Castiglion Fiorentino

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

Satellite / Cable TV

Entertainment

Hair Dryer

Bathroom

Dishwasher

Microwave

Freezer

Kitchen

Oven

Stove

Toaster

Fridge

High Chair

Coffee Maker

Cooking Essentials

Kitchen & Dining

Cot / Crib

Washing Machine

Bedroom & Laundry

Swimming Pool

Private Pool

Wellness & Fitness

Wi-fi

Laptop Friendly Workspace

Internet & Office

Air Conditioning

Central Heating

Fireplace

Heating & Cooling

Parking Available

Free Parking On Premises

Private Entrance

Parking & Access

Barbeque

Garden

Sun Loungers / Beach Chairs

Patio / Terrace

Balcony

Outdoor

Mosquito Net

Nice to haves

Pets Allowed

Pets

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 

Kitchen Utensils

Hot Tub

Outdoor Pool

Private Parking

Free Parking

Beach / Pool Towels

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

Bathtub

Espresso Machine

Pod Coffee Machine

Hangers

Fenced Property

Stand on the flower festooned balcony of this large, stone-built farmhouse in the rolling Tuscan countryside and just take a few moments. With idyllic views over the estate's olive grove to the forest-clad hills beyond, we're sure you'll feel inspired. This gorgeous rural residence is perfect for groups looking for seclusion and tranquillity. 

Spend your days lounging by the pool or relaxing in the shade of the loggia. Enjoy dinner under the gazebo, and then when the light starts to fade, retire to the spacious interior. Here, a blend of classic period details – terracotta tiled flooring, wrought iron mezzanine balconies, brick arches and wooden beams – combine with sumptuous furnishings to create a convivial home. Wind up the vintage gramophone or entertain your guests at the piano in the living room – this is a home designed to be filled with music and laughter.

When you feel like exploring, head to the walled city of Castiglion Fiorentino, known for its annual festivals and its Etruscan archaeological sites, five kilometres away.



Gramophones & Gazebos

Iron

Ironing Board

Self Check-in / Check-out

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

Desk / Workplace

Ceiling Fans

Outdoor Seating

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

Smart TV

Kettle

Wine Cellar

Private Washing Machine

Drying Rack

Outdoor Fireplace / Firepit

Outdoor Shower

Sun Umbrellas

Welcome Hamper

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Smoke Detector

Other

Tucked between olive groves and a pine forest, this cosy villa is a scenic drive away from Cortona, Arezzo and Pienza – but you might not want to leave once you're here. The three bedrooms (each with their own bathroom) are downstairs, while upstairs it’s all about spending time together – cooking in the kitchen, chatting around the travertine island, or sharing a bottle of local wine at the glass-and-timber table made from a tree that once grew on the property. Outside, you’ve got a pool, a jacuzzi, and a rooftop terrace with front-row seats to the sunset over Castiglion Fiorentino. It’s peaceful, spacious and completely private – a proper countryside escape without feeling remote.

A Tuscan Sunrise

Child Friendly

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

Toiletries

Blender

Wine Cooler

Shared Washing Machine

Extra Pillows and Blankets

EV Charger

Courtyard

Hammock

Breakfast Included

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

Sauna

Free Parking On Street

Single-Level Home

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

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

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

Perched high on a hillside above the medieval town of Camucia, this stone cottage is perfect for couples seeking relaxation in Tuscany. Surrounded by olive groves and rolling hills, the home offers stunning valley views. Days can be spent relaxing by the private swimming pool or dining alfresco under the cool shade of the gazebo. Inside this two-storey home, you'll find a cosy lounge with a fireplace and plenty of original features such as beams. This place is situated just under 10 kilometres from Cortona, with its piazza filled with cafes and restaurants.

Tuscan Stone & Olive Trees

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

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

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

Playground

Pool / Snooker Table

Sound System

Dryer

Exercise Equipment

This luxurious villa is the perfect setting for a relaxing holiday in Tuscany. The home is set in a large park filled with plants and flowers, with a beautiful infinity pool at its centre. There’s a vegetable garden that you can choose produce from for your meals, perhaps prepared on the barbecue or in the wood-burning oven. When you want to take your vacation relaxation to the next level, head to the wellness centre to soak in the Jacuzzi and unwind in the sauna. This home in the heart of the Val di Chiana is a stunning choice for large groups. 

