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Satellite / Cable TV

Entertainment

Hair Dryer

Bathtub

Bathroom

Dishwasher

Microwave

Espresso Machine

Oven

Stove

Kitchen Utensils

Toaster

Fridge

High Chair

Coffee Maker

Kettle

Kitchen

Kitchen & Dining

Iron

Washing Machine

Cot / Crib

Ironing Board

Dryer

Hangers

Drying Rack

Bedroom & Laundry

Swimming Pool

Hot Tub

Private Pool

Exercise Equipment

Wellness & Fitness

Wi-fi

Laptop Friendly Workspace

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Private Parking

Self Check-in / Check-out

Free Parking On Premises

Private Entrance

Parking & Access

Barbeque

Garden

Outdoor Seating

Balcony

Outdoor Shower

Outdoor

Mosquito Net

Nice to haves

Pets Allowed

Pets

Sitting on the peaceful border between Tuscany and Umbria, adventurers will be glad to know this home isn't too far off the beaten track. In one direction, Chiusi beckons you to visit the Museo Archeologico Nazionale and, the other way, Città della Pieve calls you into Pieve Co-Cathedral – both are a seven-kilometre drive. One thing's for certain when you come here, lots of fresh air and hilly picnics.

Ideal for groups craving a sense of space, this idyllic home spreads out over three separate apartments. With plenty to do among the fruit trees and flowers, how about a morning workout in this open-air gym? Maybe relaxing in the hot tub would suit you better, or dipping your toes in the infinity pool to keep cool during those sunny afternoons. If you're staying in the winter, just imagine dining on Italian-inspired dishes with your dearest ones – farm-to-table cooking couldn't be easier thanks to the abundant vegetable garden.

Against the Golden Wall

DVD Player

Freezer

Pod Coffee Machine

Cooking Essentials

Parking Available

Set against the backdrop of Umbria’s green rolling hills and topaz sky, this exposed stone villa on the outskirts of Città della Pieve holds the promise of uninterrupted rest and relaxation. Inside, a blend of elegance and farmhouse traditionalism creates a feeling of unmistakable serenity in the living room, with its beamed ceilings and simple hearth adding warmth and rustic flair. Paired with the dining room’s ornate chandelier and the bright, modern kitchen, the home wears its country chic style with effortless grace. Factor in the three comfortable bedrooms with their countryside views, including the enviable master bedroom’s private balcony, and you’ve got rural romance in spades. Outside, the large swimming pool with its waterfall feature is where you’ll want to spend long, sunny afternoons, while evenings call for poolside drinks around the well–style table as you watch the sun set behind the hills. Fire up the grill while the little ones entertain themselves in the garden’s playhouse and slide, then gather together for an alfresco meal under the pergola as the stars come out one by one.

Cara Mia

Outdoor Pool

Fireplace

Free Parking

Sun Loungers / Beach Chairs

Child Friendly

Other

You’ll find this rustic villa set among Tuscany’s rolling hills and endless countryside. Inside, there’s a warm ambience thanks to the terracotta tiles, homespun furnishings and farmhouse-style kitchen. If you’ll be spending time outside, we bet you’ll be relaxing by the private pool with a refreshing beverage in hand. Spend afternoons dipping in and out of the water before sitting down to an Italian-inspired feast at the alfresco dining table. 

If exploring sounds like a good idea, take the short drive to charming Chiusi for a stroll around the honey-hued streets and an espresso in a traditional cafe. Should a day trip be on the cards, travel north to Arezzo – visit the hilltop cathedral, Basilica di San Domenico and the imposing Medicean Fortress. Return to your abode in the early evening for a glass of wine or two on the terrace followed by a night of blissful sleep in the comfortable bedrooms.

Sunshine Burst

Desk / Workplace

Herb Garden

Patio / Terrace

Frescoed cherubs and exposed stone walls; this villa is the epitome of old Italian charm. It sits in the Umbrian countryside, an eight-minute drive from Castiglione del Lago, on the shore of Lake Trasimeno. Delightful day trips are on the cards with the Etruscan history of Chiusi a twenty-minute drive away and the hilltop enclave of Perugia reachable in forty minutes. 

