Book Luxury Holiday Apartments in San Leo

Award-winning homes from £98

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Home spotlights in San Leo

Tuscan Villa

Tuscan Villa

  • 8 guests

  • 4 bedrooms

Bucine, Arezzo

This elegant stone villa is nestled rather picturesquely amidst rolling hills and vineyards in the Tuscan countryside, approximately a thirty-minute drive from Arezzo. You’ll enjoy stunning scenery here, especially since you’ll have a large garden at your disposal.

Tuscany in Bloom

Tuscany in Bloom

  • 18 guests

  • 9 bedrooms

Cortona, Arezzo

Made for outdoor living and large family gatherings, this home is sure to jump high up on your wishlist. We love the space this home has, and with two apartments independent from the main villa, it’s perfect for extended families where two couples are seeking a bit of added privacy.

The Vine Song

The Vine Song

  • 8 guests

  • 4 bedrooms

Castelnuovo Berardenga, Siena

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 Chianti Hills

The Chianti Hills

  • 8 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

This marvellous Tuscan villa is perfect for groups eager to sample the unique delights of the Chianti region. Set back from civilisation in the region's rolling hills, up to eight guests can rest comfortably across four en-suite bedrooms, or wander the expansive grounds dotted with trees and surrounded by olive groves.


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

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Most popular homes in San Leo

Chianti Classico

Chianti Classico

  • 12 guests

  • 6 bedrooms

Radda in Chianti, Tuscany

Rossini's Opera

Rossini's Opera

  • 48 guests

  • 16 bedrooms

Cesolo, San Severino Marche

Between the Vines

Between the Vines

  • 8 guests

  • 4 bedrooms

Terranuova Bracciolini, Arezzo

Peaceful Love

Peaceful Love

  • 10 guests

  • 5 bedrooms

Bucine, Arezzo

Forever Views

Forever Views

  • 10 guests

  • 5 bedrooms

Civitella in Val di Chiana, Tuscany

A Home's Embrace

A Home's Embrace

  • 2 guests

  • 1 bedrooms

Pietrapiana, Tuscany

Villa Tosca

Villa Tosca

  • 16 guests

  • 8 bedrooms

La Chiocciola, Rignano sull'Arno

The Vines of the Vineyard

The Vines of the Vineyard

  • 2 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

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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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