Book Luxury Winter Rentals in Tuscany

We selected the 1225 homes worth renting in this location

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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.

Thermae

Thermae

  • 4 guests

  • 2 bedrooms

San Miniato, Pisa

A sixteenth-century villa in the hilly outskirts of Florence that, 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.

Tuscan Rose

Tuscan Rose

  • 10 guests

  • 3 bedrooms

Terranuova Bracciolini, Arezzo

Tucked away in vineyards and verdant pastures as far as the eye can see, this home promises tranquillity with breathtaking views to boot. You'll find it tucked away in Terranuova Bracciolini, surrounded by natural beauty and just a thirty-minute drive from Arezzo.

Rosemary & Olive

Rosemary & Olive

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

For a taste of authentic Italian living, this stylish home opens its doors to the beauty of southern Siena. Located in the historic town of Montalcino (renowned for its Brunello wine), this is the perfect setting to experience the warmth and depth of Italian living.


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

Explore the 1225 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

The Breadbasket

The Breadbasket

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

Casa Dolce Vita

Casa Dolce Vita

  • 2 guests

  • 1 bedrooms

Montepulciano, Siena

Upon the Pathway

Upon the Pathway

  • 4 guests

  • 1 bedrooms

Lucca, Tuscany

Aqua Olive

Aqua Olive

  • 8 guests

  • 4 bedrooms

Manciano, Grosseto

Hillside Sunset

Hillside Sunset

  • 10 guests

  • 5 bedrooms

Lucca, Tuscany

A Midsummer Daydream

A Midsummer Daydream

  • 6 guests

  • 3 bedrooms

Barberino Tavarnelle, Florence

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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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