with reduced mobility. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There is parking available on the proper...
Staying in this charming apartment gives you a taste of authentic Florence. It’s in a historic building – so there’s no lift – and boasts classic Florentine decor including wooden beams. The owners have lovingly decorated it in a warm, romantic style, blending the old and new. There’s a convenient kitchen, though with so many restaurants nearby, you won’t need to cook unless you really want to. Galleria dell’Accademia, Piazza della Signoria, and the Duomo are all within 500 metres – this is a remarkably central base. *This apartment is on the second floor of a building with no lift, so it may not be suitable for those with reduced mobility. There are forty-three stairs to the entrance. Air Conditioning Central Heating Child Friendly Coffee Maker Drying Rack Espresso Machine Fire Extinguisher Freezer Fridge Hair Dryer Iron Ironing Board Kettle Kitchen Utensils Microwave Paid...
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...
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...
This charming apartment is on the ground floor of a renovated farmhouse in the Italian countryside. It’s surrounded by vast gardens with a shared swimming pool, and you’ll have private outside space too – what’s better than dining alfresco on holiday? Enjoy views of the surrounding hills while you cook on the barbecue or whip up pasta dishes in the well-equipped kitchen. This comfortable home is ideal for a family seeking a restful escape in a rural setting. You’ll be close to San Gimignano and Siena, giving you great options for day-trips. *The swimming pool is shared with the other residents. It’s open from 1st May to 30th September. *There’s free parking at this home. *Your host can provide a cot for little ones. *The laundry facilities are shared here. Barbeque Carbon Monoxide Detector Central Heating Child Friendly Coffee Maker Cot / Crib Fenced Property Fire Extinguisher Free Parkin...
If you’re celebrating something special or simply looking for a huge, luxury home to gather together in the beautiful Tuscan countryside (ten minutes from Lucca), this is the spot for you. Dating back to the 17th century, you can feel the history of this home in the frescoed ballroom (seating up to 50 people for dinner), lounges set around ancient fireplaces and the shining farmhouse-style kitchen. Bedrooms are spread across the main villa, a converted hunting lodge and former stables in the grounds. Speaking of, the rose gardens, herb gardens and vine-twisted pergolas seem to go on forever. Apart from an inviting outdoor swimming pool, the crowning glory is the dedicated spa with its Turkish bath, sauna and hydrotherapy centre. *A complimentary housekeeping service is included throughout your stay. *This home consists of three separate buildings – the main villa sleeping 12 guests, a former hunting lodge housing four apartments...
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...
If you’re in search of a traditional Tuscan escape, this home delivers a great solution. Just 10 kilometres from Cortona, this rustic sanctuary consists of three independent apartments (each with its own entrance) – making it a great option for groups and families. It’s worth noting some of the furnishings are a little dated, but you will find a peaceful garden, a private pool and a large terrace with a barbecue. Your host can also help organise a range of extra services, including cooking classes and spa treatments. From here, it’s just a short drive to local amenities, while majestic cities like Arezzo and Siena are also within easy reach. *Please note this home is spread across three floors and consists of three apartments. Each floor has its own kitchen and entrance. There is also an adjoining annexe with a dining room. *While not all of the rooms are photographed, expect the style and quality to be consistent with the rest ...
This charming cottage is surrounded by vineyards, tucked away in the small medieval village of Scrofiano. The cottage boasts lush gardens with an above-ground swimming pool and a covered veranda where you can admire the views and cook on the barbecue. Inside, the cottage is traditional and as charming as they come – look forward to exposed wooden beams, terracotta floors, and stone arches. At full occupancy, two guests will sleep on a sofa bed in the living room, which we think is best suited to children. From this delightful home-from-home, you can reach the thermal baths of Rapolano in twenty minutes, and Siena in thirty. *At full occupancy, two guests will sleep on a sofa bed in the living room. *There’s parking for two cars at this home. *There’s a spiral staircase here that may not be suitable for those with reduced mobility. *The swimming pool is open from 1st May-30th September. *Your host can provide a cot and...
This 17th-century villa in the heart of the Chianti countryside offers far-reaching views across the vineyards and olive groves out to Siena. You're within walking distance of Lecchi, as well as being a fifteen-minute drive from Radda in Chianti for dreamy day trips exploring the region. A car is recommended to get the most out of your stay here. Outside, you'll find a well-kept garden lined with cypress trees, as well as a private pool. But our favourite spot has to be up on the dining terrace, which provides some beautiful views over the hilly surroundings and is ideal for alfresco feasts together. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There’s private parking for up five cars. The drive will be hilly and often uneven at times. *The home consists of a main house and a separate annexe. *The twin beds can be configured as double if required – you’ll need to request this in a...
