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Luxury Villas in Monteriggioni

Experience la dolce vita in Tuscany's charming hilltop town of Monteriggioni. Discover luxurious villas, rich history, and breathtaking landscapes - the perfect blend for a unforgettable Italian holiday.

Villas in Monteriggioni

Beautiful apartment in villa with WIFI, pool, TV, patio, pets allowed, panoramic view and parking
£143  night
4
2
1
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Chiara Country home
4.9/5
£449  night
14
6
7
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Lovely apartment in villa for 3 guests with ALovely apartment in villa for 3 guests with A/C, pool, TV and parking, close to Siena/C, pool, TV and parking, close to Siena
£114  night
3
1
1
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Villa dei 2 Ulivi (Abbadia Isola)
5.0/5
£395  night
23
6
4
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Farmhouse Ebbio in exclusive- Monteriggioni 10 Rooms 5 Bathrooms
£1312  night
24
10
5
Details View Offers
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
5.0/5
£221  night
5
2
2
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Bellosguardo, Castellina in Chianti, Siena and Chianti
£315  night
6
3
2
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Casina di Teo In Monteriggioni, Tuscany
4.9/5
£221  night
4
1
2
Details View Offers
Villa la Quercia Comfortable holiday residence
£2426  night
14
6
7
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Villa la Quercia By MMega
5.0/5
£498  night
14
6
7
Details View Offers
Villa Rosanna - wonderful villa with swimming pool
£216  night
5
2
2
Details View Offers
Beautiful apartment in villa for 2 guests with ABeautiful apartment in villa for 2 guests with A/C, pool, TV and parking, close to Siena/C, pool, TV and parking, close to Siena
£114  night
2
1
1
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15th century barn fully renovated in a stylish style with gorgeous swimming pool
5.0/5
£613  night
8
3
3
Details View Offers
Villa Villa "Le Vallecchie" overlooking Siena and with private swimming pool"Le VallecchieVilla "Le Vallecchie" overlooking Siena and with private swimming pool" overlooking Siena and with private swimming pool
4.8/5
£338  night
8
4
4
Details View Offers
Idyllic Countryside Retreat with Rustic Elegance
5.0/5
£572  night
14
7
8
Details View Offers
Villa Isaia 31 Stunning villa medieval borgo with pVilla Isaia 31 Stunning villa medieval borgo with p/pool and tennis/pool and tennis
£7128  night
31
16
16
Details View Offers
Family friendly Villa with private garden, 30 min walk to city centre
5.0/5
£168  night
6
3
2
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Il Boschetto an oasis of peace and nature in Siena
4.9/5
£395  night
10
5
3
Details View Offers
Villa Rinaldi 6, Emma Villas
£667  night
6
4
3
Details View Offers
Stunning private villa with WIFI, private pool, TV, patio, pets allowed, panoramic view and park...
£645  night
23
9
5
Details View Offers

Why a holiday villa in Monteriggioni

Monteriggioni, perched atop a hill in Tuscany, is a medieval walled town that exudes charm and history. A villa holiday here allows you to experience the authentic essence of Italy, where time stands still and la dolce vita is truly alive. Imagine waking up each morning in your luxurious villa, surrounded by rolling hills and vineyards, with the sound of birds singing and the scent of fresh olive groves wafting through the air.

As you explore Monteriggioni's narrow streets and alleyways, you'll discover hidden gems like ancient towers, quaint shops, and restaurants serving up delicious local cuisine. The nearby cities of Siena and Florence are also within easy reach, offering a wealth of art, history, and culture to explore. Whether you're looking for relaxation, adventure, or simply a chance to unwind in a beautiful setting, Monteriggioni's villas offer the perfect blend of tranquility and excitement.

When to rent a villa in Monteriggioni

Tuscany's climate is renowned for its mildness, making it an ideal destination for a villa holiday at any time of the year. However, if you're looking for the most comfortable and pleasant weather, spring (April-May) and autumn (September-October) are the best times to visit Monteriggioni. During these periods, the temperatures are mild, with average highs ranging from 18°C to 22°C, making it perfect for outdoor activities like exploring the town's narrow streets, visiting local wineries, or simply enjoying a glass of wine in your villa's garden.

