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Villas in San Gimignano: Luxury Accommodations

Experience la dolce vita in Tuscany's iconic hilltop town, San Gimignano. Discover enchanting villas amidst medieval charm, rolling hills & vineyards. Your dream Italian getaway awaits!

Villas in San Gimignano

Villa with private pool overlooking San Gimignano. Exclusive use of the property
5.0/5
£521  night
12
6
6
Details View Offers
Stunning villa for 4 people with hot tub, private pool, WIFI, TV, terrace and parking
5.0/5
£132  night
4
2
1
Details View Offers
Private Villa with WIFI, private pool, TV, balcony, pets allowed, parking, close to San Gimignano
4.0/5
£271  night
12
6
5
Details View Offers
Villa Salvucci with private pool in San Gimignano
£395  night
10
5
6
Details View Offers
Casa Spina - Apartment with pool near San Gimignano in Tuscany
£282  night
6
3
3
Details View Offers
SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI
5.0/5
£910  night
18
9
9
Details View Offers
Lovely apartment in villa for 7 guests with pool, ALovely apartment in villa for 7 guests with pool, A/C, WIFI, TV and parking/C, WIFI, TV and parking
£186  night
7
3
3
Details View Offers
Villa with private pool walking distance from San Gimignano
4.9/5
£421  night
9
4
4
Details View Offers
Lilium, splendid villa with outdoor space, on the hills of San Giminiano
4.8/5
£223  night
7
3
4
Details View Offers
Villa Barbarella - Villa with a private pool in San Gimignano
£895  night
10
5
4
Details View Offers
Villa with swimming pool among vineyards 2 km from San Gimignano
5.0/5
£343  night
6
3
3
Details View Offers
Luxury villa, infinity pool, chef, pizzaiolo, massages, yoga, grocery delivery
5.0/5
£352  night
12
5
5
Details View Offers
Villa Giorgia 14 pax
£864  night
14
7
8
Details View Offers
Private villa near Certaldo and San Gimignano with swimming pool and large garden.
4.7/5
£258  night
10
4
4
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
Villa Le Ripe - Gambassi Terme, Toscana
5.0/5
£455  night
19
7
6
Details View Offers
Stunning private villa with WIFI, private pool, TV, patio, pets allowed, panoramic view and park...
£338  night
10
5
3
Details View Offers
Il Pascolo, San Gimignano, Siena and Chianti
£322  night
6
4
3
Details View Offers
Nido del Merlo 8 In San Gimignano, Tuscany
4.9/5
£330  night
9
4
3
Details View Offers
Entire big villa with private pool San Gimignano
£429  night
15
7
7
Details View Offers

Why a holiday villa in San Gimignano

San Gimignano is a medieval walled town perched on top of a hill in Tuscany, offering visitors a unique and unforgettable experience. Staying in a villa here means immersing yourself in the authentic charm of Italy's countryside, surrounded by rolling hills, cypress trees, and vineyards as far as the eye can see.

Imagine waking up each morning to the sound of birds singing and the warm sun rising over the terracotta-tiled roofs. Spend your days exploring the narrow streets and alleys of San Gimignano, admiring the stunning skyline of 14th-century towers and taking in the breathtaking views from the top of the town's highest point. In the evenings, return to your villa and relax on the private patio or poolside with a glass of wine, watching the stars twinkling above.

As night falls, the sky is painted with hues of pink and orange as the sun sets over the Tuscan hills. The gentle breeze carries the scent of fresh herbs and the sound of crickets fills the air, creating an atmosphere that's at once peaceful and enchanting. This is what a villa holiday in San Gimignano has to offer – a chance to disconnect from the world and reconnect with nature, beauty, and the simple pleasures in life.

Staying in a luxury villa here means having your own private haven, where you can relax and unwind in style. Many villas come with private pools, outdoor kitchens and beautifully manicured gardens, perfect for al fresco dining or simply enjoying the warm sunshine. Others offer breathtaking views of the surrounding countryside, while some are located just outside San Gimignano's historic center, within easy walking distance to all the town's shops, restaurants and attractions.

From villas with private pools and outdoor kitchens to those with stunning views of the Tuscan countryside, there's a perfect accommodation for every taste and budget. Whether you're looking for a romantic getaway or a fun family holiday, San Gimignano's villas offer the ultimate Italian experience – immerse yourself in la dolce vita and make unforgettable memories in this enchanting hilltop town.

