Cortona

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Entertainment

Hair Dryer

Bathroom

Dishwasher

Freezer

Fridge

Oven

Stove

Kitchen

Coffee Maker

Kitchen Utensils

Cooking Essentials

Kettle

Kitchen & Dining

Washing Machine

Iron

Ironing Board

Cot / Crib

Hangers

Bedroom & Laundry

Sauna

Wellness & Fitness

Wi-fi

Desk / Workplace

Laptop Friendly Workspace

Internet & Office

Air Conditioning

Central Heating

Fireplace

Heating & Cooling

Parking Available

Free Parking On Street

Private Entrance

Single-Level Home

Free Parking On Premises

Self Check-in / Check-out

Parking & Access

Balcony

Garden

Outdoor Seating

Barbeque

Outdoor

Smoke Detector

Carbon Monoxide Detector

Other

Florence and Pisa steal the limelight for Tuscan cities, yet Cortona is a hidden gem brimming with character. Authentically Italian and undoubtedly pretty, the sleepy streets and welcoming ambiance is the perfect immersion into the local lifestyle. For true convenience, you're expertly placed to explore every part of the town.

The town centre is just three minutes away, giving you instantly access to the charming cafes, restaurants and shops. Spend leisurely afternoons moseying around the quaint streets, finding chic clothing in the aisles and delicious food in the eating spots.

If you wanted to keep things private and intimate, your host can arrange a private chef to rustle up some top-notch dishes at home. When the weather is warm, you can enjoy each sumptuous bite on the cute outdoor table in the garden. 

Even if you're not eating, the garden is a dreamy spot to spend the evening. Pick up a bottle of wine from town and share a glass or two with the beautiful view as your background.





View From The Evening

Satellite / Cable TV

Microwave

High Chair

Balcony / Patio

Located in Cortona’s historic centre, this handsome apartment blends rustic charm with modern comforts to create a memorable, relaxing stay. 

Housed in a historic building, you’ll find plenty of traditional features here including exposed dark wood beams and terracotta floor tiles sitting alongside inviting contemporary furnishings to create the perfect mix of old meets new. 

Make yourself at home on the living room’s sofa – a good book and a coffee in hand – or retreat to the small private balcony for a sundowner after a day of exploring. The dining table beckons sociable soirées when you’re not out sampling the local trattorias, while the two bedrooms – with their beamed ceilings and rooftop views – are a treat to come back to after a day of sightseeing, or enjoying one of the many tours and cooking classes on offer through your host. 

Outside of your home, you’ll find Piazza della Repubblica a one-minute walk away, Porta Sant'Agostino a seven-minute stroll and the ​​Diocesan Museum three minutes away on foot. 


Sunflower Beams

Patio / Terrace

Welcome Hamper

Nice to haves

This charming holiday apartment lies in the heart of Cortona, ideal for a romantic getaway. The terrace boasts lovely views of the surrounding landscape, though the outdoor space is overlooked by nearby buildings, so it doesn't feel the most private. Your host can provide a free high chair here and little ones will love the garden, though the interior decor is quite traditional and won't be for everyone. You'll find public parking a short walk away, but Cortona's mouth-watering restaurants and picturesque churches are reached easily on foot, so you won't need a car.

Garden Oasis Retreat

Espresso Machine

Pets Allowed

Pets

If you're a frequent visitor to Tuscany and looking for somewhere that's slightly off the beaten track for your next trip, the medieval town of Cortona is a lovely choice and this apartment on the outer edges will help you see the best of it.

Spread across two floors, the interior is a distinctive mix of period features, such as the flagstone floors and wooden ceiling beams, and modern touches, like the monochrome kitchen and smart grey bathroom. Compared to a lot of other apartments for two, there's a pleasing amount of space inside and nothing feels cramped.

The local town is one that's easy to explore on foot and you'll discover plenty of restaurants and ice cream parlours, plus a couple of museums, during your wanderings. The Basilica of Saint Margaret of Cortona and Fortress of Girifalco are both only twenty minutes away on foot, too.