Golden Dahlia

DVD Player

DVD Library

Indoor Pool

Heated Pool

Lift Access

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

Library of Books

Cafetiere

Herb Garden

Tucked away on the Tuscan hillside, this home is an idyllic retreat for larger groups seeking a slice of dolce vita. Tiled floors, exposed beams and warm tones stay true to the house’s origins and also provide a cool respite from sweltering summer temperatures outside. Upon arriving, drop your bags and dive straight into the impossibly large pool, or if swimming isn’t your thing, retreat to the library and curl up with a good book. Dinners are a breeze thanks to the wood-fired pizza oven – you can even pick your own toppings from the vegetable garden – what could be better than that? If can bear to leave your remote Tuscan idyll, you're within striking distance of Florence, just over an hour away, which is the birthplace of the Renaissance movement and one of the world's greatest art cities.

Vita Toscana

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

Board Games

Baby Bath

Cleaning Products

Umbrellas

This home is a true haven nestled right in the heart of Arezzo. With its luscious garden and rustic interior, it's the perfect place to kick back and relax away from the hustle and bustle. 

Step inside, and you'll be enchanted by the traditional touches, from the terracotta tiles to the original fireplace and wooden ceiling beams. Budding chefs can whip up their favourite dishes in the kitchen, using the fresh Italian herbs provided. And, the leafy garden provides the ideal spot for a sundowner – open a bottle of Pinot Grigio and relax on the patio as you make some plans for the following day. 

The hilltop Arezzo Cathedral is not to be missed – admire the painted ceilings before strolling through the medieval town, gelato in hand. The nearby Piazza Grande is one of the most beautiful in the region, and is an awe-inspiring setting for a coffee or something stronger. And, if you want to explore more of eastern Tuscany then there's plenty to see just a short drive away – from vineyards to castles, there's something for everyone. 

Pistachio Pesto

Relaxation is the order of the day at this 19th-century farmhouse in Tuscany's Ranchetto region. Located within its own natural park, lined by tall oak and chestnut trees, it's perfect for those after unwavering peace and privacy. 

Upon arrival, the home's stone exterior, wooden shutters and juniper roofing hark back to the place's history, and we can't help but swoon over the warm and inviting living space inside. Beamed ceilings and terracotta floors add plenty of visual interest, while the very earthy and natural colour palette will soon have you feeling right at home. Cook up a storm in the country-style kitchen, then spill out into the beautiful communal outdoor areas. 

With a completely-fenced garden of about 3000 sq/m, full of green foliage and potted flowers, you'll have no choice but to slow right down, adopt the pace of nature and unwind. Whether you're tucking into a lazy alfresco lunch on the terrace, cooling off with a few up and downs in your glistening pool or enjoying an apéritif under the pergola, you're sure to feel completely at ease. 

If you can muster up the energy to leave this beautiful home, there's so much exploring to do nearby. Start with a visit to the traditional neighbouring town of Castiglion Fiorentino, where age-old buildings, museums and artwork make for a great historical trip, just a twenty-eight-minute drive away. You'll also find the popular hilltop town of Cortona and the attractive city of Arezzo in less than thirty minutes by car. 

Old Tuscan Farmhouse

Black-Out Blinds

Surrounded by olive groves and ancient woods, this traditional farmhouse welcomes you to an authentic stay in the heart of Tuscany. 

Located on Pomaio hill with sweeping views across the countryside, this is a wonderful setting to retreat into the heart of nature. And from the moment you arrive, you’ll want to savour the rustic simplicity and charm of this home – it’s the perfect place to connect with the timeless beauty of Italy. 

Families and friends will love gathering here – the communal spaces feel warm and intimate, inviting you to slow down and enjoy quality time together. And whether you’re drinking your morning coffee in the garden, swimming in the pool or cooking in the cosy kitchen, this is the kind of home that enriches daily living. 

Outside, follow the garden path out into the surrounding countryside for an inspiring stroll, or make the short drive into the majestic city of Arezzo – just ten–minutes away. Whether you’re admiring 15th century frescoes and abbeys, or olive trees and vineyards, this home is the perfect setting to celebrate the authentic taste of Tuscany. 

