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Holiday Villas with Pool in Italy

Below you will find our entire range of Italian holiday villas with pool. To narrow down the list, you can select the number of persons, and additional amenities (private pool, child safe pool, heated pool, near the beach, etc.). Then click the search button.

Casa dell’Ambasciatore
Vivo d'Orcia

Casa dell’Ambasciatore

2 BR Cottage in Southern Tuscany, village in walking distance - UNESCO World Heritage

Casa dell’Ambasciatore is a charming country house standing on its own on the edge of the hamlet, surrounded by a garden and wide stretching views onto open field...

Key activities:

cultural sightseeing, winemaking area, spas, excellent food, beautiful hiking, wild nature

As from 1498.00 €

4 2 2 Pool Internet Access Florence: 150 km
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Aster
Frassanelle

Aster

A friendly holiday apartment in the Veneto on flowered courtyard with portico

The farm buildings of the estate are surrounded by the English style park, cultivated farmland and - literally bordering on the estate - the Natural Park of the Eug...

Key activities:

Sightseeing, golf, hiking whithin the estate, excellent restaurants

As from 1100.00 €

6 3 2 Pool Internet Access Venice: 68 km
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Chiarentana – Ronda
Chiarentana

Chiarentana – Ronda

Apartment for 6 built around a magical courtyard and dominating the Orcia valley

Chiarentana was once a medieval fortress and has been 'de-gentrified' over the centuries, becoming one of the main farm buildings on the property.

The 6 holiday ...

Key activities:

Siena, Florence, Montalcino, Montepulciano, Pienza, Orvieto, Cortona

As from 2121.00 €

6 3 3 Pool Internet Access Florence 150km
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Casa del Camino
La Montecchia

Casa del Camino

Charming holiday rental for 2 on a top wine estate near Venice

Casa del Camino is a charming ground floor apartment flooded with light. It lies next to the offices of the wine estate. While one might see the odd visitor during ...

Key activities:

Visit the wine estate, cultural sightseeing, golf, tennis, retaurant with a Michelin star, wine producing area

As from 306.00 €

2 1 1 Pool Internet Access Venice airport: 60 km
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Villa La Foce
La Foce

Villa La Foce

A Renaissance luxury villa with pool near Siena - CLASS LISTED/LANDMARKED BUILDING

Villa La Foce is the Origo family house. It was originally built at the end of the XVth century as a wayside tavern, but soon became the centre of an estate belongi...

Key activities:

cultural sightseeing, winemaking area, tennis, spas, hiking

As from €

24 12 12 Pool Internet Access Florence: 150 km
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Torretta – Silene
Frassanelle

Torretta – Silene

Stylish holiday rental studio with pool on historical estate near Padua and Venice

The elegant farm buildings of the Frassanelle estate date back to the 17th century. What used...

Key activities:

Sightseeing, golf, hiking whithin the estate, excellent restaurants

As from 700.00 €

2 1 1 Pool Internet Access Venice: 68 km
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Casa Faraona
San Polo in Rosso

Casa Faraona

Secluded Chianti villa with pool and wheelchair accessibility.

Enjoy an authentic and idyllic rural holiday at this secluded villa with a pool found deep in Chianti. Sitting on the edge of a hamlet, the beautifull...

Key activities:

touring towns, cultural sightseeing, visiting wineries, spa treatments, hiking, biking

As from 3775.00 €

6 3 3 Pool Internet Access Rome Fiumicino airport 275km – 3h, Florence airport 70km – 1h10, Pisa airport 115km – 1h50
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Chiarentana – Bersagliere
Chiarentana

Chiarentana – Bersagliere

6 generous apartments overlooking the Val d'Orcia, with salt water pool

Chiarentana was once a medieval fortress and has been 'de-gentrified' over the centuries, becoming one of the main farm buildings on the property.

The 6 apartmen...

Key activities:

Siena, Florence, Montalcino, Montepulciano, Pienza, Orvieto, Cortona

As from 1022.00 €

2 1 1 Pool Internet Access Florence 150km
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Ringoni
Via del Pellegrino

Ringoni

Tuscan farmhouse holiday rental with heated pool in the Val d'Orcia

A charming 300 years old stone farmhouse, lying high up in the Orcia valley, facing south-west with a stunning view over hills of what is considered one of the most...

Key activities:

cultural sightseeing, winemaking area, spas, hiking, mountain biking

As from 5000.00 €

10 5 4 Pool Internet Access Perugia 1 hour, Florence 1.5 hours, Rome and Pisa 2 hours
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Castelrotto
Castelnuovo Tancredi

Castelrotto

An authentic, beautifully restored farmhouse on an organic wine estate near Montalcino south of Siena

Nestled within gently rolling vineyards, olive groves and grain fields, this lovingly renovated farmhouse is part of a vast 600-hectare estate which has been owned ...

Key activities:

touring towns, cultural sightseeing, visiting wineries, spa treatments, hiking, biking, golf.

As from 8400.00 €

20 10 8 Pool Internet Access 115 km Florence, 200 km Rome
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