Castiglion Fiorentino

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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

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

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

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

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

With views across the Val di Chiana, this beautiful 18th Century villa is rich in the warmth and charm of the Tuscan countryside. 

Filled with character, there’s an atmospheric presence to this home that feels enchanting. It’s the kind of space that offers a wonderful glimpse into traditional Italian life – inviting you to savour the joy of being together in a beautiful setting. And whether you’re preparing your morning coffee in the kitchen, lounging by the pool or sitting around the table, there’s an understated luxury to this home that feels inspiring. 

Outside, follow the spectacular views to the hilltop town of Cortona – only a twenty–minute drive, or admire the stunning renaissance architecture in Montepulciano – a thirty–minute drive away. 

As the day draws to a close, you’ll love gathering in the garden of this home. It’s the perfect setting to light up the barbecue and watch the sunset across the valley. 

A Gift of Laurel

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

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

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 

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

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

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

We selected the 3108 homes worth renting in this location

Who's coming along?

Home spotlights in Castiglion Fiorentino

GOLDEN
DAHLIA

A TUSCAN
SUNRISE

THE TUSCAN
SONG

We've selected the top 3% homes in Castiglion Fiorentino.

Most popular homes in Castiglion Fiorentino.

Casa
Castagna

The
Lucia

A Gift
of Laurel

By and
By

Noah's
Son

The Valley
of Angels

Tuscan
Shadows

The Etruscan
Lady

Casa
Castagna

The
Lucia

A Gift
of Laurel

By and
By

Noah's
Son

The Valley
of Angels

Tuscan
Shadows

The Etruscan
Lady

Check rates and availability for Castiglion Fiorentino.

Book with Plum Guide.

Frequently Asked Questions

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

We selected the 3108 homes worth renting in this location

Home spotlights in Castiglion Fiorentino

GOLDENDAHLIA

A TUSCANSUNRISE

THE TUSCANSONG

We've selected the top 3% homes in Castiglion Fiorentino.

Most popular homes in Castiglion Fiorentino.

CasaCastagna

TheLucia

A Giftof Laurel

By andBy

Noah'sSon

The Valleyof Angels

TuscanShadows

The EtruscanLady

CasaCastagna

TheLucia

A Giftof Laurel

By andBy

Noah'sSon

The Valleyof Angels

TuscanShadows

The EtruscanLady

Check rates and availability for Castiglion Fiorentino.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Castiglion Fiorentino?

GOLDEN
DAHLIA

A TUSCAN
SUNRISE

THE TUSCAN
SONG

Casa
Castagna

The
Lucia

A Gift
of Laurel

By and
By

Noah's
Son

The Valley
of Angels

Tuscan
Shadows

The Etruscan
Lady

Casa
Castagna

The
Lucia

A Gift
of Laurel

By and
By

Noah's
Son

The Valley
of Angels

Tuscan
Shadows

The Etruscan
Lady