A big swimming pool sits in the manicured lawn, where the old stone villa seems to admire itself in the water’s reflection. Alfresco dining is set up beneath gazebos that wouldn’t look out of place at a Rennaisance fair and the view is of endless rolling vineyards all around. Two built-in barbecues provide chefs with plenty of room to cook outdoors. 

Heading inside, a warren of archways lead to grand lounges and chandelier-clad dining rooms. Wooden ceiling beams and painted frescos on the walls feel as though you’ve stepped into the 18th century and the kitchen is a vision of old-world charm. This feeling continues in each beautiful bedroom, where four-poster beds are swathed with silk curtains and the two main bedrooms come with free-standing slipper tubs. 

Umbrian Fairytale

Sound System

Blender

Surrounded by olive groves and rolling Umbrian countryside, this rustic farmhouse retains its original character and charm. We loved the timber and exposed brickwork ceilings, Venetian plaster walls and traditional furnishings that make the place feel like home. Wake up to a light breakfast in the charming kitchen then spend your day lounging by the secluded pool or floating about in its cool water. 

Enjoy a quiet moment with a good book on the wisteria-covered pergola, surrounded by the scent of potted lavender, before heading out to explore. Stroll around the village of Panicale, right on your doorstep, or drive over to Perugia for a tour of the excavations under San Lorenzo cathedral, followed by a mosey around Porta Sole, the city’s creative quarter. When dusk falls, pick out a family-run restaurant for a selection of hearty local dishes. 

Wisteria & Lavender

Playground

Ceiling Fans

Hammock

Fire Extinguisher

Spend just a few moments relaxing in the jacuzzi, appreciating the views of the Umbrian countryside, and you'll see why we love this rural farmhouse. The hosts have carefully restored all the historic features and rustic charm you'd expect in a place like this – think colourful tile flooring in the downstairs kitchen, exposed stone walls in the bedrooms, and plenty of antique walnut furniture. But it's not just the traditional character we love. This home offers plenty of modern comforts, too, with two kitchens, a sparkling swimming pool and a whirlpool bathtub. Whether you're napping in the cosy living areas, sunbathing by the pool or sipping apéritifs on the shady patio, you'll feel right at home here. Swing the day away in the hammocks before firing up the built-in barbecue or wood oven for a tasty alfresco dinner made with ingredients from the garden. Then, watch the sunset over the olive groves. The location is perfect for exploring the region – scenic Lake Trasimeno is just a twenty-minute drive, while artsy Perugia is just under an hour away.

Terracotta & Stone

Standing high and proud above sea level, this turreted fortress gazes down at the stunning, surrounding countryside. Planted neatly between the delights of Tuscany and Umbria and with Lake Trasimeno in the foreground, a medieval trail of monuments, spas, and villages await to be explored. The villa itself is like an ancient towerhouse, rising up between the trees. The 360-degree view from its highest point overlooks the vast grounds, so you can survey the lands like a king or queen. Kids can play Rapunzel in the tower, or run around on the lawn and splash in the pool. With so many sheltered seating spots, from terraces to balconies, there’s plenty of spots to escape with a good book and bask in the peace and quiet. A cute, consecrated chapel sits within the grounds, should you be visiting for nuptials, and the four-poster master bed with its velvet curtains is the stuff of honeymoon suite dreams. With pines, cypresses, vivid blooms, and even an orchard and vegetable garden, this home is suitably overflowing with flora to sit within the green heart of Italy. 

Flora Fortress

For a true Italian escape, head to this home in the Tuscan hills. You’ll be welcomed by sweeping vistas, a large garden and a private swimming pool. The terrace provides the perfect spot for alfresco dining, while the first floor balcony makes it easy to switch off and enjoy the views. It’s worth noting one of the bedrooms is located in an independent annexe, but this is a great option for those seeking a little extra privacy. You’ll also find plenty to explore with Siena, Cortona and Montepulciano all within driving distance. 

A View of the Moon

Toiletries

Cleaning Products

Extra Pillows and Blankets

Desk

Lift Access

Free Parking On Street

Paid Parking On Premises

Single-Level Home

Safe

First Aid Kit

This elegant apartment is located in the main square of the charming town of Città della Pieve. It’s in Umbria but is just 7 kilometres from Tuscany, making this home a great choice of base if you plan on seeing more of Italy. We recommend hiring a car to get the most out of your stay. The apartment is equipped with everything you might need for a short break, including a desk for those working remotely during their stay. 

