Book Luxury Winter Rentals in Tuscany

We selected the 1347 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Under 1

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Home spotlights in Tuscany

The Tuscan Farm

The Tuscan Farm

  • 14 guests

  • 7 bedrooms

Sovicille, Tuscany

Whether you’re here for the famous landscapes, rich history, culture or cuisine, one thing’s for sure, if you want to experience Tuscany at its finest, this charming villa is the place to be. In an idyllic countryside location, this home is surrounded by luscious greenery, rolling hills and landscapes, making it the ideal spot for sunset views and stargazing.

Artistic Grapes

Artistic Grapes

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

If you love the artsy side of life, you'll thrive in this contemporary loft. Colourful art pieces stand out, with some splashes of colour added by the feature walls.

Fairytale in Fresco

Fairytale in Fresco

  • 2 guests

  • 1 bedrooms

Certaldo, Florence

In a sleepy town in Tuscany, this breathtaking apartment is a unique find. Set in a former palazzo, it boasts classical Tuscan features like high ceilings, traditional archways, and a grand red brick exterior.

Verdant Valley

Verdant Valley

  • 15 guests

  • 8 bedrooms

Poggibonsi, Siena

This elegant home in Tuscany is in a dreamy spot in a valley, in a countryside setting that leads to absolute relaxation. The villa is full of character, with antique furniture and wooden beams, in addition to mesmerising views.


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

Explore the 1347 most perfect homes in our collection

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Most popular homes in Tuscany

Beyond the Bridge

Beyond the Bridge

  • 7 guests

  • 3 bedrooms

Colle di Val d'Elsa, Siena

Hazy Days of Summer

Hazy Days of Summer

  • 8 guests

  • 4 bedrooms

Marina di Pietrasanta, Pietrasanta

Thermae

Thermae

  • 4 guests

  • 2 bedrooms

San Miniato, Pisa

Tuscan Rose

Tuscan Rose

  • 10 guests

  • 3 bedrooms

Terranuova Bracciolini, Arezzo

Giardino Joy

Giardino Joy

  • 6 guests

  • 3 bedrooms

Reggello, Florence

Tuscan Welcome

Tuscan Welcome

  • 7 guests

  • 3 bedrooms

Orentano, Castelfranco di Sotto

The Breadbasket

The Breadbasket

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

Rosemary & Olive

Rosemary & Olive

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

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Check upcoming rates & availability for Tuscany Vacation Rentals for Winter


Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in Tuscany, 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 Tuscany. 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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