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We selected the 3218 homes worth renting in this location

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Home spotlights in San Gimignano

A Glass Of Chianti

A Glass Of Chianti

  • 2 guests

  • 1 bedrooms

Montespertoli, Florence

This apartment shares its location with a family-run farm in pretty Montespertoli. The family produces wine and olive oil from a picturesque spot amid the gentle Chianti hills, surrounded by vineyards, olive groves and woods – it’s delightfully rustic.

San Gimignano Views

San Gimignano Views

  • 4 guests

  • 2 bedrooms

San Gimignano, Siena

With stunning views of the surrounding vineyards and olive groves from this apartment’s private terrace, this place has a wonderful setting. There are also panoramic views of San Gimignano to enjoy from the communal grounds which include a shared swimming pool.

Heart of Tuscany

Heart of Tuscany

  • 2 guests

  • 1 bedrooms

San Gimignano, Siena

Flooded with light, courtesy of the arched windows, this home is perfect for a couple’s getaway. Traditional in style, the main thing missing here is an oven – but isn’t that the perfect excuse to dine out on fine Italian cuisine instead?

Tuscan Trees

Tuscan Trees

  • 6 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

This beautiful home is one of a kind. It allows guests to experience Tuscan life in an authentic way, with everything you might need at your fingertips.


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

Explore the 3218 most perfect homes in our collection

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Most popular homes in San Gimignano

A Touch of Tuscany

A Touch of Tuscany

  • 7 guests

  • 3 bedrooms

San Gimignano, Siena

Tempo Giusto

Tempo Giusto

  • 6 guests

  • 3 bedrooms

San Gimignano, Siena

The Magic Valley

The Magic Valley

  • 43 guests

  • 18 bedrooms

Poggibonsi, Siena

Love & Romance

Love & Romance

  • 12 guests

  • 6 bedrooms

Gambassi Terme, Florence

Sunset in the Hills

Sunset in the Hills

  • 4 guests

  • 2 bedrooms

San Gimignano, Siena

Medieval Lullabies

Medieval Lullabies

  • 8 guests

  • 3 bedrooms

Torri, Poggibonsi

A Tuscan Adventure

A Tuscan Adventure

  • 4 guests

  • 2 bedrooms

Gambassi Terme, Florence

Stone & Vine

Stone & Vine

  • 2 guests

  • 1 bedrooms

San Gimignano, Siena

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Check upcoming rates & availability for San Gimignano Family Friendly Rentals


Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in San Gimignano, Siena, Tuscany, Italy. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent San Gimignano Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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