Italian Tastes

Sauna

This period stone villa, filled with antique furnishings, is what we call love at first sight. You will have four spacious floors all to yourself for a dream Tuscan escape with your loved ones. The property sits in the open countryside among rolling hills dotted with cypress trees. Outside, in the manicured gardens, you can make the most of the sunny days and read a book beside the pool or unwind in the Jacuzzi with a cocktail. You will never get weary of listening to the rustling oaks and orchard trees or inhaling the scent of herbs and roses. Sweat out any remaining stresses in the sauna, then whip up some fresh pasta in the kitchen and round up everyone for dinner under the gazebo. Should you need anything more, you’re just a one-minute drive from Sarteano, with its charming medieval houses, wine bars, restaurants and shops. 

Rustling Oaks

Games Room

Ping Pong Table

Outdoor Fireplace / Firepit

Set out over three levels, with a different perspective over the stunning landscapes around every corner, this vast hilltop villa is guaranteed to impress. The interior is pure traditional Tuscany, with brick archways, exposed beams and terracotta flooring to ground you as you wander from room to room. 

Each of the individually decorated bedrooms brings its own charm, while the main bedroom – with direct patio access and stunning marble en-suite is set to dazzle even the most seasoned of travellers. The open-plan seating area and dining room form an integral heart of the home and would be the focus almost anywhere else. However, life in Tuscany is best lived outdoors, and you're blessed with a number of balconies, rooftop terraces, poolside patios and landscaped gardens (plus seating areas in each one) that ensure there's always a corner to claim as your own. We imagine you'll spend most of your days sprawled out by the pool, only interrupting your tanning time to grill some lunch and take part in sporadic table tennis tournaments.

The surrounding area is well worth exploring. In under ten minutes, you can reach the timeless medieval town of Cetona. Here, the scent of cypress trees fills the air as you explore the winding streets of one of Italy's most beautiful towns. Slightly further afield, you're also within an hour of Val d'Orcia, one of Tuscany's six world heritage sites and the subject of countless Renaissance paintings.

Maremma Amara

Pool / Snooker Table

Bicycles

We could get used to this – a rustic Italian villa that oozes charm, surrounded by lush Umbrian countryside. A short drive takes you to the shops and cafes of medieval Città della Pieve, and charming destinations like Trasimeno Lake and Perugia are within easy reach too. This is a seriously good spot. In the home itself, Persian rugs sit adorn the polished tiled floors, lending a feeling of laid-back luxury, while a grand fireplace takes centre stage in the open living area. The kitchen is dominated by stainless steel and provides everything you need to realise your culinary dreams. Then, share your meals with nine of your favourite people at the garden table outside, with views of the countryside as your backdrop. Handily, there is also a separate, self-contained annexe for those who require some extra privacy. It comes with its own kitchen, en-suite and billiard table. Outside, the large, inviting pool is where we suspect you’ll spend most of your time. The well kept garden surrounding the villa is an extremely relaxing place to unwind – get the outdoor pizza oven on and set the world to rights until the sun goes down. Then do it all again tomorrow.

Where Olives Grow

Library of Books

The Italian countryside has a magnetic charm. Could it be the holy trinity of wine, food and verdant views? Definitely. Or the temperate Mediterranean climate? Certainly. But it’s also because it’s where you’ll find glorious holiday homes like this one. 

Set in the hills of San Casciano dei Bagni and Chiusi, this magnificent stone farmhouse straddles the border between two fairytale regions – Tuscany and Umbria. Explore both of their charming towns, cultures, and cuisines with ease from this central base. We recommend the neighbouring hillside towns of Cetona and San Casciano dei Bagni, but if you’d like to venture a bit further afield, the nearby railway station in Chiusi allows for breezy day trips to Cortona, Siena and Montepulciano. 

But for all that, you'll have more than enough to keep you busy with all this home has to offer. The well-selected modern furniture and fixtures blend beautifully with the terracotta floors, brick-vaulted ceilings, stone arches and fireplaces. The classical rustic interior transports you to the past, especially with the countryside views from nearly every room. 

And there’s a lot to see – sitting proudly on a five-hectare estate, the home looks out onto both cultivated land and woodland, a lush garden of flowers and cypress trees. Outside, the rolling landscape is best enjoyed by the shimmering stone pool or the romantic, shaded pergola. In the heat of the afternoon, read in the cool of the study before returning to the patio. Lounge until sunset, where the fiery colours linger longer, and are best enjoyed alongside a bold Tuscan red from the cellar.

