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Siena Villas - Authentic Tuscany Experiences

Experience la dolce vita in Tuscany's heart - Siena. Discover charming villas, authentic Italian culture, and breathtaking landscapes in this medieval gem.

Villas in Siena

Villa Colombini by MMega
£398  night
14
7
5
Details View Offers
Nice apartment in villa with pool, WIFI, TV, patio, pets allowed, panoramic view and parking
4.0/5
£133  night
4
2
2
Details View Offers
Private Villa with WIFI, private pool, APrivate Villa with WIFI, private pool, A/C, TV, patio, panoramic view, close to Montepulciano/C, TV, patio, panoramic view, close to Montepulciano
4.9/5
£349  night
10
4
3
Details View Offers
Villa Salvucci with private pool in San Gimignano
£395  night
10
5
6
Details View Offers
Casalone | Luxury Villa + Winery + Pool in Tuscany
£4604  night
18
7
7
Details View Offers
Beautiful apartment in villa for 2 people with WIFI, TV, patio and parking
£56  night
2
1
1
Details View Offers
From this area you can easily reach Florence, Arezzo, Siena, Chianti
4.9/5
£281  night
4
2
2
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Stunning private villa for 4 guests with pool, WIFI, TV and parking
5.0/5
£238  night
4
2
2
Details View Offers
Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views
4.8/5
£397  night
14
7
7
Details View Offers
Villa Mealli Large Private Pool, WiFi
4.6/5
£196  night
9
5
3
Details View Offers
Beautiful private villa for 8 guests with WIFI, private pool, TV, patio, pets allowed and parking
£180  night
8
4
3
Details View Offers
Villa Justina Tuscany
£1805  night
14
6
6
Details View Offers
Podere Gragnano 12, Emma Villas
£845  night
12
7
7
Details View Offers
Villa with private pool and large garden
4.7/5
£384  night
7
4
3
Details View Offers
Villa Giorgia 14 pax
£864  night
14
7
8
Details View Offers
Lovely apartment in villa for 4 people with ALovely apartment in villa for 4 people with A/C, WIFI, pool, TV and parking/C, WIFI, pool, TV and parking
4.0/5
£130  night
4
2
2
Details View Offers
Delightful villa in the heart of Tuscany
5.0/5
£1496  night
38
12
14
Details View Offers
Montebendico 6, Emma Villas
£480  night
6
4
2
Details View Offers
Solaria di Santa Maddalena 14, Castelnuovo Berardenga, Siena and Chianti
5.0/5
£687  night
14
7
7
Details View Offers
Beautiful private villa for 12 guests with ABeautiful private villa for 12 guests with A/C, WIFI, private pool, TV, terrace and parking/C, WIFI, private pool, TV, terrace and parking
£1313  night
12
6
8
Details View Offers

Why a holiday villa in Siena

Siena, Italy is a treasure trove of medieval charm and Tuscan beauty, making it the perfect destination for a villa holiday. This medieval city is nestled in the rolling hills of Tuscany, surrounded by vineyards, cypress trees and olive groves. With its well-preserved historic center, charming streets, and stunning piazzas, Siena offers an authentic Italian experience that will leave you enchanted.

Imagine waking up each morning in your own private villa, surrounded by the sights and sounds of rural Tuscany. Spend your days exploring the city's narrow alleys, visiting local markets, and sampling some of the world's best wines. Alternatively, relax in the peace and tranquility of your villa surroundings, enjoying a leisurely lunch on the patio or a game of tennis on the lawn. With its unique blend of culture, history, and natural beauty, Siena is the perfect destination for a villa holiday that will leave you with memories to last a lifetime.

The villas available in and around Siena are diverse in style, ranging from rustic farmhouses to elegant country estates. Many have been lovingly restored to retain their original charm, while others have been modernized to provide luxurious amenities. Whether you're looking for a romantic getaway or a family vacation, there's a villa to suit every taste and budget. So why not come and experience the authentic Italy that Siena has to offer?

When to rent a villa in Siena

When it comes to planning your villa holiday in Siena, Italy, timing is everything. The Tuscan countryside experiences a Mediterranean climate, with warm summers and mild winters. If you're looking for a relaxing getaway without the crowds, consider visiting Siena in the spring (April-May) or autumn (September-October). During these periods, the weather is usually pleasant, with temperatures ranging from 18-22°C (64-72°F), making it ideal for outdoor activities like hiking and biking. The countryside is also at its most vibrant during this time, with wildflowers blooming in every color of the rainbow.

If you're looking for a more festive atmosphere, summer might be the perfect time for your villa holiday in Siena. June to August brings warm weather (average high temperature around 28°C/82°F) and long days, making it ideal for exploring the city's historic center or enjoying water activities at one of the nearby lakes. However, keep in mind that this is peak tourist season, so expect larger crowds and higher prices. If you're a winter sports enthusiast, December to February is the best time to visit Siena for skiing and snowboarding, with many nearby resorts offering excellent facilities and stunning views of the Tuscan countryside blanketed in snow.