The Terracotta Sun

Set in 30,000 square metres of grounds, this home is the Tuscan dream. There’s a turquoise swimming pool for hot summer days, a volleyball and football pitch, and a well-tended orto (vegetable garden) where you can help yourself to seasonal sun-ripened produce and cook just like a local. If the weather is fine a barbecue might be in order – there are plenty of places to sit and enjoy a meal around the garden – plus an annex with a fully-equipped gym for burning off the feast the night before. Inside the traditional villa, there’s a luxuriously modern feel, yet the old Tuscan charm has been retained. Uplighting illuminates exposed brick archways and vaulted ceilings as though proudly displayed in a museum, and antique furniture sits alongside modern, comfy sofas. The sleek, minimalist kitchen has everything you need for an Italian feast from the orto and dinner can be accompanied by a bottle of local red from the stocked wine cellar (wine is not included in the rental price). This home is split between the main villa and a garden cottage. The garden cottage houses a full spa with massage rooms, a sauna and a Jacuzzi – just ask your host to make a booking. You’re in the Valdichiana hills here, looking out over olive groves and the rolling scenery Tuscany is famous for, and it’s a twenty-minute drive to the beautiful Etruscan town of Cortona.

Ten Green Bottles

Foosball / Table Football

Piano

Ping Pong Table

Bicycles

Tennis Court

When staying in Tuscany, who doesn’t want a 16th-century villa, with life-size frescoes and acres of grounds to explore? This place sits between the medieval borgo of Monte San Savino (a ten-minute drive) and the alluring city of Arezzo (a fifteen-minute drive). 

This villa’s swimming pool really grabbed us – a long, turquoise triangle, covered at one end to keep you shaded during the heat of the day. Loungers sit beneath parasols and the huge, outdoor dining table is shaded by an L-shaped pergola, dappled with jasmine. There are sprawling lawns for the kids to run free, and a tennis court and ping pong table too.

Inside, each apartment has its own living area, from the grand lounge set around an ancient stone fireplace to the book-lined family snug and TV room. The kitchen is sleek and modern in slate grey and white but sits beneath the old wooden ceiling of this 16th-century villa for a touch of the past.  

Between The Olive Groves

Nothing says ‘la dolce vita’ quite like this authentic Italian villa, which you’ll find tucked away on the outskirts of Castiglion Fiorentino. Nestled deep in the heart of the Tuscan countryside, this rustic home dates back to the 17th century, so it’s no wonder that stepping inside feels like travelling back in time. Don’t worry though – there are plenty of modern amenities on-site to make your stay as comfortable as possible, so whether you need to join a last-minute Zoom meeting or want to spend the evening curled up in front of the TV, this Italian abode has got you covered.  

However you plan to spend your day, we’d recommend starting your morning with a leisurely coffee in the wooded garden, where you’ll be able to feast on views of the verdant Tuscan hills. When you’re finished, grab your swimming costume and take a dip in the shimmering infinity pool, or get dressed and wander down to the grocery store – just a ten-minute walk away – to pick up some fresh ingredients for lunch. If you fancy doing some sightseeing, it’s an eight-minute drive – or forty-five-minute walk – to Castiglion Fiorentino, the perfect place to learn more about the region’s rich history. When you’ve had your fill of ancient attractions – think the Cassero fortress and Pinacoteca Comunale – grab a bite to eat in one of the city’s pizzerias or head home and let yourself drift off in front of the villa’s gorgeous stone fireplace. Bliss.

Casa Castagna

If you’re in search of a traditional Tuscan escape, this home delivers a great solution. Just 10 kilometres from Cortona, this rustic sanctuary consists of three independent apartments (each with its own entrance) – making it a great option for groups and families. It’s worth noting some of the furnishings are a little dated, but you will find a peaceful garden, a private pool and a large terrace with a barbecue. Your host can also help organise a range of extra services, including cooking classes and spa treatments. From here, it’s just a short drive to local amenities, while majestic cities like Arezzo and Siena are also within easy reach. 