Cypress Hill

Set amidst Umbria’s rolling hills and verdant woods, this home is a true escape from the hustle and bustle of city life. Less than a five-minute drive from the medieval village of Monteleone d'Orvieto, it’s a relaxing retreat full of sensory romance. Breathe in the sweet-smelling flowers that frame the home’s grounds, look out onto the forested paths beyond the front gates and feel right at home within its pretty pink walls. Inside, contemporary and vintage furnishings combine with an elaborate hearth and cowhide rug in the first-floor living room, while downstairs, rustic charm abounds in the bright, white dining room. Exit through the French doors to reach the lush garden, where a jade green swimming pool invites swimming and sun-soaking aplenty. In the evening, the pool takes on a magical lantern-lit glow, perfect for sundown dips. Steal yourself away for an intimate drink under the stone portico, then sit down for an al fresco meal, courtesy of the barbecue. When it’s time for bed, canopied beds and a private suite under the home’s eaves will treat you to a dreamy night's sleep. 

The Cat's Meow

A hideaway in the Tuscan countryside, this beautiful home has an air of old Italy about it, without sacrificing modern comforts. Surrounded by the gold and green hills, it's a home for those who want to take a break from the everyday and bring the entire family along to do it with. With two houses and a sprawling garden, there is definitely enough room to accommodate everyone. In the mornings, step outside for an espresso before taking a refreshing dip in the pool. Relax under the Italian sun on one of the loungers — or retreat to the covered pergola with a good book. Inside, the home has retained many of its original features, including wood-beamed ceilings, an open stone hearth in the living room, and tall, arched windows looking out over the grounds. Sunflower-yellow walls throughout are sure to put a smile on your face. When golden hour hits, step outside to take in views of the Tuscan countryside, golden-hued and changing by the second, this is what the term 'sundowner' was made for. 

Texture Like Sun

Parking On Street

This 19th-century farmhouse has been beautifully restored, preserving all period features like terracotta tiles, oak floors and a travertine marble staircase. The sumptuously decorated dining rooms, living room and rustic-style kitchen are all interconnected without being totally open-plan, and there are as many dining room options as there are meals of the day. Sit up, formal-style under chintsy candelabra, country-style around the hardwood table, or alfresco, under the shade of the pergola. Outside you’re surrounded by rolling hills covered in vineyards and olive groves. Under the shade of oaks, cypresses, peach and apricot trees, and among the fragrant flowers, herbs and figs, you can easily believe the Garden of Eden is in Tuscany. At dusk, let the barbecue sizzle and sip celebrated local wines while listening to the songs of cicadas and crickets. In the morning, tip-toe to the pool for a refreshing swim and breakfast on the sundeck. There is a separate annexe for your personnel or for guests that might pop in at the last minute. A small annexe offers games for the kids, so adults can have some quiet time. You’re also a six-minute drive from Cetona where you can stock up on groceries or dine out.  

The Orchard Song

Board Games

This refurbished 18th century home is perfectly perched to explore both Tuscany and Umbria. The entrance hall, with roped-off antique chairs, gilded ceilings and busts on the balustraded balcony is like stepping into a museum. The theme continues in the bedrooms, which feel like they’ve each been lovingly curated to reflect the history of the home with frescoed ceilings, pastoral murals, huge antique beds and hand-painted dressers. Spend mornings here lounging by the aquamarine private pool, like a gem amidst the emerald lawns. The peaceful grounds are surrounded by old oak trees and vibrant local flora shades outdoor dining areas (there’s even a full outdoor kitchen in the open veranda), yet it’s just a short drive away from popular sights like the hilltop town of Cortona and Lake Trasimeno. In the afternoons, find a cosy reading nook – perhaps in the plant-filled library where the sun streams through stained glass windows, or in the splendid living room where vintage furnishings, chandeliers, lush carpets lend a luxurious touch. We love the details here – a standalone bathtub in one bedroom, a large vintage map of the world in another and a sauna and gym that somehow sit seamlessly against the panelled walls of yesteryear. 

Museum of Light

Wheelchair Access

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.