Noah's Son

Bathtub

Sitting on the first floor of a noble palazzo in the typically Tuscan town of Cortona, this apartment will put a smile on the face of anyone fond of the opulence of yesteryear.

Wander about the home and you'll spot everything from intricate frescoes and high vaulted ceilings to a black marble fireplace and handsome wooden furnishings. This tasteful interior is bathed in natural light from the large windows, which also offer guests lovely views of the townscape and the wider valley.

We don't want to give you the impression that the address is a museum piece, however. The kitchen is plenty large enough for whipping up Tuscan feasts, plus the presence of a bathtub will be appreciated by those that like to end the day with a relaxing soak.

When you're in the mood to explore, the local town is small enough to get about on foot, although there are enough attractions with which to fill an itinerary, including the Diocesan Museum only five minutes' walk away and a good choice of restaurants dotted along the medieval streets.

Fresco Fantastico

Toiletries

Changing Table

Toaster

Extra Pillows and Blankets

Cleaning Products

Drying Rack

Swimming Pool

Outdoor Shower

Sun Loungers / Beach Chairs

Mosquito Net

Travel can fill us with a sense of wonder, openness and possibility. And this elegant villa is the perfect setting to discover the timeless beauty of Tuscany. 

Perched on the mountains above Cortona, this is a wonderful place for families and friends to gather and experience the authentic charm of Italian living. With its traditional features, earthy tones and elegant styling, you’ll want to savour the calming presence and rustic simplicity of this home. 

From waking up to views across the valley to leisurely breakfasts in the garden, this is the kind of space that inspires a sense of joy and appreciation for life’s little luxuries. Like spending a slow day by the pool, reading, cooking with fresh local produce and exploring the beautiful Tuscan countryside. 

As the sun sets, this home is a wonderful place to retreat into the heart of nature. Light up the pizza oven and gather around the table for an authentic taste of Italy. 

The Angelico 

Found on the second floor of a noble palazzo, this apartment overlooks Cortona and the rolling Italian landscape beyond. Though it is a little more rustic, which might not be everyone's cup of tea, we think it charming. The balcony is its best feature, and we recommend sunset drinks to fully appreciate the views. As for your location, you're pretty central. This means a quick walk can get you to everything from restaurants to museums. Perfect for immersing yourself in this picturesque village. 

The Bello

Private Pool

If you’re in search of a rustic getaway, this 18th-century home ticks all the right boxes. Surrounded by trees, the garden offers beautiful views, as well as a swimming pool (open seasonally), a barbecue and a wood-burning pizza oven. You’ll find the main house consists of two independent apartments, while the garden cottage has an additional two bedrooms – providing plenty of space for groups to spread out and enjoy quality time together. Some of the furnishings are a little dated, but there’s plenty of charm and character. It’s also just a short drive from the picturesque hilltop town of Cortona (2.5 kilometres away), while the nearest amenities are also just a short drive away.

The Valley of Angels 

Blender

Wine Cooler

Shared Washing Machine

Outdoor Pool

EV Charger

Courtyard

Hammock

Sun Umbrellas

Breakfast Included

First Aid Kit

Safe

Security Cameras

Perched on the hills overlooking the Val di Chiana, this beautiful home seamlessly blends rustic charm with elegant Tuscan style to create a truly unforgettable stay. 

Less than a fifteen–minute walk from the centre of Cortona, the owners have thoughtfully restored this traditional farmhouse into a welcoming space that exudes charm. And with its abundant garden and breathtaking views, this is the perfect setting for a retreat into the heart of nature. 

Stepping inside, you’ll find an uplifting space designed to enrich your stay with the simple pleasures of Italian living. From luminous mornings watching the sun rise over the valley to cosy evenings curled up by the fire, this is the kind of space that adapts to suit the needs of the moment. And for the ultimate sense of relaxation, the swimming pool is perfectly poised for refreshing swims and lazy afternoons reading under a tree. 

