San Gimignano Luxury Rentals

We selected the 652 homes worth renting in this location

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Home spotlights in San Gimignano

The Lago Sky

The Lago Sky

  • 12 guests

  • 6 bedrooms

Iano, Montaione

Amid scenic landscapes on the Tuscan hillside, the façade of this home resembles a countryside castle. Meanwhile, the interiors and amenities are just as impressive.

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.

The Tuscan Moon

The Tuscan Moon

  • 10 guests

  • 5 bedrooms

Castellina in Chianti, Tuscany

Nestled between the pretty hilltop towns of Chianti, this home offers a traditional Italian sanctuary. Enjoy breathtaking views across vineyards while relaxing on the terrace.

Kind Love

Kind Love

  • 14 guests

  • 7 bedrooms

Barberino Tavarnelle, Florence

Immersed in the natural beauty of Tuscany, this home sets the tone for an idyllic Italian escape. Outside, days can be spent lounging by the pool, swaying in the hammock and sipping drinks on the terrace.

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

Explore the 652 most perfect homes in our collection

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Most popular homes in San Gimignano

Grande Amore

Grande Amore

  • 2 guests

  • 1 bedrooms

Pescia, Pistoia

Sensory Overload

Sensory Overload

  • 12 guests

  • 6 bedrooms

Barberino Tavarnelle, Florence

Moonlight Moments

Moonlight Moments

  • 12 guests

  • 5 bedrooms

Lucciana, Casole d'Elsa

Envelope For A Love Letter

Envelope For A Love Letter

  • 6 guests

  • 3 bedrooms

Gambassi Terme, Florence

Pearl Romance

Pearl Romance

  • 8 guests

  • 5 bedrooms

Capo d'Arco, Rio

From Volterra, With Love

From Volterra, With Love

  • 15 guests

  • 9 bedrooms

Volterra, Pisa

La Fantasia

La Fantasia

  • 4 guests

  • 2 bedrooms

Walled City, Lucca

Tesoro

Tesoro

  • 8 guests

  • 4 bedrooms

Walled City, Lucca

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Frequently asked questions

A handpicked selection of the best luxury homes in San Gimignano, Siena, Tuscany, Italy, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.

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