Castelfranco Piandiscò

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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 a challenging trail along the Pratomagno mountains.

Sing, Prima Donna

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Enjoy a fairytale setting when you stay on this Tuscan estate, nestled amid scenery said to have inspired da Vinci's paintings. Designed by a famous architect, we love how this home retains its traditional character with an ancient fireplace and a loggia overlooking the communal square. On-site, there's also a seasonal pool to share with your neighbours, a restaurant, and a concierge to help you plan tours. Fancy a road trip? Florence and Arezzo are less than an hour away by car.

The Orange Sun

This charming villa, nestled among the olive trees in Tuscany, is ideal for those looking for fuss-free comfort. Inside the home, you'll find an upside-down layout, while outside, there are two balconies overlooking the square and Pratomagno mountain, as well as a private garden to stroll around. There’s also a large, shared infinity swimming pool and games room with a billiards table. If you don't fancy cooking, guests have access to an on-site restaurant for meals, and the concierge can help organise tours, so it’s easy to explore cities such as Florence nearby.

Casa San Giorgio

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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 Pian di Scò takes just over twenty minutes to reach on foot if you fancy a change of scenery.

Nearest & Dearest

Tucked away in rural Tuscany, this picturesque villa sits on a working olive farm, although it used to be a 17th-century convent. Surrounded by natural beauty, this historic place invites you to roam the woodland right outside your front door. Perhaps you'll drive out to Florence for a cultured outing, where Renaissance masterpieces await. Arezzo lies in the opposite direction, but we wouldn't blame you if you didn't want to venture too far.

Bursting with storybook charm, this quaint retreat is furnished with antiques to honour the age of the home. While sipping Italian espresso at this intimate dining table, gather your loved ones and discuss your oil-tasting experience at the on-site olive mill. Why don't you stop by the impressive library and read about performing arts before taking to the stage at the theatre? Alternatively, imagine making new friends in the shared infinity pool or booking a relaxing massage – we just love how much there is to do around here. What better way is there to end the day than with a sunset barbecue on your stony terrace?

A Playwright's Paradise

This breathtaking villa is one of the oldest in the hamlet of Castelfranco Piandiscò, and it wears its history with pride. The traditional stone exterior gives way to a charmingly traditional living space – you'll be enchanted by the rustic wooden beams, collection of antique furniture and terracotta tiles. The ancient Valdarno fireplace is a beautiful centrepiece, and you'll find a second feature fireplace in the kitchen. The four bedrooms are wonderfully peaceful, and one even has access to the balcony, where you can sip your morning espresso in the fresh air. In, fact, you're spoilt for choice when it comes to outdoor space – from the beautiful garden, full of greenery and flowers, to the smart patio, you can't help but adopt an alfresco lifestyle here. Pick a book or magazine from the extensive home library, and bask in the Italian sunshine before taking a refreshing dip in the infinity pool. Adventurers can explore the stunning scenery surrounding the commune, wandering through olive groves and beech woods in true tranquility. And, if you fancy a day in the city, both Arezzo and Florence are only thirty kilometres away – their world-famous cultural relics have to be seen to be believed. 

Golden Silence

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.

Tuscan Casa

Espresso Machine

Private Pool

Desk

Located just outside the atmospheric medieval town of Pian di Scò, this stunning villa offers an idyllic countryside retreat, perfect for spending quality time with family and friends under the Italian sun. Thanks to the secluded garden, private outdoor pool and covered porch, you'll be able to enjoy the alfresco lifestyle throughout your stay. 

Step inside, through any of several French doors lining the villa's facade, and you'll uncover a traditional Tuscan interior with rustic terracotta tiled floors, antique furniture and plenty of exposed wood. Elsewhere, each of the four individually decorated bedrooms boasts its own en-suite. 

There are several other properties and shared facilities on the farm, including a vast library with a wide selection of books and magazines, a theatre for hosting musical events, and a network of walkways crisscrossing the grounds that'll lead you on enchanting walks through mature forests, passing streams and waterfalls along the way. If that all sounds a bit sedate, your hosts will happily arrange white-knuckle mountain bike rides along trails in the nearby forests. 

Elsewhere, the area is dotted with charming small towns and hilltop hamlets that are a delight to explore. Further afield, but well within day-trip distance, the Renaissance cities of Florence and Arrezzo are well worth an afternoon's exploration. 


Amarillo Sky

Located in the picturesque area of Valdarno, in a farmland territory off the beaten track lies this gorgeous villa. An ancient stone bridge will lead you to the entrance of this home, up on the first floor, where you can sink into the plush sofas and make yourself right at home. The loggia by the kitchen brings the outdoors in and helps this home feel like perpetual summertime. There are plenty of communal facilities within the farm for guests to take advantage of, including a pool where you can catch some rays or escape the summer heat in the calm waters, or a library for those who want to do some work or study, or who are just looking for something new to read. Treat yourself to an in-house massage or a scenic walk along the stream of the private natural park under clear blue skies.

