Casole d'Elsa

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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

Situated a short drive outside the bustling medieval city of Siena, this villa offers a true escape in the Tuscan countryside. Originally constructed as a watchtower, its 12th-century exterior has been updated with a stunning glass pavilion that offers 270-degree views of rolling Tuscan hills covered in cypress trees and olive groves. Beyond the sliding doors, an oxygen-cleaned pool offers a relaxing spot to while away your days, with a counter-current swim machine if you're feeling active. And though it's technically capable of accommodating up to four people, it makes for a perfect romantic retreat for two.


Tuscan Haven

Whether you’re in search of a dream-worthy Italian escape, a quiet retreat or an immersive sightseeing adventure, this beautiful home welcomes you to enjoy it all from the rolling hills of Tuscany. 

With views stretching far across the horizon towards the walled town of Volterra (just 14km away), the owners have designed this home to feel like a natural sanctuary – one that celebrates life’s simple (and luxurious) pleasures. 

From slow mornings watching the sunrise to leisurely swims in the pool (heated upon request) and long soaks in the jacuzzi, it’s easy to fall in love with the quiet charm of this setting. 

By sunset, the outdoor dining area transforms into the perfect backdrop to idyllic evening drinks and barbecue meals. And when the weather draws you inside, you’ll find the living room inviting you to get cosy by the wood-burning fire. 

For explorations further afield, days can be spent admiring ancient sights, sampling delicious local cuisine, following nearby hiking trails and simply basking in the beauty of Italian living. 

Colours of the Sky

Tucked in a restored farmhouse, this apartment sets the tone for a magical stay in Tuscany. You will need a car to get around here, but it’s just a short drive to San Gimignano and it’s a fantastic base for day trips to Siena and Florence. You can spend your days sightseeing, hiking and sampling fresh local produce in nearby markets. And when it comes to rest and relaxation, this home features a private terrace for blissful evening drinks. Inside, the rooms are traditional, simple and well suited to families. 

Ancient Embrace

Immerse yourself in a traditional Tuscan lifestyle at this hilltop home. Once an ancient oratory, with original features dating from the 15th century, this home is now dedicated to praising Chianti's most famous delicacy – wine. Naturally, there's plenty of space for entertaining, including two outdoor dining areas accompanied by sweeping vineyard views – though the estate's independent annexe is perfect for guests looking for a touch more privacy. Retreat to the balcony to enjoy a locally-produced bottle, or hop in the car to explore nearby wine estates and charming hilltop villages – but a day lounging by the pool might be just as tempting. 

Noble House

This beautiful villa is nestled in the rolling countryside of Val d’Elsa. The medieval villages of Casole d’Elsa, Colle Val d’Elsa, and San Gimignano are all within easy reach, giving you plenty of options for day-trips. Perfect for large groups, this home is split into several independent units, so everyone can enjoy their own space before coming together to swim in the private pool, stroll the grounds, play ping pong on the terrace, or dine together outside. Wine, olive oil, cheese, and cured meats are produced on the estate – why not book a private chef to whip up the ultimate local feast? 

Rustic Embrace

A traditional stone villa set deep in the Tuscan hills, with no neighbouring properties in view and surrounded by nature. The double-height living room – exposed beams, a large fireplace, arched glass doors onto the terrace – is the kind of space that makes evenings unhurried. Outside, a private pool sits among olive trees and aromatic herbs, with wrought iron beds lending every bedroom an authentically Tuscan feel. Volterra's Etruscan and medieval streets are a sixteen-minute drive when you're ready to explore.

Wild Wine

Nestled away in the countryside outside the idyllic hilltown of San Gimignano, this extraordinary villa combines exquisite interior design and a sprawling collection of amenities to make for an address that is sure to win over even the most discerning of guests.

As you walk about the house for the first time, you might find it difficult to single out a favourite room. There's a timeless elegance to the dining room surrounded by floor-to-ceiling windows and centred around a grand piano, while the neighbouring kitchen is surprisingly modern in style and is sure to excite those with a culinary calling. 

