Book Luxury Winter Rentals in Tuscany

We selected the 1409 homes worth renting in this location

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Age 1 to 12

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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.

Lighthouse Island

Lighthouse Island

  • 4 guests

  • 2 bedrooms

Grosseto, Tuscany

This unique home offers an unparalleled escape to a private island in Tuscany, where the sea sparkles and time slows. Once a lighthouse, it's been beautifully restored, blending historic character with effortless luxury.

Thermae

Thermae

  • 4 guests

  • 2 bedrooms

San Miniato, Pisa

An open space in a sixteenth-century building, in the hilly outskirts of Florence that, at time at times, has been both a stables and a nightclub, Thermae is one of the most spectacular places we’ve seen in Italy. Its restoration has been a labour of love for the host, Giovanni, and the way that he’s incorporated technology into the original structure is simply impressive.

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 1409 most perfect homes in our collection

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Most popular homes in Tuscany

Artistic Grapes

Artistic Grapes

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

Fairytale in Fresco

Fairytale in Fresco

  • 2 guests

  • 1 bedrooms

Certaldo, Florence

Pistachio Pesto

Pistachio Pesto

  • 8 guests

  • 2 bedrooms

Arezzo, Tuscany

 The Hills of Montaione

The Hills of Montaione

  • 6 guests

  • 2 bedrooms

Montaione, Florence

Escaping Time

Escaping Time

  • 7 guests

  • 3 bedrooms

Sovicille, Tuscany

The Breadbasket

The Breadbasket

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

Rustic Honey

Rustic Honey

  • 4 guests

  • 2 bedrooms

Casciana Terme Lari, Tuscany

The Olive Tint

The Olive Tint

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

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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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