Citta di Castello

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

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

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

Perched high on a hill and part of a boutique hotel estate, this villa straddles the Tuscan and Umbrian border with an effortless sense of escape. The infinity pool gazes out across forested valleys – an especially arresting place to be as the sun drops. On the ground, hectares of gardens unfold into a rose loggia, a vine-covered alfresco dining area, a tennis court, and a dedicated spot for sundowners. Three semi-independent sections make it well-suited to larger groups – especially those who prefer their Italian homesteads with just the right amount of historic character.

Umbrian Allure

Perched on a hill overlooking the Umbrian countryside, this villa is a scenic spot for your Italian getaway. It’s a great option for a big family trip or group holiday, with six individual apartments and generous gardens offering ample room to relax. Enjoy having your own space to spread out, while sharing picturesque pool days and leisurely lunches on the terrace. Time for a spot of sightseeing? Explore nearby Citta di Castello, where you’ll find elegant palazzos and galleries. Or head further afield to Arezzo, which hosts a monthly antique fair – perfect for picking up special souvenirs.

Valley Serenity

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

Tucked against the Roman walls of medieval Spello, this villa puts you a short stroll from cobbled, flower-lined streets, the main piazza, and the magic of Italian life. It's also the perfect base for sightseeing with Assisi and its UNESCO World Heritage Basilica di San Francesco within easy driving distance. Back at home, the balcony offers views across the Umbrian hills – perfect with a glass of local wine in hand. Inside, bold, eclectic art fills the living room, while the kitchen and dining area open directly onto that view through French windows.

Peaceful Sundown

Few apartments can claim an address like this. Overlooking Piazza del Campo in the heart of Siena, this top-floor penthouse gives you a bird's-eye view of Europe's great medieval squares. The living room windows frame the piazza in full, so you can watch the square shift from afternoon gold to the soft glow of evening without leaving the sofa. Panoramas aside, the interiors are a mix of historic charm and contemporary design. Three en-suite bedrooms give everyone their own space to retreat to after a day of exploring – and with Siena’s sights, sounds, and landmarks right on your doorstep, there will be plenty of adventures on the cards.

Campo at Sunset

This villa captures the rustic charm of old Italy. Surrounded by 40 hectares of land boasting olive groves, vineyards, orchards, and meadows with grazing horses, it’s an idyllic escape into the Tuscan countryside. A country road leads to the UNESCO hamlet of Castiglione d'Orcia. The garden is home to a rustic outdoor cooking station, a large, shaded table, and a full outdoor lounge. There’s a touch of modernity to the private, heated pool and you’ll find a sauna hidden amid the trees. The main villa is split across two levels and is a vision of old-world Italy and there is a separate annexe with further bedrooms, a second full kitchen and an open-plan living room. 

Rusticana Retreat

Adorned with traditional features that take you back to a time when things moved a bit slower, this nostalgic farmhouse oozes serenity and peaceful relaxation. Choose to spend lazy days by the pool, on the terrace or in any of the wonderfully comfortable bedrooms. We would, however, recommend having a car so that you can easily get around and explore all that this wonderful part of the country has to offer. Make sure to try all the local produce and cuisine – foodies will find themselves in heaven here.

East of the Sun

The views at this Umbrian home are truly spectacular. The villa stands in vast private grounds just a ten-minute drive from the hilltop town of Montone, looking out over the hills and valleys of the Umbrian countryside. It’s a secluded retreat, but still within easy access to all that Umbria has to offer. The villa is rustic, with a simple and comfortable decor – expect cotto floors, beamed ceilings and exposed original stonework, plus a few antiques. The gardens have been designed to make the most of the wraparound views, so you’ll find many a terrace and quiet corner to enjoy. We love the fig tree by the pool – time your visit right and you can pick sun-warmed fruit straight from the tree for breakfast. 

Drink in the Serenity

Tucked away in the Tuscan countryside, this villa is just the spot to switch off and relax. We love the seamless blend of traditional and modern and the opportunity to find space for socialising or solitude. The outdoor space is sure to be a firm favourite – with a private pool, sun-kissed terraces, ample opportunity for alfresco dining and far-reaching views, it’s not hard to see why this home caught our eye. When you’re ready to explore, the local village of San Sano has a restaurant and small grocery store, or you can hop in the car for a trip to Siena. 

Terracotta & Vine

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

Chic, contemporary and packed full of all the necessary ingredients for a relaxing stay, this villa is an ideal base for a small family or group of friends on an Italian getaway. The cherry on the cake for us is the outdoor space. Sun-kissed terraces allow you to gaze out at the sparkling lake views, or you can cool off in the Perugian sun with a swim in the private pool. Lake Trasimeno is a mere stone’s throw away, perfect for when you fancy a day on the water or a simple refreshing stroll around the shore. 

Book a stay in one of the best homes in Citta di Castello.

We selected the 2734 homes worth renting in this location

Who's coming along?

Home spotlights in Citta di Castello

SUNFLOWER
BEAMS

UMBRIAN
ALLURE

VALLEY
SERENITY

We've selected the top 3% homes in Citta di Castello.

Most popular homes in Citta di Castello.

Ten Green
Bottles

Peaceful
Sundown

Campo at
Sunset

Rusticana
Retreat

East of
the Sun

Drink in
the Serenity

Terracotta &
Vine

Under A
Tuscan Moon

Ten Green
Bottles

Peaceful
Sundown

Campo at
Sunset

Rusticana
Retreat

East of
the Sun

Drink in
the Serenity

Terracotta &
Vine

Under A
Tuscan Moon

Sunshine
Rhapsody

Check rates and availability for Citta di Castello.

Book with Plum Guide.

Frequently Asked Questions

Book a stay in one of the best homes in Citta di Castello.

We selected the 2734 homes worth renting in this location

Home spotlights in Citta di Castello

SUNFLOWERBEAMS

UMBRIANALLURE

VALLEYSERENITY

We've selected the top 3% homes in Citta di Castello.

Most popular homes in Citta di Castello.

Ten GreenBottles

PeacefulSundown

Campo atSunset

RusticanaRetreat

East ofthe Sun

Drink inthe Serenity

Terracotta &Vine

Under ATuscan Moon

Ten GreenBottles

PeacefulSundown

Campo atSunset

RusticanaRetreat

East ofthe Sun

Drink inthe Serenity

Terracotta &Vine

Under ATuscan Moon

SunshineRhapsody

Check rates and availability for Citta di Castello.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Citta di Castello?

SUNFLOWER
BEAMS

UMBRIAN
ALLURE

VALLEY
SERENITY

Ten Green
Bottles

Peaceful
Sundown

Campo at
Sunset

Rusticana
Retreat

East of
the Sun

Drink in
the Serenity

Terracotta &
Vine

Under A
Tuscan Moon

Ten Green
Bottles

Peaceful
Sundown

Campo at
Sunset

Rusticana
Retreat

East of
the Sun

Drink in
the Serenity

Terracotta &
Vine

Under A
Tuscan Moon

Sunshine
Rhapsody