Book Luxury Villas in San Gimignano

We selected the 1762 homes worth renting in this location

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Home spotlights in San Gimignano

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.

A Tuscan Adventure

A Tuscan Adventure

  • 4 guests

  • 2 bedrooms

Gambassi Terme, Florence

You’ll find this villa nestled on a resort alongside two other homes, surrounded by landscaped gardens that are perfect for making the most of the Tuscan sun. Granted, its traditional interiors may not be everyone’s cup of tea, but the location makes it easy to explore some of the area's most iconic towns.

Tales of Sunsets

Tales of Sunsets

  • 4 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

This 19th-century Tuscan farmhouse that sits 450 metres above sea level has been brought into stylish 21st-century style, all while retaining its rustic charm and characterful Italian romance. Featuring its original windows and tall beamed ceilings alongside contemporary decor, it’s a space that’s been reimagined with rest and relaxation in mind, not to mention a showstopping outdoors that is certain to have you basking in its beauty from dawn till dusk.

Pulpa de Tomate

Pulpa de Tomate

  • 10 guests

  • 5 bedrooms

San Gimignano, Siena

Take a step back in time at this 18th-century estate, overlooking the rolling Tuscan countryside. With gorgeous outdoor space and stunning views for miles, it's the perfect place to press pause and relax.


We selected the top 3% holiday homes in San Gimignano Villas

Explore the 1762 most perfect homes in our collection

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Most popular homes in San Gimignano

Love in Tuscany

Love in Tuscany

  • 7 guests

  • 4 bedrooms

San Gimignano, Siena

Mambo Beats

Mambo Beats

  • 4 guests

  • 3 bedrooms

Certaldo, Florence

Love & Romance

Love & Romance

  • 12 guests

  • 6 bedrooms

Gambassi Terme, Florence

An Ode to Tuscany

An Ode to Tuscany

  • 10 guests

  • 4 bedrooms

San Giorgio, Poggibonsi

Castle in Green

Castle in Green

  • 12 guests

  • 6 bedrooms

Barberino Tavarnelle, Florence

Into the Olive Grove

Into the Olive Grove

  • 10 guests

  • 5 bedrooms

San Filippo a Ponzano, Barberino Tavarnelle

Tempo Giusto

Tempo Giusto

  • 6 guests

  • 3 bedrooms

San Gimignano, Siena

The Sun Kingdom

The Sun Kingdom

  • 10 guests

  • 5 bedrooms

Tignano, Barberino Tavarnelle

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Frequently asked questions

Secure a luxury stay in one of the remarkable Villas in our San Gimignano, Siena, Tuscany, Italy collection. Our quality and consistency is unmatched, with only the top 3% of homes making it onto our site. Our meticulous home experts test everything from shower pressure to a home's feel and atmosphere, so there really is no need to worry about a thing. Your chosen home is also guaranteed to be fully furnished, with an excellently-equipped kitchen, essential bathroom toiletries, and linens all included. Acquire the help of our friendly experts, on standby 24/7 and always eager to assist you in your hunt for the finest luxury Villa in the entirety of San Gimignano.

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