Rent Luxury Self-Catering Apartments in Gaiole in Chianti

We selected the 3682 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Gaiole in Chianti

Chianti Sunset

Chianti Sunset

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

Nestled in the Chianti countryside between Siena and Florence, this home has serenity running through its core. Sat atop a hill, surrounded by olive groves and vineyards (the site is actually an active organic winery), it’s impossible not to relax here.

A Guide to the Hills

A Guide to the Hills

  • 9 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

Overlooking the Chianti hills, this home is the ideal setting for a restorative Tuscan getaway. Spread across two floors (connected by external stairs), there are two kitchens, family-friendly rooms and plenty of space for groups to stretch out and enjoy quality time together.

Villa Splendente

Villa Splendente

  • 4 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

With resplendent views of rolling hills from the comfort of a shaded infinity pool, this tiered stone villa is a Tuscan gem. The home is comprised of two independent apartments, affording your group some extra privacy.

Tuscan Idyll

Tuscan Idyll

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

Offering views of the surrounding hills and the owner's vineyard, this eco-friendly villa is set within the Chianti countryside. While the interior is fairly subdued and the unpaved road leading here isn't the best drive, this home promises a paradisal outdoor living space.


We selected the top 3% holiday homes in Gaiole in Chianti Self-Catering Apartments

Explore the 3682 most perfect homes in our collection

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Most popular homes in Gaiole in Chianti

The Tuscan Hills

The Tuscan Hills

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

The Olive Vine

The Olive Vine

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

The Alabaster Breeze

The Alabaster Breeze

  • 8 guests

  • 4 bedrooms

Cavriglia, Arezzo

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

The Chianti Grape

The Chianti Grape

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

The Olive Tint

The Olive Tint

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

The Hilltop Dream

The Hilltop Dream

  • 12 guests

  • 6 bedrooms

Radda in Chianti, Tuscany

The Chianti Hills

The Chianti Hills

  • 8 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

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Frequently asked questions

Book luxury Self-Catering Apartments in Gaiole in Chianti, Siena, Tuscany, Italy, and enjoy a memorable stay for all the right reasons. We leave no stone unturned in our pursuit of the most remarkable homes, vetting everything from shower pressure to design aesthetic. Every home in our collection of luxury Gaiole in Chianti Self-Catering Rentals comes fully furnished with a well-equipped kitchen, all linens, and essential bathroom toiletries included. And should you need any help in finding the perfect home, our friendly experts are always on hand to help.

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