In the heart of Tuscany, surrounded by vineyards and olive groves, this home is a true haven. Contemporary and calming, you can’t help but relax here, while the flexible bedroom setup makes it an ideal choice for larger groups. The icing on the cake for us is the outdoor space, with sun-kissed terraces, a private pool and plentiful alfresco dining opportunities to enjoy – there’s something for everyone. Ready to explore? The town of Vagliagli is a stone’s throw away, while Siena and Florence are within easy reach. *There's no air conditioning here, but fans are provided for guests' comfort. *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, open between the end of April and the end of September, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *Single beds may be pushed together in s...
Ten minutes from Sarteano town and an easy drive from Montepulciano, this charming Tuscan estate has its own outdoor pool and wellness facilities. The gym and spa are well-equipped, with a heated indoor pool, Finnish sauna and professional exercise equipment. Made up of a main home and an annexe, there's plenty of room for large groups to spread out, and for kids and pets to tire themselves out in the garden. You'll have privacy and countryside views, plus it's a great base to explore the Val d'Orcia and Valdichiana regions by car. *Not all bedrooms and bathrooms are photographed, but we expect consistency in style and quality throughout. *We highly recommend hiring a car to make the most of your stay. *This home is made up of a main house which sleeps sixteen guests, and an annexe which sleeps a further ten. *Several of the bedrooms can be configured as twins or doubles by pushing the beds together. The bedrooms in the an...
This traditional farmhouse will captivate anyone in search of a rustic retreat in the heart of Tuscany. It commands a lofty position with stunning views and a wonderful sense of character. There’s also a heated swimming pool, sauna, gym, and lots to explore in the surrounding area. From here, it’s just a forty-minute drive to Florence and Arezzo, with beautiful towns like Siena and San Gimignano also within easy reach. Your host is also on hand to help organise a range of extra services including wine tastings with a local wine producer. *While not all of the rooms are photographed, we expect the style and quality to be consistent with the rest of the home. *Due to this home's location, we recommend hiring a car to get the most out of your stay. *Alongside the main house there’s an independent annexe with three bedrooms – for those with reduced mobility, there are two ground-floor bedrooms and bathrooms here. *Mid-week ...
Surrounded by olive and cypress trees, this home perfectly embodies the timeless charm of Tuscan living. Dating back to the 15th-century, it began its life as a monastery, transitioned into a farm and now exists as the ideal setting for an immersive Italian escape. Inside, you’ll be welcomed by a wonderful sense of character along with plenty of space to stretch out and enjoy quality time together. There is also a games room, a fitness room and a wine cellar. Outside, you can stroll through the gardens, relax by the private pool and enjoy games of tennis on the private court. You will need a car to get around here, but it’s just 10 kilometres to Siena, while Florence and Arezzo are also within driving distance. *This home consists of a main house with three floors and an adjoining annexe with a laundry room, fitness room and wine cellar. *The tennis court can transform into a basketball court. Rackets are available to use. *D...
Surrounded by countryside, you won’t find it hard to relax in this Tuscan home. Comfortable for up to twelve guests, there’s plenty of space for everyone to spread out and enjoy some quiet time or come together as a group, with the added bonus of en-suites to all bedrooms. While there’s no air conditioning here, a refreshing dip in the private pool will have you cooling down in no time. And when it’s time to explore, you can reach Florence or Siena within an hour’s drive. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There's private parking available here. *There's no air conditioning available here. It could get a little hot during the summer. *The swimming pool, open between 1st June and 30th September, isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. For pool opening times outside of this period, please speak to your host. *The sixth ...
In the heart of Chianti Classico, this charming old stone villa offers a haven for wine enthusiasts. Surrounded by vineyards producing world-renowned wines, you can easily explore local wineries and historic towns like Radda. If you’re not sampling the local grapes, back home, you’ll find everything needed for a comfortable stay. Granted, there’s no air conditioning here, but with sun-dappled terraces, panoramic views and a private pool, you’re sure to be drawn outdoors anyway. Locally, a trip to Radda is a must, reached easily in under ten minutes in the car. *There's no air conditioning here. It could get a little hot during the summer. *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 September, isn't fenced. Children will need to be supervised at all times. *The twin bedroom can be set up as a double upon request. *We...
