Book Luxury Winter Rentals in Sicily

We selected the 585 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Sicily

Market Symphony

Market Symphony

  • 4 guests

  • 2 bedrooms

Syracuse, Sicily

Directly facing the historic Ortigia market, this beautifully curated apartment offers a symphony for the senses, all while providing a design-led space that’s as chic as it is comfortable. Housed in an early 20th-century building, you’ll immediately be immersed in the colours, scents and sounds of local Ortigian life from the home’s beautiful balconies – allowing you to people-watch over a morning cup of coffee or evening glass of red, courtesy of the home's wine cellar.

Sicilian Sun

Sicilian Sun

  • 12 guests

  • 6 bedrooms

Pantelleria, Trapani

Discover the Sicilian island of Pantelleria from this gorgeous villa. It has a contemporary feel with elements of a dammuso, a typical Pantelleria home, and is surrounded by two acres of fragrant Mediterranean garden.

A Pleasant Oasis

A Pleasant Oasis

  • 10 guests

  • 4 bedrooms

Santa Maria di Licodia, Sicily

This home immerses you in Sicily's volcanic heritage. Lying on the slopes of Mount Etna, the two guesthouses that make up this villa are built from distinctive lava stone, and you have practically uninterrupted views of Etna from the gardens.

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.


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

Explore the 585 most perfect homes in our collection

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Most popular homes in Sicily

Ionian Marble

Ionian Marble

  • 8 guests

  • 4 bedrooms

Plemmirio, Syracuse

Torre Salsa

Torre Salsa

  • 8 guests

  • 4 bedrooms

Montallegro, Libero consorzio comunale di Agrigento

Centre of Light

Centre of Light

  • 4 guests

  • 2 bedrooms

Centro, Catania

Early Riser

Early Riser

  • 4 guests

  • 2 bedrooms

Modica, Ragusa

Opulent Vista

Opulent Vista

  • 12 guests

  • 5 bedrooms

Noto, Syracuse

Ocean Terrace

Ocean Terrace

  • 8 guests

  • 5 bedrooms

Noto, Syracuse

The Sun Bay

The Sun Bay

  • 8 guests

  • 4 bedrooms

Taormina, Messina

The Ancient Olive Press

The Ancient Olive Press

  • 8 guests

  • 4 bedrooms

Milo, Catania

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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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