Città della Pieve

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

The Tuscan Castle

Unwind amidst the stunning surroundings of Tuscany's Val d'Orcia at this expansive home. Spread across a large estate with a main villa, guesthouse, and an independent apartment, there are plenty of spots from which to admire the views – the saltwater pool offering perhaps the best vantage point. There's abundant produce in the orchards and kitchen garden to create your favourite Tuscan dishes, which you can cook in the large Italian kitchen or outside on the barbecue. It would be too easy to spend all day on the terrace, taking in the hilltop views, but there's also a gym and sauna, and it's just a short walk or cycle into the nearby town.

Heaven's Domain

Set on an expansive 27-acre estate in the peaceful Umbrian countryside, this home benefits from the hosts' passionate care for the 18th-century villa and its surrounding grounds. The modern amenities in this cosy apartment are welcome, but you can feel the history of the building, too, like the exposed wooden beams and stone walls. Although the open-plan living room isn't huge, you'll likely spend most of your time outside, whether exploring the vegetable garden, lavender fields, or olive groves (ask nicely and you might be able to sample some homemade olive oil). Cool off in the shared pool and then retreat to the patio with drinks at sunset to round off a dreamy Italian getaway.

Olive Ridge

Nestled near Paciano on the border between Umbria and Tuscany, this home is in a charming spot. Lake Trasimeno is nearby too, which is a particularly picturesque place for a swim or a stroll. Back at the apartment, you’ll find everything you need to get comfy, including a characterful kitchen for homemade meals. There’s also a communal pool (perfect on sunny days), along with space to enjoy dinner and drinks in the garden. Or you could walk into the village, where you’ll find a grocery shop, bar, and a handful of local eateries.

Wonderful Stone

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

Texture Like Sun

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

Terracotta & Stone

This Tuscan villa is a dream escape, where rustic charm meets timeless beauty. Set across a main building, annexes and private apartments with their own entrances, it balances privacy with shared spaces, making it ideal for group getaways. Inside, wooden beams, stone walls and a traditional fireplace create a warm and inviting atmosphere. The main kitchen is made for feasts, while the long table is perfect for lingering over local wine. Step outside and you’ll find a sparkling pool, shaded terraces and lawns that flow into the rolling hills beyond. It’s a place where lazy afternoons turn into golden evenings under the pergola. Charming restaurants are just a minute’s walk away, plus a complimentary tasting of local specialities is included in your stay. While you might want a car for exploring further, every breathtaking view and moment here makes it more than worth it.

Romantic View

The view from this 13th-century tower-turned-villa could be the envy of every Italian landscape painter. The hills of the Monte Rufeno national park, kissed golden at sunset and sunrise, sprawl before you and there’s probably no better place to take it all in than from the edge of the infinity pool. If the Italian sun gets too much, retreat to the lounge and dining area beneath the vine-dappled pergola – there’s a traditional stone-built pizza oven and grill out here for the chef of the group to try some regional classics alfresco. 

You can still dine with a view indoors, thanks to the sunroom with its walls of glass – the ideal spot for breakfast. While the rest of the tower and annexe is all wood-beam ceilings and terracotta floors, the kitchen feels sleek and modern with a dedicated wine fridge to chill your orvietos and pinot grigios. Apart from aspiring chefs, there’s plenty to entertain all kinds of visitors here – hit the gym and unwind with a sauna session after, head to the media room for a movie night or tuck yourself away with a book from the big collection of holiday reads. Winding your way up the staircases of the old tower, the view gets better and better. You’ll find bedrooms on the upper levels, with fabulous antique beds and ensuites – some with slipper tubs for a long soak.

Out here on the Tuscan- Lazio-Umbrian border, hiking trails snake through the Monte Rufeno national park and vineyards tumble town the hillsides (in fact, there’s a winery on the estate). Should you wish to stock up on supplies or explore the medieval streets of the nearest picturesque Tuscan town, Orvieto is a short drive away.  

The Landscape Artist

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

Wisteria & Lavender

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

Where Olives Grow

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

Cypress Hill

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

Sunshine Burst

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Types

Book a stay in one of the best homes in Città della Pieve.

We selected the 1962 homes worth renting in this location

Who's coming along?

Home spotlights in Città della Pieve

THE TUSCAN
CASTLE

HEAVEN'S
DOMAIN

OLIVE
RIDGE

We've selected the top 3% homes in Città della Pieve.

Most popular homes in Città della Pieve.

Wonderful
Stone

Texture Like
Sun

Terracotta &
Stone

Romantic
View

The Landscape
Artist

Wisteria &
Lavender

Where Olives
Grow

Cypress
Hill

Wonderful
Stone

Texture Like
Sun

Terracotta &
Stone

Romantic
View

The Landscape
Artist

Wisteria &
Lavender

Where Olives
Grow

Cypress
Hill

Sunshine
Burst

Check rates and availability for Città della Pieve.

Book with Plum Guide.

Frequently Asked Questions

Book a stay in one of the best homes in Città della Pieve.

We selected the 1962 homes worth renting in this location

Home spotlights in Città della Pieve

THE TUSCANCASTLE

HEAVEN'SDOMAIN

OLIVERIDGE

We've selected the top 3% homes in Città della Pieve.

Most popular homes in Città della Pieve.

WonderfulStone

Texture LikeSun

Terracotta &Stone

RomanticView

The LandscapeArtist

Wisteria &Lavender

Where OlivesGrow

CypressHill

WonderfulStone

Texture LikeSun

Terracotta &Stone

RomanticView

The LandscapeArtist

Wisteria &Lavender

Where OlivesGrow

CypressHill

SunshineBurst

Check rates and availability for Città della Pieve.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Città della Pieve?

THE TUSCAN
CASTLE

HEAVEN'S
DOMAIN

OLIVE
RIDGE

Wonderful
Stone

Texture Like
Sun

Terracotta &
Stone

Romantic
View

The Landscape
Artist

Wisteria &
Lavender

Where Olives
Grow

Cypress
Hill

Wonderful
Stone

Texture Like
Sun

Terracotta &
Stone

Romantic
View

The Landscape
Artist

Wisteria &
Lavender

Where Olives
Grow

Cypress
Hill

Sunshine
Burst