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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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Villa Tombolino
Tombolino Bolgheri

Villa Tombolino

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 9340.00 €

12 6 6 Pool Internet Access Pisa airport 67 km (under one hour)
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Rocchetto
Le Rocchette

Rocchetto

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 1600.00 €

6 3 3 Pool Internet Access Florence: 110 km
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Palazzetto
Barberino

Palazzetto

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 €

16 8 7 Pool Internet Access Florence: 45 km
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Casa Vecchia
Podere Tesorino

Casa Vecchia

Stylish country house with private pool and fab views on a beautiful hillside in Tuscany

Casa Vecchia is a 300 year old, typically Tuscan farm, set on a hill, surrounded by an seemingly endless succession of hills with olive groves, meadows and small sp...

Key activities:

Beaches, Thermal springs, Biking, Hiking, Culture

As from 3020.00 €

9 9 4 Pool Internet Access Roma Fiumicino: 197 km, Pisa Galileo Galilei: 182km
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Castello
Marsiliana

Castello

The former traditional hunting castle

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 3000.00 €

15 8 4 Pool Internet Access Roma Fiumicino: 120 km
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Il Mulino
La Badia

Il Mulino

Stunning villa with pool on organic estate in central Tuscany

Mulino in Italian means Mill and this house used to be the mill of the La Badia estate. It still...

Key activities:

Excellent starting point to visit most of Tuscany, cultural sightseeing, excellent food, hiking within the estate, tennis in the village

As from 3130.00 €

10 6 5 Pool Internet Access Florence: 110 km
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Torre alle Tolfe
Le Tolfe

Torre alle Tolfe

A beautifully restored villa on an organic wine estate near Siena

Crowning a hilltop in the world-famous Chianti wine region and only three kilometers from stunning Siena, this former watch tower has been converted into a magnific...

Key activities:

cultural sightseeing, visiting wine producers and cheese makers, spa treatments, hiking, biking.

As from 6900.00 €

29 17 18 Pool Internet Access Florence 80 km, Pisa 115 km, Rome 265 km
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Villa Spada
Orbicciano Lucca

Villa Spada

Villa with private pool in the hills above Lucca - experience superbly comfortable country style

Set high in the idyllic landscape of the hills north west of Lucca, this patrician country house dating back to the 1700's was once the hunting lodge of the aristoc...

Key activities:

cultural sightseeing, the famous villas around Lucca, beachlife, excellent food

As from 2742.00 €

10 5 4 Pool Internet Access Pisa: 50 km
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Maramai
Tenuta di Gracciano

Maramai

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 2500.00 €

9 5 5 Pool Internet Access Florence: 120 km
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Castello di Galbino
Galbino

Castello di Galbino

A fairy tale castle in the country of Saint Francis - CLASS LISTED / LANDMARKED BUILDING

Tucked away into the hills of Arezzo lies the magic Castello di Galbino, a large and welcoming family castle surrounded by seemingly endless fields and hills covere...

Key activities:

Cultural sightseeing, discovery of an unknown Tuscany, excellent resturants, tennis (village)

As from €

19 9 8 Pool Internet Access Florence: 120 km
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