For explorations further afield, it’s just a short atmospheric stroll to the church of Santa Maria Nuova as well as the town centre. Days can be spent meandering the majestic streets, pausing in a local bar or restaurant and savouring the stunning views.

The Ancient Stone

Ping Pong Table

Rain Shower

Pod Coffee Machine

Private Parking

Built as a farm at the end of the 19th century, this rural home has oodles of charm and Tuscan character. We're swooning over the original terracotta-vaulted ceilings, the exposed cork beams and the huge fireplace, which is the perfect spot to snuggle up with a cup of tea on wintery nights. Every room captures the essence of old-world Tuscany – warm, cosy and pastoral – but there are modern conveniences too, like rainfall showers and a ping-pong table in the garden.

Surrounded by a sea of olive trees and with vistas of the mountains, the garden is utterly enchanting. Start the morning off with an espresso on the outdoor sofa, cool off on sunny afternoons with a swim in the pool, then fire up the stone barbecue and dine under the wisteria-covered pergola on summer evenings. 

If you fancy exploring, there are plenty of places to discover. Just down the road is artsy Cortona, an Etruscan town with views across the Chiana Valley. Want to stretch your legs? Lace up your walking shoes and go for a hike through the hilly countryside – there are many scenic outlooks and trails within easy reach. Or really pick up the pace with a visit to Arezzo or Perugia, both about forty-five minutes by car and excellent spots for day trips. 

The Softest Crimson

DVD Player

Foosball / Table Football

Cafetiere

Vacuum Cleaner

Multiple Sets of Keys

Fenced Property

Herb Garden

Umbrellas

Child Friendly

Fire Extinguisher

This quintessentially Italian home is nestled in the countryside just 5 kilometres from the beautiful town of Cortona. Days here can be spent hiking, cycling and exploring the historic hilltop towns of Tuscany. There’s also a private pool, a bocce court and a terrace with a barbecue – perfect for magical sunset meals. Inside, the rooms are traditional and full of character with plenty of space across the two floors to spread out. One of the rooms has bunk beds – making this a great option for families travelling with children. 

The Lucia

Black-Out Blinds

Beach Essentials

Stair Gates

Set amidst the verdant greenery of the Tuscan countryside, this elegant home invites you to experience the timeless charm of Italian living. 

And from the moment of arrival, the atmospheric presence of the villa feels inspiring. Formerly a church that belonged to an old noble property, the owners have sensitively restored this building into a home that shines with character and poetic beauty. 

From the traditional features to the art and objects, every detail brings a quality of joy to daily life. And whether you’re gazing at the garden views from the kitchen, sipping coffee on the terrace or soaking in the bathtub, it’s easy to settle in and feel at home here. 

Stepping outside, you’ll discover an idyllic sanctuary – a natural haven perfectly poised for refreshing morning swims, long lunches and sunset drinks. Take a short stroll and you’ll find the village of Pergo is just fifteen–minutes away – there’s a supermarket here for any basic amenities you might need. And for explorations further afield, the picturesque hilltop town of Cortona is just a ten–minute drive away. From here you can meander through the medieval streets, stop for gelato and savour the beauty of the Valdichiana valley. 

A Sweet Symphony 

Hot Tub

Free Parking

Nestled quietly in the countryside, this beautiful home will enchant you from the moment you first set eyes on it. With views over the Val di Chiana and Cortona, this home has it all – stunning stonework, exposed beams, comfortable furnishings and rich gardens. Spend your days swimming in the panoramic infinity pool which is unique, thanks to its telescopic closure system – close the walls and roof and you can access the pool directly from the living room. 

Combining traditional Italian rustic charm with elegance and class, it won't just be the terracotta accents helping you feel the warmth of this home. Dine with loved ones in the wonderfully open-plan space or even share a pizza at the outdoor wood oven, before snuggling around the fireplace to enjoy a bottle of wine and good conversation. With the main villa alongside two annexes, there’s space for privacy but enough to keep the whole family entertained, making this home the perfect backdrop to an Italian adventure. 