Where to go in Siena

Siena's picturesque countryside offers a wide range of settings for your villa holiday, each with its own unique character. For those seeking a peaceful retreat, the hills surrounding Siena are dotted with secluded villas that provide breathtaking views and tranquil surroundings. Take a leisurely walk through the vineyards and olive groves, or simply relax in the garden of your private villa, surrounded by nature's splendor.

Alternatively, you may want to consider a villa located in one of Siena's charming neighborhoods, such as Pianore or San Gimignano. These areas offer easy access to the city's historic center, where you can explore the narrow streets, visit local markets and restaurants, and enjoy the lively atmosphere that comes with being in the heart of Tuscany. For those seeking a more vibrant experience, Siena has a number of villas located near the nearby towns of Volterra and Castellina, which offer a range of amenities and activities, including wine tastings and cooking classes.

Picture of two young girls swimming in a pool with their floatation rings
Family friendly villas
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Image of a woman swimming in a pool at a holiday home
Private pool villas
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Picture of a Titleist golf ball on the edge of the hole on a golfing green
Villas near golf course
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Discover regions within Siena

Unione dei Comuni Valdichiana Senese
Unione dei Comuni Valdichiana Senese
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Gaiole in Chianti
Gaiole in Chianti
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Unione dei Comuni Amiata Val d'Orcia
Unione dei Comuni Amiata Val d'Orcia
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Radda in Chianti
Radda in Chianti
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San Gimignano
San Gimignano
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Castelnuovo Berardenga
Castelnuovo Berardenga
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Montalcino
Montalcino
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Castellina in Chianti
Castellina in Chianti
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Asciano
Asciano
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Casole d'Elsa
Casole d'Elsa
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Poggibonsi
Poggibonsi
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Colle di Val d'Elsa
Colle di Val d'Elsa
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Monteriggioni
Monteriggioni
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Buonconvento
Buonconvento
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Radicondoli
Radicondoli
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Villas in Siena

Villa Colombini by MMega
£398  night
14
7
5
Details View Offers
Nice apartment in villa with pool, WIFI, TV, patio, pets allowed, panoramic view and parking
4.0/5
£133  night
4
2
2
Details View Offers
Private Villa with WIFI, private pool, APrivate Villa with WIFI, private pool, A/C, TV, patio, panoramic view, close to Montepulciano/C, TV, patio, panoramic view, close to Montepulciano
4.9/5
£349  night
10
4
3
Details View Offers
Villa Salvucci with private pool in San Gimignano
£395  night
10
5
6
Details View Offers
Casalone | Luxury Villa + Winery + Pool in Tuscany
£4604  night
18
7
7
Details View Offers
Beautiful apartment in villa for 2 people with WIFI, TV, patio and parking
£56  night
2
1
1
Details View Offers
From this area you can easily reach Florence, Arezzo, Siena, Chianti
4.9/5
£281  night
4
2
2
Details View Offers
Stunning private villa for 4 guests with pool, WIFI, TV and parking
5.0/5
£238  night
4
2
2
Details View Offers
Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views
4.8/5
£397  night
14
7
7
Details View Offers
Villa Mealli Large Private Pool, WiFi
4.6/5
£196  night
9
5
3
Details View Offers
Beautiful private villa for 8 guests with WIFI, private pool, TV, patio, pets allowed and parking
£180  night
8
4
3
Details View Offers
Villa Justina Tuscany
£1805  night
14
6
6
Details View Offers
Podere Gragnano 12, Emma Villas
£845  night
12
7
7
Details View Offers
Villa with private pool and large garden
4.7/5
£384  night
7
4
3
Details View Offers
Villa Giorgia 14 pax
£864  night
14
7
8
Details View Offers
Lovely apartment in villa for 4 people with ALovely apartment in villa for 4 people with A/C, WIFI, pool, TV and parking/C, WIFI, pool, TV and parking
4.0/5
£130  night
4
2
2
Details View Offers
Delightful villa in the heart of Tuscany
5.0/5
£1496  night
38
12
14
Details View Offers
Montebendico 6, Emma Villas
£480  night
6
4
2
Details View Offers
Solaria di Santa Maddalena 14, Castelnuovo Berardenga, Siena and Chianti
5.0/5
£687  night
14
7
7
Details View Offers
Beautiful private villa for 12 guests with ABeautiful private villa for 12 guests with A/C, WIFI, private pool, TV, terrace and parking/C, WIFI, private pool, TV, terrace and parking
£1313  night
12
6
8
Details View Offers