Holiday Villas in Italy with Private Pool
Below you will find our entire range of holiday villas with private pools in Italy. To narrow down the list, you can select the number of persons and additional amenities (heated pool, child safe pool, near the beach, etc.). Then click the search button.
- Overview
- Search result: 30 Villas available
- Agriturismo cottages in Italy
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- Villas with private pools in Italy
- Holiday villas with pools in Italy (shared and private)
- Child friendly villas in Italy
- Seaside villas in Italy
- Holiday villas in Italy with air condition
- Villas with wheelchair access in Italy
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![Maramai](https://www.trustandtravel.com/wp-content/uploads/2016/06/000-Pool-1-Maramai-2.jpg)
Comfortable villa with great pool on wine estate near Montepulciano and Pienza
Maramai, now a charming country house, used to be a small farm with 3 separate buildings. It is named after the Tuscan farmer’s family who lived there until the e...
Key activities:
visiting the wine estate, cultural sightseeing, excellent food, hiking, tennis (village)
As from 3350.00 €
![Palazzonaccio](https://www.trustandtravel.com/wp-content/uploads/2016/06/00-DSCN0084-copia.jpg)
Old stone farmhouse turned holiday house in southern Tuscany - beautiful design, solar heating, pool
Palazzonaccio lies high up overlooking the majestic Orcia valley. It was the first house to be restored by the international designer Ilaria Miani here in the Orcia...
Key activities:
cultural sightseeing, winemaking area, spas, hiking, mountain biking
As from 5375.00 €
![Castiglione Ugolino](https://www.trustandtravel.com/wp-content/uploads/2019/10/Castiglione-Ugolino-01.jpg)
Newly restored medieval castle in Umbria with infinity pool
The 11th-century Castiglione Ugolino sits within the Murlo estate atop a hill overlooking the rolling hills of Umbria. Completely restored in 2019, the ancient cast...
Key activities:
Sightseeing, golf, swimming, walks, discover restaurants, wine tasting, fishing, mountain-biking
As from €
![Palazzetto](https://www.trustandtravel.com/wp-content/uploads/2016/06/000-Palazzetto-28.jpg)
A small jewel of Renaissance architecture in Chianti - CLASS LISTED / LANDMARKED BUILDING
The villa looks onto the main street of the historical village Barberino Val d’Elsa (which is...
Key activities:
cultural sightseeing, visiting wine producers, excellent restaurants, tennis (village)
As from 4000.00 €
![Rocchetto](https://www.trustandtravel.com/wp-content/uploads/2016/06/000-Rocchetto-Square.png)
Delightful 3 BR villa with great pool between Siena and Arezzo
Small villas (this one sleeps 4 to 6 guests) with private pools are a rarity. Rocchetto is perfectly located, has great charm, and a lovely pool.
Over the last t...
Key activities:
Excellent starting point to visit most of Tuscany, cultural sightseeing, excellent food, hiking within the estate, tennis in the village
As from 2300.00 €
![Casuzza](https://www.trustandtravel.com/wp-content/uploads/2016/06/00-Casaccia.jpg)
Villa with private pool on Sicily's southern coast
La Casuzza is reached over a small country road bordered by dry stone walls that leads up the hill from the coast. The house sits above a small valley dotted with C...
Key activities:
Beachlife, visiting baroque Sicily, fishing, on the trail of Inspector Montalbano
As from 2500.00 €
![Villa dell’Orso](https://www.trustandtravel.com/wp-content/uploads/2016/06/Villa-dell-orso-on-the-sea-in-Sardinia-1.jpg)
Exceptional beachfront villa on Sardinia's most beautiful coast
Villa dell’Orso is situated on the northern tip of Sardinia on a white sandy beach overlooking a large bay with the islands of the national Park La Maddalena in t...
Key activities:
Private access to the sea, sailing, surfing, scuba diving, snorkeling, fishing, sightseeing, walks along the coast
As from €
![Fontalgozzo](https://www.trustandtravel.com/wp-content/uploads/2016/06/00-Fontalgozzo-DJI_0016.jpg)
Converted farmhouse with the best known view in Tuscany
The house stands on its own, surrounded by olive groves, wheat fields and cypresses, and looks onto the famous cypress road that winds up the 'crete' on the opposit...
Key activities:
cultural sightseeing, winemaking area, tennis, spas, hiking
As from 4600.00 €
![Sassaia](https://www.trustandtravel.com/wp-content/uploads/2022/09/01-sassaia-facade-copy.jpg)
Spacious country villa with pool in the famous Val d'Orcia
Sassaia sits on the slopes of the famous Orcia valley and is surrounded by magnificent evergreen oak trees typical of Tuscany. Beyond are open fields and views acro...
Key activities:
Siena, Florence, Montalcino, Montepulciano, Pienza, Orvieto, Cortona
As from 7490.00 €
![Villa Tombolino](https://www.trustandtravel.com/wp-content/uploads/2016/06/00-villa-bolgheri-garden-terrace.jpg)
Elegant beachfront villa on the famous Bolgheri coastline
Unspoilt beaches fringed with dunes are backed by hillsides covered in Mediterranean scrub and olive groves, crested by charming hill-top villages. The reclaimed fl...
Key activities:
direct access to the beach, wine tasting, excellent restaurants, visiting the surrounding hilltop towns
As from €