Just a few kilometres from Castiglion Fiorentino and delightful Cortona, explore their beauty by meandering through the streets, following the scent of the most divine local cuisine, before returning to your charming rural retreat. 

Wrapped in Jasmine & Aloe

Located just one mile from the hilltop town of Cortona, this Tuscan villa is made up of two apartments in one charming and traditional farmhouse. Both apartments have their own separate entrances, making this a great choice for large groups. Outside, the private pool is fenced and perfectly placed for stunning views, and children will love the expansive grounds. Animal lovers can bring their furry friends along, but it's important to note that a couple of dogs and even a friendly donkey live on the land, and the owner of the home lives nearby. Despite this though, you'll be granted full privacy during your stay.

Valley Vista Villa

Smart TV

Dryer

Lift Access

Beach / Pool Towels

Dating back to the 18th century, this home provides the perfect setting for a dreamy Tuscan retreat – one that’s filled with the majestic beauty of the Italian countryside. And from the moment of arrival, you’ll want to pause to admire the unique charm of this setting. 

Surrounded by trees, the abundant garden fills the house with a wonderful sense of peace and tranquillity – inviting you to put down your bags and make your way inside. 

From the elegant styling, rustic stone and traditional features to the air-conditioned bedrooms (each with its own bathroom), the owners have honoured the building’s heritage whilst integrating contemporary comforts – including a lift to travel between floors. And with an abundance of living space, both inside and out, this is the perfect location to celebrate the simple pleasures of Italian living. So whether you’re enjoying a quiet morning coffee on the terrace, swimming in the pool, relaxing in the shade or sharing Italian-inspired feasts as the stars fill the sky, every moment promises to be enriched by the natural beauty of the surroundings. 

Beyond this private sanctuary, it’s just a short scenic drive to the hilltop town of Cortona, while the region is brimming with opportunities for long hikes, sightseeing, wine tasting and simply admiring the views across the Chiana Valley.

The Main Event

Pool / Snooker Table

This 17th-century Tuscan villa boasts a large private pool, lovely views, and a private chapel on its expansive grounds. The interior is traditional and elegant, and perhaps won't be to everyone's taste. But most of the bedrooms enjoy their own en-suites, and the gardens are great for pets –there's more than enough space for alfresco dining, or just relaxing under the century-old trees. Your host can arrange all manner of extras, from private chefs to wine tours in Chianti, to make your stay special. We recommend having a car here to get the most out of your stay – the idyllic hilltop village of Cortona and the gorgeous Lake Trasimeno are an easy drive away.

Blossom & Shutter

Private Washing Machine

Parking On Premises

Made for outdoor living and large family gatherings, this home is sure to jump high up on your wishlist. We love the space this home has, and with two apartments independent from the main villa, it’s perfect for extended families where two couples are seeking a bit of added privacy. With traditional interiors, it’s a comfortable place to call home – but it was the outdoor space that caught our eye. Sun-kissed terraces, alfresco dining opportunities, a private pool and hot tub, and all a short drive from the beautiful hilltop town of Cortona. 

Tuscany in Bloom

Whether you're splashing about in the private pool, admiring the Tuscan scenery from the patio or dining on Italian delicacies in the setting sun, this charming villa is the perfect place to call home. Inside, every room oozes traditional character – stone walls here, wooden-clad ceilings there – creating a cosy, comfortable sanctuary. Each floor has its own sitting area and kitchen, making it ideal for groups wanting plenty of privacy and space to spread out.

The garden offers postcard-worthy views as soon as you step outside – and there are oodles of spots to sit back with a glass of wine and take it all in. Dish up lunch under the shade of the age-old trees before sprawling out on the loungers for a poolside afternoon snooze. When the sun begins to set, make a beeline for the terrace to watch the entire countryside glow golden.

