San Leo

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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

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

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

Situated a scenic, ten-minute stroll from Cortona, this villa is the ideal setting for sampling life in Tuscany. The walled town’s rich history and traditional restaurants are within close reach, and the rest of the region is easy to explore by car. As for the house, it’s characterful and comfortable (if a little rustic in parts), while outside the swimming pool invites leisurely laps while admiring the scenery. If you’re looking for an authentic Tuscan experience, where you can embrace a slower pace, this is a charming option.

Grace & Bronze

Nestled between the valleys and fields of central Italy, this luxury, eco-conscious country house provides the perfect base for a rural getaway. What was once an abandoned farmhouse has been sensitively restored to reflect the bountiful Marche countryside, honouring its traditional characteristics while adding a flair of modernity. Inside, terracotta tiles and wooden beamed ceilings blend harmoniously with chic, minimalist furniture and a modern, farmhouse-style kitchen. 

The interior is beautiful, but we imagine you’ll be spending most of your time making the most of the outdoors. Especially when considering the outdoor kitchen, fully equipped for trying your hand at local dishes. Spend days lounging by the saltwater pool, taking a dip to cool off, while soaking in the rural surroundings. And spend evenings beneath the pergola, white curtains gently swaying in the wind, tucking into a fresh barbecue dinner around the dining table. After nights of tipsy piano playing and a few games of pool, you’ll love sinking into your cosy beds, already looking forward to waking up to the verdant, rolling views that both bedrooms are met with. 

If you never wanted to leave this slice of countryside heaven, we’d get it. But this corner of Italy is one of the last areas that isn’t yet on the tourist trail, so you can explore the region of Marche and its beaches, walled cities, and archaeological sites with ease. 

Memories from Marche

Located near Morciano di Romagna, in the province of Rimini, this villa is ideal for nature lovers who want to enjoy some peace and quiet. There’s no better place to soak up the countryside panoramas than from the edge of the swimming pool or from the dining terrace with a spread of local delicacies. A big plus is the fenced grounds, making the place suitable for pets and small children. Fancy a change of scenery? It’s a short drive to Altamarea Beach and the town of Cattolica. 

The Art of Dreams

Head into the Tuscan hills just outside the charming village of Cellai and keep an eye out for an imposing villa with its own bell tower. Almost unbelievably, this stunning property will be your home from home for however long you decide to stay.

Step inside your apartment, and you'll discover a typically Tuscan scene, with tiled terracotta floors, exposed wooden ceilings and frescoes painted directly on the walls. Four individually decorated bedrooms, each as enchanting as the last, will serve as your soothing sanctuaries for you to unwind at the end of each day. The spacious interior includes not one but two seating areas, so you can always claim a secluded spot as your own for the afternoon if you want to get lost in the pages of a good book. Meanwhile, the kitchen and dining area are perfect for sociable meals with family and friends in true Italian style. 

Outside in the shared garden, you'll find yourself surrounded by pristine landscaped gardens with a vine-covered pergola, terraced seating and perhaps most importantly, a pool. 

Start each day by visiting Forno La Chiocciola, where you can stock up on fresh bread, including Florentine speciality flatbread, schiaccata. Then, when you're not laying out on poolside loungers and sipping wine in the sun, the stunning Renaissance city of Florence is less than half an hour away. Why not get to know the artistic, architectural and cultural history of Tuscany, spending an afternoon or three wandering its streets and taking it all in. 


The Legendary Giulia

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

Taking up a significant patch of lush land in a small Umbrian village near the Tuscan border, this villa is spread across the main house and annexe, making it the perfect destination for family reunions or intimate events. The traditional interior is what you'd expect from an older Sicilian home, and though some might find it a little outdated, it's a fair trade for the ample space, inside and out, and a private gym and spa. Admire the Lisciano Niccone hills from the private pool or the patio tables – ideal for alfresco dining before driving to Castello di Lisciano or Lake Trasimeno. 