This home is perfect for those who want to get away from everything and reconnect with nature – you'll find yourself immersed in olive groves and forests, bursting with native plants and wildlife. Natural water springs and expansive wooded areas allow you to go on some truly scenic walks, challenging hikes, or even a family picnic. Book a tour at the on-site olive factory where you'll get a taste of some freshly-made olive oil, or see a show at the on-site theatre. It's easy to get the most out of your holiday before you've even left the park, but a day trip up to Florence or down to Arezzo will give you that perfect variety.

The Stonewall

Although this villa shares facilities like an infinity pool, restaurant and games room with five other villas, it’s the only one on the complex with its own private pool. Set in luxurious lawns, it’s a tranquil spot to while away the days. French windows lead from the living room to the garden and bless the spaces with lots of sunlight during the day. Old hearths inside speak of days gone by and the kitchen has everything you need for self-catering. The decor might feel a little old-fashioned, but there’s plenty of space for the group to spread out. Tuscany is on your doorstep and Florence is an easy drive away for a day trip.

My Italian Song

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Ideally located in rural Tuscany, this country villa will provide the perfect base for holidays spent relaxing, wine tasting and hiking around this stunning part of northern Italy. With 8 hectares of olive trees and gardens at your disposal, you’ll want to spend most of your time enjoying the pool, hot tub and alfresco dining area. Inside, you’ll find some of the bedrooms have double beds made up of singles which will give you flexibility, while the separate annexe is perfect for couples seeking extra privacy. And when you want to explore the real Italian Dolce Vita lifestyle, have your host arrange an olive oil tour or truffle hunting excursion.

The Grapes of Violetta

Part of a complex of six similar villas, this place sits in the Tuscan countryside, within day-tripping distance of Florence. If you’re not exploring the medieval hilltop towns and rolling vineyards, there is plenty your host can organise on-site – wine tasting, breakfast, dinner and lunch in the restaurant or trips into the countryside. Guests here have access to a shared infinity pool and a games room. Within the villa, you’ll find a full kitchen and two dining areas. Some might call the living room dated, but it blends in with the wood-beamed ceilings and old fireplaces. 

Luxurious Views

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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.

Between the Vines

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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 sleeping quarters, spend mornings in the fully-equipped country kitchen, brewing espressos or tucking into breakfast on the veranda. 

Fringed by lush, landscaped grounds, including a home-grown vegetable garden that you're encouraged to forage, this home beckons you to relax in the splendour of your surroundings. Here, a saltwater infinity pool takes centre stage, a glistening oasis amidst the perfectly clipped emerald lawn. Spend your days poolside, soaking up the sun or relaxing beneath the shade of the rose garden nearby. 

Tuscan Rose

Pod Coffee Machine

Tucked away amongst olive groves and vineyards in the countryside of Chianti, within easy reach of the vibrant cities of Florence, Siena, and Arezzo, this home makes a great base for exploring gorgeous Tuscany. The home itself is typically Tuscan, with antique decor and terracotta tiled floors – but the garden is the sparkliest jewel in the crown, where you'll find a gorgeous dining terrace with climbing vines that provide ample shade, plus a private outdoor pool for making happy memories in the sunshine.

Sweet Orange Peel

Rain Shower

Private Dryer

Tennis Court

Breakfast Included

Standing boldly amid the rolling hills and meadows of Tuscany, it’s easy to see why this home caught our eye. Not only is it visually striking, but it also boasts great views, a private pool and exceptional service. Breakfast is included in your stay, butler service is available throughout the day and a private chef can be arranged for lunch and evening meals. Tennis lovers will also appreciate the access to the estate courts (just a ten-minute drive away), while those in search of an Italian adventure will love exploring nearby Florence – just a thirty-minute drive away. 

Tuscan Spirit

A traditional manor house located in Tuscany’s Val d'Arno, this pet-friendly home welcomes large groups with open arms. The outside space is all about taking advantage of the sunshine – there’s a swimming pool,  table tennis to keep the youngsters entertained and a shaded terrace complete with a barbecue for alfresco meals. Should you fancy swapping the countryside for the city, Siena is an excellent day trip destination, or why not nip into nearby Poggibonsi for rustic cafes and eateries?

Olives & Roses

With a simply dreamy location in the middle of the Tuscan Hills, this villa treats guests to glorious views of verdant countryside and an uninterrupted skyline.

The question that arises, therefore, is from which spot to enjoy this beautiful panorama. The table on the covered balcony is a lovely spot for an alfresco dinner, perhaps cooked on the stone barbecue and pizza oven found on the storey below. If that sounds a little too sedate, you can just as easily enjoy the scenery from the swimming pool complete with a slide, or while playing a few matches on the tennis court.