Summer (June-August) is also a great time to visit Monteriggioni, with warm weather and long days perfect for outdoor pursuits. However, it can get quite hot during this period, with temperatures sometimes reaching up to 30°C. If you're looking for a more relaxed atmosphere, consider visiting in the shoulder season (April-May or September-October), when the crowds are smaller and prices tend to be lower. Winters (December-February) are generally cooler, but still pleasant, with average highs around 12°C. If you don't mind cooler weather and want to explore Monteriggioni's Christmas markets or enjoy a quiet winter retreat, this might be the perfect time for your villa holiday.

Where to go in Monteriggioni

Monteriggioni is a charming hilltop town surrounded by rolling hills and vineyards, making it the perfect base for exploring Tuscany's countryside. For those seeking a relaxed and peaceful atmosphere, consider staying in one of the quieter areas surrounding the town, such as the hamlet of Casalino or the nearby village of Poggio a Caiano. These locations offer breathtaking views, picturesque walks, and easy access to local wineries and olive groves.

For a more vibrant experience, head to the historic center of Monteriggioni itself, where you'll find charming piazzas, quaint shops, and a selection of excellent restaurants serving up traditional Tuscan cuisine. The town also hosts various events throughout the year, including medieval reenactments and wine festivals, which add to its unique charm. If you're looking for a more lively atmosphere, consider staying in the nearby towns of Siena or Florence, which offer a wealth of cultural attractions, nightlife, and dining options.

Picture of two young girls swimming in a pool with their floatation rings
Family friendly 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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Private pool villas
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Villas in Monteriggioni

Beautiful apartment in villa with WIFI, pool, TV, patio, pets allowed, panoramic view and parking
£143  night
4
2
1
Details View Offers
Chiara Country home
4.9/5
£449  night
14
6
7
Details View Offers
Lovely apartment in villa for 3 guests with ALovely apartment in villa for 3 guests with A/C, pool, TV and parking, close to Siena/C, pool, TV and parking, close to Siena
£114  night
3
1
1
Details View Offers
Villa dei 2 Ulivi (Abbadia Isola)
5.0/5
£395  night
23
6
4
Details View Offers
Farmhouse Ebbio in exclusive- Monteriggioni 10 Rooms 5 Bathrooms
£1312  night
24
10
5
Details View Offers
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
5.0/5
£221  night
5
2
2
Details View Offers
Bellosguardo, Castellina in Chianti, Siena and Chianti
£315  night
6
3
2
Details View Offers
Casina di Teo In Monteriggioni, Tuscany
4.9/5
£221  night
4
1
2
Details View Offers
Villa la Quercia Comfortable holiday residence
£2426  night
14
6
7
Details View Offers
Villa la Quercia By MMega
5.0/5
£498  night
14
6
7
Details View Offers
Villa Rosanna - wonderful villa with swimming pool
£216  night
5
2
2
Details View Offers
Beautiful apartment in villa for 2 guests with ABeautiful apartment in villa for 2 guests with A/C, pool, TV and parking, close to Siena/C, pool, TV and parking, close to Siena
£114  night
2
1
1
Details View Offers
15th century barn fully renovated in a stylish style with gorgeous swimming pool
5.0/5
£613  night
8
3
3
Details View Offers
Villa Villa "Le Vallecchie" overlooking Siena and with private swimming pool"Le VallecchieVilla "Le Vallecchie" overlooking Siena and with private swimming pool" overlooking Siena and with private swimming pool
4.8/5
£338  night
8
4
4
Details View Offers
Idyllic Countryside Retreat with Rustic Elegance
5.0/5
£572  night
14
7
8
Details View Offers
Villa Isaia 31 Stunning villa medieval borgo with pVilla Isaia 31 Stunning villa medieval borgo with p/pool and tennis/pool and tennis
£7128  night
31
16
16
Details View Offers
Family friendly Villa with private garden, 30 min walk to city centre
5.0/5
£168  night
6
3
2
Details View Offers
Il Boschetto an oasis of peace and nature in Siena
4.9/5
£395  night
10
5
3
Details View Offers
Villa Rinaldi 6, Emma Villas
£667  night
6
4
3
Details View Offers
Stunning private villa with WIFI, private pool, TV, patio, pets allowed, panoramic view and park...
£645  night
23
9
5
Details View Offers