Book Luxury Winter Rentals in Sicily

We selected the 535 homes worth renting in this location

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Home spotlights in Sicily

Colours of The Desert

Colours of The Desert

  • 2 guests

  • 1 bedrooms

Syracuse, Sicily

Contemporary living meets Sicilian charm in this traditional home. Located in the historic area of Ortigia, you'll be surrounded by ancient streets contrasting this stylishly modern apartment.

In the Heart of Ortigia

In the Heart of Ortigia

  • 4 guests

  • 2 bedrooms

Syracuse, Sicily

Modern and bright, this apartment offers a comfortable base for those looking to stay in the heart of Isola di Ortigia. You'll be a short walk from Fonte Aretusa, Syracuse Cathedral and the vibrant marina’s waterfront eateries and bars, while the Ionian waters of Cala Rossa are within easy reach.

Centre of Light

Centre of Light

  • 4 guests

  • 2 bedrooms

Centro, Catania

Right in the centre of Catania, this home allows you to explore the city with total ease. History buffs will love it here, due to local landmarks only being a short walk away.

A Violin for Violet

A Violin for Violet

  • 16 guests

  • 6 bedrooms

Castelvetrano, Trapani

Set within acres and acres of olive groves, this villa is all about Sicily’s peace and quiet. If you do want to catch a bit of the island’s buzz and stock up on supplies, the historic town of Castelvetrano is a short drive away.


We selected the top 3% holiday homes in Sicily Vacation Rentals for Winter

Explore the 535 most perfect homes in our collection

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Most popular homes in Sicily

The Lady of Ortigia

The Lady of Ortigia

  • 8 guests

  • 4 bedrooms

Syracuse, Sicily

Sunny Sicily

Sunny Sicily

  • 3 guests

  • 2 bedrooms

Letojanni, Messina

Siciliana Rhythm

Siciliana Rhythm

  • 4 guests

  • 1 bedrooms

Bochini, Sicilia

Sicilian Sun

Sicilian Sun

  • 12 guests

  • 6 bedrooms

Pantelleria, Trapani

Chasing Bliss

Chasing Bliss

  • 4 guests

  • 1 bedrooms

Bochini, Sicilia

Ionian Marble

Ionian Marble

  • 8 guests

  • 4 bedrooms

Plemmirio, Syracuse

Sisters Are Doing It For Themselves

Sisters Are Doing It For Themselves

  • 10 guests

  • 5 bedrooms

Noto, Syracuse

Opulent Vista

Opulent Vista

  • 12 guests

  • 5 bedrooms

Noto, Syracuse

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Check upcoming rates & availability for Sicily Vacation Rentals for Winter


Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in Sicily, Italy. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Sicily. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.

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