Book Luxury Vacation Rentals with a Private Chef in San Gimignano

We selected the 3216 homes worth renting in this location

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Home spotlights in San Gimignano

Groves & Vines

Groves & Vines

  • 8 guests

  • 4 bedrooms

Gambassi Terme, Florence

This Tuscan farmhouse is in a peaceful spot, nestled among olive groves and vineyards. The home consists of two apartments, each with its own entrance, garden, and patio, so is a great choice for a group – you can holiday together and still enjoy your own space.

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.

One of the Greats

One of the Greats

  • 10 guests

  • 5 bedrooms

San Gimignano, Siena

Nestled away in the countryside outside the idyllic hilltown of San Gimignano, this extraordinary villa combines exquisite interior design and a sprawling collection of amenities to make for an address that is sure to win over even the most discerning of guests. As you walk about the house for the first time, you might find it difficult to single out a favourite room.

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.


We selected the top 3% holiday homes in San Gimignano Vacation Rentals with a Private Chef

Explore the 3216 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

Marble & Olives

Marble & Olives

  • 4 guests

  • 2 bedrooms

San Gimignano, Siena

The Lago Sky

The Lago Sky

  • 12 guests

  • 6 bedrooms

Iano, Montaione

A Tuscan Adventure

A Tuscan Adventure

  • 4 guests

  • 2 bedrooms

Gambassi Terme, Florence

The Noble Hour

The Noble Hour

  • 10 guests

  • 5 bedrooms

San Gimignano, Siena

Heart of Tuscany

Heart of Tuscany

  • 2 guests

  • 1 bedrooms

San Gimignano, Siena

Chestnut & Stone

Chestnut & Stone

  • 16 guests

  • 8 bedrooms

Gambassi Terme, Florence

Moonlight Moments

Moonlight Moments

  • 12 guests

  • 5 bedrooms

Lucciana, Casole d'Elsa

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Frequently asked questions

Explore our unbeatable collection of luxury Vacation Rentals with a Personal Chef in San Gimignano, Siena, Tuscany, Italy. Each and every home in our range comes fully furnished with excellently-equipped kitchens, essential bathroom toiletries, and all necessary linens included. Tested aspects of any home range from Wifi speed and shower pressure to a space's feel and design, so there really is nothing left to chance on our mission to discover the greatest properties on offer. Enjoy a stay in one of the Holiday Rentals in San Gimignano with a Private Chef today, and remember your trip for all the right reasons. And don't hesitate to contact our team of experts if you require any assistance, as it is their pleasure to help make the process easy.

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