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...
Nestled in the Tuscan countryside with a private pool, serene outdoor space and views across Chianti’s vineyard-laced hills – what’s not to love about this home? Comfortable for a family or group of friends, inside, you’ll find a seamless blend of traditional and modern. And, when you fancy a spot of sightseeing or some authentic Italian cuisine, you can walk to the hilltop town of Radda, just two minutes away, or for jaunts further afield, hop in the car for a day trip to Florence or Siena. *There's no air conditioning here, but fans are provided for guests' comfort. *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 mid-October, isn't fenced. Children will need to be supervised at all times. *There are steps to access this home. It may not be the best option for those with reduced mobility. *We recommend hiring a car to get t...
Set in the foothills fringing the medieval town of Cortona and surrounded by olive and fir trees, the setting of this traditional cottage couldn't be more Tuscan if it tried. The interiors may be too rustic for some, but they would perfectly suit a small family or group of friends looking for a fuss-free stay. That lengthy pool fringed by vast lawns for little ones to have a runabout is all yours – and there's a ping pong table to break up pool time. Location-wise, Cortona is within walking distance, just 800 metres away – albeit uphill. And just a little further, discover Lake Trasimeno in Umbria. *There is ample private parking outside the villa. *If you’re travelling with little ones, the pool area has gated access for added peace of mind. *This cottage is semi-detached alongside a separate dwelling which is permanently occupied. The owner's cottage is also within the grounds. The use of the swimming pool is solely for yo...
Everyone is welcome at this hillside villa. Outside, you can enjoy expansive views across olive groves and there’s a swimming pool for refreshing dips. Afternoons can be spent relaxing on the terrace or soaking up the sun on a lounger. Inside, the rooms are contemporary, fresh and family friendly. You’ll also find plenty of opportunities for wine and olive oil tasting in the region, while the main market towns of Chianti are all within easy driving distance. It’s also just a short drive to the lively village of Gaiole. *Private parking is available for two cars on the drive. *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 *Well behaved pets are welcome to join you here. Air Conditioning Barbeque Beach / Pool Towels Child Friendly Coffee Maker Cot / Crib Dishwasher F...
The journey to this home is magical – you’ll travel along winding roads through vineyards, olive groves and the hills of the Florentine countryside. And when you want some culture, this apartment is only twenty minutes from Florence. There’s a private terrace to relax on, as well as shared gardens where you can enjoy the amazing views, alfresco dinners at sunset or do some stargazing. Housed in a former convent from the 1400s, inside this home, modern interiors blend with the character features. This apartment is perfect for couples, friends, and families looking to stay in a rural retreat with easy access to the cities and towns of Tuscany. *There's no lift here. You'll need to be able to climb stairs to reach the third floor entrance of the home. *There's a private terrace here, while some areas of the grounds are shared with other residents of this complex. *There are a couple of steps down to one of the bedrooms. *...
In the countryside just outside of the spa town of Gambassi Terme, this delightful villa looks out over the Volterra Hills. It’s peaceful and pretty, surrounded by typical Tuscan vegetation including cypresses, chestnuts, and olive trees. The well-kept garden – full of vibrant flowers and aromatic herbs – boasts a beautiful swimming pool, a lawn, and a gazebo for alfresco dining. The terrace is a splendid spot for sunset. Perfect for a couple of families travelling together, this home is spread between the farmhouse and the converted barn, so everyone can enjoy their own space. *The swimming pool is open from the last Saturday in April until the first Saturday in October. *Your host can provide a cot and high chair for little ones. *This home is spread between the farmhouse and barn so you won’t all be sleeping under the same roof. *There are stairs to climb at this home so it may not be suitable for those with reduced mo...
Whether you're swimming laps in the pool, lounging in bed or sipping a sundowner in the garden, this country home serves up breathtaking views from almost every angle. Surrounded by olive groves, world-famous vineyards and just a short drive from Siena, it’s a picture-perfect base for exploring the Chianti region. Inside, it’s packed with character — grand but with a touch of eccentricity, from exposed beams and stone staircases to chandeliers and canary-coloured walls. Did we mention it comes with staff, including a chef? After a hard day of wine tasting, nothing beats coming home to find dinner ready and waiting. *While not all of the bedrooms and bathrooms are photographed, expect the style and quality to be consistent with the rest of the home. *This home comes with its own private chef and team of staff who can help with anything you might need while always respecting your privacy. *The swimming pool isn't fenced. If you...