When you finally head inside, you'll find a home that's rather traditional in style, with a grand fireplace, terracotta tiling underfoot and chandeliers hanging on the ceiling. The villa itself is actually two independent apartments, which offers an extra degree of privacy and flexibility for large groups.

Although the address feels wonderfully isolated, there are plenty of small towns that sit nearby, including Loro Ciuffenna ten minutes' drive away. The cities of Arezzo and Florence take fifty minutes and just over an hour to reach by car respectively, too.

Comfort Food

Smart TV

Sauna

This beautiful home can be found in Reggello, close to Florence and only 4 kilometres from some of the best shopping in Tuscany. It’s a modern home-from-home, cool and comfortable, with a delightful outside space. A private pool sits in a vibrant garden filled with flowers and aromatic plants, where there’s a barbecue for alfresco dining, and an air-conditioned gym. Sliding doors connect the relaxing garden with the stylish villa, with its open-plan living and dining space. You won’t want to leave. 

Giardino Joy

This traditional Tuscan home is a peaceful retreat just 26 kilometres southeast of Florence. Consisting of a main house and an independent annexe (with its own kitchen), this is a great option for families and groups in search of authentic Italian charm in a beautiful location. It’s worth noting some of the furnishings and decor are a little dated, but you will find plenty of socialising space and a fantastic garden. There is also a sauna and a private pool, plus your host can help organise a range of extra services – including wine tastings and spa treatments. And for explorations further afield, the restaurants and shops of Leccio are just 3 kilometres away. 

The Sweetness of Being

DVD Player

Surrounded by its own private gardens, this historic and beautifully renovated villa is perfect for those seeking a relaxing retreat in the Tuscan countryside, as well as groups wanting a base to explore thriving cultural and nature hubs nearby – the charming commune of Terranuova Bracciolini is a mere five minutes' walk away. Day trips to Florence, the home to many Renaissance masterpieces, is less than an hour drive away too. For the nature lovers amongst us, there are two nature reserves in the Arezzo province and the River Arno is just minutes from your door. Alternatively, you can take in the stunning views of the idyllic natural surroundings just by lounging by the pool or from the bedroom in the ancient lookout tower. Inside, elegant furniture and large windows provide plenty of natural light to the sectioned, open-plan living spaces. This home dates way back to ancient Roman times – you’ll feel its rich history from the ancient-vaulted ceiling and stone archways the moment you step foot over the threshold. 

Olive Groove Nest

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. 

Green & White

Just a short walk from Loro Ciuffenna, this ground-floor apartment has views across the valley. The owner and their family live on the first floor and may occasionally nip down to use the pool. Otherwise, the covered terrace and garden are yours to enjoy. The design inside is minimal and uncluttered. Some of the en-suite bathrooms are a squeeze, but we love that each bedroom opens onto the garden. Loro Ciuffenna has a nice collection of cafes, restaurants and shops, but for adventures further afield, hop in the car and explore Chianti. Arezzo, Gaiole, and Radda are less than an hour's drive.

Michelangelo's Rose

Surrounded by olive groves, vineyards, and rolling hills, this hay barn conversion offers a tranquil escape. Step outside to the garden, where you'll find a private pool with panoramic vistas. Forming part of a farmstead, this two-storey home has plenty of Tuscan character and there’s a luxurious bathroom complete with a sauna and spa shower. Here, you can immerse yourself in the serenity of the Tuscan countryside while enjoying easy access to nearby towns such as Reggello, 2 kilometres away.

A Home's Embrace      

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. 

Valley Green

Courtyard

Head into the Tuscan hills just outside the charming village of Cellai and keep an eye out for an imposing villa with its own bell tower. Almost unbelievably, this stunning property will be your home from home for however long you decide to stay.

Step inside your apartment, and you'll discover a typically Tuscan scene, with tiled terracotta floors, exposed wooden ceilings and frescoes painted directly on the walls. Four individually decorated bedrooms, each as enchanting as the last, will serve as your soothing sanctuaries for you to unwind at the end of each day. The spacious interior includes not one but two seating areas, so you can always claim a secluded spot as your own for the afternoon if you want to get lost in the pages of a good book. Meanwhile, the kitchen and dining area are perfect for sociable meals with family and friends in true Italian style. 

Outside in the shared garden, you'll find yourself surrounded by pristine landscaped gardens with a vine-covered pergola, terraced seating and perhaps most importantly, a pool. 

Start each day by visiting Forno La Chiocciola, where you can stock up on fresh bread, including Florentine speciality flatbread, schiaccata. Then, when you're not laying out on poolside loungers and sipping wine in the sun, the stunning Renaissance city of Florence is less than half an hour away. Why not get to know the artistic, architectural and cultural history of Tuscany, spending an afternoon or three wandering its streets and taking it all in. 