And that's before we've even got around to the impressive grounds. On summer days, the saltwater swimming pool surrounded by leafy vegetation is sure to beckon, but there's also a wealth of peaceful spots out on the various terraces. As if that wasn't enough, guests are also blessed with a tennis court, which can be found about 500m from the home.

With this much to occupy you at the address, you just might never feel the need to leave, but San Gimignano – about 3km away – is well worth a visit. Don't just take our word, though –The historic centre is a UNESCO World Heritage Site. Both the cities of Siena and Florence are close enough to warrant a day trip, too.

One of the Greats

This Tuscan home is something special. It’s in the Val di Cecina, close to the medieval town of Pomarance, with its historic castle and walls. The villa – comprising separate apartments – is perfect for several families as there’s plenty of space to spend time together while still enjoying privacy. From its position in the hills, the villa offers beautiful views of the surrounding landscape, which can be admired from the well-kept garden and terracotta outdoor dining area. The scent of verbena, lilies, and rosemary pervades the garden. This stylish and elegant home has been renovated to add modern comforts while retaining all the charm of a typical Tuscan farmhouse. 

Verbena & Rosemary

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

Standing in the historic centre of medieval Poggibonsi, this home puts the centre of Tuscany at your fingertips. A short distance from Florence and Siena, you can venture out into the region's world-famous rolling hills for wine tasting from here, making it an ideal base for lovers of good food and drink. At home, the authentic Tuscan style, complete with frescoes, wooden beams and handcrafted furniture, make for a scenic backdrop as you relax in the evenings. And while the bathtub being in a bedroom might be inconvenient, it's still a perfect spot for unwinding.

A Dream of Tuscany

Tucked away in the picturesque Colle di Val d'Elsa, this apartment has a great location. The town is famous for its crystal glass production, medieval streets and stunning views of the surrounding Tuscan landscape. Just a short stroll away is Piazza Arnolfo, filled with charming cafes and shops. Housed in a Liberty-style building, this home has a bright living space to relax in. The traditional decor might not be to everyone's taste, but it's homely. There’s also a private patio and garden area here – perfect for evening drinks. 

Book a stay in one of the best homes in Casole d'Elsa.

We selected the 4078 homes worth renting in this location

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Home spotlights in Casole d'Elsa

THE ANCIENT
STONE

TUSCAN
HAVEN

COLOURS OF
THE SKY

We've selected the top 3% homes in Casole d'Elsa.

Most popular homes in Casole d'Elsa.

Ancient
Embrace

Noble
House

Rustic
Embrace

Wild
Wine

One of
the Greats

Verbena &
Rosemary

Campo at
Sunset

A Dream
of Tuscany

Ancient
Embrace

Noble
House

Rustic
Embrace

Wild
Wine

One of
the Greats

Verbena &
Rosemary

Campo at
Sunset

A Dream
of Tuscany

Tuscan
Shutters

Check rates and availability for Casole d'Elsa.

Book with Plum Guide.

Frequently Asked Questions

Book a stay in one of the best homes in Casole d'Elsa.

We selected the 4078 homes worth renting in this location

Home spotlights in Casole d'Elsa

THE ANCIENTSTONE

TUSCANHAVEN

COLOURS OFTHE SKY

We've selected the top 3% homes in Casole d'Elsa.

Most popular homes in Casole d'Elsa.

AncientEmbrace

NobleHouse

RusticEmbrace

WildWine

One ofthe Greats

Verbena &Rosemary

Campo atSunset

A Dreamof Tuscany

AncientEmbrace

NobleHouse

RusticEmbrace

WildWine

One ofthe Greats

Verbena &Rosemary

Campo atSunset

A Dreamof Tuscany

TuscanShutters

Check rates and availability for Casole d'Elsa.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Casole d&#39;Elsa?

THE ANCIENT
STONE

TUSCAN
HAVEN

COLOURS OF
THE SKY

Ancient
Embrace

Noble
House

Rustic
Embrace

Wild
Wine

One of
the Greats

Verbena &
Rosemary

Campo at
Sunset

A Dream
of Tuscany

Ancient
Embrace

Noble
House

Rustic
Embrace

Wild
Wine

One of
the Greats

Verbena &
Rosemary

Campo at
Sunset

A Dream
of Tuscany

Tuscan
Shutters