Book Luxury Vacation Rentals in San Leo

Award-winning homes from £98

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Home spotlights in San Leo

Montefeltro Oasis

Montefeltro Oasis

  • 17 guests

  • 8 bedrooms

San Leo, Emilia-Romagna

This showstopper of a home is a great choice for a group getaway. Standing on a hill with panoramic views across the Marecchia Valley and the Rocca di San Leo, you’ll really feel like you’ve got away from it all here.

Pristine Oasis

Pristine Oasis

  • 1 guests

  • 3 bedrooms

Pesaro, Pesaro and Urbino

Perched above the Adriatic, this charming oasis blends natural beauty with laid-back elegance. Wake to sunrise over the sea, unwind by the pool at sunset, and breathe in the scent of wildflowers on the breeze.

Umbrian Bliss

Umbrian Bliss

  • 2 guests

  • 2 bedrooms

Perugia, Umbria

Set within an expansive estate in Umbria, this villa was once a 13th-century water mill. Beautifully restored, it offers a range of impressive facilities that make for a relaxing retreat.

The Breadbasket

The Breadbasket

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

It may be less than a thirty-minute drive from the spectacular Renaissance city of Florence, but this home feels like another world. Located up in the hills, you'll discover a spectacular villa – complete with a clock tower – just outside the small village of Cellai, where time seems to stand still.


We selected the top 3% holiday homes in San Leo Vacation Rentals

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Most popular homes in San Leo

Pistachio Pesto

Pistachio Pesto

  • 8 guests

  • 2 bedrooms

Arezzo, Tuscany

Tuscan Cottage

Tuscan Cottage

  • 2 guests

  • 1 bedrooms

Radda in Chianti, Tuscany

The Legendary Giulia

The Legendary Giulia

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

The Terracotta Sun

The Terracotta Sun

  • 6 guests

  • 4 bedrooms

Arezzo, Tuscany

The Valley of Angels

The Valley of Angels

  • 14 guests

  • 7 bedrooms

Cortona, Arezzo

A Rustic Vision

A Rustic Vision

  • 25 guests

  • 6 bedrooms

Arcevia, Marche

Sunflower Beams

Sunflower Beams

  • 3 guests

  • 2 bedrooms

Cortona, Arezzo

Tuscan Rose

Tuscan Rose

  • 10 guests

  • 3 bedrooms

Terranuova Bracciolini, Arezzo

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in San Leo. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect San Leo Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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