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Luxury Villas in Gaiole in Chianti

Discover the essence of Tuscany in Gaiole in Chianti's luxury villas. Experience la dolce vita amidst rolling hills, vineyards, and cypress trees, where wine tastings, cycling, and relaxation await.

Villas in Gaiole in Chianti

Sangiovese all'Aia, Gaiole in Chianti, Siena and Chianti
£214  night
4
2
2
Details View Offers
Beautiful private villa with WIFI, private pool, ABeautiful private villa with WIFI, private pool, A/C, TV, patio, panoramic view and parking/C, TV, patio, panoramic view and parking
5.0/5
£259  night
8
3
3
Details View Offers
Villa il Roseto In Gaiole in Chianti, Tuscany
£686  night
8
4
4
Details View Offers
Villa Pianodolce - Radda In Chianti
£3984  night
12
6
6
Details View Offers
Casetta Kiwi, Gaiole in Chianti, Siena and Chianti
4.0/5
£296  night
2
2
1
Details View Offers
Siena villa rental Su
£1501  night
16
8
9
Details View Offers
Villa Gaiole - Seven Bedroom Villa, Sleeps 14
£3505  night
14
7
9
Details View Offers
Marangole 12, Emma Villas
£1374  night
12
7
8
Details View Offers
Villa in San Vincenti with 5 bedrooms sleeps 12
5.0/5
£718  night
12
5
8
Details View Offers
Lovely apartment in villa for 2 guests with pool, WIFI, TV, pets allowed, panoramic view and par...
£174  night
2
1
1
Details View Offers
Lovely apartment in villa for 2 guests with WIFI, pool, TV, pets allowed, panoramic view and par...
£137  night
2
1
1
Details View Offers
Villa on Chianti hill in heart of Tuscany, super-large pool, 14 ha plot
4.7/5
£342  night
10
5
4
Details View Offers
Sestuccina
4.9/5
£206  night
4
3
2
Details View Offers
San Sano - Holiday Country Villa with swimming pool in Chianti, Tuscany
5.0/5
£263  night
8
3
3
Details View Offers
San Marcellino, Gaiole in Chianti, Siena and Chianti
£1310  night
10
5
5
Details View Offers
Villa Montemarcoli, a haven of peace and love in Gaiole in Chianti
5.0/5
£318  night
4
2
2
Details View Offers
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
4.4/5
£132  night
4
2
2
Details View Offers
Luxury Villa in Tuscany for 10 People
£3328  night
10
5
8
Details View Offers
Sestuccia is a beautiful Tuscan villa just a short distance from Gaiole in Chianti
4.7/5
£540  night
8
4
4
Details View Offers
CASA VISTA - Four Bedroom private Villa
£656  night
8
4
5
Details View Offers

Why a holiday villa in Gaiole in Chianti

Imagine waking up to the warm Tuscan sun, surrounded by rolling hills, vineyards, and cypress trees that stretch as far as the eye can see. A villa holiday in Gaiole in Chianti is more than just a place to stay, it's an experience that will leave you feeling refreshed, renewed, and inspired.

In this charming wine region of Tuscany, you'll find a unique blend of la dolce vita (the sweet life) and rustic Italian charm. From the moment you arrive at your villa, you'll feel like you're part of a special world where time stands still and all that matters is enjoying the simple pleasures in life - great food, fine wine, and beautiful scenery. Whether you're looking to relax, explore, or simply recharge, a villa holiday in Gaiole in Chianti is the perfect way to experience la vita Italiana at its best.

When to rent a villa in Gaiole in Chianti

When it comes to planning your villa holiday in Gaiole in Chianti, Italy, timing is everything. Spring (April-May) and autumn (September-October) are generally considered the best times to visit, with mild temperatures ranging from 18°C to 25°C (64°F to 77°F). The countryside is lush and green, with wildflowers blooming everywhere, while the grapevines are in full bloom. The weather is perfect for exploring the rolling hills, visiting local wineries, and enjoying outdoor activities like cycling or hiking.

