Book Luxury Short Stay Rentals in Poggibonsi

We selected the 3148 homes worth renting in this location

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Home spotlights in Poggibonsi

Tuscan Iris

Tuscan Iris

  • 8 guests

  • 5 bedrooms

Tignano, Barberino Tavarnelle

Tuscan character abounds in this stone villa, from wood-beamed ceilings to terracotta-tiled floors. It's the garden, however, that steals the show here.

An Italian Tale

An Italian Tale

  • 14 guests

  • 7 bedrooms

Radda in Chianti, Tuscany

This former lookout tower once guarded the passage between Florence and Siena. Today, it exists as a calm sanctuary offering idyllic views, a private pool and serene grounds.

Vine & Blossom

Vine & Blossom

  • 8 guests

  • 4 bedrooms

Barberino Tavarnelle, Florence

Vineyards stretch as far as the eye can see at this Chianti villa. Settings rarely get more picturesque than this – we can already picture lazy afternoons by the private pool and alfresco drinks on the covered terrace, all while admiring the views.

Into the Olive Grove

Into the Olive Grove

  • 10 guests

  • 5 bedrooms

San Filippo a Ponzano, Barberino Tavarnelle

Conveniently located in San Filippo a Ponzano, a rural village on a hill in Chianti, from here you'll be within easy reach of Florence (a forty-five-minute drive away) and Siena (a thirty-minute drive away). Prepare to be blown away by the never-ending landscapes amidst fields of oak woods, vineyards, and olive groves upon arrival.


We selected the top 3% holiday homes in Poggibonsi Short Stay Rentals

Explore the 3148 most perfect homes in our collection

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Most popular homes in Poggibonsi

The Papessa

The Papessa

  • 6 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

Over the Chianti Hills

Over the Chianti Hills

  • 4 guests

  • 1 bedrooms

Barberino Tavarnelle, Florence

Tempo Giusto

Tempo Giusto

  • 6 guests

  • 3 bedrooms

San Gimignano, Siena

Il Nocino

Il Nocino

  • 8 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

Tales of Sunsets

Tales of Sunsets

  • 4 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

The Magic Valley

The Magic Valley

  • 43 guests

  • 18 bedrooms

Poggibonsi, Siena

Love in the Sun

Love in the Sun

  • 12 guests

  • 6 bedrooms

Barberino Tavarnelle, Florence

A Little Bit of Chianti

A Little Bit of Chianti

  • 4 guests

  • 2 bedrooms

Castellina in Chianti, Tuscany

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Poggibonsi, Siena, Tuscany, Italy. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Poggibonsi luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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