Reggello

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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. 

The Vineyard View

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

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

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

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

Situated amidst the rolling hills and sweeping meadows of enchanting Tuscany, this achingly beautiful townhouse promises an endlessly relaxing stay filled with all of the timeless charm of rural Italian living. There's so much to love about the home, from the traditional features to the art objects and modern styling. 

We think you'll spend most of your time soaking up the warm weather by your private swimming pool. With sun loungers, a cabana and a furnished summer house, you'll be spoilt for choice when deciding on a spot to enjoy your afternoon Aperol from. Complete with an outdoor shower, barbecue and a beautiful dining area, the garden and communal space are perfectly suited for balmy summer evenings spent dining alfresco with your family and friends. 

Stepping inside, you'll find a wonderfully bright and open living space that you can quickly make your own. We love the warmth of the orange-painted walls, wooden flooring and timber beams that are reassuringly rustic and homely. There's plenty of modern comfort here too. Flop down on the sumptuous modular sofa, or perch at the sociable breakfast bar for a quick coffee as you map out plans for the day ahead. 

When it's time to head out, take a short stroll to the typical Tuscan village of Pontassieve, for mini-markets selling local produce, shops and excellent restaurants. And, you can't take a trip to Tuscany without visiting Florence, just thirty minutes away by car. 

Ciao Bellissima

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

Set on a 3000-hectare estate, this villa is somewhere you can truly immerse yourself in the beauty of the Tuscan countryside. As the greenery of the valleys wraps itself around you, settle down on a sun lounger and drink in the views over a bottle of chianti with loved ones. For laid-back villa days, stroll the grounds, sit back in the sauna, or enjoy a gentle swim in the private pool – a welcome relief in the heat of the day. For those who prefer to stay active, you can hop into the private gym to expend a little energy.

Lovingly renovated, step inside and you’ll find a classic masterpiece, sophistication seeping from its walls. We love the exposed beams and elegant arches, adding a touch of class and personality. This home has a romance about it and it’s easy to see why it’s a popular spot for weddings – don’t be surprised if you fall a little bit in love with the villa itself. With vineyards aplenty in the surrounding area, do get out and explore – a tour and tasting session has to be on your agenda. Armed with bottles of local wine, you can head back home and raise a toast to unforgettable memories, in your little slice of paradise. 

Picture of Tuscany

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

Leave the gorgeous Renaissance city of Florence in your rearview mirror and head for the hills. Drive just thirty minutes or so up into the rolling Tuscan hills, and you'll come across this breathtaking villa with a soaring clock tower. Split into three units, two of which are on offer here, make your home from home in the sleepy village of Cellai where time stands still.

Step inside your apartments, and uncover an enchanting mixture of traditional Tuscan and contemporary touches that blend seamlessly together. Terracotta floors, exposed wood beam ceilings and stunning frescoes sit alongside modern additions, including a stylish farmhouse-style kitchen and monolithic fireplace. 

All eight bedrooms blend rustic charm with utmost comfort to create havens of relaxation where you can take a break from socialising and appreciate the peace and quiet of your surroundings. Throughout the spacious interiors, you'll find several seating areas where you can kick back and relax with a podcast. In addition, dining areas can comfortably accommodate the maximum number of each apartment for sociable meals with family and friends in true Italian style. Elsewhere, the bathrooms are fitted with exquisite tiles and gleaming Italian marble that adds a hint of luxury to proceedings.

Discover a lush landscape of immaculate terraced gardens, a vine-covered pergola, a tempting pool and breathtaking views over the surrounding countryside. When your hosts are in town (in the mostly vacant third unit), they've made a ritual of visiting Forno La Chiocciola, where they stock up on fresh schiaccata, a Florentine speciality, and we'd suggest you do the same. Spend your days laid out by the pool, interrupted your sunbathing sessions only for refreshing dips and trips to the kitchen to rip off a chunk of that delicious bread.

For the culture vultures, we'd suggest spending a day (at the very least) wandering the backstreets and alleyways of Florence. In our opinion, getting lost on a self-guided tour is the best way to get to know the artistic, architectural and cultural history of Tuscany.

Villa Tosca

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

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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