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Holiday Villas in Tuscany with Private Pool

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

 

Tuscany

The historical estates listed below have been carefully selected by Trust&Travel over the past years. Each property stands out for its beauty, its location, the interior decoration and the level of service. You can choose a charming agriturismo cottage, a stunning villa with private pool, an exclusive fully staffed luxury villa or a historical castle with pool.
Browse each of the following estates in Tuscany to find out more about the available rentals, their location and surroundings and the suggested services.

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Montecucco
Vivo d'Orcia

Montecucco

Restored farmhouse south of Siena with pool and views onto the vineyards of Montalcino

Villa Montecucco is located at an altitude of 400 metres above sea level, twenty minutes’ drive from the castle estate of Vivo D’Orcia. It benefits from absolut...

Key activities:

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

As from 2954.00 €

8 4 4 Pool Internet Access Florence: 150 km
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Castello
Marsiliana

Castello

A large family castle on the Tuscan Coast

From the distance, Marsiliana might look like a castle, but as you reach the top of the hill and drive through the gate the feeling is more that of an informal haml...

Key activities:

visiting the wine estate, beach life, bicling, hiking, tennis (village)

As from 3900.00 €

13 7 4 Pool Internet Access Roma Fiumicino: 120 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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Villa Melissa
Fighine

Villa Melissa

19th century luxury villa with pool in Tuscan hamlet between Florence and Rome

Villa Melissa is a large villa set within its own private garden. The beautiful swimming pool with pool house and full changing and shower facilities lies 2 minute ...

Key activities:

cultural sightseeing, visiting wine producers, excellent restaurants, spa treatments, hiking, mountain biking

As from 6099.00 €

8 4 4 Pool Internet Access Perugia 60km, Florence 120km, Rome 170km
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Casa Janine
Fighine

Casa Janine

Luxuriously amenished Tuscan farmhouse set in privately owned medieval hamlet

Casa Janine has remarkable far-reaching views over the surrounding countryside. It has its’ own private pool and garden with long expanses of lawn, a vine-covered...

Key activities:

cultural sightseeing, visiting wine producers, excellent restaurants, spa treatments, hiking, mountain biking

As from 5587.00 €

6 3 3 Pool Internet Access Perugia 60km, Florence 120km, Rome 170km
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Villa Fontanili-Ginepro
Fontanili

Villa Fontanili-Ginepro

Paradise in Maremma, the southern Tuscan coast

Surrounded by trees, the villa Il Fontanili stands in extensive landscaped grounds which blend into the olive groves and fields of the estate. The beach, 3 km. from...

Key activities:

private access to the sea, excellent sea food, cultural sightseeing, bicycling, tennis (village)

As from 1085.00 €

6 3 2 Pool Internet Access Roma Fiumicino: 100 km
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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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Villa Fontanili-Mirto
Fontanili

Villa Fontanili-Mirto

Ground floor apartment by the sea with pool in Maremma

Surrounded by trees, the villa Fontanili stands in extensive landscaped grounds which blend into the olive groves and fields of the estate. The beach, 3 km. from th...

Key activities:

private access to the sea, excellent sea food, cultural sightseeing, bicycling, tennis (village)

As from 1082.00 €

5 3 2 Pool Internet Access Roma Fiumicino: 100 km
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Chiarentana – Tiglio
Chiarentana

Chiarentana – Tiglio

6 generous apartments built around a magical courtyard

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 1505.00 €

4 2 1 Pool Internet Access Florence 150km
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