Location-wise, you're only a fifteen-minute walk from Cortona. Soak up the Etruscan history and admire the town's medieval architecture, then take a break from sightseeing and enjoy a meal in the local eateries. Your host can also arrange experiences like wine tastings, tours and hot air balloon rides – all excellent options if you fancy something extra special.

Upon a Golden Dream

Stunning countryside views. A lush garden. A swimming pool. Even a private bowls court. This Tuscan mansion sets the scene for la dolce vita. Inside, traditional charm meets a touch of eccentricity – think vaulted ceilings, eclectic furnishings, and unexpected pops of colour. And when it comes to space? There’s more than enough to go around – two kitchens and generous communal areas make it ideal for large groups of friends or family get-togethers. Cortona, Siena and Florence are all within driving distance – though with a base like this, you might be tempted to stay put.

The Etruscan Lady

Library of Books

When it comes to Tuscan idylls, this home ticks all the boxes. Set amongst Cortana’s rolling green hills, this renovated 19th century house is full of quiet corners and scenic spots waiting to welcome you into a world of rest and relaxation. Rural romance at its most beautiful, its stone exterior and wooden shutters give way to an intimate, rustic interior full of original features, exposed beams, brick archways and terracotta tiled floors. The soft mint-coloured bedrooms also have a feeling of elegant farmhouse simplicity with their wrought iron bed frames, floral accents and wood-framed windows. Here it’s the gardens, though, that are the most awe worthy. Stroll around the grounds and you’ll find a series of sunny spots and shaded nooks to while away the hours. Spend the afternoon taking dips in the pool’s cool waters then head to the viewing point at sunset to watch the sky turn amber and pink against the silhouetted hills. Enjoy a glass of wine here before fixing up a feast in the traditional kitchen, or head to the pergola for a barbecue under the stars.

Il Sogno

Leave the tourist trail behind and embrace authentic Tuscan village life during a stay at this charming four-bedroom cottage. The charming stone facade is comfortably the oldest in town, with a history dating back hundreds of years, we're sure this place would have some stories to tell.

Your hosts have lovingly renovated the building to create two self-contained two-bedroom apartments that can be effortlessly combined for multi-generational family stays and getaways with groups of friends – all while maintaining a degree of privacy. With exposed stone walls, terracotta floors, and beamed ceilings, this sympathetic renovation preserves the period features and original character so well that, at times, you'll feel as though you've stepped into a time machine. However, with all the mod cons you'd expect, there'll be no reading by candlelight and washing clothes by hand, unless you want to, of course.

The village has a small convenience store within walking distance of the home, plus plenty of hiking and biking paths, including the Path of Reclamation. This 62km-long trail runs along the banks of the Canale Maestro della Chiana through the Cortona countryside between Arezzo and Chiusi.

However, you'll need to jump in the car for easy access to larger grocery shops and restaurants, which are just a short drive away in Cortona. The city shot to fame as the unwitting star of the 2003 Hollywood film 'Under the Tuscan Sun', but has managed to retain its soul. With its Medici fortress, history of handmade ceramics and fascinating museums, it's well worth a visit.

For adventures further afield, equally beautifully cities, such as Arezzo and Siena are within an hour's drive, while Italy's east and west coasts are within day-trip distance, at approximately two-and-a-half hours drive each way.

Tuscan Tradition

Ideal for a group of friends or perhaps a multi-generational break, this farmhouse is said to be the oldest building in the village and, although it's been smartly modernised, it's still beautifully traditional. Just as it would have been when it was built, the main house is divided into separate apartments – one upstairs and one on the ground floor. With two small kitchens, two bedrooms and two bathrooms each, it's perfect if you'd like to all mingle in the outdoor space but retreat to some privacy at night. And with an additional one-bedroom guest house too, it becomes even more flexible.