The Tuscan Song

Retaining its original exposed stone structure and terracotta thatched roof, this villa stands tall just outside the small village of Alberoro. Spend mornings relaxing on the lush lawns by the private pool, where sprigs of lavender lend an air of tranquillity. Fire up the gas barbecue for an alfresco lunch in the courtyard, with striking views over the rural landscapes of the Aretine Val di Chiana and its surrounding villages. Large white umbrellas cover the many outdoor seating areas here, to shade you from the Mediterranean sun as you enjoy the views. Inside, this rustic home has luxurious touches throughout, including beautiful bathrooms with painted walls, blue velvet sofas, a 12-seater wrought iron dining table and a piano. As well as two separate living rooms, there's a light-filled library with comfy sofas, and a games room with foosball and a poker table. If you can tear yourself away, you’ll be just a short drive away from the quaint medieval town of Arezzo. 

Lavender Lawns

Sauna / Steam Room

This Tuscan villa was once a hotel, so it’s well set up for large groups. All of the bedrooms are en-suite, there’s an industrial kitchen, and the huge lounge has plenty of sofas. With an indoor and outdoor pool, you can swim in every season here. Plus there’s a sauna and two of the en-suites have Jacuzzi bathtubs. The decor feels a little dated – particularly the bathrooms – but we love the formal dining room and the conservatory overlooking the Tuscan countryside. Located in the centre of Valdichiana, there are plenty of opportunities for hiking in the area. Or you can jump in the car for a day trip to the hilltop town of Cortona or the Medieval city of Arezzo.

Rosewood Manor

Situated near Monte San Savino, this farmhouse invites guests to experience an authentic taste of the Tuscan countryside, including a complimentary wine tasting and a visit to the owner's winery. With a large garden and private swimming pool overlooking the vineyards and hills, you'll likely choose to spend much of your time out here taking in the surrounding scenery. Inside, classic designs nod to the home's Italian countryside location through features including an original oven and fireplace. While its traditional styling may not be to everyone's tastes, modern finishing touches ensure comfort and practicality are met here. 



Limestone & Antique

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

The Italian holiday of your dreams awaits at this elegant villa, based in the rolling green hills of Valdichiana Aretina, providing peace and perspective in abundance. Nestled with rich greenery, it feels like you’re tucked away in nature while still being just a short drive from the city of Arezzo, where you can roam idyllic streets and find unique bars and quaint cafes to visit.

This home has been styled with old-school opulence in mind, with ornate wooden furniture, exquisite soft furnishings and characterful decor, all making a stay here feel like a real treat. We love the stately reading room where you can grab a book from the library and enjoy some quiet time, as well as the lounge where you can sip your morning coffee while you discuss your daily itinerary with one another.

The outdoor areas here will blow you away. The private pool makes for some lovely moments of pure relaxation – especially when the sun starts to set – while the covered dining area provides the perfect spot for popping a bottle and toasting to your getaway.

Italian Iced Tea

Tucked away in Val di Chiana in the heart of the Tuscan countryside, this home promises an escape from it all. Ideal for larger groups, the main villa sleeps eight guests across four bedrooms. At the same time, the annexe accommodates four in a double and twin bedroom – perfect for those who like to holiday together yet still enjoy some privacy. The outdoor space will bring everyone together, without a doubt. Sun-kissed terraces and a private pool and hot tub, all wrapped in Mediterranean gardens. What’s not to love?

Tuscan Garden

Secured Parking

Resort Access

Stair Gates

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

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

Vacuum Cleaner

Desk

Multiple Sets of Keys

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

Tucked away in the Tuscan countryside, this home offers a taste of rural Italian life. You’re quite secluded here – the nearest supermarket is a short drive away – but the views over the Val di Chiana are well worth the price of admission. Plus, your host can arrange plenty of in-house services – think daily cleaning and private catering – so you won’t have to venture far if that’s not your bag. And if you want a bit of extra privacy at the end of the day, there’s a separate annexe with its own bedroom, offering plenty of space to unwind away from the main villa. 

Citrus & Sangiovese

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

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

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

Book a stay in one of the best homes in Castiglion Fiorentino

We selected the 2922 homes worth renting in this location

Who's coming along?

Home spotlights in Castiglion Fiorentino

We selected the top 3% holiday homes in Castiglion Fiorentino

Most popular homes in Castiglion Fiorentino

Check upcoming rates & availability for Castiglion Fiorentino

Frequently asked questions