Marbled with Flowers

Piano

Heated Towel Rail

Rain Shower

Shared Pool

EV Charger

Set within a typical Tuscan farmhouse dating back to 1800, this beautiful home takes you on a journey into the heart of Italian living.

Tuscany is a place that captivates the senses, and this home is no different. It feels traditional here, with original features and artistic touches that add warmth and character. It’s the kind of space where you’ll want to pause and savour the poetic atmosphere. 

Whether you’re sitting down to dinner, reading or having a siesta in the garden, it’s easy to feel at home here. Our highlights include waking up early to watch the sunrise across the Val di Chiana, taking a walk through the surrounding woodland and olive groves and visiting the medieval town of Montepulciano – only an eleven–minute drive away.

From thermal baths to wineries, this region is brimming with opportunities to connect with the natural beauty of Tuscany – and this home makes the perfect setting to share it with friends and family. 

The Rose Blush

Located just outside Cetona in Tuscany, this picturesque home is the perfect place to find peace and tranquility amidst the region’s renowned rolling hills and forests. A renovated stone mill, its romance is clear the moment you step inside. From its beamed ceilings, traditional kitchen and bright study that leads out in the garden, this compact but comfortable villa feels like an intimate country hideaway made for the sole purpose of your relaxation. And then there’s the bedroom with its forest palette, green gothic headboard and access to the terrace. Wake up and head outside for your morning coffee under a shady oak tree, then while away the hours in the pool or discover the babbling brook just beyond the home’s canopy of trees. The medieval town of Cetona with its sandy-hued piazza and palazzo is also just five minutes away by car. After a day luxuriating by the pool or exploring the nearby sights, come back home for a glass of wine in the stone courtyard before enjoying an intimate meal beneath the stars. 


Alberi

Black-Out Blinds

Welcome Hamper

You can't beat the views of the beautiful Val D'Orcia, itself a UNESCO World Heritage Site, from this Tuscan farmhouse lying in the Siena Province on a private two-acre estate. Tear yourself away from the vistas, and you'll find a deft renovation, combining contemporary interiors and historic charm. An excellent choice for a large group of friends or family, there's plenty of space to spill out and feel at home here. Cool off from the Tuscan sun in the infinity pool. Put to use the vast, chef-worthy kitchen (we're talking two dishwashers, two ovens, and some) for a big dinner party – a private chef is bookable for fine dining. Or keep things easy and fire up the barbecue or pizza oven outside as breath-taking views of the valley spread out before you –  best seen beneath the pergola at sunset with a glass of something chilled. And on chiller nights, hunker down beside the fireplace with a good book – there are two living rooms to choose from. When it's time to lay your head, hop in the home's elevator and take your pick from the many bedrooms, boasting king-sized beds and separate bathrooms. We'll let you decide who lucks out on that ground floor suite with bi-folds opening onto the lawned gardens. Should you ever wish to leave this idyll, you'll find you're in an excellent base to uncover Tuscany's vineyards and historic villages, starting in Sarteano, just a ten-minute drive away. With its tempting trattorias and beguiling historic charms, you'll be off to a flying start.

Little Hills

With its backdrop of rolling hills and its flourish of flowers signposting your welcome, this stone villa on the outskirts of Cetona in Tuscany is a vision of rural relaxation waiting to show you just how delicious slow living can be. Inside, exposed beams and tiled floors await you, with the main living area boasting a large hearth and country views for you to enjoy at your leisure. The farmhouse kitchen is a veritable snapshot of Tuscan traditionalism, while upstairs, three comfortable bedrooms wait to cradle you into a serene sleep. From the first floor, walk out on the geranium framed balcony for views of the lush green grounds, then walk down the stone steps to explore them up close. Here, a sunchair-lined pool invites plenty of dips in its refreshing waters while taking in views of medieval Cetona perched on its hilltop, reachable by car in five minutes. After a day luxuriating in the sun or exploring Cetona’s piazzas and palazzos, enjoy cocktails in the garden before sitting down to an alfresco feast as you watch the evening sky change to shades of pink and gold.

