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

Tempo Giusto

Tempo Giusto

  • 6 guests

  • 3 bedrooms

San Gimignano, Siena

Slow the pace at this rural hayloft converted villa, nestled in the beauty of the Chianti hills. Whether it’s the picturesque views, alluring turquoise pool, lush cypress-lined garden, or the gently shaded canopy area, this home encourages outdoor living – you’ll have no choice but to surrender yourself to the serenity of the Tuscan countryside.

Chianti Nights

Chianti Nights

  • 9 guests

  • 5 bedrooms

Barberino Tavarnelle, Florence

If you’re searching for somewhere to escape the hustle and bustle of everyday life, this Tuscan villa will be right up your street. Ideal for larger groups of friends or family, the countryside location is as peaceful as it gets.

The Magic Valley

The Magic Valley

  • 43 guests

  • 18 bedrooms

Poggibonsi, Siena

Clustered together to form its own little village, this holiday hamlet gives you access to eight homes so that large groups can be broken up into smaller parties for Tuscan weddings or big family reunions in a picturesque location. Each one of these homes has been lovingly restored and features a unique blend of rustic charm and modern touches to make it feel comfortable and homely.

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

Sensory Overload

Sensory Overload

  • 12 guests

  • 6 bedrooms

Barberino Tavarnelle, Florence

The Noble Hour

The Noble Hour

  • 10 guests

  • 5 bedrooms

San Gimignano, Siena

Tales of Sunsets

Tales of Sunsets

  • 4 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

Vine & Blossom

Vine & Blossom

  • 8 guests

  • 4 bedrooms

Barberino Tavarnelle, Florence

Love in the Sun

Love in the Sun

  • 12 guests

  • 6 bedrooms

Barberino Tavarnelle, Florence

Fairytale in Fresco

Fairytale in Fresco

  • 2 guests

  • 1 bedrooms

Certaldo, Florence

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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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