Book Luxury Monthly Rentals in San Gimignano

We selected the 3142 homes worth renting in this location

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Home spotlights in San Gimignano

A Dream of Tuscany

A Dream of Tuscany

  • 6 guests

  • 3 bedrooms

Poggibonsi, Siena

Standing in the historic centre of medieval Poggibonsi, this home puts the centre of Tuscany at your fingertips. A short distance from Florence and Siena, you can venture out into the region's world-famous rolling hills for wine tasting from here, making it an ideal base for lovers of good food and drink.

Medieval Lullabies

Medieval Lullabies

  • 8 guests

  • 3 bedrooms

Torri, Poggibonsi

Situated in a small complex amid the Tuscan countryside, this pet-friendly home centres around a 13th-century tower. With a grand fireplace and stone arches awaiting inside, there's no better base for a fairytale holiday.

Chardonnay Celebrations

Chardonnay Celebrations

  • 8 guests

  • 4 bedrooms

San Gimignano, Siena

Set in the Italian countryside and surrounded by vineyards, things feel like they haven't changed much in 200 years. Life is simpler here.

Sage and Rosemary

Sage and Rosemary

  • 10 guests

  • 5 bedrooms

Poggibonsi, Siena

Surrounded by 10 hectares of land, featuring olive groves, lush woods and picturesque vineyards, this home is the perfect introduction to the Tuscan countryside. From the terrace, you can take in the view of the region’s rolling hills, with the hilltown of Poggibonsi rising up in the distance.


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

Explore the 3142 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

Tuscan Breeze

Tuscan Breeze

  • 2 guests

  • 1 bedrooms

San Gimignano, Siena

Sunset in the Hills

Sunset in the Hills

  • 4 guests

  • 2 bedrooms

San Gimignano, Siena

A Tuscan Soul

A Tuscan Soul

  • 4 guests

  • 3 bedrooms

San Gimignano, Siena

Vine & Blossom

Vine & Blossom

  • 8 guests

  • 4 bedrooms

Barberino Tavarnelle, Florence

Moonlight Moments

Moonlight Moments

  • 12 guests

  • 5 bedrooms

Lucciana, Casole d'Elsa

Fairytale in Fresco

Fairytale in Fresco

  • 2 guests

  • 1 bedrooms

Certaldo, Florence

Love in Tuscany

Love in Tuscany

  • 7 guests

  • 4 bedrooms

San Gimignano, 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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