Book Luxury Monthly Rentals in San Gimignano

We selected the 2930 homes worth renting in this location

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Home spotlights in San Gimignano

A Tuscan Soul

A Tuscan Soul

  • 4 guests

  • 3 bedrooms

San Gimignano, Siena

Nestled on the ancient walls of the watch tower in a restored farmhouse, this home promises a tranquil escape in the Tuscan countryside. With a communal swimming pool and gardens, it’s easy to make the most of the Mediterranean climate – and this apartment boasts a private patio and courtyard, too.

Love in Tuscany

Love in Tuscany

  • 7 guests

  • 4 bedrooms

San Gimignano, Siena

Once an old stone barn, this villa has been brought back to life and promises a serene stay in the heart of Tuscany. Sure, the traditional interiors may not be everyone’s cup of tea, but you’ll find all the key ingredients for a comfortable stay here.

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.

Moonlight Moments

Moonlight Moments

  • 12 guests

  • 5 bedrooms

Lucciana, Casole d'Elsa

Surrounded by flourishing trees with sweeping views across the hills of Chianti, every detail of this home sings with the natural beauty of Tuscany. From the rustic interiors to the antique furnishings and personal touches, the owners have retained the authentic spirit of this traditional country home.


We selected the top 3% holiday homes in San Gimignano Monthly Rentals

Explore the 2930 most perfect homes in our collection

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Most popular homes in San Gimignano

Tuscan Trees

Tuscan Trees

  • 6 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

Oliva Farmhouse

Oliva Farmhouse

  • 4 guests

  • 2 bedrooms

Montespertoli, Florence

Sunset in the Hills

Sunset in the Hills

  • 4 guests

  • 2 bedrooms

San Gimignano, Siena

Tempo Giusto

Tempo Giusto

  • 6 guests

  • 3 bedrooms

San Gimignano, Siena

Chardonnay Celebrations

Chardonnay Celebrations

  • 8 guests

  • 4 bedrooms

San Gimignano, Siena

A Touch of Tuscany

A Touch of Tuscany

  • 7 guests

  • 3 bedrooms

San Gimignano, Siena

Fairytale in Fresco

Fairytale in Fresco

  • 2 guests

  • 1 bedrooms

Certaldo, Florence

Verdant Valley

Verdant Valley

  • 15 guests

  • 8 bedrooms

Poggibonsi, Siena

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in San Gimignano, Siena, Tuscany, Italy, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect San Gimignano Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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