Book Luxury Holiday Rentals in San Leo

Award-winning homes from £98

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Home spotlights in San Leo

Rosemary Breeze

Rosemary Breeze

  • 12 guests

  • 6 bedrooms

Cortona, Arezzo

In the folds of the hills, this home is all about those Tuscan sunsets. Catch the golden hour, as the sun dips below the forest-clad hills, from the terrace where curtains frame the view and dining by candlelight is a delight.

View From The Evening

View From The Evening

  • 4 guests

  • 2 bedrooms

Cortona, Arezzo

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.

Lilac Bloom

Lilac Bloom

  • 8 guests

  • 4 bedrooms

Castel San Pietro Terme, Bologna

Nestled in the verdant hills of Bologna, this villa is part of a luxurious resort that offers guests a truly unique and indulgent experience. With an array of amenities on-site, including restaurants, a spa, a tennis court, a children’s play area, and a golf course, you'll have everything you need for an unforgettable stay.

Pistachio Pesto

Pistachio Pesto

  • 8 guests

  • 2 bedrooms

Arezzo, Tuscany

This home is a true haven nestled right in the heart of Arezzo. With its luscious garden and rustic interior, it's the perfect place to kick back and relax away from the hustle and bustle.


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

Explore the 894 most perfect homes in our collection

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Most popular homes in San Leo

Pristine Oasis

Pristine Oasis

  • 1 guests

  • 3 bedrooms

Pesaro, Pesaro and Urbino

Between the Vines

Between the Vines

  • 8 guests

  • 4 bedrooms

Terranuova Bracciolini, Arezzo

The Olive Tint

The Olive Tint

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Trasimeno Treasure

Trasimeno Treasure

  • 6 guests

  • 3 bedrooms

Passignano sul Trasimeno, Perugia

The Tuscan Hills

The Tuscan Hills

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

The Legendary Giulia

The Legendary Giulia

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

The Breadbasket

The Breadbasket

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

Chianti Spirit

Chianti Spirit

  • 14 guests

  • 7 bedrooms

Greve in Chianti, Florence

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals 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 Rentals for your trip.

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