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Book Luxury Winter Rentals in Tuscany

We selected the 1206 homes worth renting in this location

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Who's coming along?

Adults

Age 13+

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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.

Beyond the Bridge

Beyond the Bridge

  • 7 guests

  • 3 bedrooms

Colle di Val d'Elsa, Siena

This charming apartment is in the old town of Colle di Val d'Elsa, a typically medieval region of Tuscany famous for crystal glass production. It’s a ten-minute stroll into the centre where you’ll find restaurants, cafés and archaeological museums beyond the ancient town walls.

The Legendary Giulia

The Legendary Giulia

  • 8 guests

  • 4 bedrooms

Cellai, Rignano sull'Arno

Head into the Tuscan hills just outside the charming village of Cellai and keep an eye out for an imposing villa with its own bell tower. Almost unbelievably, this stunning property will be your home from home for however long you decide to stay.

Tuscan Hills

Tuscan Hills

  • 4 guests

  • 2 bedrooms

Monte Sante Marie, Asciano

This hilltop haven is perfect for those looking for a quiet, calm and restful stay in Tuscany. The villa can be found thirteen minutes outside of Asciano, with its medieval centre, amid stunning rolling countryside that catches the eye from every angle.


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

Explore the 1206 most perfect homes in our collection

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Most popular homes in Tuscany

Cypress Hill

Cypress Hill

  • 12 guests

  • 6 bedrooms

Città della Pieve, Perugia

Rosemary & Olive

Rosemary & Olive

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

Artistic Grapes

Artistic Grapes

  • 2 guests

  • 1 bedrooms

Montalcino, Siena

Thermae

Thermae

  • 4 guests

  • 2 bedrooms

San Miniato, Pisa

Escaping Time

Escaping Time

  • 7 guests

  • 3 bedrooms

Sovicille, Tuscany

Bellissima Casa

Bellissima Casa

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

Latin Love Letters

Latin Love Letters

  • 18 guests

  • 9 bedrooms

Lucca, Tuscany

Chianti Classico

Chianti Classico

  • 12 guests

  • 6 bedrooms

Radda in Chianti, Tuscany

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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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