Il Pozzo

DVD Library

Cafetiere

Juicer

Fenced Garden

Sun Umbrellas

Beach / Pool Towels

Beach Essentials

Pool House

Alarm System

Carbon Monoxide Detector

Security System

Smoke Detector

Tucked within seventy hectares of countryside and surrounded by countless rows of olive groves and cypress trees, this charming Tuscan estate is the picture of rural tranquillity. Split into the main house and an independent annexe, the address has retained plenty of its original features – wooden beams, an open-hearth fireplace, stone floors and antique furniture give guests a sense of history. Start your day by pushing open the French doors in the living room and looking out over the neighbouring hills before sharing breakfast in the charming kitchen. 

Stepping outside, the home’s beautiful garden is an ideal sunbathing spot, while the sparkling swimming pool is perfect for cooling off from the midday heat. Find a cosy corner amid the plants to enjoy a cocktail at sundown, then head to the pergola, where an elegant dining table promises an unforgettable alfresco experience. If you can bear to leave your manor, the pretty town of Montepulciano is a short ten-minute drive away. Walk its winding streets and try the rare Vino Noble wine the region is so famous for.

Aglio e Olio

All we need is a harpsichord to strike up a tune and a trumpeter to announce our entrance and this home could trick us into thinking we were back in the 1700s. Built in 1690 for a notable Perugia family, the plot was recently painstakingly renovated to bring it back to its former glory. The whole building is impressive but the beautiful living space stands out with its sherbet lemon yellow walls, marble fire place and ornate chandelier. You might find yourself craning your neck upwards to gaze at the gorgeous frescos that decorate ceilings, originally painted by Mariano Piervittori in 1850. The surrounding parkland is equally as dreamy as the interiors, with an abundance of oleanders, roses, fruit trees, and a structured garden. Follow the path round to come to a swimming pool with views of the Umbrian hills. On balmy summer evenings, swap the grand formal dining room, with its oil paintings and wooden floorboards, for dinner on the terrace - there's a second kitchen a few steps away to make feasting even easier.

Evergreen Oleander

You’ll find this stunning twelfth-century watermill set among dappled woodland and 1.5 acres of flourishing gardens in the rambling Tuscan countryside. The owners, Marco and Alessandro, spent years lovingly renovating the home, restoring its timber beams, stone walls and terracotta flagstone floors while incorporating antique and custom pieces to create a warm, rustic ambience. If you’re spending time outside, we bet you’ll be relaxing under a parasol by the saltwater infinity pool – it’s built inside the trench that supplied the mill with water over 800 years ago. After a sun-soaked morning, head into the woods for secret spots and the best views of the rolling landscape. When you’re feeling peckish, indulge in Italian feasts out on the patio – or if you don’t feel like cooking, you’re only a five-minute drive from the gorgeous restaurants in Montepulciano. As the evening draws in, take a bottle of wine produced from grapes grown in the home’s own vineyards, and settle down in the chill-out area under the old oak tree for a night of stargazing. Featuring seven bedrooms – each with its own ensuite – a large group or family will enjoy spending quality time together without sacrificing their own personal space.

The Old Watermill

Secured Parking

Helipad

Courtyard

Fenced Property

Garden Games

If ever you’ve wanted to feel as though you were living a fairytale, then this Tuscan villa would be happy to oblige. A thirty-minute drive away from the spectacular Lake Trasimeno, this home sits near the border between Tuscany and Umbria and lived its former life as an actual mediaeval castle. It now makes for the perfect base for a family reunion, and invites the entire group to come walk the lush estate, wandering between the private swimming pool, the sunloungers, or any one of the many sets of garden furniture and benches. Find your nook and hunker down, or continue walking the gardens, brushing your hand over shrubs as you daydream.
 
Admittedly, the grounds are very impressive, but the home itself shouldn’t be pushed aside. In homage to its former life, it combines a regal touch with rustic elements and the result is magnetic. Musicians might find themselves especially drawn to the piano where they can sit down and play as the rest of the group gathers in front of the fireplace in the lounge. 

Come together around the breakfast table – which the housekeeper will dress with the ingredients you purchased from the market – and set off shortly after to explore the rolling Tuscan countryside. If you want to stay put, play boardgames in one of the bigger rooms or take to the pool. Evenings should be reserved for stargazing – simply choose a spot on the huge lawn and enjoy.

