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Holiday Villa Rental in Tuscany

Below you will find our entire range of holiday villa rentals 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.). Don’t forget to 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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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 1900.00 €

9 5 5 Pool Internet Access Florence: 120 km
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Palazzonaccio
Via del Pellegrino

Palazzonaccio

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 4000.00 €

11 5 6 Pool Internet Access Perugia 1 hour, Florence 1.5 hours, Rome and Pisa 2 hours
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Chiarentana – Ronda
La Foce

Chiarentana – Ronda

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:

cultural sightseeing,winemaking area, tennis, spas, hiking

As from 1430.00 €

6 3 2 Pool Internet Access Florence: 150 km
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Granaio 1
Borgo di Pietrafitta

Granaio 1

A converted granary

What used to be the granary of the estate has been cleverly converted into two ground floor apartments, each with its own private garden space.

This apartment ha...

Key activities:

cultural sightseeing, Chianti wine making, excellent restaurants, golf, hiking & biking

As from 1099.00 €

4 2 1 Pool Internet Access Florence 47km
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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 6081.00 €

6 3 3 Pool Internet Access Perugia 60km, Florence 120km, Rome 170km
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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 2420.00 €

8 4 4 Pool Internet Access Florence: 150 km
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Rombellana
Via del Pellegrino

Rombellana

Luxury villa with heated pool and air condition in southern Tuscany, stunning design

Rombellana is a large stone farmhouse wich was recently restored to the highest standard by the well known interior designer Ilaria Miani. Breathtaking contemporary...

Key activities:

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

As from 7500.00 €

19 9 9 Pool Internet Access Perugia 1 hour, Florence 1.5 hours, Rome and Pisa 2 hours
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Villa Fontanili-Mirto
Fontanili

Villa Fontanili-Mirto

Paradise in Maremma, the southern Tuscan coast

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 970.00 €

5 3 2 Pool Internet Access Roma Fiumicino: 100 km
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Casa Vecchia
Podere Tesorino

Casa Vecchia

Stylish country house with 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 3110.00 €

9 9 4 Pool Internet Access Roma Fiumicino: 197 km, Pisa Galileo Galilei: 182km
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Granaio 2
Borgo di Pietrafitta

Granaio 2

A converted Granary

What used to be the granary of the estate has been cleverly converted into two ground floor apartments, each with its own private garden space.

This apartment ha...

Key activities:

cultural sightseeing, Chianti wine making, excellent restaurants, golf, hiking & biking

As from 1008.00 €

3 2 1 Pool Internet Access Florence 47km
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