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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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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 3350.00 €

9 5 5 Pool Internet Access Florence: 120 km
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Casa della Pineta
Tombolino Bolgheri

Casa della Pineta

Beachfront cottage on the Tuscany seaside, 3 bedrooms

The apartment lies on the ground floor of a small cottage on the estate. It is a very friendly and sunny house, and nearly all the rooms have french windows opening...

Key activities:

direct access to the beach, wine tasting, excellent restaurants, visiting the surrounding hilltop towns

As from €

6 3 2 Internet Access Pisa airport 67 km (under one hour)
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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 188.00 €

4 2 2 Pool Internet Access Florence: 150 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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Casa di Donata
Chiarentana

Casa di Donata

Elegant villa with pool and tennis overlooking the Orcia valley near Pienza

Donata’s house offers all the special charm, character and seclusion of a private home and garden, with the additional advantage of having the restaurant, tennis,...

Key activities:

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

As from €

10 5 5 Pool Internet Access Florence 150km
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Chiarentana – Beco
Chiarentana

Chiarentana – Beco

6 generous holiday 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 660.00 €

4 2 2 Pool Internet Access Florence 150km
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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 3480.00 €

10 6 5 Pool Internet Access Florence: 110 km
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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 1050.00 €

6 3 2 Pool Internet Access Roma Fiumicino: 100 km
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Chiarentana – Vespa
Chiarentana

Chiarentana – Vespa

6 generous Tuscan 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 holiday ...

Key activities:

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

As from 576.00 €

4 2 2 Pool Internet Access Florence 150km
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B&B Palazzolo
La Foce

B&B Palazzolo

B&B in a traditional Tuscan farmhouse overlooking Orcia valley

B&B Palazzolo is only 500m from the central La Foce Villa, on the road that leads to Chiarentana. The house is one of the farmhouses rebuilt by Antonio Origo in...

Key activities:

cultural sightseeing, winemaking area, tennis, spas, hiking

As from €

2 2 1 Pool Internet Access Florence: 150 km
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