Deep in the Cortona countryside, it's a great base for exploring Tuscany, with Arezzo, Montepulciano, Siena and Assisi all within easy reach for a day trip by car. Get out and about on walking or cycling routes and even visit the coast if you feel like it. While you're out, don't forget to pick up some delicious local food and drink – perhaps stopping to sample the offerings at the nearby wineries. And serve dinner out on the terrace before moving inside to your characterful, comfortable quarters for the night. 

By and By

This rustic-style villa, nestled amid unspoiled swathes of the Italian countryside close to the quintessentially Tuscan town of Cortona, provides the perfect place to slow down, reconnect, and immerse yourself in the laid-back way of life this area offers. In the surrounding area, named Val d'Esse, you will find a wealth of historical, cultural, and archaeological treasures, as well as the eponymous river that runs through the valley and plenty of fantastic local eateries serving traditional delicacies – so there really is something for everyone. 

Inside, the feeling of this home is one of an authentic old farmhouse. Filled with character, charming stone features, traditional detailing, and offering a rustic kitchen at its heart, the home is warm and inviting. Enjoy coming together in these cosy spaces to cook, eat, and unwind in the company of your nearest and dearest. 

Step outside and the pool area provides the perfect spot to take some time for yourself, soaking up the sun as well as the tranquillity of the rural location. As the sun begins to set, experience that elusive sense of holiday bliss as you dine overlooking the rolling green landscape, feasting on regional delicacies and sampling some of the area's delicious wines. When you want to venture further afield, then the iconic towns of Siena, Florence, and Assisi are all accessible for a day trip too.

Under A Tuscan Moon

Ceiling Fans

Like many traditional homes in Tuscany, this gorgeous old farmhouse is full of rustic elegance, with ivy and vines creeping over the exterior, beautifully matching it to its country surroundings. With traditional wooden floors boasting large woollen rugs and thick wooden beams on the ceilings, there’s no mistaking this home's authentic and historic character. Each of the three comfortable bedrooms is bright and full of country flair while the bathrooms are fitted with Italian patterned tiles. Outside, the garden runs down to the cool, inviting swimming pool and the wide terrace is the perfect place to sit for a barbecue lunch while taking in hilltop views of the Tuscan countryside. Just a 25-minute drive over the border from Tuscany to Umbria and you’ll reach the beautiful shore of Lago Trasimeno, a large freshwater lake where you can take a boat out or enjoy a meal in a taverna on the water’s edge.


A Touch Of Ivy

Secured Parking

Resort Access

Found in the rolling Tuscan countryside, only minutes away from Cortona, this beautiful villa exemplifies the best of both worlds. Bask in the peace and tranquillity the secluded location of this home offers, but find a bit of hustle Arezzo, Perugia, or even Florence at the end of a road trip. 

Golf enthusiasts can spend crisp mornings teeing off at Golf Club Valdichiana whilst the rest of the family strolls out to Cortona for breakfast. 

The home itself cuts a pretty traditional figure, and you’ll quickly fall in love with the exposed beams, rustic furnishings and statement fireplaces. Spend mornings appreciating the homely comfort of it as you enjoy a cup of coffee in the living room. 

Dine al fresco outside – preferably a meal cooked in the stone oven – or enjoy nibbles and wine as you find shade under the gazebo. Sun lovers can listen to a podcast as they sunbathe on the lounger, cooling down in the private pool when needed.

Pietra House

Steam Room

This contemporary villa set on the edge of Terontola in southern Tuscany is just the ticket for those seeking a serene escape away from it all. Boasting modern interiors, a private pool and sun-kissed terraces, it’s a real gem. But the cherry on the cake? This home has its very own spa. So, if you fancy a sauna or massage, just wander down the steps to the lower ground floor where your sanctuary awaits. Keen to explore? Drive to historic Cortona, sample the local chocolate of Perugia, or bathe in the hot thermal springs at Bagni San Filippo – you’ll never be lost for things to do. 

