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Holiday Villas Rental in Tuscany

Below you will find our entire range of holiday villas in Tuscany, Italy. To narrow down the list, you can select the number of persons and additional amenities (private pool, near the beach, air conditioning, 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 Melissa & Casa Vittoria
Fighine

Villa Melissa & Casa Vittoria

Luxury villa set in an enchanting garden within a Tuscan hilltop hamlet

Villa Melissa and Casa Vittoria are two separate buildings within the same garden. They can be rented together for groups up to 14 guests. Both houses have their ow...

Key activities:

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

As from 9530.00 €

14 7 7 Pool Internet Access Perugia 60km, Florence 120km, Rome 170km
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Casa Livia
Cetona

Casa Livia

Medieval tower with pool, views and in walking distance of a village

Savor the best of southern Tuscany at this wonderful three-bedroom 14th century tower, set within bucolic gardens at the edge of the picturesque town of Cetona. Its...

Key activities:

touring towns, cultural sightseeing, visiting wine producers, spa treatments, hiking, biking, golf, watersports

As from 1787.00 €

6 3 3 Pool Internet Access Perugia 68km, Florence 140km, Rome 190km
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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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Sassaia
Chiarentana

Sassaia

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 €

14 7 7 Pool Internet Access Florence 150km
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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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Parretti Due
Fighine

Parretti Due

Luxury bed and breakfast with views, set in a privately owned hamlet in Tuscany

Beautifully appointed upper floor 1 bedroom apartment, ideal for guests visiting the *Michelin star restaurant of Key activities:

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

As from 295.00 €

2 1 1 Internet Access Perugia 60km, Florence 120km, Rome 170km
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Casa di Lilli
Vivo d'Orcia

Casa di Lilli

Charming 1BR cottage south of Siena - Village in walking distance - UNESCO WORLD HERITAGE

Casa di Lilli is a small 2 storeyed house located next to the romanesque church of Vivo d’Orcia. It was fully restored and turned into a charming retreat for two....

Key activities:

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

As from 784.00 €

2 1 1 Pool Internet Access Florence: 150 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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