When to rent a villa in San Gimignano

San Gimignano's Mediterranean climate means warm summers and mild winters, making it an ideal destination for a villa holiday any time of the year. However, if you're looking for a tranquil and peaceful experience, consider visiting during the shoulder season (April to June or September to October). The weather is usually pleasant, with average highs in the mid-20s Celsius (mid-70s Fahrenheit), and the crowds are smaller than during the peak summer months.

If you're looking for a more vibrant atmosphere, July and August might be the perfect time for you. These months offer warm weather, long days, and a lively party scene, with many festivals and events taking place throughout San Gimignano. However, if you prefer milder temperatures without the crowds, spring (April to May) or autumn (September to November) are excellent options. Additionally, consider visiting during the harvest season (August to October), when the local wine production is in full swing, and you can participate in wine tastings and tours at many nearby wineries. Whatever time of year you choose for your villa holiday in San Gimignano, be sure to pack accordingly, as the weather can be unpredictable, especially during the spring and autumn months.

Where to go in San Gimignano

San Gimignano's surrounding countryside offers a wide range of settings for your dream villa holiday. For those seeking tranquility and seclusion, consider villas tucked away in the rolling hills and vineyards just outside the town's historic center. Here, you can enjoy peaceful walks and bike rides through the Tuscan landscape, taking in the region's famous cypress trees and olive groves.

On the other hand, if you're looking for a villa that's within walking distance to San Gimignano's medieval charm, consider renting a property in the town's historic center or just outside its walls. This way, you can easily stroll through the narrow streets, explore the local shops and restaurants, and take in the breathtaking views from the top of the town's highest point. Some areas, such as Poggibonsi and Certaldo, offer easy access to San Gimignano while still providing a more laid-back atmosphere. No matter where you choose to stay, be sure to explore the local towns and villages for authentic Italian cuisine, wine tastings, and unique shopping experiences that will make your villa holiday in San Gimignano truly unforgettable.

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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Villas in San Gimignano

Villa with private pool overlooking San Gimignano. Exclusive use of the property
5.0/5
£521  night
12
6
6
Details View Offers
Stunning villa for 4 people with hot tub, private pool, WIFI, TV, terrace and parking
5.0/5
£132  night
4
2
1
Details View Offers
Private Villa with WIFI, private pool, TV, balcony, pets allowed, parking, close to San Gimignano
4.0/5
£271  night
12
6
5
Details View Offers
Villa Salvucci with private pool in San Gimignano
£395  night
10
5
6
Details View Offers
Casa Spina - Apartment with pool near San Gimignano in Tuscany
£282  night
6
3
3
Details View Offers
SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI
5.0/5
£910  night
18
9
9
Details View Offers
Lovely apartment in villa for 7 guests with pool, ALovely apartment in villa for 7 guests with pool, A/C, WIFI, TV and parking/C, WIFI, TV and parking
£186  night
7
3
3
Details View Offers
Villa with private pool walking distance from San Gimignano
4.9/5
£421  night
9
4
4
Details View Offers
Lilium, splendid villa with outdoor space, on the hills of San Giminiano
4.8/5
£223  night
7
3
4
Details View Offers
Villa Barbarella - Villa with a private pool in San Gimignano
£895  night
10
5
4
Details View Offers
Villa with swimming pool among vineyards 2 km from San Gimignano
5.0/5
£343  night
6
3
3
Details View Offers
Luxury villa, infinity pool, chef, pizzaiolo, massages, yoga, grocery delivery
5.0/5
£352  night
12
5
5
Details View Offers
Villa Giorgia 14 pax
£864  night
14
7
8
Details View Offers
Private villa near Certaldo and San Gimignano with swimming pool and large garden.
4.7/5
£258  night
10
4
4
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
Villa Le Ripe - Gambassi Terme, Toscana
5.0/5
£455  night
19
7
6
Details View Offers
Stunning private villa with WIFI, private pool, TV, patio, pets allowed, panoramic view and park...
£338  night
10
5
3
Details View Offers
Il Pascolo, San Gimignano, Siena and Chianti
£322  night
6
4
3
Details View Offers
Nido del Merlo 8 In San Gimignano, Tuscany
4.9/5
£330  night
9
4
3
Details View Offers
Entire big villa with private pool San Gimignano
£429  night
15
7
7
Details View Offers