A Triumph in Tuscany

Bicycles

Outdoor Fireplace / Firepit

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

Sound System

Nestled in the vibrant Tuscan landscape, surrounded by traditional beauty lies this home. Whether you're lounging by the private pool or going for a swim to stay active as the kids play in the garden, or you're getting some last-minute remote work done at the dining table, you'll find it easy to make the most of your holiday here. Head down to the private wine cellar and taste some excellent local wines, or sit out in the garden on the stone bench with a good book. The annexe is perfect for couples or guests who want a little more privacy, with its comfy sofa bed and private living quarters. Regroup in the garden under the pergola as you enjoy alfresco meals with panoramic countryside views.

This home places you in Cortona, in the heart of central Italy between the Tuscany and Umbria regions. Hiring a car or hopping on a train means travelling less than an hour to visit cities like Florence, Pienza, Assisi and Perugia. Countless days spent shopping, dining and immersing yourself in culture and history await you.

Fairytale in Cortona

In the folds of the hills, this home is all about those Tuscan sunsets. Catch the golden hour, as the sun dips below the forest-clad hills, from the terrace where curtains frame the view and dining by candlelight is a delight. Days can be spent drifting from one terrace lounge to another, or swimming laps in the pool – the sun hits the water throughout the day. There are two farmhouse-style kitchens to choose from – one is professional-grade in the basement of the main villa and the other, a smaller affair in the separate cottage. Guests can spread out between both buildings, each with its own living room, and join together for excursions to Cortona, 10 kilometres away.  

Rosemary Breeze

With views over the Chiana Valley, this Tuscan farmhouse is surrounded by picturesque scenery in every direction. Featuring a main cottage alongside a small pool-house (equipped with an independent kitchen, living area and bathroom), the space is perfect for a family or group of friends. The serene setting of the garden here puts this home in a league of its own – and you'll find plenty of perching spots to enjoy a glass of local wine. The private swimming pool, too, overlooks the Tuscan landscape, and a covered alfresco dining area calls for home-cooked Italian meals in the sunshine. While the traditional designs inside feel a little dated, they don't seem out of place, given the home's rural Italian countryside location. 


Vineyard Vistas

Set high in the Tuscan hills, this villa has everything you need for a carefree stay. With a private pool and two terraces, you'll probably spend most of your time in the garden. The hot tub is the icing on the cake – it's the best spot to admire those sweeping views. While the traditional interior isn't as impressive, there's no shortage of space. The fifth bedroom is in a separate cottage, complete with a lounge and kitchenette – perfect for grandparents or a couple wanting extra privacy. A car is a must here, but you'll be within driving distance of Arezzo (25km), Cortona (13km), and the small village of Castiglion Fiorentino (5km).

Tuscan Shadows

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

DVD Library

Hidden away in deepest Tuscany, this home is ideal for anybody eager to escape the stresses of modern life and embrace la dolce vita instead – even if only for a week or two.

The villa is a real rustic gem, with character galore in the stone walls, wooden ceiling beams and the feature wood-burning fireplace in the living room. Those fond of the latest interior design trends might not be too happy with some of the dated elements, but those not so committed to aesthetics should find no cause for complaint.

Especially when the marvellous outdoor space is taken into consideration. Across the 100 hectares of grounds, there's a long swimming pool in which to cool off during the height of summer, plus vineyards, olive groves and vegetable gardens to please the foodies in the group. The wood oven and barbecue will help you whip up lavish feasts, which can be enjoyed in the open air.

As even the most cursory of glances at the surroundings will show, the home really is isolated and quite tranquil for it. That being said, there are options for day trips only a short drive away. The town of Cortona is only 15km away and is worth a trip for the Renaissance-era architecture alone. Watersports fans might also want to head over to Lake Trasimeno, 36km away.

