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We selected the 2598 homes worth renting in this location

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Home spotlights in San Gimignano

Vineyards & Red Earth

Vineyards & Red Earth

  • 8 guests

  • 3 bedrooms

Barberino Tavarnelle, Florence

Once owned by winemaker Marchesi Torrigiani, this beautiful hillside villa still features the vineyards that were once, and will likely always be, the heart of this farmland. A beautiful sight, it’s only marginally rivalled by the view of the Chianti Hills which is sprawled out right before you from the elevated position of this home.

A Flickering Candle

A Flickering Candle

  • 10 guests

  • 5 bedrooms

Volterra, Pisa

Set amid beautiful green countryside just outside the pretty medieval town of Volterra, this striking stone home – which was originally constructed to serve as a watchtower – is brimming with quintessential Tuscan charm and a host of handy amenities, making it the perfect base from which to set out and explore the highlights of the local area. Spend days unwinding within the tranquil environs of the home and its sprawling gardens filled with mature trees and boasting a lovely fenced swimming pool area.

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.

Beyond the Bridge

Beyond the Bridge

  • 7 guests

  • 3 bedrooms

Colle di Val d'Elsa, Siena

This charming apartment is in the old town of Colle di Val d'Elsa, a typically medieval region of Tuscany famous for crystal glass production. It’s a ten-minute stroll into the centre where you’ll find restaurants, cafés and archaeological museums beyond the ancient town walls.


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

Explore the 2598 most perfect homes in our collection

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Most popular homes in San Gimignano

Love & Romance

Love & Romance

  • 12 guests

  • 6 bedrooms

Gambassi Terme, Florence

Groves & Vines

Groves & Vines

  • 8 guests

  • 4 bedrooms

Gambassi Terme, Florence

The Hillside Escape

The Hillside Escape

  • 13 guests

  • 5 bedrooms

Montespertoli, Florence

A Glass Of Chianti

A Glass Of Chianti

  • 2 guests

  • 1 bedrooms

Montespertoli, Florence

Heart of Tuscany

Heart of Tuscany

  • 2 guests

  • 1 bedrooms

San Gimignano, Siena

A Dream of Tuscany

A Dream of Tuscany

  • 6 guests

  • 3 bedrooms

Poggibonsi, Siena

Italian Serenity

Italian Serenity

  • 24 guests

  • 12 bedrooms

Poggibonsi, Siena

Chardonnay Celebrations

Chardonnay Celebrations

  • 8 guests

  • 4 bedrooms

San Gimignano, Siena

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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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