Book Luxury Holiday Apartments in San Leo

Award-winning homes from £98

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Home spotlights in San Leo

The Etruscan Lady

The Etruscan Lady

  • 17 guests

  • 8 bedrooms

Cortona, Arezzo

Stunning countryside views. A lush garden.

Chianti Dream

Chianti Dream

  • 4 guests

  • 2 bedrooms

San Sano, Gaiole in Chianti

Set in the picturesque village of San Sano, this home offers the best of both worlds – easy access to amenities and a quiet space to retreat to and relax. You won’t tire of the vineyard views here.

Sing, Prima Donna

Sing, Prima Donna

  • 6 guests

  • 3 bedrooms

Castelfranco Piandiscò, Arezzo

Sitting on a thousand-hectare olive farm in a rural part of Tuscany, this enchanting villa will win you over with its ancient character. Each morning, slide open the doors of your farmhouse kitchen, where you'll tuck into a traditional breakfast beneath wood beams.

The Legendary Giulia

The Legendary Giulia

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

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.


We selected the top 3% holiday homes in San Leo Holiday Apartments

Explore the 890 most perfect homes in our collection

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Most popular homes in San Leo

Dream of Light

Dream of Light

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

Olive Green

Olive Green

  • 4 guests

  • 2 bedrooms

Bucine, Arezzo

Stonehaven

Stonehaven

  • 12 guests

  • 6 bedrooms

Radda in Chianti, Tuscany

The Valley of Angels

The Valley of Angels

  • 14 guests

  • 7 bedrooms

Cortona, Arezzo

Sunflowers & Sangiovese

Sunflowers & Sangiovese

  • 10 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

Drink in the Serenity

Drink in the Serenity

  • 14 guests

  • 7 bedrooms

Montone, Perugia

Rosemary Breeze

Rosemary Breeze

  • 12 guests

  • 6 bedrooms

Cortona, Arezzo

Golden Silence

Golden Silence

  • 8 guests

  • 4 bedrooms

Castelfranco Piandiscò, Arezzo

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Frequently asked questions

Explore our selection of the finest luxury Holiday Apartments for your next getaway in San Leo. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that San Leo has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Apartments for your trip.

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