The Legendary Giulia

It may be less than a thirty-minute drive from the spectacular Renaissance city of Florence, but this home feels like another world. Located up in the hills, you'll discover a spectacular villa – complete with a clock tower – just outside the small village of Cellai, where time seems to stand still. 

Pad across terracotta-tiled floors, with wood beam ceilings above, and discover rooms filled with character and charm, where period features and modern touches sit effortlessly alongside one another. Nowhere is this better displayed than in the contemporary kitchen and adjoining dining room with its antique stove. Each of the four bedrooms blends rustic charm with supreme comfort, while the bathrooms are fitted out with beautiful tiles and gleaming marble for a touch of luxury.

Step outside and you'll discover a lush landscape of terraced gardens, an inviting pool and breathtaking views over the Tuscan terrain. Your hosts recommend making the trip to Forno La Chiocciola, where you can stock up on Florentine speciality flatbread, schiaccata, each morning. Afterwards, place yourself poolside and settle in for a day of sunbathing, interrupted only by refreshing dips in the water and trips to the kitchen to get some more of that delicious bread. 

The Breadbasket

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.

The White Olive Tree

Fenced Garden

This stunning villa is an oasis of colourful flowers, tropical plant life and spectacular views. Perched at the apex of the hillside, the villa exudes unbridled privacy and tranquility. 

Sit on the dining table in the mornings, cappuccino in your hand, basking in the beauty of the encompassing landscape. Peaceful and relaxing, it's a rural slice of Tuscany that's reserved just for you. 

The home oozes serenity at all times, yet its flexibility transforms it into a social hub with your favourite people. Various seating spots, a large garden, luscious pool and BBQ area are idyllic spots to chat away into the gentle hum of the evening.

Take advantage of the services available to truly immerse yourself into the Tuscan lifestyle. Cooking courses teach you some traditional dishes and walking tours showcase the picturesque landscape that forms the region.

If you fancied venturing further than your villa and the local areas, the vibrant cities of Florence and Siena can be reached in less than an hour. Visit the charming streets for delicious food, striking architecture and world-class galleries and museums. 

Branches Of Fruit

Steam Room

Herb Garden

Set within a vast estate of rolling hills and chestnut forests with an abundance of flora and fauna, this is the kind of place that captivates you from the moment of arrival. And with its location just a thirty-minute drive from Florence, this is the perfect setting to connect with the region’s most beautiful sights whilst also enjoying an immersive retreat in the countryside. 

From the traditional features to the soft lighting and personal touches, there’s an abundance of charm and character here. It feels authentically Italian – inviting you to slow down and savour the richness of the moment. So whether you’re gazing at the views from the upstairs bedroom, cooking a simple supper in the cosy kitchen or sharing a glass of wine by the fire, you’ll feel serenaded by the sweetness of this home. 

Outside, days can be spent lounging by the pool or roaming through the countryside (look out for the wild dear, goats and hares). There are some beautiful walks here, while the vineyards and idyllic villages of the Chianti region are all within driving distance. 

After a day of exploration, you’ll love coming home to relax in the spa. Featuring a hot tub and steam room, there’s everything you could need to experience the height of relaxation. 

Sun Blush

Perched at the foot of the Pratomagno hills fringing the town of Terranuova Bracciolini with its pizzerias and osterias, the setting for this Tuscan retreat is idyllic. Recently renovated, although everywhere feels light-filled, it may feel a little lacking in character for some. It’s also worth noting that the swimming pool is shared with the guests from a small neighbouring B&B – though you’ll have private poolside loungers and your own shady terraces for evening mealtimes. When it’s time to explore, take your pick between Florence and Arezzo for day trips – you’re set equidistance from them both.

To the Tuscan Hills

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. 

Whispering Cypresses

Jacuzzi

Could there be anything more Tuscan than a sentry of cypress trees guiding you up the driveway to your ancient Italian villa? This home, less than a 30-minute drive from the heart of Florence, is a private retreat away from the bustle of the famous Italian city, and feels a world away from any kind of city life. Once home to Marsilio Ficino, better known as the astrologer and educator to the Medici family, you’ll be staying in a piece of classical Italian history here. We love that this home has been decorated in a traditional Italian style – bold evergreen stripes line the sofas in the living room, citrusy oranges and yellows are used liberally in the bedrooms and bathrooms, and everywhere you look you'll spot the traditional tiles and exposed wooden beams that have been in this home for centuries. Laid out over three separate buildings, this Florentine villa is actually three homes in one. The main house plays host to the main communal rooms as well as four bedrooms, while in one annexe you’ll find a private kitchen and living room and three bedrooms. Two more bedrooms, a separate living space and another kitchen are located in the second, smaller annexe. All three buildings share access to the private, well-kept garden and large pool.

A Cypress Tree in the Lemon Grove

Single-Level Home

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. 

Tuscany Sun

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