Book Luxury Winter Rentals in Sicily

We selected the 457 homes worth renting in this location

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Adults

Age 13+

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Age 1 to 12

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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.

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.

Oasis of Blue

Oasis of Blue

  • 7 guests

  • 4 bedrooms

Taormina, Messina

With its dramatic, cliffside setting and expansive sea views, this home transports you to an instant state of relaxation. And while it feels like entering an idyllic retreat, you’ll find it’s also just a short walk from Taormina’s historic centre – providing the perfect opportunity to connect with the magic of Mediterranean living.

Blissful Daze

Blissful Daze

  • 13 guests

  • 5 bedrooms

Lipari, Messina

Positioned atop the hilly landscape of Lipari island, with unbroken views across the Tyrrhenian, this sprawling homely villa is footsteps from the sea. Days will be spent toing and froing to the sea rocks, watching steam escape from fumaroles on the distant Vulcano Island and lounging by your shimmering pool.


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

Explore the 457 most perfect homes in our collection

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Most popular homes in Sicily

Aretusa Sunset

Aretusa Sunset

  • 6 guests

  • 3 bedrooms

Syracuse, Sicily

Deep Blue

Deep Blue

  • 6 guests

  • 3 bedrooms

Scopello, Castellammare del Golfo

Villa Oltremare

Villa Oltremare

  • 12 guests

  • 6 bedrooms

Fontane Bianche, Syracuse

Seaside Seclusion

Seaside Seclusion

  • 4 guests

  • 2 bedrooms

Castellammare del Golfo, Trapani

The Stone Garden

The Stone Garden

  • 6 guests

  • 2 bedrooms

Noto, Syracuse

Ionian Marble

Ionian Marble

  • 8 guests

  • 4 bedrooms

Plemmirio, Syracuse

Sicilian Sun

Sicilian Sun

  • 12 guests

  • 6 bedrooms

Pantelleria, Trapani

The Sweet Melody

The Sweet Melody

  • 10 guests

  • 5 bedrooms

Savoca, Messina

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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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