The Tuscan Castle

It might sound impossible but we think the perfect Tuscan villa should manage to give off both a peasant and a palatial vibe at the same time. You know the kind of thing: a rambling country house that despite its impressive size – dozens of high ceilinged rooms, imposing archways, ideally a swimming pool out in the capacious grounds – still gives the impression that its occupants might just be out in their orchard picking olives. That description certainly applies to this gorgeous family-friendly villa: a classic example of super-relaxed luxury. Located in the Tuscan countryside, it’s surrounded by forests and within an hour’s drive of tourist favourites like Siena, Florence, Lucca, Pisa and Assisi. Inside you’ll find a country kitchen with a rustic dining table to seat 12; six comfortable bedrooms, colour-coded with their en-suites in earthy tones; and two large living rooms with plump, chintzy sofas. Throw back the patio doors to extensive gardens filled with lavender, olives and cypress trees, plus an outdoor lounge, a large swimming pool, barbecue and a wood-fired oven. Turns out the perfect Tuscan villa isn't impossible at all.

The Palatial Peasant

Netflix

Bathrobes

Ice Machine

Indoor Pool

Multiple Sets of Keys

Formerly a 16th century convent, this enchanting villa is bursting with character and has been renovated with every comfort and enjoyment in mind. Step into the cool stone entrance hall and you will instantly note the attention to detail. There are two distinctive reception rooms, decorated with a curated selection of original furniture, paired with custom creations from local artisans and designer touches. The kitchen is fully stocked with high spec appliances, and the dining room is the perfect place for breakfast, with views of the rolling green olive groves out of the window. 

Outside, there are plenty of spots to relax in the sun and the shade, and there is no better way to start the day than plunging into the sparkling pool. There is also an indoor hydro massage pool to relax and unwind in after a day's activities. At sunset, gather everyone for an aperitivo under the pergola, whether it’s a negroni or a bottle of red from neighbouring Montepulciano, and fire up the barbecue for an al fresco dinner. There is a vegetable garden you are welcome to pick from. If you don’t fancy cooking, a private chef can be arranged to whip up Italian delicacies. The villa is on the outskirts of Sarteano, a tiny town with picturesque stone streets, a Mediaeval castle, and some excellent Tuscan restaurants. 

Villa Monastero

Sitting pretty on sixty-five hectares of rolling countryside, this 16th-century villa has been renovated into a luxury retreat with designer touches. Even though an indoor pool, gym, wine cellar and billiard room ups the ante inside, the outdoors is where this home truly shines. Admire the views from the sprawling garden. You'll also find a private pool with ample poolside seating and a shaded veranda for alfresco dining. Location-wise, it's within driving distance of thermal spas, Siena, Florence and several other art cities. And for more active guests, Lucciola Bella Nature Reserve has various hiking trails. 

Tuscan Treasure

You'll find this traditional villa where Tuscany meets Umbria, just a few kilometres from the medieval borgo of Città della Pieve. As far as locations go, it's incredibly scenic. The region is home to rolling hills, centuries-old olive groves, and must-see cities such as Perugia and Cortona – all easily accessible by car. Back home, the private pool is ideal for afternoon dips, the terrace has alfresco dining written all over it, and the balcony is the perfect spot to unwind with a glass of wine. The layout inside is a little quirky – multiple bedrooms are connected together, and one has external access – but that's all part of the charm.

Umbrian Classic

Bread Maker

Situated on the border of Tuscany and Umbria – two of Italy's most beloved regions – you'll find this beautiful villa. With plenty of space for a larger group, it's the ideal place to kick back and relax in the Italian sunshine, or to use as a base for your adventures in the surrounding countryside. 

With exposed stone walls, traditional shutters, and wooden ceiling beams, the house is bursting with traditional charm. You'll love selecting a book from the collection, and flopping down to enjoy a peaceful read. Or, you might like to head for the kitchen – whether you're planning a three-course feast or just serving some antipasti with wine, it has everything you need. Head outside and gather your fellow guests around the dining table before opening a bottle of Prosecco and making a toast to the good life. There's even a beautiful swimming pool where you can take a dip on hot days, or simply stretch out on a lounger. 

The medieval village of Fabro, with its 12th-century castle, is just a twelve-minute drive away, while Città Della Pieve is a little further. And, with close access to the motorway, you can easily drive to Orvieto, Terni, or even further afield to Florence and Rome for a day trip. Nature lovers will also be happy here – cycle, hike or horse-ride through the beautiful rolling landscapes, stopping off at the tiny hilltop villages along the way. 