Through the Brick Arch

Nestled in the rolling hills of Marche, this home is the definition of rural charm. The 200-year-old farmhouse is now a charming, four-bedroom villa showcasing both modern amenities and traditional style. Admire the exposed wooden beams and fireplace in the living space, and take in the views from the master bedroom's private balcony – whoever takes this room is very lucky indeed. The garden is an attraction in its own right, with flourishing flowers and shaded dining areas where you can enjoy breakfast in the morning. Relax by the pool with a book and soak up the views, returning to the house only to rustle up lunch in the kitchen to enjout in the conservatory, one of our favourite spots. If it's even possible, the gardens perhaps look more charming after the sun goes down, when the pool lights up and lamps cast the trees in a warm glow. Gather out here for a barbecue, and afterwards curl up in the historic living room for a nightcap. While this home's charm comes from its rural location, you're just a twenty-minute drive from Pesaro, a coastal city where you can visit palaces and take to the many cycling trails. 

The Rest Is History

Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding. The interiors have preserved the grace of earlier ages while adding the essential modern cons and amenities.  Exposed wood beam ceilings, tiled floors covered with vibrant carpets, and gorgeous vintage furniture make you feel at home, yet so far away from the current era. The master bedroom comes with a four-poster bed, and overall, all sleeping quarters exude a pampering feel accentuated by the gorgeous period furniture. We love the huge dining room, the walls of which are lined with well-stocked bookshelves. After a hearty meal, grab a book, amble outside to the sundeck and lose yourself in another world. When the warmth overwhelms you, take a cooling dip in the massive pool. In the evening you can savour wine and antipasti on the veranda or under the vine-wrapped pergola. If you get the itch to explore, a thirty-minute drive will take you to Siena where you can enjoy dining, shopping and sightseeing. 

The Vine Song

Tucked away in the Umbrian countryside, this traditional villa has tranquillity running through its core. While the upper level is reserved for the owner’s family, there’s more than enough space on the lower level for a family or group of friends to enjoy a comfortable stay. And the cherry on top is the outdoor space. Sun-kissed terraces, shady alfresco dining spots and a private pool – what’s not to love? When you’re ready to explore, it’s a mere fifteen-minute drive to Puglia, where authentic Italian cuisine awaits. 

Lavender, Basil & Rosemary

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Book a stay in one of the best homes in San Leo.

Who's coming along?

Home spotlights in San Leo

NOAH'S
SON

SUNFLOWER
BEAMS

THE MAIN
EVENT

We've selected the top 3% homes in San Leo.

Most popular homes in San Leo.

Grace &
Bronze

Memories from
Marche

The Art
of Dreams

The Legendary
Giulia

View From
The Evening

Through the
Brick Arch

The Rest
Is History

The Vine
Song

Grace &
Bronze

Memories from
Marche

The Art
of Dreams

The Legendary
Giulia

View From
The Evening

Through the
Brick Arch

The Rest
Is History

The Vine
Song

Lavender, Basil
& Rosemary

Check rates and availability for San Leo.

Book with Plum Guide.

Frequently Asked Questions

Book a stay in one of the best homes in San Leo.

Home spotlights in San Leo

NOAH'SSON

SUNFLOWERBEAMS

THE MAINEVENT

We've selected the top 3% homes in San Leo.

Most popular homes in San Leo.

Grace &Bronze

Memories fromMarche

The Artof Dreams

The LegendaryGiulia

View FromThe Evening

Through theBrick Arch

The RestIs History

The VineSong

Grace &Bronze

Memories fromMarche

The Artof Dreams

The LegendaryGiulia

View FromThe Evening

Through theBrick Arch

The RestIs History

The VineSong

Lavender, Basil& Rosemary

Check rates and availability for San Leo.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in San Leo?

NOAH'S
SON

SUNFLOWER
BEAMS

THE MAIN
EVENT

Grace &
Bronze

Memories from
Marche

The Art
of Dreams

The Legendary
Giulia

View From
The Evening

Through the
Brick Arch

The Rest
Is History

The Vine
Song

Grace &
Bronze

Memories from
Marche

The Art
of Dreams

The Legendary
Giulia

View From
The Evening

Through the
Brick Arch

The Rest
Is History

The Vine
Song

Lavender, Basil
& Rosemary