Book Luxury Winter Rentals in Sicily

We selected the 440 homes worth renting in this location

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Home spotlights in Sicily

Sicilian Song

Sicilian Song

  • 10 guests

  • 5 bedrooms

Fontane Bianche, Syracuse

With the beach just a 200-metre stroll away, this home delivers the ideal spot for a blissful coastal escape. Days can be spent on the seafront or relaxing by the private pool (open seasonally).

Seaside Seclusion

Seaside Seclusion

  • 4 guests

  • 2 bedrooms

Castellammare del Golfo, Trapani

Perched on the hillside on the Sicilian coast, the view from this home’s terrace is simply sublime. Light stone surrounds the lagoon-shaped swimming pool which invites you for a cooling dip in the heat of the Sicilian sun and, wending your way around the terraced gardens, you’ll find a ping pong table, outdoor dining area and summer kitchen for days spent alfresco, all with a sea view.

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.

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.


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

Explore the 440 most perfect homes in our collection

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Most popular homes in Sicily

Sicilian Sun

Sicilian Sun

  • 12 guests

  • 6 bedrooms

Pantelleria, Trapani

The Stone Garden

The Stone Garden

  • 6 guests

  • 2 bedrooms

Noto, Syracuse

Early Riser

Early Riser

  • 4 guests

  • 2 bedrooms

Modica, Ragusa

Colours of The Desert

Colours of The Desert

  • 2 guests

  • 1 bedrooms

Syracuse, Sicily

Ionian Marble

Ionian Marble

  • 8 guests

  • 4 bedrooms

Plemmirio, Syracuse

The Sicilian Sun

The Sicilian Sun

  • 4 guests

  • 2 bedrooms

Noto, Syracuse

Power of Zen

Power of Zen

  • 8 guests

  • 4 bedrooms

Syracuse, Sicily

The Scent of Sicily

The Scent of Sicily

  • 16 guests

  • 7 bedrooms

Ciavolo, Marsala

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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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