If you're looking for a more relaxed pace, consider visiting during the shoulder season (June-August), when the summer crowds have dissipated but the temperatures are still pleasant (around 25°C to 30°C or 77°F to 86°F). The evenings can be warm, but the cool mornings and breezy afternoons make it ideal for outdoor activities. If you're a fan of la dolce vita, come during the winter months (December-February) when Gaiole in Chianti is quieter, and enjoy wine tastings, cozying up by the fireplace, or simply taking in the tranquility of the Tuscan countryside.

Where to go in Gaiole in Chianti

Gaiole in Chianti is a charming hilltop town perched on top of a hill, surrounded by some of Tuscany's most renowned vineyards and olive groves. The perfect base for your villa holiday, Gaiole offers a relaxed and peaceful atmosphere, with narrow streets to explore, charming shops, and a weekly market selling local produce and handicrafts. For those seeking a more vibrant experience, the nearby town of Greve in Chianti offers a range of restaurants, bars, and wine shops, while the historic city of Siena is just a short drive away.

But it's not all about urban excitement - Gaiole in Chianti is also perfectly situated for exploring the beautiful Tuscan countryside. Take a leisurely walk through the rolling hills, visit a local winery or two, and enjoy the stunning views from the top of Monti di Siena. If you're looking for something more active, try hiking, horseback riding, or cycling through the scenic landscapes - whatever your pace, Gaiole in Chianti is the perfect place to experience la dolce vita at its best.

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Family friendly villas
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Private pool villas
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Villas near golf course
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Villas in Gaiole in Chianti

Sangiovese all'Aia, Gaiole in Chianti, Siena and Chianti
£214  night
4
2
2
Details View Offers
Beautiful private villa with WIFI, private pool, ABeautiful private villa with WIFI, private pool, A/C, TV, patio, panoramic view and parking/C, TV, patio, panoramic view and parking
5.0/5
£259  night
8
3
3
Details View Offers
Villa il Roseto In Gaiole in Chianti, Tuscany
£686  night
8
4
4
Details View Offers
Villa Pianodolce - Radda In Chianti
£3984  night
12
6
6
Details View Offers
Casetta Kiwi, Gaiole in Chianti, Siena and Chianti
4.0/5
£296  night
2
2
1
Details View Offers
Siena villa rental Su
£1501  night
16
8
9
Details View Offers
Villa Gaiole - Seven Bedroom Villa, Sleeps 14
£3505  night
14
7
9
Details View Offers
Marangole 12, Emma Villas
£1374  night
12
7
8
Details View Offers
Villa in San Vincenti with 5 bedrooms sleeps 12
5.0/5
£718  night
12
5
8
Details View Offers
Lovely apartment in villa for 2 guests with pool, WIFI, TV, pets allowed, panoramic view and par...
£174  night
2
1
1
Details View Offers
Lovely apartment in villa for 2 guests with WIFI, pool, TV, pets allowed, panoramic view and par...
£137  night
2
1
1
Details View Offers
Villa on Chianti hill in heart of Tuscany, super-large pool, 14 ha plot
4.7/5
£342  night
10
5
4
Details View Offers
Sestuccina
4.9/5
£206  night
4
3
2
Details View Offers
San Sano - Holiday Country Villa with swimming pool in Chianti, Tuscany
5.0/5
£263  night
8
3
3
Details View Offers
San Marcellino, Gaiole in Chianti, Siena and Chianti
£1310  night
10
5
5
Details View Offers
Villa Montemarcoli, a haven of peace and love in Gaiole in Chianti
5.0/5
£318  night
4
2
2
Details View Offers
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
4.4/5
£132  night
4
2
2
Details View Offers
Luxury Villa in Tuscany for 10 People
£3328  night
10
5
8
Details View Offers
Sestuccia is a beautiful Tuscan villa just a short distance from Gaiole in Chianti
4.7/5
£540  night
8
4
4
Details View Offers
CASA VISTA - Four Bedroom private Villa
£656  night
8
4
5
Details View Offers