Shades of Green

Just outside the charming village of Sarteano, this cosy villa is surrounded by woodland and rolling Tuscan countryside. We love the arched window looking out over the garden – the perfect spot to curl up on a plushy sofa with a good book. To cool down, take a long swim in the pool before drying off for an aperitif on the terrace, just one of the many outdoor lounging areas. Indulge in long lunches under the shade of the greenery before a round of table tennis on the lawn. If you’re looking to add a touch of luxury to your holiday, the spa resorts of Chianciano Terme, Bagno Vignoni, and Bagni San Filippo are just half an hour away. Wine connoisseurs might enjoy a trip to Montepulciano to wash down a cheese tasting in Pienza. Art lovers will no doubt take the hour’s drive to Siena or Arezzo for a day drip. No matter what little adventures you decide to go on, be sure to stop and smell the flowers in the garden and feel the soft grass between your toes. 

Sartini

Electricity Adaptors

Tucked away at the end of a four-kilometre dirt road, Casa Rossa provides guests with complete privacy and serenity for a most relaxing stay in the rolling hills of the Valdichiana. Welcoming up to twelve guests, this is an excellent choice for a group of friends or a family gathering. Casa Rossa boasts a contemporary look that creates both a refreshing contrast to its rural setting and offers guests plenty of modern luxuries, from the sleek kitchen to the indoor fire pit. Step outside and make the most of the expansive lawn, large pool and outdoor dining set up. Although you're about an hour and a half from Florence, you can always create your own Bistecca alla Fiorentina on the barbecue. What a way to spend a vacation.

Casa Rossa

Jacuzzi

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 how spaced out this home feels, with a separate annex to sleep two – perfect for those wanting that little extra privacy. While upstairs in the main house, the cool, lofty bedrooms invite a blissful night's sleep in their comfortable beds. And you'll love waking up to those views of the Tuscan hills each morning. 

Little Borghis

Mini Bar

This swoon-worthy Tuscany villa presents a dreamy fairytale-like setting amidst the quiet, green woodland of Sarteano. Unveiling romantic and characteristic scenery, the home itself is also brimming with charm and personality throughout. Stone walls, exposed wooden beams and terracotta tiling invite guests in for a true taste of Tuscan design. With a combination of modern and traditional furnishings, the home boasts both comfort and practicality, all while remaining true to its quintessentially Italian identity. Stylish, warm and welcoming, the space allows guests to soon feel relaxed and at ease upon arrival. 

A stone patio separates a three-storey annexe from the front of the main building, meaning guests can benefit from the extra added privacy of having two separate living spaces – perfect for groups of multiple families. The annexe features two en-suite double bedrooms, with its own lounge and kitchen. 

Beyond the house, you'll have full access to the serene gardens (spread over 5000 square metres) and an abundance of flora and fauna that fills the air with an array of seasonal scents all year round. Perch by the garden's big oak tree for a secluded spot to relax and unwind with a glass of wine. And when the weather is particularly warm, there's no better place to cool off than over at the swimming pool which overlooks the rolling Tuscan hills in the distance. 

If you can manage to pull yourselves away from this delightful slice of paradise, Sarteano is located just eight minutes from the villa where you'll find all the necessary shops and amenities in the backdrop of a stunning village setting. You'll also find famous spa resorts like Chianciano Terme (just a twenty-minute drive away) as well as Bagno Vignoni and Bagni San Filippo (reachable in thirty minutes). 

Food and wine fans should head to the towns of Montepulciano and Pienza (both forty minutes away), where local wines and cheeses can be sampled for a truly authentic Italian experience. Shopaholics are also in for a treat here, as the Valdichiana Outlet Village in Foiano della Chiana is just positioned around a forty-minute drive away from the villa too.



The Italian Dream

Smart TV

Wine Cooler

Breakfast Included

With a private swimming pool, sun-drenched terraces and a private spa that includes a sauna, Turkish bath and massage table, it’s impossible not to relax here. Set just five kilometres from the centre of historic Cortona, this charming villa is an ideal retreat for a family or group of friends. With daily breakfast included, you can start the day in a leisurely fashion on the terrace, just the spot for sunny alfresco dining. And if having breakfast prepared has given you the taste for taking it easy, you’ll find a selection of eateries nearby for authentic Tuscan food. 

Tuscany Soul

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