Rural Dreamscape

A truly idyllic escape to rural Tuscany requires rolling hills, a rustic farmhouse and panoramic views across olive groves and vineyards. And you'll have all of this and more at this beautiful home deep in the countryside between Arezzo and Cortona. Surrounded by its own lush, terraced gardens, it's a stone-built gem with flexible accommodation to suit a large group. Packed with character features, you'll be welcomed by tiled floors, ancient wooden beams and traditional shuttered windows. The main house is divided into two apartments, each boasting its own kitchen and cosy living room, and with two bedrooms on each of the two floors. Allowing for as much or as little socialising as you require, there's also a stunning dining room with a table big enough to seat up to ten guests. And it has its own kitchenette to make life easier. Elsewhere in the garden, you'll find an additional one-bed guesthouse with its own bathroom – perfect if you really value your privacy. Spend your days swimming in the private pool on a lower level of the garden and eating outside on the huge terrace, pouring local wine and admiring the incredible views. If you want to do some shopping, Arezzo is just half an hour away by car, with Cortona and the Valdichiana Outlet Village around the same.  

Wild Rosemary

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.

A Tranquil Place

Indoor Pool

Heated Pool

Wheelchair Access

A traditional Tuscan villa nestled in the pristine countryside just a thirty-five-minute drive from Arezzo, this home is every bit as magical as it looks. Steeped in history and packed with period features and antiques, it's a slice of old-world romance that's suitable for a large group holiday or a special celebration. Surrounded by olive groves and with views over the Val di Chiana, it's set in a commanding position on a hilltop.

Terracotta tiles, ancient fireplaces and ornate vaulted ceilings are the order of the day inside, with tall, arched windows and vintage rugs. There's a corner bar in the living room and one of the most imposing fire surrounds we've ever seen, while the dining area can seat up to twenty-four guests – perfect for events. And you're welcome to cook for yourselves but for the ultimate in luxury, why not hire a private chef to do all the hard work in the stainless steel, professional kitchen for you? 

Nine en-suite bedrooms, some with their own sitting rooms and Jacuzzis, provide plenty of space and there's the option to add more beds if necessary. And for an additional fee, you can use the beautiful indoor pool and its sauna.

Outside, undulating lawns and flower beds give way to a large terrace with sun loungers, parasols and a dining pergola – not to mention a private pool of an excellent size. You can arrange for this villa to come with staff, becoming more of a hotel experience, or opt for independence. Either way, it's a perfect choice for a special break in the Tuscan countryside.   

Now and Forever

Surrounded by olive trees in the Tuscan countryside, this villa is a peaceful escape for a large family or group of friends. The rustic interiors are rich with charm, and two living areas and kitchens mean plenty of space for everyone to feel comfortable. Outside, you’ll find a large garden with knockout views of the rolling landscape. Better still, there is also a swimming pool, hot tub, and terrace where you can enjoy homemade Italian meals. When you're ready to explore, it's just a ten-minute drive to Cortona, where you'll find plenty of restaurants, shops, and historic landmarks.

Italian Heart & Soul

Tucked away in the heart of Tuscany, this serene stone house sets the scene for many happy holiday memories made with your loved ones. It sits on a green and leafy spot, with some wonderful views over the Tuscan hills in the distance that you can enjoy from one of the many sitting areas in the gardens and on the terrace. There's a dreamy private pool here so you can stay refreshed in the Tuscan heat, as well as an outdoor kitchen with a barbecue and wood oven for alfresco feasts. Inside, the interiors are a little lacking in light, but they feel peaceful and secluded, and feature all you need for a home-from-home stay.

Timeless in Tuscany

Juicer

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.

Tuscan Sunflower

Overlooking the lush Chiana Valley, this former farmhouse boasts views you won’t be forgetting any time soon. There are plenty of spots to sit back and soak it all in, but the pergola’s one of our favourites, perched right next to the pool and offering plenty of room for dining alfresco. The vineyard at the bottom of the garden is lovely too – and, while the interior’s a little dated, there’s a gorgeous stone fireplace to cosy up by if you’re visiting out of season.

Fresh As a Vine

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